Phenolic Compounds in Foods and Natural Health Products PDF
Preview Phenolic Compounds in Foods and Natural Health Products
Phenolic Compounds in Foods and g acs.orw001 Natural Health Products bs.9.f u0 p9 p://5-0 htt00 9 | k-2 0b er 22, 2010.1021/ ctobdoi: 6 on O2005 | 131, 34.y 2 3.ul 6J 89.1ate: y D d bon deati ac wnloPubli o D In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. g acs.orw001 bs.9.f u0 p9 p://5-0 htt00 9 | k-2 0b er 22, 2010.1021/ ctobdoi: 6 on O2005 | 131, 34.y 2 3.ul 6J 89.1ate: y D d bon deati ac wnloPubli o D In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. ACS SYMPOSIUM SERIES 909 Phenolic Compounds in Foods and Natural Health Products g acs.orw001 bs.9.f u0 p9 p://5-0 htt00 9 | k-2 0b er 22, 2010.1021/ MFeemroeriidalo Uonniv eSrshitya ohfi Ndeiw, fEoudnidtloanrd ctobdoi: 136 on O1, 2005 | RutgerCs, hTih-eT Satanteg U Hniove,r Esitdy iotof Nre w Jersey 34.y 2 3.ul 6J 89.1ate: y D d bon deati ac wnloPubli o D Sponsored by the ACS Division of Agricultural and Food Chemistry, Inc. American Chemical Society, Washington, DC In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. Library of Congress Cataloging-in-Publication Data Phenolic compounds in foods and natural health products / Fereidoon Shahidi, Chi-Tang Ho, editor. p. cm.—(ACS symposium series ; 909) Includes bibliographical references and index. ISBN 0-8412-3891-X (alk. paper) g acs.orw001 1. Phenols—Physiological effect—Congresses. 2. Functional foods—Congresses. bs.9.f I. Shahidi, Fereidoon, 1951- II. Ho, Chi-Tang, 1944- III. Series. u0 p9 p://5-0 QP801.P4P455 2005 htt00 9 | k-2 612'.0157—dc22 2005041203 0b er 22, 2010.1021/ TNMhaaettie orpniaaaplls eS, rtA anuNsdSeaIdr dZ i3nfo9 .rt4 h8Iin-sf1 o9pr8mu4ba.lt iiocant ioSnc iemnceeest—s tPheer mmanineinmcuem o f rPeqaupeirre mfoern tPsr inotfe dA mLiebrriacrayn ctobdoi: Copyright © 2005 American Chemical Society 6 on O2005 | Distributed by Oxford University Press 131, 34.y 2 All Rights Reserved. Reprographic copying beyond that permitted by Sections 107 or 3.ul 108 of the U.S. Copyright Act is allowed for internal use only, provided that a per 89.16ate: J -2c2h2a pRteorse fweeo oodf $D3r0i.v0e0, Dplaunsv $er0s.7, M5 Ape 0r 1p9a2g3e, UisS pAai.d R teop uthbeli cCaotipoynr ioghr tr eCplreoadrauncctioe nC efontre sra, lIen c., ded by ation D opef rpmaigsseiso nin r tehqiuse bsotso kto i sA pCeSrm Citotepdy riognhlty O ufnfidceer, lPicuebnlsicea ftrioonms ADCivSis.i Donir, e1c1t 5th5e s1e6 tahn Sd toretheet,r wnloaPublic NTh.We c.,i tWatiaosnh inogf ttorand, eD nCa m20e0s3 6a.n d/or names of manufacturers in this publication is not to be o D construed as an endorsement or as approval by ACS of the commercial products or services referenced herein; nor should the mere reference herein to any drawing, spec -ification, chemical process, or other data be regarded as a license or as a conveyance of any right or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publi -cation, even without specific indication thereof, are not to be considered unprotected by law. PRINTED IN THE UNITED STATES OF AMERICA In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. Foreword The ACS Symposium Series was first published in 1974 to pro vide a mechanism for publishing symposia quickly in book form. The purpose of the series is to publish timely, comprehensive books devel oped from ACS sponsored symposia based on current scientific re search. Occasionally, books are developed from symposia sponsored by g acs.orw001 oauthdeire nocreg.a nizations when the topic is of keen interest to the chemistry bs.9.f u0 Before agreeing to publish a book, the proposed table of con p9 p://5-0 tents is reviewed for appropriate and comprehensive coverage and for 9 | httk-200 interest to the audience. Some papers may be excluded to better focus er 22, 20010.1021/b ctahhpeap prbotoeprorsika ;at eroe, t hopevereesr r-mvrieaevywi e bwoere daid npdtrreoidod rut octo to prfryion vacil hdaeac pcctoeerpmst apnarrecehe eanodsrdi vreeedjn.e ecsDtsir.o anWf,t sha neondf ctobdoi: manuscripts are prepared in camera-ready format. 136 on O1, 2005 | papers aAres ian crluulde,e do ninly t hoer ivgoinlualm reess.e Varecrhb aptiamp erresp aronddu cotriiognins aol fr epvreievwi 34.y 2 ously published papers are not accepted. 3.ul 6J 89.1ate: y D d bon ACS Books Department deati ac wnloPubli o D In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. Preface Phenolic and polyphenols compounds in foods and natural health products represent one of the most widely distributed plant secondary metabolites with varied structured characteristics, properties and health effects. Many of the beneficial health effects of plant phenolics are due to their antioxidant activity and their role in balancing g or1 the deleterious effects of oxidants. However, this is not always the case. 9 | http://pubs.acs.k-2005-0909.pr00 mTtiynhpagetero eshrd yeoi eafdn ltcithssae napacsnreeodrsm, naocanattidruod rnaitho l aevhc aeptsiarcvoluitcthlyea srpo srdf o iopdsfehu aacestgneseo , ilcniaacgups.t aoiTb ismlh eiun ms ot,uf h nceneo e ncud sotuirnsamotlrripodztliei noοrgsfn , cro eiefna rfctflaotaiiomvnde ctober 22, 200doi: 10.1021/b pmooxeylcyghpeanhn eiaTsnnmhodil ssoo fvt ahaorecleruta imoosx neoi, dfrp earrpneootsd resutapscr ecttcihhoiee n sa,l naiandtne dtsdht i hesd ecbeauovlstdeshlye oe spi fsfmt ehoceeft nismrt suoc hfci nhed mitfihnfieest ertperreynhs,te t an.p noraloildcy usacinstds, 6 on O2005 | and phenolics thereof. We are grateful to the authors of different chap 131, ters for their state-of-the-art contributions that made publications of this 34.y 2 book possible. 3.ul 6J wnloaded by 89.1Publication Date: DMFeeeprmaeoritdrmioaeol nUnt n oSifv hBearihsoicitdyh ieo mf iNsterwy foundland o D St. John's, Newfoundland A1B 3X9 Canada Chi-Tang Ho Department of Food Science Rutgers, The State University of New Jersey New Brunswick, NJ 08901-8520 xi In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. Chapter 1 Phenolics in Food and Natural Health Products: An Overview Fereidoon Shahidi1 and Chi-Tang Ho2 1Department of Biochemistry, Memorial University of Newfoundland, bs.acs.org 9.ch001 2Department6 o5fS DFt.uo Jdoodleh ySn c'Rsie,o nNacdeew,, N fRoeuuwnt gdBelarrsun,nd Ts Awhe1ic BSkt ,3a NXteJ9 ,U0 C8n9ai0vne1ar-d8sai5t 2y 0o f New Jersey, u0 p9 p://5-0 9 | httk-200 0b er 22, 2010.1021/ Phenolic and polyphenols compounds occur in food as ctobdoi: secondary metabolites. Different classes of phenolics are 6 on O2005 | eofffteecnt se nrecolautendte rteod thine ifro aondtsi oaxnidda ntht eascet ievxietyrt, cbheenmefoicpiraelv ehnetailvteh 131, effect and anticarcinogenic potential, among others. These 34.y 2 activities are often governed by the structural characteristics 3.ul 89.16ate: J ooff thfoeo bdiso amctiigvhe tc oamffepcotn enthtse pcrehseemntic. alI na anddd itaicotniv, iptryo coefs sitnhge ded by ation D compounds involved. wnloaPublic o D Introduction Phenolic compounds in foods and natural health products originate from one of the main classes of secondary metabolites in plants derived from phenylalanine or tyrosine (/). The term 'phenolic' or 'polyphenol' can be defined as a substance which possesses an aromatic ring bearing one or more hydroxyl substituents, including functional derivatives (esters, methyl ethers, glycosides etc.) (2). Most phenolics have two or more hydroxyl groups and are bioactive substances occurring widely in foods. © 2005 American Chemical Society 1 In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. 2 Occurrence of Phenolics The phenolics which occur commonly in foods and natural health products may be classified into simple phenols, hydroxybenzoic acid and hydroxycinnamic acid derivatives, flavonoids, stilbenes, lignans and hydrolyzable as well as condensed tannins. The Simple Phenols and Phenolic Acids The simple phenols include monophenols such as p-cresol isolated from several fruits and diphenols. Diphenols such as hydroquinones are probably the g most widespread simple phenols (3). bs.acs.or9.ch001 hydrToxhyercein naarme ict wacoi dsc.l aEssxecse pot fi np cheerntaoilnic r eadc ifdrus,i tsh aynddro oxnyiboennsz, otihce accoindtse nat nodf u0 9 | http://pk-2005-09 haimcyidpdro ourtxsayunbat lelsnyoz uoorciccce u aroc fii dngs ap lillnaicn etasdc iiibdnl ews ophulibaclnhet issf o i3sr,m 4u, s5au-sta rlcilhayyt edvcrehorixyny lbeosewtnez r(os/i,) c.q uaTcienidaic (c 4aac)n.i dGb eaesl ltaiecnr er 22, 20010.1021/b tohre h hyTydhdreoro lhyxyzydabbreolnexz ytoacinicnn naincasimd. sic i anc fiodosd asn. dH tyhdeirro xdyecriivnantaivmeisc aarcei dms oarned c tohmeimr odner tihvaanti vaerse ctobdoi: are almost exclusively derived from p-coumaric acid, caffeic acid, and ferulic 6 on O2005 | hacyiddr owxyhceirnenaasm siinca apcicid sa ciind fios,o din hgaesn ebreael,n leresvs ieewnceodu nbtyer eHde. rrTmhaen no c(cJu)r.r eCnacfef eoicf 34.13y 21, acid and its esterified derivatives are the most abundant hydroxycinnamic acids 3.ul in a variety of fruits. On the other hand, ferulic acid and its derivatives are the 6J 89.1ate: most abundant hydroxycinnamic acids found in cereal grain (6). by n D ded atio wnloaPublic Flavonoids o D Flavonoids are ubiquitous in plants; almost all plant tissues are able to synthesize flavonoids. There are also a wide variety of types - at least 2000 naturally occurring flavonoids. Flavonoids are present in edible fruits, leafy vegetables, roots, tubers bulbs, herbs, spices, legumes, tea, coffee, and red wine (1,2,7). They can be classified into seven groups: flavones, flavanones, flavonols, flavanonols, isoflavones, flavanols (catechins), and anthocyanidins. The structures of these flavonoids are given in Figure 1. Examples of common flavonoids in foods are listed in Table I. In general, the leaves, flowers, and fruits or the plant contain flavonoid glycosides; woody tissues contain aglycones, and seeds may contain both. In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. 3 g bs.acs.or9.ch001 u0 p9 p://5-0 9 | httk-200 0b er 22, 2010.1021/ ctobdoi: 6 on O2005 | 131, 34.y 2 3.ul 6J 89.1ate: by n D ded atio wnloaPublic o D Flavanol (catechin) Anthrocyanidin Figure 1. Sturctures of flavonoids. In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005. 4 Table I. Different Classes of Flavonoids, Their Substitution patterns and Dietary Sources Class Name Substitution Dietary Source Flavone Apigenin 5,7-OH Parsley, celery Rutin 5,7,3',4'-OH, Buckwheat, citrus 3-O-rutinose, Tangeretin 4,5,6,7,4'- Citrus OCH 3 Flavanone Naringin 5,4' - OH Citrus Naringenin 5,7,4' - OH Orange peel g Flavonol Kaempferol 3,5,7,4' - OH Broccoli, tea bs.acs.or9.ch001 Quereetin 3,5,7,3',4'-OH Oapnpiloens,, bbreorcriceosl i, u0 p9 p://5-0 Flavononol Taxifolin 3,5,7,3',4' -OH fruits 9 | httk-200 Isoflavone Genistein 5,7,4' - OH Soybean er 22, 20010.1021/b DPuaeidrazreiinn 4g7l', u4-c 'Oo-OsHeH, 7, -80-- KSouydbzeua n ctobdoi: C-glucose 6 on O2005 | Flavanol (-)-Epicatechin 3,5,7, 3',4' -OH Tea 131, (catechin) 3.34.uly 2 (-)-epigallocatechin 3,5,7, 3',4',5'- Tea 6J by 89.1n Date: (-)-epigallocatechin O5,H7, 3',4',5'- Tea ded atio gallate OH, 3-gallate wnloaPublic Anthocyanidin Cyanidin 3,5,7,3',4'-OH Cherry, Do strawberry Delphinidin 3,5,7, 3',4',5'- Dark fruits OH As a result of their ubiquity in plants, flavonoids are an integral part of the human diet. It is estimated (<S) that the average American's daily intake of flavonoids is close to 1 g per person. However, this estimated daily intake of flavonoids may be too high when compared to the results of the Zutphen Elderly Study by Hertog et al. (Ρ). They measured the content of selected flavonoids, In Phenolic Compounds in Foods and Natural Health Products; Shahidi, F., el al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2005.
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