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Wine and grape Metabolomics Chapters 1-2

The document outlines a module on untargeted metabolomics in oenology and viticulture, detailing learning outcomes such as understanding wine metabolome terminology and familiarizing students with methods and applications. It consists of 30 hours of lectures, interactive exercises, and group lab work, with prerequisites in chemistry and statistics. The final assessment includes a written test and possibly an oral presentation, focusing on students' knowledge of metabolomics in wine production.

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The allegory of the cave
What do you aspect from this module?
C3A Applied Metabolomics in oenology and viticulture Semester II Year III Hours 30 English Objects This module will introduce the students into the untargeted metabolomics concept and its applications in the field of oenology and viticulture. Learning outcomes: 1. Understand and learn the wine metabolome terminology/ontology. 2. Account for methods, the techniques and the instruments used in untargeted metabolomics. 3. Be familiar with the workflow of the untargeted metabolomics studies. 4. Account for applications for untargeted metabolomics in enology and viticulture. 5. Learn to think in holistic way as far as the wine metabolome. + get familiar with the English oenological terminology
C3A Applied Metabolomics in oenology and viticulture Semester II Year III Hours 30 English Description This 30 hours module includes: - Lectures (general theory and published applications). - Interactive classroom exercises (computer tools, software, databases) (optional) - Group exercises in the laboratory (optional) Moreover, will be proposed to the students material and resources (publications, books, websites) to explore the topics of the course in depth. Be aware that the material in Italian is poor. Is strongly advised to participate to the frontal lessons. Prerequisites For the most profitable attendance of the course, the student should have preferably completed the exams of English; Mathematic and statistics, General Chemistry; Organic chemistry; Wine chemistry and microbiology; and Enology 1.
C3A Applied Metabolomics in oenology and viticulture Semester II Year III Hours 30 English Final exam The final exam consists of a written test (compulsory), and a possible oral exam that could include a group oral presentation based on the carried out activities. The exam will investigate the student's ability to demonstrate theoretical and practical knowledge on the topics of metabolomics applied in vine-oenology, including the proposed teaching material.
C3A Applied Metabolomics in oenology and viticulture Calendar MON TUE WED THU FRI SAT SUN MON TUE WED THU FRI SAT SUN 1 2 3 1 2 3 4 5 4 5 6 7 8 9 10 6 7 8 9 10 11 12 11 12 13 14 15 16 17 13 14 15 16 17 18 19 18 19 20 21 22 23 24 20 21 22 23 24 25 26 25 26 27 28 29 30 31 27 28 29 30 31 MON TUE WED THU FRI SAT SUN MON TUE WED THU FRI SAT SUN 1 2 3 4 5 6 7 1 2 8 9 10 11 12 13 14 3 4 5 6 7 8 9 15 16 17 18 19 20 21 10 11 12 13 14 15 16 22 23 24 25 26 27 28 29 30 MARCH APRIL MAY JUNE
What is important to know before to enter in Wine Metabolomics  What is metabolomics?  What is metabolite?  How do we measure the metabolites? Prerequisites – first step The first part of the module will focus in three subjects:  Wine organic chemistry – Wine metabolome  Basic knowledge about Chromatography and Mass Spectrometry  Basic statistic knowledge
1. INTRODUCTION
(Metabol)-omics: definitions System biology Systems biology is a biology-based interdisciplinary field of study that focuses on complex interactions within biological systems, using a holistic approach (holism instead of the more traditional reductionism) to biological research. The systematic study of the complete DNA sequences of an organism. The systematic study of the complete complement of proteins of an organism. The systematic study of the gene expression (messengerRNA) of an organism. “Proteomics, transcriptomics: what's in a name?” Nature 402:715 Dec 16, 1999
(Metabol)-omics: definitions What can the cell potentially do? What is currently being turned on? What enzymes are currently active? What is being produced/consumed? System biology Sirén et al. (2019) Multiomics and potential applications in wine production. Current Opinion in Biotechnology
Metabolomics: definitions metabolomics is the "systematic study of the unique chemical fingerprint that specific cellular processes leave behind", the study of their small-molecule metabolite profiles (Daviss 2005) metabolomics is a newly emerging field of "omics" research concerned with the comprehensive characterization of the small molecule metabolites in biological systems. (Metabolomics Society) metabolomics is the comprehensive and holistic study of the metabolome the complete set of small-molecule metabolites to be found within a biological sample metabonome: the complete set of metabologically regulated elements in cells
From targeted to untargeted
Targeted versus Untargeted
Targeted versus Untargeted
Targeted versus Untargeted
Metabolomics: metabolite What is a metabolite? Product and intermediate of the metabolism – small organic molecules
2. Grape/Wine Metabolome
Wine Chemistry – Wine Composition How big is the grape/wine metabolome?
Metabolomic: what is and what is not How big is the metabolome? Sigma-Aldrich has ~55K commercial available chemicals Kegg contains 18K metabolites HMDB is based in ~42K metabolites Plant metabolome is estimated to cover 200K metabolites PubChem ID contains more than 10M entries CAS contains over 90M unique organic and inorganic chemicals ChemSpider contains over 57M compounds from 530 data sources
Plant metabolome is estimated to cover 200 000 metabolites #ofmetabolites5-21% ethanol g/L mg/L µg/L ng/L pg/L fg/L How big is the metabolome? Wine Chemistry – Wine Composition
#ofmetabolites5-21% ethanol g/L mg/L µg/L ng/L pg/L fg/L Plant metabolome is estimated to cover 200 000 metabolites How big is the metabolome? Wine Chemistry – Wine Composition
Wine Chemistry – Wine Composition #ofmetabolites g/L mg/L µg/L ng/L pg/L fg/L 95-79% water 5-21% ethanol 0-100 g/L sugars (glucose/fructose) 1-6 g/L tartaric acid 0-4 g/L malic acid 0-4 g/L lactic acid 0.5-1.5 g/L succinic acid 0.2-1.5 g/L acetic acid 4-15 g/L glycerol 0.1-10 g/L CO2 0.02-1.3 g/L argine glutamine, alanine, glutamic acid, proline, glycine, histidine arabinose, xylose, rhamnose Fe, Cu, B, Mn methanol, acetaldehyde, SO2 proteins thiamine, riboflavin, niacin, biotin, pantothenate and vitamin C phenolics polysaccharide
Wine Chemistry – Wine Composition Waterhouse, Understanding wine chemistry, 2016
Grape/Wine Chemistry
Wine/Grape Chemistry Koutroumanidis et al
Wine/Grape Chemistry – Phenolics
Wine/Grape Chemistry – Phenolics – Classification according the skeleton C6 C6-C3 C6-C3-C6 O OH O OH C6-C2-C6 phenolic acids cinnamics acids stilbenoids flavanoids O OH OH O OH OH OH O OH OH OH OH OH OH OH O OH OH OH O OH OH O OH OH OH OH OH OH OH OH O OH OH OH O OH OH O OH O A C B 7 2 3 45 6 2' 8 3' 4' 5' 6' 2' : 2 prime (not apostrophe)
Wine/Grape Chemistry – Phenolics – Phenolic acids shikimic acid O OH OH O OH OH OH O OH OH OH OH gallic acid UV-Vis spectrum nm250 300 350 400 450 500 550 270 nm nm250 300 350 400 450 500 550 280 nm • Wooden barrel • Non Vinifera • Hydrolysable tannins gallic acid O HO HO OH O HO O OH OH OH glucogallin
Wine/Grape Chemistry – Phenolics - Cinnamates shikimic acid phenylalanine cinnamic acid coumaric acid coutaric acidfertaric acid caftaric acid caffeic acidferulic acid
Wine/Grape Chemistry – Phenolics - Cinnamates coutaric acid Wine 15 mg/L
Wine/Grape Chemistry – Phenolics - Cinnamates nm250 300 350 400 450 500 550 caffeic acid UV-Vis spectrum 324 nm
fertaric acid Wine/Grape Chemistry – Phenolics - Cinnamates coutaric acid 4-vinyl phenol 4-vinyl guaicol 4-ethyl guaicol 4-ethyl phenol OH O O OH O OH OH O OH O O OH O OH OH O O CH3 OH CH2 O CH3 OH CH3 O CH3 OH CH3OH CH2
Wine/Grape Chemistry – Phenolics - Flavonols shikimic acid phenylalanine cinnamic acid naringenin myricetinsyringetin quercetin keampferol isorhamnetin naringenin chalcone
Wine/Grape Chemistry – Phenolics - Flavonols quercetin quercetin 3-rabinoside quercetin 3-glucuroside quercetin 3-galactose quercetin 3-rhamnosidequercetin 3-glucose
Wine/Grape Chemistry – Phenolics - Flavonols Mattivi et al JAFC 2006 myricetin syringetin quercetin keampferol isorhamnetin
Wine/Grape Chemistry – Phenolics - Flavonols Mattivi et al JAFC 2006 myricetin syringetin quercetin keampferol isorhamnetin
Wine/Grape Chemistry – Phenolics - Flavonols UV-Vis spectrum
Wine/Grape Chemistry – Phenolics - Anthocyanins shikimic acid phenylalanine cinnamic acid naringenin naringenin chalcone cyanidin delphinidin pelargonidin malvidin peonidin
Wine/Grape Chemistry – Phenolics - Anthocyanins O + OH OH O OH O OO OH OH OH OH O O OH OH OH OH O + OH O OH O OO OH OH OH OH OH O + OH O OH O OO OH OH OH O O OH OH O + OH O OH O OO OH OH OH O O OH OH OH O + OH O OH O OO OH OH OH O O OH O + OH O OH O OH
Wine Chemistry – Phenolics - Anthocyanins OH OOH OH OH OH OH O + OH O OH O OO OH OH OH OH O + O OH OH O O OH OH OH OH OH O OH O OH OH OH OH O + O OH OH O O OH OH OH OH O OH OH O OH OH OH OH O + OH OH O OH O OO OH OH OH OH
Wine Chemistry – Phenolics - Anthocyanins O + OH OH O OH O OO OH OH OH OH O + O OH OH O O OH OH OH OH O O O + O OH OH O O OH OH OH OH O O OH O O + OH O OH O OO OH OH OH OH OH p-coumaric acid
Wine/Grape Chemistry – Phenolics - Anthocyanins UV-Vis spectrum nm250 300 350 400 450 500 550 O OH HO OH OH OH cyanidin
Wine Chemistry – Phenolics - Anthocyanins
Wine Chemistry – Phenolics - Anthocyanins Bobeica et al Frontiers 2016
Mattivi et al JAFC 2006 cyanidin delphinidin pelargonidin malvidin petunidin Wine/Grape Chemistry – Phenolics - Anthocyanins
Wine/Grape Chemistry – Phenolics - Anthocyanins O + O OH OH OH O O OH OH OH OH O O + OH OH OH OH O O OH OH OH OH OH O + O OH OH OH O O OH OH OH OH O + OH OH OH OH O O OH OH OH OH O + O OH OH OH O O OH OH OH OH OH + + +
Wine/Grape Chemistry – Phenolics - Flavanols cyanidin delphinidin pelargonidin OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OOH OH OH OH + + + epicatechin catechin epigallocatechin gallocatechin epiafzelechin afzelechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate
Wine/Grape Chemistry – Phenolics – Flavanols (dimers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OH OOH OH OH OH OH OOH OH O OH OH OH OH O OH OH OH OOH OH OH OH OH OOH OH O OH OH O OH OH OH OOH OH OH OH OH OOH OH O OH OH OH O OH OH OH
Wine/Grape Chemistry – Phenolics – Flavanols (oligomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
Wine/Grape Chemistry – Phenolics – Flavanols (oligomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
Wine/Grape Chemistry – Phenolics – Flavanols (polyomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH O OH OH OH OH O OH OH OH
Wine Chemistry – Phenolics – Flavanols (astringent and bitter taste) OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH epicatechin catechin gallocatechin OOH OH O OH O OH OH OH OH (epi)catechin-gallate epicatechin is more bitter than catechin OOH OH OH OH OH catechin The galloyl-ation increase the astringency Cheynier et al. ACS Symposium 1997
Wine Chemistry – Phenolics – Flavanols (astringent and bitter taste) Polymerization decrease bitterness (dimers, trimers and tetramers are more bitter than astringent) polymerization slightly increase the astringency (high degree or polymerization may decrease astringency) (the maximum is reached ~ 8 units) Cheynier et al. ACS Symposium 1997 OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
Wine/Grape Chemistry – Phenolics – Flavanols (degree of polymerization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ean degree of polymerization = mDP O OH OH OH OH OH
Wine Chemistry – Sugars/Carbohydrates O OH OH OH OH OH O OH OH OH OH OH glucose O OH OH OH OH OH fructose O OH OH OH OH arabinose OH OH OH OH OH OH OH OH OH O OH OH OH OH OH O α β glucuronic acid glycerol inositol 1 2 3 4 5 6
Wine Chemistry – Amines O NH2 OH O NH2 NH OH O NH2 OH O NH2 OH tryptophan phenylalanineleucine isoleucinealanine N H O NH2 NH2 NH2 OH NH2 N N O 3-Isobutyl-2-methoxypyrazine indole putrescine tyramine2-aminoacetophenone N O 2-acetylpyrroline O NH2 OH
Wine Chemistry – Tryptophan metabolites OH NH2 N H O O NH2 OH O OH N H OH O OH N H OH N H TOL N OH O OH N H O NH O N H OH NH2 shikimic OH OH OH OOH OOH NH2 O NH2 O O N H OH O OH OH OH OH OH O OH OH OH OH OH O OH OH OH OH OH O NH N H O O O NH2 N H O epicatechin procyanidin B2 phenylalanine tryptophan melatoninserotonin tryptophan ethyl ester N-acetyl-tryptophan ethyl ester kynurenic anthranillic kynurenine indole-3-pyruvic acid indole-3-lactic acid indole-3-acetic acid tryptophol 2-aminoacetophenone OOH NH2 anthranillic
Wine Chemistry exercise Design 1. glucose 2. alanine 3. phenylalanine 4. p-coumaric acid 5. catechin
Wine Chemistry Design 1. glucose 2. alanine 3. phenylalanine 4. p-coumaric acid 5. catechin OOH OH OH OH OH O NH2 OH O OH OH OH OH OH O NH2 OH
Grape Sensorial analysis: grape What is the odor of a grape berry? Inspired by Il respire del vino of L. Moio
Grape Sensorial analysis: grape Aromatic grape Moscato, Gewϋrztraminer Wine smell as the grape Non-aromatic grape a) silenced and b) not-silenced Sauvignon blanc Must non-aromatic, wine aromatic
Grape Sensorial analysis: grape aromatic part aromatic part sugar O OOH OH OH OH OH enzymatic or chemical hydrolysis
Grape aromatic compounds: terpenoids Isoprene Hydrocarbon 5 x Carbons 2 x Isoprene Monoterpenes 10 x Carbons 3 x Isoprene Sesquiterpene 15 x Carbons 4 x Isoprene Diterpenes 20 x Carbons 5 x Isoprene Sesteterpenes 25 x Carbons 6 x Isoprene Triterpenes 30 x Carbons Terpene + Oxygen or Nitrogen = terpenoids
OH α-terpineol linalool OH geraniol OH OH citronellol myrcene limonene O eucaliptolo α-pinene Grape aromatic compounds: terpenoids
Grape aromatic compounds: volatiles thiols O SH OH SH O SHO 4-mercapto-4-methylpentan-2-one 4MMP 3-mercaptohexan-1-ol 3MH 3-mercaptohexyl-acetate 3MHA
Grape aromatic compounds: volatiles thiols
OH S O NH2 OH Grape aromatic compounds: volatiles thiols aromatic part cysteine
β-carotene O O O O O Grape aromatic compounds: norisoprenoids
O Grape aromatic compounds: norisoprenoids megastigmane non-megastigmane TDNβ-damascenone vitispirane O β-ionone
Grape aromatic compounds: norisoprenoids Time Quantity carotenoids more sun Veraison Maturity Over maturity
Grape aromatic compounds: methoxypyrazine N N R
Grape Sensorial analysis: must Aromatic grape Moscato, Gewϋrztraminer continuity
Grape Sensorial analysis: must O 1-hexanol OH OH OH OO Non-aromatic grape (but aromatic in taste) 1-hexanal 3-trans-hexan-1-ol 3-trans-hexan-1-al 3-cis-hexan-1-ol 3-cis-hexan-1-al
Grape Sensorial analysis: must O 1-hexanol OH OH OH OO 1-hexanal 3-trans-hexan-1-ol 3-trans-hexan-1-al 3-cis-hexan-1-ol 3-cis-hexan-1-al O OH O OH linoleic acid linolenic acid
Grape Sensorial analysis: must Cabernet Sauvignon, Sauvignon blanc, Cabernet Franc, Merlot N N R • Amplification of herd odor • Not mature grapes
Grape Sensorial analysis: must White grapes: Honey, dry fruits, chamomile Red grapes: comfiture of red berries
Grape Sensorial analysis: alcoholic fermentation OH O O O OH OH OH OH OH O O OH O glucose pyruvic acid acetaldehyde ethanol
O NH2 OH O NH2 R OH O O R OH O R OH R O NH2 NH OH O NH2 OH O NH2 OH Must sensorial analysis: alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine O NH2 OH
O NH2 OH O NH2 R OH OH R O NH2 OH O NH2 OH Must sensorial analysis: alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine O NH2 NH OH O NH2 OH
OH O NH2 OH O NH2 NH OH OH NH O NH2 OH O NH2 OH OH OH Must sensorial analysis: alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine OH phenyl-ethanol ethanol 3-methyl-butanol tryptophol2-methyl-butanol 4-197 mg/L 6-490 mg/L 2-150 mg/L 2-30 mg/L O NH2 OH
O NH2 OH O NH2 NH OH OH NH O NH2 OH O NH2 OH OH OH Must sensorial analysis: alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine OH phenyl-ethanol ethanol 3-methyl-butanol tryptophol2-methyl-butanol amino acid in must ft Cultivar Maturity Viticulture practices Turbidity O NH2 OH OH
OH OH Must sensorial analysis: alcoholic fermentation / Ehrlich reaction phenyl-ethanol 3-methyl-butanol 2-methyl-butanol volatiles threshold 300 mg/L Adolf and Versini, 1999 OH
Must sensorial analysis: alcoholic fermentation OH O O O OH OH OH OH OH O O OH O glucose pyruvic acid acetaldehyde ethanol O OH acetic acid
Must sensorial analysis: alcoholic fermentation O OH acetic acid OH O OH O OH O OH O OH O 2-methylpropanoic acid 3-methylbutanoic octanoic acid acid (caprilic acid) Hexanoic acid (capronic acid) butanoic acid (butyric acid) OH Odecanoic acid acid (caprinic acid)
Must sensorial analysis: alcoholic fermentation / half time OH O OH O OH O OH O 3-methylbutanoic octanoic acid acid (caprilic acid) Hexanoic acid (capronic acid) butanoic acid (butyric acid) O O O O O O O O isoamyl acetate ethyl butanoate ethyl hexanoate ethyl octanoate
Wine sensorial analysis: the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
Wine sensorial analysis: the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
Wine sensorial analysis: the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
Wine sensorial analysis: aging Time
Wine sensorial analysis: aging Time ethyl esters Alcohols superior Phase I Phase II Phase III
Wine sensorial analysis: barrel aging Time Fermentation barrique aromatic or non-aromatic silenced cultivar
Wine sensorial analysis: barrel aging Time Fermentation barrique non-aromatic cultivar
Wine Chemistry exercises
Wine Chemistry Design 1. linalool 2. pheyl-ethanol 3. isoamyl acetate 4 3-mercaptohexan-1-ol 5. β-damascenone linalool OH OH SH 3-mercaptohexan-1-ol 3MH phenyl-ethanol O O isoamyl acetate O β-damascenone OH

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Wine and grape Metabolomics Chapters 1-2

  • 2.
  • 3.
    What do youaspect from this module?
  • 4.
    C3A Applied Metabolomics in oenologyand viticulture Semester II Year III Hours 30 English Objects This module will introduce the students into the untargeted metabolomics concept and its applications in the field of oenology and viticulture. Learning outcomes: 1. Understand and learn the wine metabolome terminology/ontology. 2. Account for methods, the techniques and the instruments used in untargeted metabolomics. 3. Be familiar with the workflow of the untargeted metabolomics studies. 4. Account for applications for untargeted metabolomics in enology and viticulture. 5. Learn to think in holistic way as far as the wine metabolome. + get familiar with the English oenological terminology
  • 5.
    C3A Applied Metabolomics in oenologyand viticulture Semester II Year III Hours 30 English Description This 30 hours module includes: - Lectures (general theory and published applications). - Interactive classroom exercises (computer tools, software, databases) (optional) - Group exercises in the laboratory (optional) Moreover, will be proposed to the students material and resources (publications, books, websites) to explore the topics of the course in depth. Be aware that the material in Italian is poor. Is strongly advised to participate to the frontal lessons. Prerequisites For the most profitable attendance of the course, the student should have preferably completed the exams of English; Mathematic and statistics, General Chemistry; Organic chemistry; Wine chemistry and microbiology; and Enology 1.
  • 6.
    C3A Applied Metabolomics in oenologyand viticulture Semester II Year III Hours 30 English Final exam The final exam consists of a written test (compulsory), and a possible oral exam that could include a group oral presentation based on the carried out activities. The exam will investigate the student's ability to demonstrate theoretical and practical knowledge on the topics of metabolomics applied in vine-oenology, including the proposed teaching material.
  • 7.
    C3A Applied Metabolomics in oenologyand viticulture Calendar MON TUE WED THU FRI SAT SUN MON TUE WED THU FRI SAT SUN 1 2 3 1 2 3 4 5 4 5 6 7 8 9 10 6 7 8 9 10 11 12 11 12 13 14 15 16 17 13 14 15 16 17 18 19 18 19 20 21 22 23 24 20 21 22 23 24 25 26 25 26 27 28 29 30 31 27 28 29 30 31 MON TUE WED THU FRI SAT SUN MON TUE WED THU FRI SAT SUN 1 2 3 4 5 6 7 1 2 8 9 10 11 12 13 14 3 4 5 6 7 8 9 15 16 17 18 19 20 21 10 11 12 13 14 15 16 22 23 24 25 26 27 28 29 30 MARCH APRIL MAY JUNE
  • 8.
    What is importantto know before to enter in Wine Metabolomics  What is metabolomics?  What is metabolite?  How do we measure the metabolites? Prerequisites – first step The first part of the module will focus in three subjects:  Wine organic chemistry – Wine metabolome  Basic knowledge about Chromatography and Mass Spectrometry  Basic statistic knowledge
  • 9.
  • 10.
    (Metabol)-omics: definitions System biology Systemsbiology is a biology-based interdisciplinary field of study that focuses on complex interactions within biological systems, using a holistic approach (holism instead of the more traditional reductionism) to biological research. The systematic study of the complete DNA sequences of an organism. The systematic study of the complete complement of proteins of an organism. The systematic study of the gene expression (messengerRNA) of an organism. “Proteomics, transcriptomics: what's in a name?” Nature 402:715 Dec 16, 1999
  • 11.
    (Metabol)-omics: definitions What canthe cell potentially do? What is currently being turned on? What enzymes are currently active? What is being produced/consumed? System biology Sirén et al. (2019) Multiomics and potential applications in wine production. Current Opinion in Biotechnology
  • 12.
    Metabolomics: definitions metabolomics isthe "systematic study of the unique chemical fingerprint that specific cellular processes leave behind", the study of their small-molecule metabolite profiles (Daviss 2005) metabolomics is a newly emerging field of "omics" research concerned with the comprehensive characterization of the small molecule metabolites in biological systems. (Metabolomics Society) metabolomics is the comprehensive and holistic study of the metabolome the complete set of small-molecule metabolites to be found within a biological sample metabonome: the complete set of metabologically regulated elements in cells
  • 13.
    From targeted tountargeted
  • 14.
  • 15.
  • 16.
  • 17.
    Metabolomics: metabolite What isa metabolite? Product and intermediate of the metabolism – small organic molecules
  • 18.
  • 19.
    Wine Chemistry –Wine Composition How big is the grape/wine metabolome?
  • 20.
    Metabolomic: what isand what is not How big is the metabolome? Sigma-Aldrich has ~55K commercial available chemicals Kegg contains 18K metabolites HMDB is based in ~42K metabolites Plant metabolome is estimated to cover 200K metabolites PubChem ID contains more than 10M entries CAS contains over 90M unique organic and inorganic chemicals ChemSpider contains over 57M compounds from 530 data sources
  • 21.
    Plant metabolome isestimated to cover 200 000 metabolites #ofmetabolites5-21% ethanol g/L mg/L µg/L ng/L pg/L fg/L How big is the metabolome? Wine Chemistry – Wine Composition
  • 22.
    #ofmetabolites5-21% ethanol g/L mg/L µg/L ng/L pg/L fg/L Plant metabolomeis estimated to cover 200 000 metabolites How big is the metabolome? Wine Chemistry – Wine Composition
  • 23.
    Wine Chemistry –Wine Composition #ofmetabolites g/L mg/L µg/L ng/L pg/L fg/L 95-79% water 5-21% ethanol 0-100 g/L sugars (glucose/fructose) 1-6 g/L tartaric acid 0-4 g/L malic acid 0-4 g/L lactic acid 0.5-1.5 g/L succinic acid 0.2-1.5 g/L acetic acid 4-15 g/L glycerol 0.1-10 g/L CO2 0.02-1.3 g/L argine glutamine, alanine, glutamic acid, proline, glycine, histidine arabinose, xylose, rhamnose Fe, Cu, B, Mn methanol, acetaldehyde, SO2 proteins thiamine, riboflavin, niacin, biotin, pantothenate and vitamin C phenolics polysaccharide
  • 24.
    Wine Chemistry –Wine Composition Waterhouse, Understanding wine chemistry, 2016
  • 25.
  • 26.
  • 27.
  • 28.
    Wine/Grape Chemistry –Phenolics – Classification according the skeleton C6 C6-C3 C6-C3-C6 O OH O OH C6-C2-C6 phenolic acids cinnamics acids stilbenoids flavanoids O OH OH O OH OH OH O OH OH OH OH OH OH OH O OH OH OH O OH OH O OH OH OH OH OH OH OH OH O OH OH OH O OH OH O OH O A C B 7 2 3 45 6 2' 8 3' 4' 5' 6' 2' : 2 prime (not apostrophe)
  • 29.
    Wine/Grape Chemistry –Phenolics – Phenolic acids shikimic acid O OH OH O OH OH OH O OH OH OH OH gallic acid UV-Vis spectrum nm250 300 350 400 450 500 550 270 nm nm250 300 350 400 450 500 550 280 nm • Wooden barrel • Non Vinifera • Hydrolysable tannins gallic acid O HO HO OH O HO O OH OH OH glucogallin
  • 30.
    Wine/Grape Chemistry –Phenolics - Cinnamates shikimic acid phenylalanine cinnamic acid coumaric acid coutaric acidfertaric acid caftaric acid caffeic acidferulic acid
  • 31.
    Wine/Grape Chemistry –Phenolics - Cinnamates coutaric acid Wine 15 mg/L
  • 32.
    Wine/Grape Chemistry –Phenolics - Cinnamates nm250 300 350 400 450 500 550 caffeic acid UV-Vis spectrum 324 nm
  • 33.
    fertaric acid Wine/Grape Chemistry– Phenolics - Cinnamates coutaric acid 4-vinyl phenol 4-vinyl guaicol 4-ethyl guaicol 4-ethyl phenol OH O O OH O OH OH O OH O O OH O OH OH O O CH3 OH CH2 O CH3 OH CH3 O CH3 OH CH3OH CH2
  • 34.
    Wine/Grape Chemistry –Phenolics - Flavonols shikimic acid phenylalanine cinnamic acid naringenin myricetinsyringetin quercetin keampferol isorhamnetin naringenin chalcone
  • 35.
    Wine/Grape Chemistry –Phenolics - Flavonols quercetin quercetin 3-rabinoside quercetin 3-glucuroside quercetin 3-galactose quercetin 3-rhamnosidequercetin 3-glucose
  • 36.
    Wine/Grape Chemistry –Phenolics - Flavonols Mattivi et al JAFC 2006 myricetin syringetin quercetin keampferol isorhamnetin
  • 37.
    Wine/Grape Chemistry –Phenolics - Flavonols Mattivi et al JAFC 2006 myricetin syringetin quercetin keampferol isorhamnetin
  • 38.
    Wine/Grape Chemistry –Phenolics - Flavonols UV-Vis spectrum
  • 39.
    Wine/Grape Chemistry –Phenolics - Anthocyanins shikimic acid phenylalanine cinnamic acid naringenin naringenin chalcone cyanidin delphinidin pelargonidin malvidin peonidin
  • 40.
    Wine/Grape Chemistry –Phenolics - Anthocyanins O + OH OH O OH O OO OH OH OH OH O O OH OH OH OH O + OH O OH O OO OH OH OH OH OH O + OH O OH O OO OH OH OH O O OH OH O + OH O OH O OO OH OH OH O O OH OH OH O + OH O OH O OO OH OH OH O O OH O + OH O OH O OH
  • 41.
    Wine Chemistry –Phenolics - Anthocyanins OH OOH OH OH OH OH O + OH O OH O OO OH OH OH OH O + O OH OH O O OH OH OH OH OH O OH O OH OH OH OH O + O OH OH O O OH OH OH OH O OH OH O OH OH OH OH O + OH OH O OH O OO OH OH OH OH
  • 42.
    Wine Chemistry –Phenolics - Anthocyanins O + OH OH O OH O OO OH OH OH OH O + O OH OH O O OH OH OH OH O O O + O OH OH O O OH OH OH OH O O OH O O + OH O OH O OO OH OH OH OH OH p-coumaric acid
  • 43.
    Wine/Grape Chemistry –Phenolics - Anthocyanins UV-Vis spectrum nm250 300 350 400 450 500 550 O OH HO OH OH OH cyanidin
  • 44.
    Wine Chemistry –Phenolics - Anthocyanins
  • 45.
    Wine Chemistry –Phenolics - Anthocyanins Bobeica et al Frontiers 2016
  • 46.
    Mattivi et alJAFC 2006 cyanidin delphinidin pelargonidin malvidin petunidin Wine/Grape Chemistry – Phenolics - Anthocyanins
  • 47.
    Wine/Grape Chemistry –Phenolics - Anthocyanins O + O OH OH OH O O OH OH OH OH O O + OH OH OH OH O O OH OH OH OH OH O + O OH OH OH O O OH OH OH OH O + OH OH OH OH O O OH OH OH OH O + O OH OH OH O O OH OH OH OH OH + + +
  • 48.
    Wine/Grape Chemistry –Phenolics - Flavanols cyanidin delphinidin pelargonidin OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OOH OH OH OH + + + epicatechin catechin epigallocatechin gallocatechin epiafzelechin afzelechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate
  • 49.
    Wine/Grape Chemistry –Phenolics – Flavanols (dimers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OH OOH OH OH OH OH OOH OH O OH OH OH OH O OH OH OH OOH OH OH OH OH OOH OH O OH OH O OH OH OH OOH OH OH OH OH OOH OH O OH OH OH O OH OH OH
  • 50.
    Wine/Grape Chemistry –Phenolics – Flavanols (oligomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
  • 51.
    Wine/Grape Chemistry –Phenolics – Flavanols (oligomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
  • 52.
    Wine/Grape Chemistry –Phenolics – Flavanols (polyomers) (epi)catechin epigallocatechin OOH OH O OH O OH OH OH OH OOH OH O OH O OH OH OH OH OH (epi)catechin-gallate (epi)gallocatechin-gallate OOH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH O OH OH OH OH O OH OH OH
  • 53.
    Wine Chemistry –Phenolics – Flavanols (astringent and bitter taste) OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OH epicatechin catechin gallocatechin OOH OH O OH O OH OH OH OH (epi)catechin-gallate epicatechin is more bitter than catechin OOH OH OH OH OH catechin The galloyl-ation increase the astringency Cheynier et al. ACS Symposium 1997
  • 54.
    Wine Chemistry –Phenolics – Flavanols (astringent and bitter taste) Polymerization decrease bitterness (dimers, trimers and tetramers are more bitter than astringent) polymerization slightly increase the astringency (high degree or polymerization may decrease astringency) (the maximum is reached ~ 8 units) Cheynier et al. ACS Symposium 1997 OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH OOH OH OH OH OH
  • 55.
    Wine/Grape Chemistry –Phenolics – Flavanols (degree of polymerization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ean degree of polymerization = mDP O OH OH OH OH OH
  • 56.
    Wine Chemistry –Sugars/Carbohydrates O OH OH OH OH OH O OH OH OH OH OH glucose O OH OH OH OH OH fructose O OH OH OH OH arabinose OH OH OH OH OH OH OH OH OH O OH OH OH OH OH O α β glucuronic acid glycerol inositol 1 2 3 4 5 6
  • 57.
    Wine Chemistry –Amines O NH2 OH O NH2 NH OH O NH2 OH O NH2 OH tryptophan phenylalanineleucine isoleucinealanine N H O NH2 NH2 NH2 OH NH2 N N O 3-Isobutyl-2-methoxypyrazine indole putrescine tyramine2-aminoacetophenone N O 2-acetylpyrroline O NH2 OH
  • 58.
    Wine Chemistry –Tryptophan metabolites OH NH2 N H O O NH2 OH O OH N H OH O OH N H OH N H TOL N OH O OH N H O NH O N H OH NH2 shikimic OH OH OH OOH OOH NH2 O NH2 O O N H OH O OH OH OH OH OH O OH OH OH OH OH O OH OH OH OH OH O NH N H O O O NH2 N H O epicatechin procyanidin B2 phenylalanine tryptophan melatoninserotonin tryptophan ethyl ester N-acetyl-tryptophan ethyl ester kynurenic anthranillic kynurenine indole-3-pyruvic acid indole-3-lactic acid indole-3-acetic acid tryptophol 2-aminoacetophenone OOH NH2 anthranillic
  • 59.
    Wine Chemistry exercise Design 1.glucose 2. alanine 3. phenylalanine 4. p-coumaric acid 5. catechin
  • 60.
    Wine Chemistry Design 1.glucose 2. alanine 3. phenylalanine 4. p-coumaric acid 5. catechin OOH OH OH OH OH O NH2 OH O OH OH OH OH OH O NH2 OH
  • 61.
    Grape Sensorial analysis:grape What is the odor of a grape berry? Inspired by Il respire del vino of L. Moio
  • 62.
    Grape Sensorial analysis:grape Aromatic grape Moscato, Gewϋrztraminer Wine smell as the grape Non-aromatic grape a) silenced and b) not-silenced Sauvignon blanc Must non-aromatic, wine aromatic
  • 63.
    Grape Sensorial analysis:grape aromatic part aromatic part sugar O OOH OH OH OH OH enzymatic or chemical hydrolysis
  • 64.
    Grape aromatic compounds:terpenoids Isoprene Hydrocarbon 5 x Carbons 2 x Isoprene Monoterpenes 10 x Carbons 3 x Isoprene Sesquiterpene 15 x Carbons 4 x Isoprene Diterpenes 20 x Carbons 5 x Isoprene Sesteterpenes 25 x Carbons 6 x Isoprene Triterpenes 30 x Carbons Terpene + Oxygen or Nitrogen = terpenoids
  • 65.
  • 66.
    Grape aromatic compounds:volatiles thiols O SH OH SH O SHO 4-mercapto-4-methylpentan-2-one 4MMP 3-mercaptohexan-1-ol 3MH 3-mercaptohexyl-acetate 3MHA
  • 67.
    Grape aromatic compounds:volatiles thiols
  • 68.
    OH S O NH2 OH Grape aromatic compounds:volatiles thiols aromatic part cysteine
  • 69.
  • 70.
    O Grape aromatic compounds:norisoprenoids megastigmane non-megastigmane TDNβ-damascenone vitispirane O β-ionone
  • 71.
    Grape aromatic compounds:norisoprenoids Time Quantity carotenoids more sun Veraison Maturity Over maturity
  • 72.
    Grape aromatic compounds:methoxypyrazine N N R
  • 73.
    Grape Sensorial analysis:must Aromatic grape Moscato, Gewϋrztraminer continuity
  • 74.
    Grape Sensorial analysis:must O 1-hexanol OH OH OH OO Non-aromatic grape (but aromatic in taste) 1-hexanal 3-trans-hexan-1-ol 3-trans-hexan-1-al 3-cis-hexan-1-ol 3-cis-hexan-1-al
  • 75.
    Grape Sensorial analysis:must O 1-hexanol OH OH OH OO 1-hexanal 3-trans-hexan-1-ol 3-trans-hexan-1-al 3-cis-hexan-1-ol 3-cis-hexan-1-al O OH O OH linoleic acid linolenic acid
  • 76.
    Grape Sensorial analysis:must Cabernet Sauvignon, Sauvignon blanc, Cabernet Franc, Merlot N N R • Amplification of herd odor • Not mature grapes
  • 77.
    Grape Sensorial analysis:must White grapes: Honey, dry fruits, chamomile Red grapes: comfiture of red berries
  • 78.
    Grape Sensorial analysis:alcoholic fermentation OH O O O OH OH OH OH OH O O OH O glucose pyruvic acid acetaldehyde ethanol
  • 79.
    O NH2 OH O NH2 R OH O O R OH O R OH R O NH2 NH OH O NH2 OH O NH2 OH Must sensorial analysis:alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine O NH2 OH
  • 80.
    O NH2 OH O NH2 R OH OH R O NH2 OH O NH2 OH Must sensorial analysis:alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine O NH2 NH OH O NH2 OH
  • 81.
    OH O NH2 OH O NH2 NH OH OH NH O NH2 OH O NH2 OH OH OH Must sensorial analysis:alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine OH phenyl-ethanol ethanol 3-methyl-butanol tryptophol2-methyl-butanol 4-197 mg/L 6-490 mg/L 2-150 mg/L 2-30 mg/L O NH2 OH
  • 82.
    O NH2 OH O NH2 NH OH OH NH O NH2 OH O NH2 OH OH OH Must sensorial analysis:alcoholic fermentation / Ehrlich reaction tryptophanphenylalanine leucine isoleucinealanine OH phenyl-ethanol ethanol 3-methyl-butanol tryptophol2-methyl-butanol amino acid in must ft Cultivar Maturity Viticulture practices Turbidity O NH2 OH OH
  • 83.
    OH OH Must sensorial analysis:alcoholic fermentation / Ehrlich reaction phenyl-ethanol 3-methyl-butanol 2-methyl-butanol volatiles threshold 300 mg/L Adolf and Versini, 1999 OH
  • 84.
    Must sensorial analysis:alcoholic fermentation OH O O O OH OH OH OH OH O O OH O glucose pyruvic acid acetaldehyde ethanol O OH acetic acid
  • 85.
    Must sensorial analysis:alcoholic fermentation O OH acetic acid OH O OH O OH O OH O OH O 2-methylpropanoic acid 3-methylbutanoic octanoic acid acid (caprilic acid) Hexanoic acid (capronic acid) butanoic acid (butyric acid) OH Odecanoic acid acid (caprinic acid)
  • 86.
    Must sensorial analysis:alcoholic fermentation / half time OH O OH O OH O OH O 3-methylbutanoic octanoic acid acid (caprilic acid) Hexanoic acid (capronic acid) butanoic acid (butyric acid) O O O O O O O O isoamyl acetate ethyl butanoate ethyl hexanoate ethyl octanoate
  • 87.
    Wine sensorial analysis:the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
  • 88.
    Wine sensorial analysis:the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
  • 89.
    Wine sensorial analysis:the first battle O O O O O O ethyl butanoate ethyl hexanoate ethyl octanoate O O isoamyl acetate OH OH phenyl-ethanol 3-methyl-butanol 2-methyl-butanol superior alcohol versus esters OH
  • 90.
  • 91.
    Wine sensorial analysis:aging Time ethyl esters Alcohols superior Phase I Phase II Phase III
  • 92.
    Wine sensorial analysis:barrel aging Time Fermentation barrique aromatic or non-aromatic silenced cultivar
  • 93.
    Wine sensorial analysis:barrel aging Time Fermentation barrique non-aromatic cultivar
  • 94.
  • 95.
    Wine Chemistry Design 1.linalool 2. pheyl-ethanol 3. isoamyl acetate 4 3-mercaptohexan-1-ol 5. β-damascenone linalool OH OH SH 3-mercaptohexan-1-ol 3MH phenyl-ethanol O O isoamyl acetate O β-damascenone OH