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Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
Glycosides by Ellen Kamhi PhD RN, The Natural Nurse
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Glycosides by Ellen Kamhi PhD RN, The Natural Nurse

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  • Thank you Dr. Kamhi for this very informative slideshow. I appreciate the depth of your study to the chemical level. This is the type of schooling I'm searching for, and would be very interested in knowing where you took your studies. I hope I find more of your work on the internet. Kandi
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  • 1. Glycosides: DefinitionSUGAR + AGLYCONE= GLYCOSIDE- Myriad of Sugars- Huge variety of Aglycones Sugar molecule:enhances absorptionand bioavailability of aglycone. Plants will make glycosides by adding a sugar molecule to an aglycone in order to enhance solubility in water GINSENOSIDE – glycoside in Ginseng to transport the molecule.
  • 2. Glycosides: Definition• Multitude of glycosides• Glycosides are not related to each other botanically or chemically• “Business End of a Glycoside is the Aglycone, not the sugar Salicin-found in White Willow Bark,Oil of Wintergreen, Meadowsweet First Isolated from Meadowsweet
  • 3. Glycosides:ClassificationGlycosides may be classified by the number of sugar units , or the specific aglycone structure that it contains.1. SUGAR UNIT:Many glycosides are 5 carbon (pentose sugars ) or 6 carbon (hexose sugars)However the sugar may be a mono, di, or oligosaccharide GlucosidesGlucose RhamnosidesRhamnose2. AGLYCONE STRUCTURE:The business end of the molecule; most classification systemsfocus on the Aglycone
  • 4. Glycosides:Classification Classes of Glycosides: Examples:• Cardioactive glycosidesDigitalis, Convallaria• Anthraquinone glycosidesCascara, Senna, Aloe• Saponin glycosidesGlycyrrhiza• Cyanophore glycosides Amygdalin(laetril), Prunisin• Isothiocynate glycosidesWild mustard• Flavonoid glycosidesQuercetin• Alcohol glycosidesSalicin• Aldehyde glycosidesVanillin (Vanilla orchid)• Lactone glycosidesSweet & Red clover• Phenolic glycosidesUvaUrsi, (arbutin)• Tanninsglycosides polymerized by polyphenol oxidase
  • 5. Glycosides:Anthraquinones• Many are found in laxative plants• Strong cathartic action• May damage epithelial cells, leading to changes in absorption,secretion and motility• Damaged cells are found as apoptotic bodies in dark pigmented mucosa- pseudomelanosis coli, can be caused by laxative abuseVideo of Pseudomelanosis:http://daveproject.org/viewfilms.cfm?film_id=882
  • 6. Glycosides:Anthraquinones• Red-orange pigments• Water/alcohol soluble• Function as stimulants/ laxatives/purgatives• Excessive use can cause pathological changes in colon• Anthraquinones are characterized by two aromatic rings fused to Aloe, Buckthorn, Cascara the central ketone-bearing Sagrada, Rhubarb, Senna ring LG
  • 7. Glycosides:Anthraquinones LaxativesAloeBuckthorn(Rhamus frangula)Cascara sagrada(Rhamus purshiana)Chinese rhubarb(Rheum palamtum)Senna(Senna alexandrina) Rheum rhabarbarum NOT LAXATIVE
  • 8. FDA LAXATIVE WARNING"NOTICE (or WARNING): Contains herbs (insert name of herbs) that can act as stimulant laxatives. Prolonged steeping time can increase the risk of adverse laxative effects, including: nausea, vomiting, abdominal cramps, and diarrhea. Chronic use of laxativescan impair colon function. Use of laxatives may be hazardous in the presence of abdominal pain, nausea, vomiting, or rectal bleeding.Laxative-induced diarrhea does not significantly reduce absorptionof food calories. Acute or chronic diarrhea may result in seriousinjury or death.“http://www.pueblo.gsa.gov/cic_text/health/teatime/597_tea.html
  • 9. Glycosides:AnthraquinonesSenna:Glycoside: Sennoside ADimeric glycoside two 3 UNIT Phenolic groups attached with hydrogen bonding
  • 10. Glycosides:Anthraquinones Cascara Glycoside: Cascarosides glucose glucoseLG
  • 11. Glycosides:AnthraquinonesCascara (Rhamnus purshiana)• The bark of the tree• Grows in Washington and BC,Canada• Collected in May• Dried for one year to oxidize glycosides to give them a milder action• Never use in UC, Crohns , IBS• Pregnancydon’t use Except if labor has stalledLINK: mechanism of action study:http://www.ncbi.nlm.nih.gov/pubmed/2289777?dopt=Abstract
  • 12. Glycosides:Anthraquinones Cascara• Aged bark is a mild stimulant laxative• Cascarosides are one of many anthraquinone glycosides; some of these are also anticarcinogenic• Excessive use can cause pathological changes in colon mucosa glucose glucose Cascaroside ALG
  • 13. Glycosides:AnthraquinonesAloeGlycosides:aloe-emodin and emodin- anthraquinones
  • 14. Glycosides:Anthraquinones• Aloe gel does not contain anthraquinones• Aloe resin: aloe-emodin & its glycosides, aloin (barbaloin), aloinoside• Aloe-emodin is anti- carcinogenic; also found in Turkey Rhubarb(Rheum palmatum) ingredient in Essiac formulaLink to study: http://www.ncbi.nlm.nih.gov/pubmed/12445860?dopt=AbstractLG
  • 15. Glycosides:AnthraquinonesChinese Rhubarb( also called Turkey Rhubarb):Glycoside:GlucorheinRhein ( aglycone)Favorite Chinese catharticRoot of plant is usedPrevents kidney damageLi X, Wang H. Chinese herbal medicine in the treatment of chronic kidney disease. Adv Chronic Kidney Dis. 2005;12:276-81.
  • 16. Glycosides:AnthraquinonesSennaGlycosides: sennosides, glycosides of „dianthrones‟ - molecules made with two anthraquinone skeletons glucose glucoseLG
  • 17. Glycosides: Saponins„Saponins‟ come from the word saponify soap-likeWater soluble sugars attached to either a lipophilic steroid(C 27) or triterpenoid (C 30)Wide array of diverse plants contain saponinsCommon Characteristics:Bitter tasteHemolytic activityForm stable foam in water upon shaking
  • 18. Glycosides: SaponinsHydrophobic-Hydrophilic Asymmetrylowers surface tension- causes soaplike foamingeffect
  • 19. Glycosides: SaponinsThree main classes of Saponins: Triterpenoid glycosides ( 5 rings) Steroidal glycosides (4 rings) Steroidal alkaloid glycosides
  • 20. Glycosides: SaponinsMEDICINAL EFFECTS :• Adaptogenic/amphoteric• Alterative• Antihelminthic• Antifungal• Antimicrobial/Immunomodulation (both humoral and cellular)• Anti ulcerogenic• Cholesterol-lowering• Expectorant (via reflex irritation and lowering surface tension)• Hemolytic• Hepatoprotective (Bupleurem’s saikosaponins)• Adrenotrophic hormone releasers (ACTH)• Calcium channel blockers (Panax)• Diuretic• Vascular tonics/anti-exhudativeAesculus• AntiinflammatoryGlycyrrhiza, Guaicum
  • 21. Glycosides: SaponinsNatural surfactants, Foamingagents-soaps and shampoos.Antifungal, antibacterialinhibits cancer cell growth.Lowers blood cholesterol by binding with bile acids
  • 22. Glycosides: SaponinsThousands of herbs contain saponins: Eleuthero Smilax Licorice Astragalus Panax spp. Calendula Phytolacca Codonopsis Dandelion Dioscoria Mullein Legumes -soy, alfalfa Also Many Vegetables
  • 23. Glycosides: SaponinsLicorice Root (Glycyrrhiza glabra) Glycosides: Glycyrrhizin (glycyrrhizinic acid) Liquiritin
  • 24. Glycosides: Saponins Licorice Root• Isoliquiritigenin : - inhibits aldose reductase : may reduce diabetic neuropathy - inhibits MAO (Monoamine oxidase): may support mood balance• Licochalcones: anti-parasitic: eg. Leishmania has been used for malaria…• Butein, isoliquiritigenin : stops growth of melanoma cells in vitroLG
  • 25. Glycosides: Saponins Licorice Root• Liquiritigenin (a flavonoid) & its glycoside, liquiritin, contribute to the anti-inflammatory & antispasmodic action of Licorice• May also be involved in ulcer-healing properties• Antimicrobial• MAO inhibitor LG
  • 26. Glycosides: SaponinsLicorice Root• Glycyrrhizin (glycyrrhizinic acid): main triterpenoid saponin in root• Anti-inflammatory (synergistic with the flavonoids)• Inhibits secretion of stomach acid• Inhibits deactivation of cortisol• Responsible for raising blood pressure w/excess ingestion ( sodium & water retention, potassium excretion, diuresis)• Immunostimulating, antihepatotoxic, antiviralLG
  • 27. Glycosides: SaponinsLicorice Root Glycyrrhetinic acid • antitussive • flavoring agent- masks bitter taste, used in Chinese formulas for this purpose • anti-inflammatory • relieves peptic ulcers- inhibits gastric secretion but stimulates pancreatic and mucous secretion
  • 28. Glycosides: SaponinsLicorice Root • The structure of glycyrrhetinic acid is similar to that of cortisone. • Both molecules are flat and similar at position 3 and 11. • This might be the basis for licorices anti-inflammatory action.
  • 29. Glycosides: Saponins• Cortisone • Glycyrrhitinic acid
  • 30. Glycosides: Saponins Steroidal Saponins• Cholesterol: example of solid sterol
  • 31. Glycosides: CardiacSteroidal Saponins Highly specific- powerful action on cardiac tissue. Sugars are attached to the 3 position of the steroid nucleusTwo broad categories of Cardiac glycosides:Cardenolides, C 23, more prevalent in natureBufadienolides (Buf-adi-eno-lides) (derived from the skin of toads (sounds like witches brew!)
  • 32. Glycosides: Cardiac• Cardiac steroids: strongest heart regulators, but most toxic ( eg. Digitalis)• Phosphodiesterase inhibitors: indirectly raise cAMP, nontoxic and extremely useful for CHF ( congestive heart failure) (eg. Hawthorne (Crataegus spp.)• Direct adenylate cyclase stimulants :can also be useful (eg. Forskolin)
  • 33. STEROIDAL SKELETON:• Sourcehttp://www2.odn.ne.jp/~had26900/constituents/cardiac_steroid_skeleton.gif:
  • 34. Glycosides: Cardiac Actions:• actions include both beneficial and toxic effects on the heart.• Documented since 1500 B.C. as poisons, arrow poisons, emetics, diuretics, and heart tonics.• Used in modern treatment of congestive heart failure , atrial fibrillation and flutter• Toxicity issues must be kept in mind
  • 35. Glycosides: CardiacActions:Positive inotropic activity- increases contraction of heart muscle- important in heart failureInhibits NA+, K+ , ATPase, increasing intracellular NA+,which then increases intracellular Ca+, which leads toenhanced contraction of the cardiac muscle fibers http://www.sbirc.ed.ac.uk/cyril/gfx/cp_neurophysio2_NaK-pump.jpg
  • 36. Glycosides: CardiacActions: • Increase strength of systolic contractions- decrease length of systole- increase length of diastole • Increases the heart‟s resting tone • Improves cardiac output • Improves renal flow • Decreases edema- Pulmonary and Systemic
  • 37. Glycosides: Cardiac• The sugar portion of the molecule confers solubility and distribution• The more OH groups on the cardiac glycoside molecule, the more: Rapid action Water soluble Easily excreted – Safer, but requires more frequent dosing
  • 38. Glycosides: CardiacCautions:• Avoid electrolyte depletion and other sources of calcium• Some are (+) ionotrophic (increased force of contraction) but negatively (-)chronotrophic (decreases beats, slows heart)• Also affect vascular smooth muscle, REDUCING AFTERLOAD on heart muscle• Reduce sympathetic tone• Effect purkinje fibers and Bundle of HIS, – slowing down conduction
  • 39. Glycosides: Cardiachttp://www.personal.psu.edu/mjm5267/blogs/202c/heart%202.jpg
  • 40. Glycosides: Cardiac Dr. William Withering published Use of Digitalis to Treat Dropsy 1785
  • 41. Glycosides: CardiacDropsy : swelling of the body, often occurs with congestive heart disease, when heart does not pump sufficiently, which causes accumulation of fluidMain symptoms: swelling of the whole body especially legs gastrointestinal symptoms tingling sensation in the skin tenderness in the calf muscles increased intra-ocular pressure (glaucoma)
  • 42. Glycosides: Cardiac Digitalis for Dropsy• William Withering (a prominent physician in his time) is credited with „discovering‟ digitalis as a cure for dropsy in 1775• In reality, he learned it from a local „gypsy‟ or „old woman‟ who was curing cases of heart failure with a formula including Foxglove … an „old family recipe‟LG
  • 43. Glycosides: Cardiac• Foxglove has ~ 30 different cardenolides including digitoxin/digitalin, gitoxin, & gitaloxin• Powerful cardiac agents that increases contractility of heart muscle, cardiac output, cardiac work capacity, heart rate, arterial resistance; narrow range of safety• „Purified‟ glycosides currently used in medicine; whole leaf previously usedLG
  • 44. Glycosides:Cardiac• Small doses used clinically for controlling congestive heart failure• Larger doses are cardiac poisons• Native peoples use/d them as arrow poisons• Steroidal glycosides with an extra lactone ring attachedLG
  • 45. Glycoside:Cardiac • Isolated digitoxin is used in contemporary pharmacy • Cardiac glycoside, extracted from Foxglove (Digitalis purpurea or D. lanata)
  • 46. Glycosides: Cardiac DIGITALIS• INDICATIONS: CHF, supra-ventricular tachycardia, atrial flutter, atrial fibrillation• USUAL DOSE: 1-2 grams USP crude drug proceed to 100-200 mg for maintenance• REDUCE DOSE by 25% for the elderly or overly thin client, more for obese• ONSET OF ACTION: 2-4 hours• DISSIPATION OF DRUG: 2-3 weeks• Digitalis is particularly likely to cause toxicity as its cardiac glycosides are – less polar, – less water soluble – (MORE LIPOPHILIC) and have a longer half life
  • 47. Glycosides:CardiacLilly of the Valley(Convallaria spp.)
  • 48. Glycosides:CardiacConvalleriaUsed for cardiac irregularities with mechanical impediments – Mitral valve insufficiency – Feeble circulation with low arterial tension – Dropsy of cardiac origin – Palpitation with arrhythmias and vehement (violent) heart action – Dyspnea – Feeble quickened pulse – Used with Crateagus, it is valuable in BRADYCARDIA – Use before digitalis, which is more applicable in SEVERE CHF
  • 49. Glycosides:CardiacConvalleria • ~ 40 different glycosides based on several different aglycones; variable • Convallatoxin highly active, but generally no more than 10% of the amount ingested can be absorbed • Positive inotropic effect; used for mild cardiac insufficiency LG
  • 50. Convalleria Glycosides:Cardiac• Contains anthraquinones-excessive doses cause diarrhea 1st- before toxicity ensues• Contains highly water soluble ‘safer’ gycosides: Convallotoxin, convalloside, convallotoxol• High in Flavonoids• Dose is usually 5-30 drops of 1:5 tincture per day• Favorite of Dr. Bastyr, Founder of Bastyr University of Naturopathic Medicine: CCC Cardiac Combo Crateagus, Cactus & ConvallariaNOTE: Cactus and Crateagus have NO CARDIAC GLYCOSIDES but instead have flavonoids and other vasoactive amines which help weak & feeble heart
  • 51. Hawthorn• Hyperin, a glycoside of quercetin, is the main flavonoid in Hawthorn• Also contains OPC‟s• Helps heart muscle to work more efficiently, strengthens contractions, stabilizes rhythm• Enhances the utilization of oxygen in cells• Contains many antioxidants• Antispasmodic, anti-inflammatoryLG
  • 52. Variability: Developmental StageOPC levels in Hawthorn flowers are ~ 4x higherin the bud stage than in open flowers
  • 53. Cardiovascular DrugsHerbal Support: Hawthorne Hawthorne (Crataegus: laevigata, oxyacantha, monogyna, spp.) 53 53
  • 54. Cardiovascular Drugs Herbal Support: HawthorneThe Hawthorne is a tree/shrub in the rose family that is widely distributedand grows in the USA, Europe, western Asia and North Africa. Many partsof the plant are used. The berries are similar to crabapples and traditionalmedicinal and edible preparations used this fruit. Since active constituentshave been isolated and extracted, many more modern medicinalpreparations use mainly the leaves and flowers.The use of Hawthorne as a heart tonic probably originated due to the„doctrine of signatures‟ which proposes that plants give „cosmic clues‟about their potential use. Hawthorne berries have a similarity in color andshape to the heart. By the first century AD, the Greek medicinal herbalist,Dioscorides, reported using hawthorne as a heart tonic, among other uses. 54 54
  • 55. Cardiovascular Drugs Nutrient Depletion: HawthorneCrataegus spp. Hawthorne Oligomeric procyanidins,vitexin,vitexin 4’-O-rhamnoside,quercetin, Rutin Leaves and flowers have highest flaonide content,esp. OPC Also, increases strength of collagen 20 fold Use in OA a.w.a.CV Dz 55
  • 56. Cardiovascular Drugs Herbal Support: HawthorneMechanism of Action - Cardiovascular effects:• Decreases blood pressure and total peripheral resistance• Economizes myocardial function : reduces work loa=d on the heart• Decreases cardiac preload in healthy people• Inotropic effects (Inotropic: Affecting the force of muscle contraction)• The inotropic effects of hawthorn may be caused by inhibition of 3,5- cyclic adenosine monophosphate diesterase , which in turn decreases inflammation• Anti-oxidant activity is protective to heart muscle and circulatory system due to high flavonoid content 56
  • 57. Cardiovascular Drugs Herbal Support: HawthorneRecommended Dosage:Standardized Extract (18.75% oligomeric procyanidins) 60 mg 3 X/day or or 80 mg 2 X per day.Standardized ( 2.2 % flavonoids ) 100 – 300 mg 3 X per day Tincture: 300-900 mg/ day in divided doses Capsules Standardized (2% vitexin-2"-0- rhamnoside) 300-1000 mg/ day in divided doses 57
  • 58. Cardiovascular Drugs Herbal Support: HawthorneProduct Examples Hawthorn leaf capsules, 325 mg Standardized (2% vitexin-2"-0-rhamnoside)http://www.iherb.com/Nature-s-Answer-Hawthorn-Leaf-Extract-60-Veggie-Caps/8143?at=0 Hawthorn extract (leaf, flower) tablets, 80 mg (18.75% OligomericProcyanidins)http://www.iherb.com/Nature-s-Way-HeartCare-Hawthorn-Extract-120-Tablets/1987?at=0 Hawthorn Berry Veggie Caps, 500 mghttp://www.iherb.com/Nature-s-Answer-Hawthorn-Berry-120-Veggie-Caps/8115?at=0 58
  • 59. Cardiovascular Drugs Herbal Support: HawthorneStudiesElango, C. , et. al. Hawthorn extract reduces infarct volume and improvesneurological score by reducing oxidative stress in rat brain followingmiddle cerebral artery occlusion. ( 2009) International Journal ofDevelopmental Neuroscience. 2009 Aug 25. [Epub ahead of print]http://www.ncbi.nlm.nih.gov/pubmed/19712738?itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVDocSum&ordinalpos=3Pittler MH, et. al. , (2008) Hawthorn extract for treating chronic heartfailure, Cochrane Database of Systemic Reviews. Jan 23;(1):CD005312.“AUTHORS CONCLUSIONS: These results suggest that there is asignificant benefit in symptom control and physiologic outcomes fromhawthorn extract as an adjunctive treatment for chronic heart failure.”http://www.ncbi.nlm.nih.gov/pubmed/18254076?ordinalpos=1&itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_SingleItemSupl.Pubmed_Discovery_RA&linkpos=5&log$=relatedreviews&logdbfrom=pubmed 59
  • 60. Cardiovascular Drugs Herbal Support: HawthorneAdverse EffectsProven safe for long term use in centuries of traditional use with minimumreports of adverse effectsAllergiesAvoid if allergic to hawthorn or to members of the Crataegus genus. Thereis a case report of an immediate-type hypersensitivity reaction to hawthornplants. It is not known if this applies to formulations taken by mouth.Side Effects and WarningsThere are limited reports of adverse effects associated with hawthorn.Numerous human trials, observational studies including over 4,500patients, and case reports have noted rare adverse effects, includingabdominal discomfort, nausea, agitation, dizziness, headache, fatigue,shortness of breath, skin rash, insomnia, sweating, and rapid heart rate.Pregnancy and BreastfeedingNot recommended due to lack of sufficient data. No reports of adverseeffects. 60
  • 61. Cardiovascular Drugs Herbal Support: HawthorneDrug InteractionsAntiarrhythmic medications: Laboratory studies report that constituents contained inhawthorn have antiarrhythmic activity which may alter the effects of these medications andpossibly the dose needed for treatment. Use with caution. Potential/Theoretical AdditiveEffects – These drugs include amiodarone, bretylium tosylate, adenosine, dofetilide, propafenone, lidocaine, tocainide, flecainide, ibutilide fumarate, moricizine, quinidine, disopyramide, procainamide, mexiletine, verapamil, digoxin, propranolol, sotalol, esmolol, acebutolol.ACE inhibitors: Laboratory studies report that constituents contained in hawthorn haveACE inhibiting activity which may alter the effects of these medications and possibly thedose needed for treatment. Use with caution. Potential/Theoretical Additive Effects – These drugs include benazepril, captopril, enalapril, lisinopril, fosinopril,moexipril, quinapril, ramipril, trandolapril, perindopril erbumine.Cardiac glycosides: Laboratory studies report that constituents contained in hawthorn havecardiac activity which may alter the effects of these medications and possibly the doseneeded for treatment. Use with caution. Potential/Theoretical Additive Effects – These drugs include digoxin. Note: all interactions are supported by studies unless noted by potential/theoretical 61
  • 62. Cardiovascular DrugsHerbal Support: HawthorneDrug InteractionsAntihypertensive medications: Laboratory studies report that constituents contained inhawthorn have hyper/hypotensive activity which may alter the effects of these medicationsand possibly the dose needed for treatment. Use with caution. Potential/TheoreticalAdditive Effects – These drugs include amlodipine, bepridil, diltiazem, felodipine, isradipine, nicardipine, nifedipine, nimodipine, nisoldipine, verapamil, benazepril, captopril, enalapril, lisinopril, fosinopril,moexipril, quinapril, ramipril, trandolapril, perindopril erbumine, atenolol, esmolol, betaxolol, penbutolol, carteolol, bisoprolol, pindolol, metoprolol, timolol, sotalol, acebutolol, nadolol, propranolol, labetalol, carvedilol, methyldopa, clonidine, guanfacine, guanabenz, brimonidine tartrate, dipiprazole, levobunolol, levobetaxolol, metipranolol, reserpine, prazosin, terazosin, doxazosin meylate, guanadrel, guanethidine, isosorbide monohydrate, isosorbide dinitrate, nitroglycerin, hydralazine, minoxidil, papaverine, isoxsuprine, losartan, valsartan, eprosartan mesylate, telmisartan, candesartan cilexetil, irbesartan. Vasoconstrictor medications : such as phenylephrine (Neo-Synephrine®), ephedrine or norepinephrine. Hawthorn may have Potential/Theoretical Antagonistic Effects Note: all interactions are supported by studies unless noted by potential/theoretical 62
  • 63. Cardiovascular DrugsNutrient Depletion: Coleus• Antihypertensive medications: Laboratory data has reported that constituents contained in coleus leaf have antihypertensive activity which may alter the effects of these medications and possible the dose needed for treatment. Use with caution. Potential/Theoretical – Drugs include amlodipine, bepridil, diltiazem, felodipine, isradipine, nicardipine, nifedipine, nimodipine, nisoldipine, verapamil, benazepril, captopril, enalapril, lisinopril, fosinopril,moexipril, quinapril, ramipril, trandolapril, perindopril erbumine, atenolol, esmolol, betaxolol, penbutolol, carteolol, bisoprolol, pindolol, metoprolol, timolol, sotalol, acebutolol, nadolol, propranolol, labetalol, carvedilol, methyldopa, clonidine, guanfacine, guanabenz, brimonidine tartrate, dipiprazole, levobunolol, levobetaxolol, metipranolol, reserpine, prazosin, terazosin, doxazosin meylate, guanadrel, guanethidine, isosorbide monohydrate, isosorbide dinitrate, nitroglycerin, hydralazine, minoxidil, papaverine, isoxsuprine, losartan, valsartan, eprosartan mesylate, telmisartan, candesartan cilexetil, irbesartan. 63
  • 64. Glycosides: Flavonol Quercitin • More than 135 different glycosides exist in leaves, fruits, flowers • Rutin (quercetin-3-rutinoside) used for capillary fragility & venous integrity • Hyperin (hyperoside; quercetin-3-galactoside), main flavonoid in Hawthorn; also in St. Johnswort – helps prevent cataracts; may contribute to antidepressive activity • Quercetin inhibits mast cell degranulation • Powerful anti-inflammatory • Rich dietary sources: Onion, Kale, Broccoli, Lingonberry, Cranberry, Black Currant, TeaLG
  • 65. Isoflavones: AglyconesLG
  • 66. Isoflavones: Glycosides Most isoflavones actually occur as the glucose conjugates; aglycones are present in the plants, butLG only in small amounts
  • 67. Anthraquinones in Yellow Dock • Emodin, chrysophanol, rhein & related glycosides • Contribute to aperient activityLG
  • 68. Chromones • Related to the flavonoids • Khellin (from Ammi visnaga) • Cardiovascular tonic: for angina, atherosclerosis, high cholesterol • Vasodilator • Antispasmodic • Also used for asthma (bronchodilator) & is antitussive via CNSLG action Photo © Werner Arnold 2003
  • 69. Quinones: Naphthoquinones Drosera (Sundew) contains plumbagin: antibacterial, antispasmodic (for cough), immunostimulantLGPhoto © Richard Bailey 2003 The Carnivorous Plant Society www.thecarnivorousplantsociety.org
  • 70. Anthraquinones in Hypericum • St. Johnswort contains a complex anthraquinone relative, hypericin (a „bianthraquinone‟) • Aka a „naphthodianthrone‟ • Occurs with pseudohypericin • Colors the oil red • Contributes to antiviral & antidepressant activities • Responsible for photoreactivity • Synergistic with the flavonoids, xanthones, & hyperforinLG
  • 71. Cardiac Glycosides in Milkweeds • Found in all species of Asclepias • Components of the milky latexLG • Toxic to vertebrates, but not to butterflies
  • 72. Isoflavones: GlycosidesMost isoflavones actually occur as the glucoseconjugates; aglycones are present in the plants, butonly in small amounts

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