Grape and Wine Fenolics - Observations and Recient Findings

8/22/2019 Grape and Wine Fenolics - Observations and Recient Findings

1/14

revision de literatura

Cien. Inv. Agr. 35(2): 107-120. 2008

www.rcia.puc.cl

Introduction

W phc mp qycmp h cb h c, ,

f f w. ahgh phc cmpf w c g fm mcb k c, h mjy f h phcc f w gp-.i wh w, h m mp phccmp h hyxycmc c of minor quantities, the avan-3-ol monomers.

th cmp mp wh g h qy f wh w.

i w, hcy h m mp phc c. tcb h mhf f w b hy fm pgm pym cwh h hcy p h bpgm q g w g-m c by.

Wmk hy hmpc f gp w phc w qy, y cgy, c

gp w phc chmy h

made it difcult to remain current in our

g. th cmpx f myrecent ndings has also made it at times difcult

ppy h cc wy h c b

pccy. th w mmy f c f g h whan emphasis on recent ndings.

Grape phenolics

Compounds and distribution. th mj phccmp fm w qy ppc h hyxycmc c, hcy, (syn: phcy ctannins) (Ribreau-Gayon, 1965-1963, 1959,

Figures 1-3). The identication of these

cmp h b ccmph hb h gp by h b wcm (Fg 4).

Biosynthesis, accumulation and management.th byh f gp phc h b bjc f g cy (Bget al., 2007, 2005; dx et al., 2005; X et al.,2003; Winkel-Shirley, 2001; Boss et al., 1996).

th byh f h phc cmph mp w qy h cmm phwy (Fg 5). Wh my fthe genes in this pathway have been identied,

p f m pc. i pc,

Grape and wine phenolics: Observations and recent ndings

Jm a. Ky1dpm f F scc tchgy

Oregon State University, Corvallis, OR 97331, USA

Abstract

J.A. Kennedy. 2008. Grape and wine phenolics: Observations and recent fndings. Cien.

Inv. Agr. 35(2):107-120. Wh cm w h cm f mgmpcc fm h y h g. a ch, h c hcmp f w h m f cmp, mp hw pcpcc ffc w chmy. Bc phc cmp mp h

qy f w, hy h bjc f g hgh h w. th wis a summary of current knowledge and some recent ndings that have taken place in this

.

Key words: ahcy, phcy, w, , Vitis vinifera.

Received 16 October 2007. Accepted 21 April 2008.1 Corresponding author: [email protected]


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108 CienCia e investiGaCion aGraria

O+

OH

HO

OH

R 2

R 1

OH

O H

H

OH

H

H

HO

H

O R 3

A

B

C

1

3

5

7 6'

4'2'

1' 4'

OH

O

O OH

OHO

OO

O

Acetate ester Coumarate ester Caeoate ester

R3= OH or or or

phcy pc p cmpy (dx et al., 2005).dp h, c c h b mwh g h fc h g g (Bg et al., 2007).

th cc f gp phc chgh by pm. Bgg f wh xp wgh b, hyxycmc c c (dwy et al., 2003; Kennedyet al., 2001, 2000; d F et al., 2000;rmy et al., 1983). Beginning at vraison,hcy ccm h by c g f pg. th c

h gg h hcy c c by pm (Ky et al., 2002).

i ccp h phc cmp mp h qy f w hf cb m f ch h bc w h g f hwvineyard management practices inuence their

cc gp.Figure 1. Hyxycmc c f Vitis vinifera.

Figure 2. ahcy f Vitis vinifera.

r3 b:

O

OR3

R2

HO

R1

Hyxycmc ac r1 r2

p-cmc H Hcffc oH Hfc oCH3 Hpc oCH3 oCH3

O

HO

O

OH

OH

OH

tartaric acid

r3 esterication

ahcy My r1 r2

cy oH Hp oCH3 Hph oH oHp oCH3 oHm oCH3 oCH3


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109VOL 35 N2 MAYO - AGOSTO 2008

i w bh h phc y whg (C et al., 2007, b; P r Ky, 2006; dwy et al., 2003;rb-Gy, 1972), fhm, hh c pcc m

h pg f c ffc cmp(P-n et al., 2007; sm et al., 1988).Fruit exposure inuences phenolic production in

h gp (C Ky, 2006; dwyet al., 2004; Bgq et al., 2001; dkz

Figure 3. Flavan-3-ols found in grapes with an oligomer shown with various interavonoid bonds as well as anthocyanin

hy mfc.

Figure 4. db wh h gp by f cmp mp w qy.

Flavan-3-ol Monomer

(+)-catechin

(-)-epicatechin

(-)-epigallocatechin

(-)-epicatechin-3-0-gallate

R2

H

H

OH

H

OH

OH

OH

R1

OH

OH

OH

O

O

OH

HOOH

OH

O

R2

R1

OH

OMe

OMeO

O

O

O

OO

OH

OH

OH

OH

OH

OH

HO

OH

HO

HO

HO

HO

HO

HO

HO

HO

HO

HO

HO

HO

HO HO

HO

OH

OH

OHOH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OH

OHOH

OH

OH

OH

OH

OH

OH

OHOH

HO

HO

HO

OH

OH

OH

OH

OH

OGlc

OMe

OGlc

O

O

O

O

O

O

O

O

O

OMe

OH

Skin

Anthocyanins

Proanthocyanidins

Flavor compounds

Pulp

Water

Organic acids

Sugars

Flavor compounds

Seed

Proanthocyanidins

Coombe, 1987

1 mm


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Kw, 1996; Pc et al., 1995; G Ch, 1994; Kw t, 1972;Kw, 1977). rch cy by spy etal. h hw h xp ffc c b mp gh ffc (spy et al.,2002). It is logical that the observed ndings

fm cmmy b pcc ymgm c b p fm chg h xp gh/mp m h f (C et al., 2005; Kyet al., 2002, 2000; oj et al., 2002; Met al., 2001).

Phenolic extraction during wine production

oc gp h phc cmp h w bcm p p pcg h wy. Wh h xcp f pp- hyxycmc c, phc fm h k mk ph mjy f h phc p p w, wh m- phc mkg m cmp f c. dmg h qy f phc cmp hf wmk c.

Bc hcy cz h k f m gp c, fm mc h pf ffc hamount of anthocyanin present in the nal

w. a xm xmp f h w b hp f h p f h gp byfm h jc wh kw mcg w wh c.spkg w m fm c. P gp xmp f hw c cb xc.

Cy, bc f h cz fhcy wh p c c,ff b c. dff mpy h pc by whch cmp mfm g f hgh cc w g f w cc (..: fm h pc h w). Cg h gyb xc c f hcy(rb-Gy Mh, 1970; rb-

Gy et al., 1970) h ffc h wpcg b h h f hcmp xc, h pc gy c wh ff. dff p p h fwg: 1. tmp,

2. Mc wgh/z yp f mc,3. Concentration gradient, 4. Cell permeability,

5. sfc h cc g, 6. Cmp f xc mm (ch h cc).

i c b mc z, hb cb py h fff. tm, f c, mpb f xc.

P ch h hw h y gfm, m mp h wcc b mg h mm f hcy p w (a

Ky, 2007; Zmm et al., 2002; Kcet al., 1992; My et al., 1994; scm-smh et al., 1990; ab Px, 1969;ogh am, 1961; Bg akyh,1956). F hcy, hgh mpc h m mxmm cc, c h mxm m. B hm b b f m mp,h h b by py hcy xc. dmg hrelative importance, however, is difcult because

f h cmp f h ffc.

Wh g , h ff b cb b,wmk h g pfc whg h g f h : k . i gy hgh h k- p h h f h , f m p w pf, hk . o xp fh mpm qy wh pc f my h h c h pp f k- . ug cy p yc mh (Pydes Gachons, and Kennedy, 2003), Pastor del

r Ky (2006) f h w mfm cgy m gp c h pp f -. th b c whg w y xp f qy mpm.

a ch gg hw h c h pp f k ( m) p m xp fw qy mpm (C et


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Proanthocyanidin

O

O

OH

OH

OH

OH

OH

OH

OH

OH

OH

HO

HO

O

OH

OH

OHHO

procyanidin

O

HO HO

Ocinnamic acid

C4H

PAL

phenylalanine

HO

NH2

HO

C3H

OH

OH

OH

Ocaeic acid

p-coumaric acid

OH

OH OH

OH

OHO

O

O

O

HO

CHS HO

caftaric acid

StSy

naringenin chalcone

CHI

OH

OH O

HO

OH

HO O

OOH

resveratrol

naringenin

OH

OH

F3H

F35H

OHO

O

F3H

OH

OH

OH

OH

OHOH

HO O

leucocyanidin

eriodictyol

OH

OH

OH

OHOH

OH

OHO

DFR

dihydroquercetin

O

O

O

OH

OH

OH

OH

OHO

O

FLS

OH

OH

OH

OH

OH

HO

HO

OH

OH

OH

UFGT

quercetin

quercetin-3-glucoside

OGlc

peonidin-3-glucoside

OH

OH3

OGlc

OGlc

OH

OH

HO

HO

OH UFGT

cyanidin-3-glucoside

MT

O+

O+

cyanidin

O+HO

OH

OH

OH

(-)-epicatechin

ANR

LDOX

OH

OHO

OH

OHLAR

(+)-catechin

OHO

OH

OH

Abbreviations:ANR - anthocyanidin reductaseCH - p-coumarata- 3-hydroxylaseC$H - cinnamate-4-hydroxylaseCHI - chalcone isomeraseCHS - chalcone synthaseDFR - dihydroavonol-4 -reductaseF3H - avonone-3-hydrox ylaseF3H - avonoid-3- hydroxylaseF35H - avono id-3, 5-hydroxyla seFLS - avonol synthaseLAR - leucoanthocyanidin reductaseLDOX - leucoanthocyanidin dioxygenaseMT - methyl transferasePAL - phenylalanine ammonia lyaseStSy - stilbene synthaseUFGT - UDP glucose: avonoid-3-O -glucosyl transferase

Flavan-3-ol Monomer

Flavan-3-ol Polymerization(Biochemical Process Remains Speculative)

Flavan-3-ol Monomer

3 malonyl-CoA

Hydroxycinnamic Acid

Stilbene

Trihydroxylated

B-ring

Flavonoids

Flavonol

Anthocyanin

al., 2005). G h b, ph c cg h my c k pp, mpm qy h bb wh c h ppf k f w. sk gy xc y fm h mc m c, h whch xc c(Peyrot des Gachons and Kennedy, 2003).

t xc w c hghfm (rb-Gy et al., 1970) hf, m p mh p h w. th ck fm wmkg ppc w b pmz y h qy f xc, b

h pp f k .

In the nal wine, the skin and seed tannin

pp gy ff h hf h by (Fg 6). i

gp my mc m, c h y (C Ky, 2006;C et al., 2005) h g f bychg (pbh ) h b fto inuence the proportion of skin and seed

w. ug h cqcf m cmp fm pcp p h g m ky g h b g f mgg w qy bh h y hwy.

th mb c h chmc(Fg 6) b p c xpmcc c. P n. Gp xc h f h k

, m p f h qy f f h gp xc g w pc. Fy,h mc f h xc f k .

Figure 5. Phypp byhc phwy f h mj phc c f w.


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Grape

tannin

Wine

tannin

89%in SeedTissue

11%in SkinTissue

6%of SeedTannin

Extracted

29%of SkinTannin

Extracted9%

Extracted DuringMaceration

36%From Skin

Tissue

64%From Seed

Tissue

Figure 6. schmc p f k xc g mc.

Wine aging

oc w p, h cc fgp phc mxm, cg hf(ng Wf, 1979). i wh w, gg

fm gh w-c w m py yw c (sg Kmg, 1976). i w, h b- c hcy fm bck- pgm. th ph f w c c b q p p hbg y gp- hcymg. i h pc f w ch h fc w c f w cy.

i gy cgz w hgrape-derived anthocyanins become modied

wh h cmp f w. orecently identied example of a modied

hcy cmb h y mbpyc c wh hcy fm a(Fc et al., 1998; Bkk tmbk,1997). v a fm y f fmh cmp (schwz et al., 2003) and hash fm bck- c f w

pp w w whch m bybp 520 m.

a w g, xp xyg h ffc f x (Wh

l, 2006). a pc f w x h, whch x pc fh x (W sg,1974). ec f h cp w phc pym h b cy

b c wh g ppf h phc pym (dk et al.,2007, b). i h b b f m mthat ethanal formation leads to a modication of

w c (Bkk tmbk, 1997;tmbk B, 1976; t, 1908-c).

th fm f h pyhcyin wine has subsequently led to the identication

f h c cph cghydroxycinnamic acids and ethanal-avan-3-

c pc (H et al., 2006; Met al., 2004, 2003; Benabdeljalil et al., 2000,Fg 7). i h mc c, c wk h hwh h x f w c hx f gyc gychy, hcphc pc (l Wh,2006, b).

th bgg chg f w c

chczg h g mc wghpgm m p w.sm m g, c w ppf pgm pym bc fh pc f phcy, h


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w pc hcy phcy (rb-Gy et al.,1983; Haslam, 1980; Somers, 1971; Jurd, 1969,

1967, b). th cccy f h pchas been conrmed (Salas et al., 2004; v-Q et al., 2002; rmy et al., 2000; e-Sa et al., 1999, Fg 8), h chmyh b x hgh mc wghmaterial (Hayasaka and Kennedy, 2003). It is

g h pgm pymbg fm y w f (eget al., 2004).

Sensory properties of phenolics

th cmpxy f phc pcp pp wh y z h w phc

c b by gh, m, , ch.of h, gp phc gy g - hf hy c bm. ahcy hyxycmcc m b p h

component in wines. Flavan-3-ol monomers

b h h . th phcy g, bcf h cmpx pcp, m c f

h fw.

t cmp h m bg by b hb fg. t ccmph h bcf h by b gy p(Hm, 1998). Bgh bck w, gy c h w b h f bc h bg pcpg y p. t p mpy, g, by g

(Gw, 1998; nb, 1994). agcy c hf, wfeel . thg h cmm m cb w: mhf.

By gcy, c pb, whch bgh b by h w mc wgh (Khk et al., 1997; rbch nb, 1990; a et al., 1980). i gyc h mch b w

b b p h c h w mc wgh bg by m, h my p c xp f why qymp wh f my.

Cg pcp , hgcy f h c mppc h pcp (ihkw nb,1995). Wh w h xc qyf , h gcy f h w cg by h f h cmp. thpc gy hgh f bgb.

ahgh b gcy f w, cp h f pc g. i, wmk cb m h pbqy fm. sy c chm h p cb m f

m yg h m bpc f pcp (Fz etal., 2007; lch nb, 2005; vet al., 2004a, 2003; Gawel et al., 2001, 2000;Chy et al., 1998).

Figure 7. Examples of malvidin-3-O-glucoside-basedpyranoanthocyanins that have been identied in red wine.

O+

O

HO

OH

OMe

OMe

OGlc

O+

O

HO

OH

OMe

OMe

OGlc

CO2H

O+

O

HO

OH

OMe

OMe

OGlc

OH

OH

O+

O

HO

OH

OMe

OMe

OGlc

OH

O

OH

OH

OH

HO

R

O+

O

HO

OH

OMe

OMe

OGlc

OH

O

OH

OH

OH

HO

R

vitisin A vitisin B

pinotin A ethyl-avan-3-ol adduct

portisin


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OHO

OH

OH

OH

OH

OHO

OH

OH

OH

OH

O+HO

OH

OGlc

OH

OMe

OMe

OHO

OH

OGlc

OH

OMe

OHO

OH

OH

OH

OH

OHO

OH

OH

OH

OH

OMe

OHO

OH

OGlc

OH

OMe

OO

OH

OH

OH

OH

OHO

OH

OH

OH

OH

OMe

OHO

OH

OH

OH

OH

OHO

OH

OH

OH

OH

O OH

OH

GlcO

HO

MeO

OMe

T-A type Trimer

A-T type Trimer

Bicyclic form Ethyl-bridged Trimer

Figure 8. Examples of malvidin-3-O-glucoside proanthocyanidin derivatives.

Fm h g, c h hpcp f gcy w c binuenced by many components in wine

cg h (Fch nb, 1994),cy (Pg et al., 1998; Fch nb,1994), cy (smh et al., 1996), mpg (B et al., 2004), pycch(v et al., 2004b; r et al., 2001) hcy (v et al., 2004b). icgyh bg p h wyh h mpc pcp (dCm-ly et al., 2006). It is difcult

to convey how difcult these studies are tocc bc f h hmp gcy b (Fchet al., 1994). M, h cmpx cbw h mcmc

f w (d F et al., 2003; Riouet al., 2001; sc et al., 1997, b) ch fy g h f pcp w c b chgg f ch.

Php g wy f ccpzg pcp h hp bw cp gp cmp hkabout how different grape components inuence

pcp f (Fg 9). H c bc wh h g

pycch. a wmk, h g bc h cmp w.iy, wh pck y, w w h cy h xc cywith a deciency in polysaccharides, sugar and


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h. a h f bcm m m, hcmp bcm m bc hcp bcm m p. a wmkh h by m w cp byadjusting the balance accordingly. The gure as

pc wh ch pcp.

Fm h ch gh , cgh byh f h pm f h by, h pc h mgg h chg h gp cc h m h k y pg gp pcpcc. M, h chg h cc

g by m (Ky, 2002) h xpc changes that positively inuence the quality of

.

th c pg gp wphc ch my wy w p hcg pm f yc chmy.th c pg g cy mch b yc c.a pg yc chmy

h b m cy xcg

h bg c w mkgyc fm y cq p(Fz ag, 2007; Mc et al.,2007; Czz et al., 2006). th cw ky mpm gp w phc mgm.

Resumen

l q cm pb cmc pcc mj q p y ccy cp. Cmg, p c b cmpc mm cm, mp cmp cm fc

pcc mj cmpc qmc . db q cmp fctienen tal importancia sobre la calidad nal del

, cmp h bj gc m. e m ccmc y g cbm cq h c .

Palabras clave: ac, p-c, , , Vitis

vinifera.

Figure 9. schmc p f h cp f b p w cmp.

Component

Physiological

Response

Wine

Descriptor

EthanolSugar

PolysaccharidesTanninAcid

BodySweetness

FatThick

BitternessAstringencySourness

Silky

Velvety

Ripe

Hard

Green

Coarse

Unripe


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