An Organic Chemists's Perspective on Paleo by Mat Lalonde, PhD

An Organic Chemist’s Perspec3ve on “Paleo” Mathieu P. Lalonde, Ph. D. Ancestral Health Symposium August 6th 2011

Credibility: The Presenter’s Currency Harvard Department of Chemistry Pﬁzer Lecture Hall and Chemical Biology

The Evolu3onary Approach: Observa3on ≠ Causa3on Our ancestors and modern hunter-‐gatherers consumed a diet mostly devoid of grains, legumes, and dairy. Our ancestors and modern hunter-‐gatherers were virtually free of diseases of civilizaFon. Invalid inference: Consuming a diet mostly devoid of grains, legumes, and dairy will allow us to be free of diseases of civilizaFon. Rader, A. W.; Sloutsky, V. M. Processing of Logically Valid and Logically Invalid CondiFonal Inferences in Discourse Comprehension. Journal of Experimental Psychology: Learning, Memory, and Cogni=on 2002, 28(1), 59–68.

Observa3onal Epidemiology as a Tool for Genera3ng Hypotheses Mixture of saturated, polyunsaturated and monounsaturated fats in hunter-‐ gatherer and typical western diets The Paleo Diet Update v3, #3 -‐ The Paleo Concept Typical Hunter-‐ Western Diet gatherer diet Ques3ons: 1) Is saturated fat is responsible for the poor health outcomes in the Western diet? 2) What if saturated fat is beneﬁcial but hunter gatherers were not consuming enough due to its scarcity? 3) Were the levels of polyunsaturated faYy acids in hunter-‐gatherers diets too high? Invalid inference: EmulaFng the dietary faYy acid proﬁle of hunter-‐gatherers will lead to improved health.

Observa3onal Epidemiology as a Tool for Genera3ng Hypotheses Ques3ons: 1) Are Americans consuming too many calories from carbohydrate? 2) Are Americans not consuming enough protein? Invalid inference: The calculated average macronutrient raFo of hunter-‐gatherer populaFons is the healthiest. Cordain, L.; Friel, J. NutriFon 101. The Paleo Diet for Athletes: A Nutri=onal Formula for Peak Athle=c Performance, 1st ediFon; Rodale Books, 2005, pp. 84.

Food: A Selec3ve Agent in Evolu3on “The immense biological variability among individuals has overpowering significance. The examples shown above lend support to this thesis. Much theore=cal and prac=cal knowledge can be gained from study of biological individuality. Nutri=onal variability on an interna=onal level requires that we be aware of these intricacies and interac=ons. The global approach necessitates cau=on in implemen=ng worldwide nutri=onal programs based on mean requirements derived in a specific culture. This narrow orienta=on overlooks the importance of man’s nutri=onal individuality, a reflec=on of evolu=on.” Kretchmer, N.; Food: A SelecFve Agent in EvoluFon. In Food, Nutri=on and Evolu=on; Walcher, D. N.; Kretchmer, N., Eds.; Masson Publishing USA, Inc.: New York, 1981, pp. 48.

Tishkoﬀ, S. A.; Reed, F. A.; Ranciaro, A.; Voight, B. F.; BabbiY, C. C.; Silverman, J. S.; Powell, K.; Mortensen, K. M.; Hirbo, J. B.; Osman, M.; Ibrahim, M.; Omar, S. A.; Lema, G.; Nyambo, T. B.; Ghori, J.; Bumpstead, S.; Pritchard, J. K.; Wray, G. A.; Deloukas, P. Convergent AdaptaFon of Human Lactase Persistence in Africa and Europe. Nature Gene=cs 2006, 39, 31–40.

Perry, G. H.; Dominy,N. J.; Claw, K. G.; Lee, A. S.; Fiegler, H.; Redon, R.; Werner, J.; Villanea, F. A.; Mountain, J. L.; Misra, R.; Carter, N. P.; Lee, C.; Stone, A. C. Diet and the EvoluFon of Human Amylase Gene Copy Number VariaFon. Nature Gene=cs 2007, 39(10), 1256–1260.,

Food: A Selec3ve Agent in Evolu3on Invalid inference: We evolved over millions of years without consuming foods that became readily available upon the advent of agriculture, hence, we are not adapted to these evoluFonary novel foods.

Food: A Selec3ve Agent in Evolu3on Is it safe to assume that we are not adapted to any food that became readily available and part of the human diet a7er the advent of agriculture? Doesn’t this suggest that a species cannot discover a new, be=er source of food? Didn’t our ancestors discover a new, be=er source of food when they began scavenging bone marrow and brains and didn’t this impact their development? Does this mean that all foods that were available prior to the advent of agriculture a re inherently healthier? Invalid inference: We evolved over millions of years without consuming foods that became readily available upon the advent of agriculture, hence, we are not adapted to these evoluFonary novel foods.

The Evolu3onary Approach: Beware of the Selec3on Bias Remember that, at the end of the day, all hypotheses must be tested before they can be shown to be valid or invalid. Even if some may appear less valid than others when considering testability, simplicity, scope, fruiVulness, and conserva3sm. Approaching a problem by thinking the solu3on is at hand because the hypothesis relies on evolu3on will only lead to poor science.

The Periodic Table of the Elements

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Valence Electrons, Bonding & Geometry Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Valence Electrons HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LF C N O alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H HCopyright Structure P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Kekulé Mathieu H C H H N H H O H F F H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 109.5° 104.5° Molecular Geometry H H C H N H O F FCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu Fluorine P. Lalonde 107.3° Hydrogen Methane Ammonia WaterCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Linear LinearCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde TetrahedralCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Hydrocarbons Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH H opyright Mathieu P. Halonde Copyright MH H P. Lalonde H L H H athieu Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu H. Lalonde H H C H C C P C H CCopyright Mathieu P. Lalonde Copyright Mathieu P. LC H H C H C alonde Copyright Mathieu P. Lalonde H C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H H HH H H HH HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Methane Ethane Propane ButaneCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LH H H CH H H HMH H H P. Lalonde H HH HH H H H H H H H H H alonde opyright athieu Copyright MC C C PCLalonde Copyright C athieu P. Lalonde Copyright Mathieu P. Halonde H C athieu . H H C C C MC C C C C C C C C C C C C C LCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HH H H HH HH HH HH HH HH HH HH HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu POctadecaneopyright Mathieu P. Lalonde Pentane . Lalonde CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde The bond angles in the chain are drawn as 120 ° for convenience Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Double Bond Geometry Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H HCopyright Mathieu P. LCC C alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C H C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde trans: hydrogen atoms on opposite cis: hydrogen atoms on the same sides of a disubstituted double bond. side of a disubstituted double bond.Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH H H H H athieu P. Oalonde CH H H H Mathieu P. Lalonde O H H H H H H H H H H opyright M L H H H opyright Copyright C C C C C . Lalonde C opyright Mathieu P. C alonde C opyright Mathieu P. Lalonde HO C C C Mathieu P C C C C CC C C C C H HO L C C C C C C C C H C H HH HH HCopyright Mathieu P. Lalonde Copyright Mathieu P. LH H H HCH H H H Mathieu P. Lalonde H HH HH HH H H H HH HH HH H alonde opyright C C C C H H C C C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright H athieu P. Lalonde M H HH HH HH HCopyright Mathieu Acidalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Elaidic P. L (18:1n-9) Oleic Acid (18:1n-9)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde trans-Octadec-9-enoic Acid omega carbon cis-Octadec-9-enoic AcidCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Bond-‐Line Formulas Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu PH Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H H H H H H H . H H H H H H H H O C C C C C C C C C HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO C C C C C C C C C HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Acid (18:0) P. Lalonde H H H H H H H H H H H H H H H H H H Stearic Mathieu Stearic Acid (18:0)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H H H H H H H O C C C C C HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO C C C C C H H H H H H HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H H H H H H C H C C C C C C C H CH3 HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright M(18:1n-9) P. Lalonde H H H H H H H H Oleic Acid athieu Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Oleic Acid (18:1n-9)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu H . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H P H H H H C H C C H C HCopyright Mathieu H . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O C HC C H C PC CH C H C C OCopyright Mathieu HH LH C C C Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO C C C H C C P. Halonde H C H HO Me H H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H H H H Docosahexaenoic Acid (22:6n-3) Docosahexaenoic Acid (22:6n-3)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mre implied and omi]ed. Hydrogen atoms a athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Ldrawn bCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Carbon atoms are not alonde ut implied to be located at the end and junc3on of every line. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Electron pairs can be drawn or omi]ed. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Stereochemistry Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Dichlorofluoromethane BromochlorofluoromethaneCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde mirror mirrorCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MHathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H HCopyright MCathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Br athieu P. Lalonde F Cl Cl F F Br M F Cl Cl Cl ClCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MHathieu P. Lalonde Hopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C H HCopyright MCathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C C CCopyright Mathieu F Cl P. Lalonde Copyright Mathieu P. Lalonde Copyright F athieu P. Lalonde F Cl F Br M Cl Cl Cl Cl BrCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lmirror images (S) (R) superimposable alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright mirror images Lalonde non-superimposable Mathieu P. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Enantiomers

Basic Organic Chemistry Knowledge is Important hYp://www.greenmedinfo.com/blog/franken-‐thyroxine-‐making-‐your-‐thyroid-‐condiFon-‐worse

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structure and Func3on: Thyroxine Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde mirrorCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde I O O I HO I I OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde NH2 NH2 I O O ICopyright Mathieu P. LIalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde ICopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde L-Thyroxine, T4 LevothyroxineCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (thyroid hormone) NaOH 180 °Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde I O I O HO I HO ICopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LOH O alonde Na [H2O]xCopyright Mathieu P. Lalonde 2Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde NH NH2 I O I OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde I ICopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Levothyroxinealonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Mathieu P. L sodium Dextrothyroxine (thyroid hormone) (cardiac side-effects)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structure and Func3on: Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Elaidic vs Oleic Acid Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright 1Mathieu P. Lalonde O •Increases CETP activityCopyright Mathieu P. Lalonde Copyright MCH3 •Induces dyslipidemia2,3 athieu P. Lalonde Copyright Mathieu P. Lalonde HO •Impairs endothelium function3Copyright Mathieu P. Acid (18:1n-9) Elaidic Lalonde Copyright Mathieu P. Lalonde insulin sensitivity.4•Decreases Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Diastereomers: stereoisomers that are not mirror imagesCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde •Improves glycemic tolerace through increased HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde glucagon-likeMathieu P. Lalonde secretion of Copyright peptide-15Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH3 •Reduces blood pressure.6Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Oleic Acid (18:1n-9)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 1) Abbey, M.; Nestel, P. J. Plasma Cholesteryl Ester Transfer Protein AcFvity is Increased when Trans-‐Elaidic Acid is SubsFtuted for Cis-‐Oleic Acid in the Diet. Atherosclerosis 1994, 106, 99–107. 2) Bendsen, N. T.; Chabanova, E.; Thomsen, H. S.; Larsen, T. M.; Newman, J. W.; Stender, S.; Dyerberg, J.; Haugaard, S. B.; Astrup, A. Eﬀect of Trans FaYy Copyright Mathieu P. LL.; Katan, M. B. Replacement of Dietary Saturated P. LAcids by Trans Copyright Mathieu P. Lalonde alonde Copyright Mathieu FaYy alonde FaYy Acids Lowers Serum HDL Cholesterol and Impairs Acid Intake on Abdominal and Liver Fat DeposiFon and Blood Lipids: A Randomized Trial in Overweight Postmenopausal Women. Nutri=on and Diabetes 2011, doi:10.1038/nutd.2010.4. 3) de Roos, N. M.; Bots, M. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Endothelial FuncFon in Healthy Men and Women. Arterioscler. Thromb. Vasc. Biol. 2001, 21, 1233–1237. 4) ChrisFansen, E.; Schnider, S.; Palmvig, B.; Tauber-‐Lassen, E.; Pederson, O. Intake of a Diet High in trans Monounsaturated FaYy Acids or Saturated FaYy Acids. Eﬀects on Postprandial Insulinemia and Glycemia in Obese PaFents with NIDDM. Diabetes Care 1athieu P Lalonde Copyright Mathieu P Lalonde Copyright Mathieu P Lalonde Copyright M 997, 20, 881–887. . . .

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structure and Func3on: Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Glucose vs Fructose Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH HO OH HO OH O Copyright Mathieu P. OH Lalonde OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH HO OH HO OH O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO HO HO OH HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH!-D-(+)-Glucopyranose "-D-(+)-GlucopyranoseCopyright Mathieu P. Lalonde Copyright Mathieu PD-Fructofuranose (36.4% in solution) (63.6% in solution) . (32% in solution) Lalonde Copyright Mathieu P. Lalonde D-Fructopyranose (68% in solution)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH O OH OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO HO HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH OH OCopyright Mathieu P. LO C6H12 6 alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde C6H12O6Copyright Mathieu P. Hexose Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Aldose, Lalonde Ketose, HexoseCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde D-(+)-Glucose "-D-(–)-Fructose (0.003% in solution)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structure and Func3on: Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Adrenaline Biosynthesis Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu Phenylalanine Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O P. Lalonde O Tyrosine O hydroxylase hydroxylase HO Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P2. Lalonde NH2 HO NH2 HO NH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Phenylalanine (amino acid) Tyrosine (amino acid) L-DOPA (precursor to catecholamine neurotransmitters) Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde DOPA decarboxylase Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright OH athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde M H OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MHO HO N Phenylethanolamine N-methyltransferase HO NH2 Dopamine !-hydroxylase athieu P. Lalonde NH2 CH3 Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MHO HO HO athieu P. Lalonde (stress hormone, Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright neurotransmitter) Epinephrine (a.k.a. adrenaline) Norepinephrine Dopamine (stress hormone, neurotransmitter) (neurotransmitter, neurohormone) Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structure and Func3on: Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Biologically Ac3ve Phenethylamines Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH OH opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH H OH HCopyright Mathieu P. Lalonde CN NH2 opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde N N CH3 CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH3 CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Phenethylamine Albuterol (+)-Pseudoephedrine (–)-PseudoephedrineCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (psychostimulant) (bronchodilator) (Sudafed, decongestant) (bronchodilator)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu OH Lalonde Copyright Mathieu P. Lalonde O P. H CH3O NH2 HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde NH2 N N H2NCopyright 3 athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH M CH3 CH3O CH3 CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO CH3OCopyright Mathieu (psychostimulant) opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (+)-Amphetamine (psychostimulant) P. Lalonde C (+)-Methamphetamine Labetalol (antihypertensive drug) Mescaline (psychoactive drug)Copyright Mathieu P. Lalonde Copyright Mathieu possible stereoisomers mixture of all 4 P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Natural Products

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Plant-‐Derived Natural Products Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Structural: Biologically Active Natural CompoundsCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH3 Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde N opyright Mathieu P. Lalonde HO OH N C OCopyright HOathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde M O O NCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde N CH3 OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O opyright Mathieu P. Lalonde HO O H3C CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH Caffeine nCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright (psychoactive stimulant) Mathieu P. Lalonde CelluloseCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OCopyright Mathieu P. Lalonde Copyright Mathieu P. L3alonde Copyright Mathieu P. Lalonde H C H3C OHCopyright Mathieu P. Lalonde Copyright Mathieu P. 3Lalonde Copyright Mathieu P. Lalonde H H C O N OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H O OH O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH CH3Defense: Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Paclitaxel O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (mitotic inhibitor used in cancer therapy) HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde N H3CO CHCopyright Mathieu P. Lalonde Copyright 3 athieu P. Lalonde Copyright Mathieu P. Lalonde M OCopyright Mathieu P. LCapsaicinopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde alonde C

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Plant-‐Derived An3nutri3onal Factors Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright enzyme inhibitors Tannins Digestive Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Proanthocyanidins R1 OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (forage legumes) OH HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO Copyright Mathieu P. Lalonde R 2 OH OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH Chlorogenic acid HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (sunflower seeds)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright Mathieu 1=R2alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Propelargonidin: R P. L =H Procyanidin: R1=OH, R2=HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Prodelphinidin: R1=R2=OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Toxic Amino AcidsCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde NH2 OCopyright O athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H2N N M OH An3nutrients or an3nutri3onal factors: Substances that Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Canavanine NH2 (leguminous plants) can reduce absorpFon and uFlizaFon of nutrients, Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Cmay produce undesirable eﬃciency of digesFon, and opyright Mathieu P. Lalonde O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde not a substance possesses HO S S OH health eﬀects. Whether or Copyright Mathieu P. Lalonde NH2 NH anFnutriFve properFes depends on the digesFve process Copyright Djenkolic acid Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Mathieu P. 2 of the animal that ingested the substance. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde (djenkol beans)

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Plant-‐Derived An3nutri3onal Factors Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Phytates N Cyanogenic Glycosides Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OO OH C Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O P O O P O O O O O Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O P O O O Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O P HO OH OH OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu N . C alonde O O O O HO PL P O O Linamarin Copyright Mathieu P. Lalonde Copyright Mathieu P. beans, flax) Copyright Mathieu P. H alonde O O O P (cassava, lima Lalonde O H L OO O O Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Phytic Acid OH HO OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu OH Lalonde (seeds) Amygdalin P. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mapricot, black cherry) (bitter almond, athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH FODMAPs Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO Oxalate O HO Copyright Mathieu P. Lalonde Copyright Mathieu O . H alonde Copyright Mathieu P. Lalonde H P LO OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O HO O OH OH Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O OH HO OH O HO OH Copyright Mathieu P. Lalonde Copyright Mathieu P. O OH Lalonde Copyright Mathieu P. Lalonde OH OH OH Raffinose Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde asparagus Mathieu P. Lalonde Oxalate (beans, cabbage, brussels sprouts, broccoli, Copyright Xylitol(occurs in many plants) (berries, oats, mushrooms) Copyright Mathieu P. Lalonde Copyright other vegetables Lalonde Copyright Mathieu P. Lalonde as well as Mathieu P. and whole grains) Copyright Mathieu iP. Lalonde Copyright Mathieu P. Lalonde Copyright & pepFdomorphins, Other an3nutrients nclude: Saponins & glycoalkaloids, prolamine proteins Mathieu P. Lalonde Copyright Mhytoestrogens. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde goitrogens, p athieu P. Lalonde

Concentra3on of an3nutrients in maize Concentra3on of an3nutrients in rice Edeogu, C. O.; Ekuma, C. E. AnFnutrient Level in Staple Food Crops in Ebonyi-‐Nigeria. Research Journal of Environmental Sciences 2007, 1(6), 302–309.

Concentra3on of an3nutrients in yams Concentra3on of an3nutrients in cassava Concentra3on of an3nutrients in cowpea Concentra3on of an3nutrients in yambean Edeogu, C. O.; Ekuma, C. E. AnFnutrient Level in Staple Food Crops in Ebonyi-‐Nigeria. Research Journal of Environmental Sciences 2007, 1(6), 302–309.

Mean concentra3on of chymotrypsin inhibitors (IU) in staple foods Edeogu, C. O.; Ekuma, C. E. AnFnutrient Level in Staple Food Crops in Ebonyi-‐Nigeria. Research Journal of Environmental Sciences 2007, 1(6), 302–309.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Saponins Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MH Me P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO athieu Copyright Mathieu P. oralonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me H L 3-Epikatonic acid HO OHCopyright MGuar sapogenin (aglycone) athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde triterpene (C30)Copyright Mathieu P. Lalonde Copyright Mathieu OH Lalonde Copyright Mathieu P. Lalonde O O PO . OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me O H O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HO OH HCopyright Mathieu Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O P. OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO Me Me Me OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H MeCopyright Mathieu P. Halonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me OH HO HO O O LO H Me MeCopyright Mathieu P. Lalonde CGuar meal saponin O H opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright H Oathieu P. Halonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO M O LCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH O OH Common saccharides: Glucose, galactose, glucuronic acid, xylose, rhamnose or methylpentoseCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright areathieu P. ofalonde oropyright Mathieu P. Lalonde ability to form Mathieu P. Lalonde Saponins M glycosides L steroids C triterpenes that were named for their Copyright stable, soap-like foamsCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde in aqueous solutions.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Terpenes Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu isopentenyl diphosphate Mathieu P. Lalonde Terpenes are biosynthesized from P. Lalonde Copyright Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O O O IsopentenylCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde diphosphate O P O P O O P O P O Dimethylallyl diphosphate (IPP)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MPPi, H+ P. Lalonde Copyright Mathieu P. Lalonde athieu Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright MO O P. Lalonde Copyright Mathieu P. Lalonde Geranyl diphosphate (GPP) athieu P P Monoterpene (C10)Copyright Mathieu P. Lalonde Copyright O athieu P. Lalonde Copyright Mathieu P. Lalonde MO O O O H3CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde IPP CH3 CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LH3C H3C alonde +Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde PPi, H CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Farnesyl diphosphate (FPP) O O HO H Lanosterone H3C CH3Copyright Mathieu P. Lalonde Copyright Mathieu P. O alonde Copyright Mathieu P. Lalonde Sesquiterpene (C15) O P O P LCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde DimerizationCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Squalene triterpene (C )Copyright M30 athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Glycoalkaloids Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright Mathieu P. Lalonde Copyright MH HO CH3 H3C athieu P. Lalonde Copyright Mathieu P. Lalonde H3C HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O OHCopyright Mathieu P. Lalonde C opyright MN HO H H3 C H athieu P. Lalonde Copyright Mathieu P. Lalonde CH3 OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H H H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O CH3 !-ChaconineCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH H3C H H3C HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu 3P. Lalonde HO HO H3C H N CH HCopyright Mathieu P. Lalonde Copyright Mathieu P. LH O O alonde Copyright Mathieu P. Lalonde H HCopyright Mathieu P. Lalonde Copyright MH O HO athieu P. LO alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright OH athieu P. LO CH3 Copyright Mathieu P. Lalonde M O alonde HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH !-SolanineCopyright Mathieu P. Lalonde Copyright Mathieu P. LOH alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mthat containLalonde Copyright Mathieu P. Lalonde Alkaloids are natural products athieu P. a basic nitrogen atomCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

In vitro study. Past experiments were performed with mulFlamellar vesicles. Keukens, E. A. J.; de Vrije, T.; Jansen, L. A. M.; de Boer, H.; Janssen, M.; de Kroon, A. I. P. M.; Jongen, W. M. F.; de Kruiﬀ, B. Glycoalkaloids SelecFvely Permeabilize Cholesterol Containing Biomembranes. Biochimica et Biophysica Acta 1996, 1279, 243–250.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde An3nutri3onal Factors: Relevant Ques3ons Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. hulling, sCopyright Mathieu P. LfermentaFon, cooking) eliminate, 1) Does processing ( Lalonde oaking, germinaFon, alonde Copyright Mathieu P. Lalonde Copyright or denature alonde Copyright r modify P. LacFvity? opyright Mathieu P. Lalonde degrade, Mathieu P. L the compound o Mathieu its alonde CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 2) Does digesFon degrade the compound or modify its acFvity? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lemploy physiologically relevant concentraFons oathieu P. Lalonde 3) Do in vitro studies alonde Copyright Mathieu P. Lalonde Copyright M r amounts of Copyright Mathieu P. re on par opyright Miathieu P. Lalonde Copyright Mathieu P. Lalonde anF-‐nutrients that a Lalonde Cwith what s present in food or diet? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu the gut amer processing and digesFon 4) Is the amount of compound that makes it to P. Lalonde Copyright Mathieu P. Lalonde sufficient to be problemaFc? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright he compound inhibit digesFve eathieu P. or possess other undesirable Lalonde 5) Does t Mathieu P. Lalonde Copyright M nzymes Lalonde Copyright Mathieu P. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde effects? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright he compound cause iopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 6) Does t Mathieu P. Lalonde C ntesFnal damage? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 7) Does the compound or its metabolites enter the bloodstream and are they Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu iP. Lhe bloodstream? Mathieu P. Lalonde Copyright Mathieu P. Lalonde problemaFc once n talonde Copyright Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde 8) Have the synergisFc effects of mulFple compounds been studied? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright part of food alonde Copyright Mathieu P. Lalonde 9) Has the compound been studied as Mathieu P. L or in isolaFon? Copyright Mathieu o. Lalonde Copyright Mathieu P. Ln humans or only in other P. Lalonde 10) Has the effect Pf the compound been studied i alonde Copyright Mathieu species? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

The mice were fed pure glycoalkaloids as well as the corresponding aglycones. Friedman, M.; Henika, P. R.; Mackey, B. E. Feeding of Potato, Tomato and Eggplant Alkaloids Aﬀects Food ConsumpFon and Body and Liver Weights in Mice. J. Nutr. 1996, 126, 989–999.

An α-‐chaconine:α-‐solanine mixture (1:1), was orally fed (3 mg/Kg/d) to mice over 21 days via their drinking water. This would amount to an 80 Kg human being eaFng 165 grams of fried potato skins every day for 21 days. Intes3nal permeability was not aﬀected in controls. If this experiment were to translate to humans, the best we could conclude is that fried potato skins might be problemaFc for individuals with IBD. Patel, P.; SchuYe, R.; Sporns, P.; Doyle, J.; Lawrence, J.; Fedorak, R. N. Inﬂammatory Bowel Diseases 2002, 8(5), 340–346. See also: Keukens, E.A. et al. Biochimica et Biophysica Acta 1995, 1240, 216–228.

Mice were fed potato skins fried in canola oil ad libitum. The commercial fried potato skins had a glycoalkaloid content of 44.2 mg/100 g (28.9 mg /100 g α-‐chaconine, 15.3 mg/100 g α-‐solanine). Iablokov, V.; Sydora, B. C.; Foshaug, R.; Meddings, J.; Driedger, D.; Churchill, T.; Fedorak, R. N. Dig. Dis. Sci. 2010, 55, 3078–3085.

Francis, G.; Kerem, Z.; Makkar, H. P. S.; Becker, K. The Biological AcFon of Saponins in Animal Systems: A Review. Bri=sh Journal of Nutri=on 2002, 88, 587–605.

Hasegawa, H.; Hung, J. H.; Matsumiya, S.; Uchiyama, M. Main Ginseng Saponin Metabolites Formed by IntesFnal Bacteria. Planta Medica 1996, 62(5), 453–457.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH HO OHCopyright Mathieu P. Lalonde Copyright OH athieu P. Lalonde Copyright Mathieu P. Lalonde M O Saponins: O O OH HOCopyright Mathieu P. LHO H O Copyright Mathieu P. Lalonde Copyright Mathieu HO. Lalonde alonde P OH O O H H H Me OH O O MeCopyright Mathieu P. LHO H alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO HO H OH H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH H Me Me Me Me Me Me Me HOCopyright Mathieu P. H alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O L Me O H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H H O H HO H H O H O O Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O O Me Me HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH Ginsenoside Rb1 HO OH Ginsenoside Rb2 OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HOCopyright Mathieu POH alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O . L OHCopyright HO athieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu HO Lalonde M O Me P. OH H HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H Me HO O O OH H H OCopyright Mathieu PMeLalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me . HO O MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Mealonde HO H Me OH H H L Ginsenoside ReCopyright Mathieu P. Lalonde Copyright Mathieu P. LHO H Me Me O H O alonde Copyright Mathieu P. Lalonde O Me Me Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. LHO alonde Copyright Mathieu P. Lalonde O H Me O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H OH HO O H O H Me Me H OCopyright Mathieu P. Lalonde Copyright Mathieu HO Lalonde Copyright MRc P. OH Ginsenoside athieu P. Lalonde HO MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OHCopyright .; Hung, J. H.; Matsumiya, S.; Uchiyama, M. Main Ginseng SMathieu P. ormed by IntesFnal opyright Medica 1996, 62(5), . 53–457. Hasegawa, H Mathieu P Lalonde Copyright aponin Metabolites F Lalonde C Bacteria. Planta Mathieu P 4 Lalonde .

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Metabolites: HO OH HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H O OH H O Me H OH O HOCopyright Mathieu HO Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde P. O Me HO HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H Me H Me Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H Me H Me HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H Me Me H Ginsenoside YCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me Ginsenoside compound K IH901 HO MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H Me Me MeCopyright Mathieu OH Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO P. HO Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H Me O HOCopyright MHO H O . Lalonde Copyright Mathieu Protopanaxadiolopyright Mathieu P. Lalonde athieu P H O OH H Me Me P. Lalonde C HO Me HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O Me H H MeCopyright Mathieu H . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Me H P Me Me Me Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me Me H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HOopyright Mathieu P. Lalonde H Me C H ProtopanaxatriolCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H Ginsenoside Mc Me Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me MeCopyright .; Hung, J. H.; Matsumiya, S.; Uchiyama, M. Main Ginseng SMathieu P. ormed by IntesFnal opyright Medica 1996, 62(5), . 53–457. Hasegawa, H Mathieu P Lalonde Copyright aponin Metabolites F Lalonde C Bacteria. Planta Mathieu P 4 Lalonde .

12 grams of ginseng extract per day for an 80 Kg human! Hasegawa, H.; Hung, J. H.; Matsumiya, S.; Uchiyama, M. Main Ginseng Saponin Metabolites Formed by IntesFnal Bacteria. Planta Medica 1996, 62(5), 453–457.

Lee, S.-‐J.; Sung, J.-‐H.; Lee, S.-‐J.; Moon, C.-‐K. Lee, B.-‐H. AnFtumor AcFvity of a Novel Ginseng Saponin Metabolite in Human Pulmonary Adenocarcinoma Cells Resistant to CisplaFn. Cancer Le`ers 1999, 144, 39–43.

Gee, J. M.; Johnson, I. T. InteracFons Between HemolyFc Saponins, Bile Salts and Small IntesFnal Mucosa in the Rat. Journal of Nutri=on 1988, 118, 1391–1397.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu H . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde PCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H Gypsogenin OH Baby’s breath Me H (a.k.a. Gypsogenic acid)Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CO O HO O opyright Mathieu P. Lalonde OH OH H H HCopyright Mathieu P. Lalonde Copyright Mathieu Me Lalonde Copyright Mathieu P. LOH Me P. HO O O alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LOH O OH O H O CH3 OH alonde H O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde COH O O H Me O O opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CO HO H O H opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O H O Me H OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HOCopyright Mathieu P. Lalonde Copyright MGypsophila Lalonde Copyright Mathieu P. Lalonde HO OH athieu P. Saponin 3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright ohnson, I. T. InteracFons alonde Copyright Mathieu ntesFnal Mucosa in the Rat. Journal of Nutri=on 1988, 118, P391–1397. Gee, J. M.; J Mathieu P. L Between HemolyFc Saponins, Bile Salts and Small I P. Lalonde Copyright Mathieu 1 . Lalonde

Gee, J. M.; Johnson, I. T. InteracFons Between HemolyFc Saponins, Bile Salts and Small IntesFnal Mucosa in the Rat. Journal of Nutri=on 1988, 118, 1391–1397.

Gee, J. M.; Price, K. R.; Ridout, C. L.; Wortley, G. M.; Hurrell, R. F.; Johnson, I. T. Saponins of Quinoa (Chenopodium quinoa): Eﬀects of Processing on their Abundance in Quinoa Products and their Biological Eﬀects on IntesFnal Mucosal Tissue. J. Sci. Food. Agric. 1993, 63, 201–209.

Maharaj, I.; Froh, K. J.; Campbell, J. B. Immune Responses of Mice to InacFvated Rabies Vaccine Administered Orally: PotenFaFon by Quillaja Saponin. Can. J. Microbiol. 1986, 32, 414–420.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Quillaja Saponins Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright OH athieu P. LH OH Copyright Mathieu P. Lalonde Me Me HO M O H OH O alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LO O alonde Copyright Mathieu P. Lalonde OH OHCopyright O athieu P. Lalonde Copyright O athieu P. Lalonde Copyright Mathieu P. Lalonde H M OH O O H M OH Me OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O O O Me Me H O OH H OO OCopyright Mathieu P. Lalonde H opyright O athieu P. Lalonde Copyright Mathieu P. Lalonde H Me C M O OH HHO O O MeCopyright H athieu P. H HO H M H Me H Lalonde Copyright Mathieu P Lalonde Copyright Mathieu P Lalonde O . H O . Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O O OH HO QS21 OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O O OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H HO O O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me O O Me O OH OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O OH H H OH OHCopyright Mathieu P. Me Me H Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Lalonde H O O OH HO OCopyright Mathieu P. Lalonde CO O O Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O H Me opyright O O OHCopyright Mathieu P. H alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde LH HO O O H Me Me H H O Me HO Me Soap bark tree HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O O O QS7Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OHCopyright a mixture ofP. Lalonde Copyright Mathieu P. Lalonde Cand QS7 are the most potent Quil A, Mathieu partially purified saponins from quillaja saponaria, opyright Mathieu P. Lalonde

Maharaj, I.; Froh, K. J.; Campbell, J. B. Immune Responses of Mice to InacFvated Rabies Vaccine Administered Orally: PotenFaFon by Quillaja Saponin. Can. J. Microbiol. 1986, 32, 414–420.

Pickering, R. J.; Smith, S. D.; Strugnell, R. A.; Wesselingh, S. L.; Webster, D. E. Crude Saponins Improve the Immune Response to an Oral Plant-‐Made Measles Vaccine. Vaccine 2006, 24, 144–150.

Could food-‐derived pepFdes that have sequences similar to human proteins trigger an autoimmune reacFon in the presence of Quillaja saponin? What about other saponins? Peiris, M.; Monteith, G. R.; Roberts-‐Thompson, S. J.; Cabot, P. J. A Model of Experimental Autoimmune EncephalomyeliFs (EAE) in C57BL/6 Mice for the CharacterisaFon of IntervenFon Therapies. Journal of Neuroscience Methods 2007, 163, 245–254.

Johnson, I. T.; Gee, J. M.; Price, K.; Curl, C.; Fenwick, G. R. Inﬂuence of Saponins on Gut Permeability and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 116(11), 2270–2277.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu H . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde P OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me MeCopyright Mathieu Me Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H P. O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde COH HO HO opyright Mathieu P. Lalonde H GypsogeninCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me H (a.k.a. Gypsogenic acid) HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CO O O H opyright Mathieu P. Lalonde H OH H OHCopyright Mathieu P. Lalonde Copyright Mathieu Me Lalonde Copyright Mathieu P. LOH Me P. HO O O alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CO CHO Mathieu P. LOH H O opyright OH O alonde 3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde COH H O OH O H opyright Mathieu P. Lalonde Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O O O O OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde COH H Me opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO H O H O H Me HO H Me HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O O HOCopyright Mathieu P. Lalonde Copyright MGypsophila Lalonde Copyright Mathieu P. Lalonde athieu P. Saponin 3Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lf Gypsophylla sp. Mathieu P. Lalonde “Gypsophylla saponins, isolated from the root o alonde Copyright (baby’s breath)” Johnson, I. T.; Gee, JMathieu PC.; Falonde nﬂuence of Saponins on athieu P and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 1P Lalonde Copyright . M.; Price, K.; Curl, . Lenwick, G. R. I Copyright M Gut Permeability Lalonde Copyright Mathieu 16(11), 2270–2277. . .

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me MeCopyright Mathieu P. Lalonde Copyright OH athieu P. Lalonde Copyright Mathieu P. Lalonde H M OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me O O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O H Me O O H O H OH O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O H H H O OHCopyright Mathieu P. Lalonde Copyright H athieu P. Lalonde Copyright Mathieu P. Lalonde OH Me O OH M OH OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH Saponarioside I OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu PMe alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde . L Me Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OH H OH OHCopyright Mathieu P. Lalonde Copyright M Me Me O O OH athieu P Lalonde Copyright Mathieu POLalonde . Me Me O . OHCopyright Mathieu P. Lalonde Copyright OH athieu P. Lalonde Copyright Mathieu P. LOHO O H Me O H O H OH O M HO H Me OO O OH alonde OHCopyright Mathieu P. Lalonde COHO H O H opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH H H O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LOH OH Me O OH OH HO O alonde O OCopyright Mathieu P. J alonde Copyright Mathieu P. Lalonde Saponarioside K Mathieu P. Lalonde Saponarioside L HO Copyright HO OHCopyright Mathieu P. Lalonde COH opyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde “Saponaria saponins from the European soapwort (Saponaria oﬃcinalis)…” Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Johnson, I. T.; Gee, JMathieu PC.; Falonde nﬂuence of Saponins on athieu P and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 1P Lalonde Copyright . M.; Price, K.; Curl, . Lenwick, G. R. I Copyright M Gut Permeability Lalonde Copyright Mathieu 16(11), 2270–2277. . .

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde CH3Copyright Mathieu P. LH H3C alonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H3CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O H N H3CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HCopyright Mathieu H P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde !-Tomatine aglycone (C ) OCopyright Mathieu P. 27alonde Copyright Mathieu P. LOH L HO H OH alonde Copyright Mathieu P. Lalonde CH3 H3CCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO O H3C H O HCopyright Mathieu P. Lalonde Copyright Mathieu P. HO O OLalonde Copyright Mathieu P. Lalonde OH O H N H H3C HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O O H HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. HO H Lalonde Copyright Mathieu P. Lalonde HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde !-TomatineCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Ls a consJtuent of gathieu omatoes, “α-‐TomaJne, a steroidal amine glycoside which i alonde Copyright M reen t P. Lalonde was obtained as a crystalline preparaJon from Sigma Chemical Co., and used as Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde purchased.” Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Johnson, I. T.; Gee, JMathieu PC.; Falonde nﬂuence of Saponins on athieu P and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 1P Lalonde Copyright . M.; Price, K.; Curl, . Lenwick, G. R. I Copyright M Gut Permeability Lalonde Copyright Mathieu 16(11), 2270–2277. . .

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde OH O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO OH O OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O OH OH H O O OHCopyright Mathieu P. Lalonde C HO OH O OH opyright Mathieu P Lalonde Copyright Mathieu P Lalonde . H O . H OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu Me. Lalonde P H H H O O OH H HCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me H Me Me O O O Me Me HO H H H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H Me Me Me HO OH HO Me H MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Me HO OH O O Soyasaponin A2Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me Soyasaponin !g HO H OH Soyasaponin VICopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde O opyright Mathieu P. Lalonde C O O O HO H O OHCopyright Mathieu P. Lalonde OHopyright Mathieu P. Lalonde Copyright Mathieu P. LOH OHO O C HO OH OH alonde Me HO OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright H Oathieu P. LOH M alonde OH OH OH HO O H OCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. LO Me alonde O H H O OH O O H H O O O MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde H H H H H Me HO H OH MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me H Me Me HO OH OH Me Me H Me Me HO OHCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Me HO Me Me MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde HO Me Soyasaponin Bc O O H Soyasaponin !aCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Soyasaponin II O HOCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde MeCopyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright M(BDH CP. Lalonde “Soy saponins were prepared from a 100-‐g sample of soybean meal athieu hemicals Ltd.). The material was mixed with sand (1:2 wt/wt) defa=ed with chloroform and Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde extracted with methanol using Soxhlet apparatus.” Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Johnson, I. T.; Gee, JMathieu PC.; Falonde nﬂuence of Saponins on athieu P and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 1P Lalonde Copyright . M.; Price, K.; Curl, . Lenwick, G. R. I Copyright M Gut Permeability Lalonde Copyright Mathieu 16(11), 2270–2277. . .

“Of the saponins used in this study, only the material derived from soy beans occurs in signiﬁcant quanJJes in the human diet.” Johnson, I. T.; Gee, J. M.; Price, K.; Curl, C.; Fenwick, G. R. Inﬂuence of Saponins on Gut Permeability and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 116(11), 2270–2277.

Friedman, M.; Tomato Glycoalkaloids: Role in the Plant and in the Diet. J. Agric. Food Chem. 2002, 50, 5751–5780.

“The small eﬀect of this material on the transmural PD suggests that it may not increase the permeability of the mucosa to the same extent as the other saponins. This is perhaps consistent with the fact that soy saponins are reported not to form addiJon compounds with cholesterol in vitro (21).” Johnson, I. T.; Gee, J. M.; Price, K.; Curl, C.; Fenwick, G. R. Inﬂuence of Saponins on Gut Permeability and AcFve Nutrient Transport In Vitro. J. Nutr. 1986, 116(11), 2270–2277.

Story, J. A.; LePage, S. L.; Petro, M. S.; West, L. G.; Cassidy, M. M.; Lighsoot, F. G.; Vahouny, G. V. InteracFons of Alfalfa Plant and Sprout Saponins with Cholesterol in vitro and in Cholesterol-‐Fed Rats. Am. J. Clin. Nutr. 1984, 39, 917–929.

“The Mechanism of acJon of saponins on the intesJnal membranes in vivo is not yet clearly understood. Ingested saponins are exposed to many potenJal ligands in the intesJne such as bile salts, dietary cholesterol and membrane sterols of the mucosal cells, and nutrients or anJnutrients in food, all of which may reduce or enhance their eﬀecJveness. It also remains to be conﬁrmed whether traces of the compound itself enter the body through the permeabilized membranes, even though all the evidence unJl now points to their non-‐absorpJon. AbsorpJon of saponin metabolites produced in the intesJne by micro-‐organisms into the body of ruminants and human subjects has, however, been demonstrated.” Francis, G.; Kerem, Z.; Makkar, H. P. S.; Becker, K. The Biological AcFon of Saponins in Animal Systems: A Review. Bri=sh Journal of Nutri=on 2002, 88, 587–605.

The eﬀect of Soyasaponins appears to be species dependent. What is it in humans? Alvarez, J. R.; Torres-‐Pinedo, R. InteracFons of Soybean LecFn, Soyasaponins, and Glycinin with Rabbit Jejunal Mucosa In Vitro. Pediatric Research 1982, 16, 728–731.

LecFns are proteins found in plants and animals that possess at least one non-‐catalyFc domain that can reversibly bind speciﬁc carbohydrates, either simple monosaccharides or more complex glycans. With a few excepFons, lecFns are found in high concentraFons in the storage organs of plants (i.e. seeds and tubers) Rüdiger, H. Plant LecFns-‐More than Just Tools for GlycoscienFsts: Occurrence, Structure, and Possible FuncFons of Plant LecFns. Acta Anatomica 1998, 161, 130–152.

Nachbar, M. S.; Oppenheim, J. D. LecFns in the United States Diet: A Survey of LecFns in Commonly Consumed Foods and a Review of the Literature. Am. J. Clin. Nutr. 1980, 33, 2338–2345.

Vasconcelos, I. M.; Oliveira, J. T. A. AnFnutriFonal ProperFes of Plant LecFns Toxicon 2004, 44, 385–403.

Vasconcelos, I. M.; Oliveira, J. T. A. AnFnutriFonal ProperFes of Plant LecFns. Toxicon 2004, 44, 385–403.

Matucci, A.; Veneri, G.; Pellegrina, C. D.; Zoccatelli, G.; Vincenzi, S.; Chignola, R.; Peruﬀo, A. D. B.; Rizzi, C. Temperature-‐Dependent Decay of Wheat Germ AggluFnin AcFvity and its ImplicaFons for Food Processing and Analysis. Food Control 2004, 15, 391–395.

•The kineFcs of PHA thermal deacFvaFon have been reported, see: Boufassa, C.; Lafont, J.; Rouanet, J. M.; Besançon, P. Thermal InacFvaFon of LecFns (PHA) Isolated from Phaseolus vulgaris. Food Chemistry 1986, 20, 295–304. •LecFns in runner beans are also destroyed by heat, see: Griebel, C. Sickness from Phaseolus vulgaris and Lathyrus =ngitanus. Z. Lebensm-‐Unters-‐Forsch. 1950, 90(3), 191–197. Bender A. E. HaemaggluFnins (LecFns in Beans). Food Chemistry 1983, 11, 309–320.

Freed, D. L. J. Do Dietary Lectins Cause Disease? British Journal of Medicine, 1999, 318, 1023–1024.

LecFns from legumes are not problemaFc to rats when fed at 1%, see: Hupriker, S. V.; Sohonie, K. HaemaggluFnins from Indian Pulses II. PuriﬁcaFon and ProperFes of HaemaggluFnin FracFons Isolated from White Pea (Pisum sp.). Enzymologia 1965, 28, 333. Bender A. E. HaemaggluFnins (LecFns in Beans). Food Chemistry 1983, 11, 309–320.

Liener, I. E. Soyin, A Toxic Protein from the Soybean I. InhibiFon of Rat Growth. The Journal of Nutri=on 1953, 49(3), 527–539. Soybean aggluFnin is inacFvated in vitro by pepsin, see: Liener, I. E. InacFvaFon Studies on the Soybean HemaggluFnin. J. Biol. Chem. 1958, 233. 401. Goitrogens in soy are destroyed by heaFng, see: Sharpless, G. R.; Pearsons, J.; Proto, G. S. ProducFon of Goiter in Rats with Raw and with Treated Soybean Flour. J. Nutr. 1939, 17, 545.

Heat Labile Lec3ns Peas Len3ls Red gram (pigeon pea) Peas, red gram and lenFls contain measurable amounts of lecFns yet show liYle to no improvements in food value when heated indicaFng the lecFns are not very problemaFc: Liener, I. E. Toxic Factors in Edible Legumes and their EliminaFon. Am. J. Clin. Nutr. 1962, 11, 281.

2 volunteers consumed 200 g of whole raw peanuts and 5 others consumed 200 g roasted, salted peanuts. Wang, Q.; Yu, L.-‐G.; Campbell, B. J.; Milton, J. D.; Rhodes, J. M. IdenFﬁcaFon of Intact Peanut LecFn in Peripheral Venous Blood Lancet 1998, 352, 1831–1832.

What happens to lecFns that remain amer the cooking process when they are consumed as part of real food? Ramadass, B.; Dokladny, K.; Moseley, P. L.; Patel, Y. R.; Lin, H. C. Sucrose Co-‐AdministraFon Reduces the Toxic Eﬀect of LecFn on Gut Permeability and IntesFnal Bacterial ColonizaFon. Diges=ve Diseases and Sciences 2010, 55, 2778–2784.

De Vincenzi, M.; Silano, M.; Luchex, R.; Carratù, B.; Boniglia, C.; Pogna, N. E. AggluFnaFng AcFvity of Alcohol-‐Soluble Proteins from Quinoa Seed Flour in Celiac Disease. Plant Foods for Human Nutri=on 1999, 54, 93–100.

Kamikubo, Y.; Dellas, C.; Loskutoﬀ, D. J.; Quigley, J. P.; Ruggeri, Z. M. ContribuFon of LepFn Receptor N-‐inked Glycans to LepFn Binding. Biochem. J. 2008, 410, 595–604.

The concentraFon of WGA in wheat germ is 300-‐350 µg/g and the average adult has a blood volume of roughly 5 liters. Kamikubo, Y.; Dellas, C.; Loskutoﬀ, D. J.; Quigley, J. P.; Ruggeri, Z. M. ContribuFon of LepFn Receptor N-‐inked Glycans to LepFn Binding. Biochem. J. 2008, 410, 595–604.

Prolamines Prolamines: a group of alcohol-‐soluble, nitrogen storage proteins with high glutamine and proline content. The family includes wheat gliadins, barley hordeins, rye secalins, oat avenins, maize zeins, etc… Fig. 13. Gliadin moFfs. Mapping of a-‐gliadin moFfs exerFng cytotoxic acFvity (red), immunomodulatory acFvity (light green), zonulin release and gut-‐permeaFng acFvity (blue), and CXCR3-‐IL-‐8 release in celiac disease paFents (dark green). Fasano, A. Zonulin and Its RegulaFon of IntesFnal Barrier FuncFon: The Biological Door to InﬂammaFon, Autoimmunity, and Cancer. Physiol. Rev. 2011, 91, 151–175.

Matysiak-‐Budnik, T.; Candalh, C.; Dugave, C.; Namane, A.; Cellier, C.; Cerf-‐Bensussan, N.; Heyman, M. AlteraFons of the IntesFnal Transport and Processing of Gliadin PepFdes in Celiac Disease. Gastroenterology 2003, 125, 696–707.

De Angelis, M.; Cassone, A.; Rizzello, C. G.; Gagliardi, F.; Minervini, F.; Calasso, M.; Di Cagno, R.; Francavilla, R.; Gobbex, M. Applied and Environmental Microbiology 2010, 76(2), 508–518. Even bacterial and fungal pepFdases have diﬃculty hydrolyzing gluten. Sourdough lactobacilli combined with fungal proteases require 72 h at 37 °C in order to hydrolyze gluten to less than 20 ppm. CombinaFons of puriﬁed lactobacilli proteases require 14 hours to fully hydrolyze immunoacitve pepFdes in gluten.

Fasano, A. Zonulin and Its RegulaFon of IntesFnal Barrier FuncFon: The Biological Door to InﬂammaFon, Autoimmunity, and Cancer. Physiol. Rev. 2011, 91, 151–175.

Drago, S.; El Asmar, R.; Di Pierro, M.; Clemente, M. G.; Tripathi, A.; Sapone, A.; Thakar, M.; Iacono, G.; Carroccio, A.; D’agate, C.; Not, T.; Zampini, L.; Catassi, C.; Fasano, A. Scandinavian Journal of Gastroenterology 2006, 41, 408–419.

Sapone, A.; Lammers, K. M.; Casolaro, V.; Cammarota, M.; Giuliano, M. T.; De Rosa, M.; Stefanile, R.; Mazzarella, G.; Tolone, C.; Russo, M. I.; Esposito, P.; Ferraraccio, F.; Carteni, M.; Riegler, G.; de Magistris, L.; Fasano, A. BMC Medicine 2011, 9, 23

Not, T.; Ziberna, F.; VaYa, S.; Quaglia, S.; Martelossi, S.; Villanacci, V.; Marzari, R.; Florian, F.; Vecchiet, M.; Sulic, A.-‐M.; Ferrara, F.; Bradbury, A.; SblaYero, D.; Ventura, A. Gut 2011, doi:10.1136/gut.2010.232900.

Hadjivassiliou, M.; Grünewald, R. A.; Kandler, R. H.; ChaYopadhyay, A. K.; JarraY, J. A.; Sanders, D. S.; Sharrack, B.; Wharton, S. B.; Davies-‐Jones, G. A. B. Neuropathy Associated with Gluten SensiFvity. J. Neurol. Neurosurg. Psychiatry 2006, 77, 1262–1266.

Hadjivassiliou, M.; Grünewald, R. A.; Lawden, M.; Davies-‐Jones, G. A. B.; Powell, T.; Smith, C. M. L. Headache and CNS White MaYer AbnormaliFes Associated with Gluten SensiFvity. Neurology 2001, 56, 385–388.

Dickerson, F.; Stallings, C.; Origoni, A.; Vaughan, C.; Khushalani, S.; Leister, F.; Yang, S.; Krivogorsky, B. Alaedini, A.; Yolken, R. Markers of Gluten SensiFvity and Celiac Disease in Recent-‐Onset Psychosis and MulF-‐Episode Schizophrenia. Biol. Psychiatry 2010, 68, 100–104.

Samaroo, D.; Dickerson, F.; Kasarda, D. D.; Green, P. H. R.; Briani, C.; Yolken, R. H.; Alaedini, A. Novel Immune Response to Gluten in Individuals with Schizophrenia. Schizophrenia Research 2010, 118, 248–255.

KárpáF, S. An ExcepFon Within the Group of Autoimmune Blistering Diseases: DermaFFs HerpeFformis, the Gluten-‐SensiFve Dermopathy. Dermatol. Clin. 2011, 29, 463–469.

Maglio, M.; Florian, F.; Vecchiet, M.; Auricchio, R.; Paparo, F.; Spadaro, R.; Zanzi, D.; Rapacciuolo, L.; Franzese, A.; SblaYero, D.; Marzari, R.; Troncone, R. Majority of Children with Type 1 Diabetes Produce and Deposit AnF-‐Tissue Transglutaminase AnFbodies in the Small IntesFne. Diabetes 2009, 58, 1578–1584.

Biesiekierski, J. R.; Newnham, E. D.; Irving, P. M.; BarreY, J. S.; Haines, M.; Doecke, J. D.; Shepherd, S. J.; Muir, J. G.; Gibson, P. R. Gluten Causes GastrointesFnal Symptoms in Subjects Without Celiac Disease: A Double-‐Blind Randomized Placebo-‐Controlled Trial. Am. J. Gastroenterol 2011, doi:10.1038/ajg.2010.487.

Ruuskanen, A.; Kaukinen, K.; Collins, P.; Huhtala, H.; Valve, R.; Mäki, M.; Luostarinen, L. Scandinavian Journal of Gastroenterology 2010, 45, 1197–1202.

Hafström, I.; Ringertz, B.; Spångberg, A.; von Zweigbergk, L.; Brannemark, S.; Nylander, I.; Rönnelid, J.; Laasonen, L.; Klareskog, L. A Vegan Diet Free of Gluten Improves the Signs and Symptoms of Rheumatoid ArthriFs: The Eﬀects on ArthriFs Correlate with a ReducFon in AnFbodies to Food AnFgens. Rheumatology 2001, 40, 1175–1179.

El-‐Chammas, K.; Danner, E. Gluten-‐Free Diet in Nonceliac Disease. Nutri=on in Clinical Prac=ce 2011, 6(3), 294–299.

FODMAPs include fructose, sucrose, fructans (inulins & fructooligosaccharides), levans, lactose, polyols (xylitol, sorbitol, erythritol, malFtol), Galactooligosaccharides (raﬃnose, stachyose, verbascose). Gibson, P. R. Shepherd, S. J. Evidence-‐Based Dietary Management of FuncFonal GostrointesFnal Symptoms: The FODMAP Approach. Journal of Gastroenterology and Hepatology doi:10.1111/j.1440-‐1746.2009.06149.x

Moshfegh, A. J.; Friday, J. E.; Goldman, J. P.; Chug Ahuja, J. K. Presence of Inulin and Oligofructose in the Diets of Americans. J. Nutr. 1999, 1407S–1411S.

Sonnenburg, E. D.; Zheng, H.; Joglekar, P.; HigginboYom, S. K.; Firbank, S. J.; Bolam, D. N.; Sonnenburg, J. L. Speciﬁcity of Polysaccharide Use in IntesFnal Bacteroides Species Determines Diet-‐Induced Microbiota AlteraFons. Cell 2010, 141, 1241–1252.

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Lindeberg, S.; Jönsson, T.; Granfeldt, Y.; Borgstrand, E.; Soﬀman, J.; Sjöström, K.; Ahrén, B. A Paleolithic Diet Improves Glucose Tolerance More than a Mediterranean-‐Like Diet in Individuals with Ischaemic Heart Disease. Diabetologia 2007, 50, 1795–1807.

Jönsson, T.; Granfeldt, Y.; Ahrén, B.; Branell, U.-‐C.; Pålsson, G.; Hansson, A.; Söderström, M.; Lindeberg, S. Beneﬁcial Eﬀects of a Paleolithic Diet on Cardiovascular Risk Factors in Type 2 Diabetes: A Randomized Cross-‐Over Pilot Study. Cardiovascular Diabetology 2009, 8, 35.

FrasseYo, L. A.; SchloeYer, M.; Mietus-‐Synder, M.; Morris, R. C.; SebasFan, A. Metabolic and Physiologic Improvements from Consuming a Paleolithic, Hunter-‐Gatherer Type Diet. European Journal of Clinical Nutri=on 2009 doi:10.1038/ejcn.2009.4

Human Evolu3on and Nutri3on “Man might be described basically as a hunter-‐gatherer who has had too liYle Fme in which to adapt fully to the new nutriFonal paYerns developed with recent food producFon technology.” Cavalli-‐Sforza, L. L.; Chapter 1: Human EvoluFon and NutriFon. In Food, Nutri=on and Evolu=on; Walcher, D. N.; Kretchmer, N., Eds.; Masson Publishing USA, Inc.: New York, 1981, pp. 1.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Adapta3on to Grain and Legume Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Consump3on Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Somewhat Copyright Mathieu P. Lalonde Copyright Mtolerant P. Lalonde Copyright Mathieu P. Lalonde athieu Tolerant Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Intolerant Copyright Mathieu Very Ialonde Copyright Mathieu P. Lalonde Very Tolerant Mathieu P. Lalonde P. Lntolerant Copyright Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde There has been insuﬃcient Fme and evoluFonary pressure for complete adaptaFon to seed Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde consumpFon to arise in Homo sapiens. As a result, individuals that tolerate grains and Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde legumes should be considered the minority, not the majority. Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

Wrangham, R.; Carmody, R. Human AdaptaFon to the Control of Fire. Evolu=onary Anthropology 2010, 19, 187–199.

Carmody, R. N.; Wrangham, R. W. The EnergeFc Signiﬁcance of Cooking. Journal of Human Evolu=on 2009, 57, 379–391.

Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Not All Grains Are Created Equal Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Wheat Oats Rice Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright roblema3c . Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde More P Mathieu P Less Problema3c Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Oat and rice seeds are unusual among cereals in that their endosperms contain relaFvely small Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde amounts of prolamine proteins. The predominant storage proteins in these cereals are Copyright Msimilar to the 11S gCopyright Mathieu P. Lalonde Cegumes). Mathieu P. Lalonde structurally athieu P. Lalonde lobulins of dicotyledons (such as lopyright Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mconsidering nutrient opyright nd athieu P. Lalonde Copyright t bathieu P. Lalonde When athieu P. Lalonde C density a M sustainability of agriculture, i Mecomes fairly clear that, if incorporated into the diet, cooked or fermented grains should be but a Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde minor part of total calories…But what about legumes? Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde Copyright Mathieu P. Lalonde

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An Organic Chemists's Perspective on Paleo by Mat Lalonde, PhD

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An Organic Chemists’s Perspective on Paleo by Mat Lalonde, PhD Presentation Transcript