Grapes vinifera : Vitis Vitis Vitis vinifera Vitis: non non- - PDF document

22/07/54 Oral Presentation CRDC 5 Grapes vinifera : Vitis • Vitis Vitis vinifera Vitis: • non non- -climacteric climacteric fruit fruit • botanically a true botanically a true berry berry • woody climbing vine woody climbing vine warm, summer, cold • grows in grows in warm, summer, cold 1

22/07/54 Oral Presentation CRDC 5 Nutritional value of Grapes 100 g Nutritional value Content Nutritional value Content Carbohydrate Carbohydrate (mg.) (mg.) Vitamin C Vitamin C Carbohydrates 18100 Vitamin C 10.8 - Sugars sucrose> Vitamin Vitamin K Vitamin K 0.022 0.022 glucose> fructose K Calcium 10 - Dietary fiber Minerals Iron 0.36 Fat 160 Protein Protein Protein 720 Magnesium 7 Vitamin B anthocyanin Thiamine (Vitamin B1) 0.069 Manganese 0.071 Rib fl Riboflavin (VitaminB2) i (Vit i B2) 0 07 0.07 Phosphorus 20 Niacin (VitaminB3) 0.188 Potassium 191 Pantothenic acid 0.05 Phenolic compound (VitaminB5) Sodium 3.02 Vitamin B6 0.086 Zinc 0.07 resveratrol Folate(VitaminB9) 0.002 Phytochemicals or phytonutrients A phytochemical is a natural bioactive compound found in plant foods that works with nutrients and dietary found in plant foods that works with nutrients and dietary fiber to protect against diseases . color Smell Other : phytosynthesis, Other : phytosynthesis, Flavor respiration, growth and Antioxidant development Enzyme activation Self defensive 2

22/07/54 Oral Presentation CRDC 5 Phytochemicals Primary metabolite Secondary metabolite Essential Oil Carbohydrate Resins and Balsums Lipids Alkaloids Proteins P i Glycosides Phenolic compounds Phenolic compounds > 8000 type Phenolic compounds are naturally occurring secondary phytochemicals. Phenolic compounds are secondary metabolites that are derivatives of the pentose phophate, shikimate, and phenylpropanoid pathways in plant. The term ‘phenolic’ is used to define substances that possess one or more hydroxy (OH) substituents bonded onto an aromatic ring. Marinova et al.,2005, Balasundram et al.,2006 3

22/07/54 Oral Presentation CRDC 5 photosynthesis 7 groups of phenolic compounds 1. Flavonoids (polyphenols): anthocyanins, isoflavones,catechins, Quercetin Quercetin, , myricetin myricetin, , apigenin apigenin , , lueteolin , kaempferol kaempferol, isorhamnetin isorhamnetin lueteolin, catechins Isoflavones ( ถั�วเหลือง ) anthocyanins apigenin apigenin myricetin myricetin Quercetin Quercetin rutin rutin kaempferol kaempferol lueteolin lueteolin 4

22/07/54 Oral Presentation CRDC 5 2. Phenolic acids: gallic acid, tannic acids, vanillin, neochlorogenic neochlorogenic acid acid, p -coumaric coumaric acid acid gallic acid ( มะม่วง ชา ) tannic acids ( ชา เบอร์รี� ) Vanillin ( วะนิลา ) p ‐ coumaric acid coumaric acid neochlorogenic acid neochlorogenic acid 3. Hydroxycinnamic acid: caffeic acid, ferulic acid chlorogenic acid caffeic acid ( แอปเปิล ) ferulic acid ( ส้ม สับปะรด ) chlorogenic acid ( กาแฟ สตรอเบอรี� ) 5

22/07/54 Oral Presentation CRDC 5 4. . Lignans Lignans: : pinoresinol pinoresinol pinoresinol ( เมล็ดงา ) 5. Tannins: condensed tannins . Tannins: condensed tannins ( ชา ) Gallic acid Flavone 6 Q i 6. Quinones, . Quinones, benzophenones Q i b b benzophenones : h h : xanthones xanthones ( th th ( มังคุด ) 7. Others: . Others: monophenol monophenol, , tyrosol tyrosol ester, ester, stilbenoids stilbenoids, , punicalagins punicalagins stilbenoids stilbenoids resveratrol glucopyranoside 6

22/07/54 Oral Presentation CRDC 5 Phenolic compound in grapes Skin Skin seed seed d anthocyanins catechin quercetin epicatechin rutin myricetin ellagic acid ll i id kaempferol resveratrol resveratrol Catechin Catechin is a polyphenolic antioxidant plant secondary metabolite. The term catechins is also commonly secondary metabolite. The term catechins is also commonly used to refer to the related family of flavonoids and the subgroup flavan-3-ols (or simply flavanols). (+)- catechin (-)- catechin http :// en . wikipedia . org / wiki / Catechin#Chemistry 7

22/07/54 Oral Presentation CRDC 5 Epicatechin Epicatechin is a polyphenolic antioxidant plant secondary metabolite . Epicatechin can be found in cacao beans. The different other enantiomers can as well be found in chocolate. (+)- epicatechin (-)- epicatechin http :// en . wikipedia . org / wiki / Catechin#Chemistry Related research Phenolic content (mg/100 g DM) Variety/clone Seeds Catechin Epicatechin AP SG1 96.9+5.9 d 106.8+1.6 d F 9 74.4+0.9 e 98.4+9.9 de ISV 2 72.9+7.0 e 88.0+0.7 e ISV RC1 60.3+8.3 e 67.9+6.2 f Merlot 138.8+0.4 bc 131.8+9.7 c Cabernet Sauv. 141.8+7.9 b 127.6+4.4 c Canaiolo 140.7+2.2 bc 205.7+3.1 a Colorino V.no 124.4+0.1 c 89.0+8.6 e Foglia Tonda 67.4+5.1 e 47.2+3.5 g Montepulciano 205.7+19.0 a 164.6+16.8 b Iacopini และคณะ , 2008 8

22/07/54 Oral Presentation CRDC 5 Related research years Sample Variables Influence on Entire dried seeds from Alonso et red grape marc after Water content in ethanol: 5–40–60–80% Yield of catechins and al. 1991 vinification Extraction time (without stirring): 3–6–12 h proanthocyanidins Entire dried seeds from Pekic et white grape marc after Water content in ethyl acetate: 3.3–5–10– al. 1998 pressing 15–20% Extraction time 1–12–24 h Yield of proanthocyanidins Manzano et al. 2004 grape seed and skin 80% ethanol Extraction time 1-5 h Yield of flavan-3-ols Solvent: ethanol, methanol, water Solvent/solid ratio: 1–3–5 (v/w) Yield of total phenols, Pinelo et Dried red and white Extraction time: 30–60–90 min Extraction concentration andantioxidant al 2005grape marc temperature: 25–37.5–50 ˚ C activity of extract Iacopini et ethanol:water:hydrochloric acid Yield of catechins and al. 2008grape seed and skin 0.12M(70:29:1 v/v/v) f: 4 h epicatechin Resveratrol • Resveratrol is a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi. • Resveratrol is found in the skin of red grapes and is a constituent of red wine 9

22/07/54 Oral Presentation CRDC 5 Structure Structure B A Content of Resveratrol and Piceid Isomers in Grape Berry Skins Extracted in Ethanol 80% at 60 ° C during 30 min Romero ‐ Perez, 2001 10

ั 22/07/54 Oral Presentation CRDC 5 Related research years Sample Variables Influence on five extraction solvents were tested: Romero- grape berries selected ethanol/water(80:20 v/v), ethanol 100%, ethyl Resveratrol and Perez et were from the Carinena acetate/methanol (50:50 v/v),acetone/water (75:25 Piceid Isomers in al. l 2001red variety 2001 d i t v/v), and acetone 100%. at 60 °C for 30 min / ) d t 100% t 60 °C f 30 i G Grape Berry Skins B Ski grapes of the Viura (white) and Tempranillo Determination of Pineiro et (red)varieties cultivated Solvent: methanol different temperatures 50, 100, trans-resveratrol in al. 2006 in Jerez (Spain) 150 ˚ C grapes Yield of total Spigno Dried powdered red Solvent: 90% ethylacetate–ethanol Faveri phenols, resveratrol and De g p grape marc (after ( Extraction time: 5–24 hExtraction temperature: 28– p and antioxidant Faveri 2007 vinification) and stems 60 ˚ C activity of extract Iacopini ethanol:water:hydrochloric acid 0.12M(70:29:1 v/v/v) et al. 2008grape seed and skin f: 4 h Yield of resveratrol Related research Marti และ สกัด resveratrol จาก grape skin Final extraction conditions were:40°C, 150 bar, คณะ 2001 ( Vitis vinifera ) 7.5% ethanol and extraction time 15 min. สกัด phenolic จาก Baccharis Piantino temperatures of 40, 50 and 60 ◦ C and pressures และคณะ 2008 of 20, 30 and 40MPa. dracunculifolia สกัด phenolic จาก roasted Gelmez pressure (148–602 bar), temperature (40–60 ◦ C) และคณะ 2009 wheat germ and time (10–60 min) สกัด resveratrol จาก Japanese Benova pressure 25–40 Mpa , temperature 50–110 ◦ C และคณะ 2010 knotweed and extraction time 5–60 min Casas และ สกัด resveratrol จาก Palomino fino pressure 100, 400 bar, temperature 35, 55 ◦ C คณะ 2010 grapes addition of modifier (5% v/v of ethanol) Castro ‐ co ‐ solvents:ethyl acetate (EtAc)and ethanol สกัด phenolic จาก guava seeds Vargas (EtOH) conditions, using 10, 20 and 30MPa and และคณะ 2010 ( Psidium guajava L.) 40,50 and 60 ◦ C. 11