profiles of potentially antiallergic flavonoids in 27 kinds of health tea & green tea infusions

8/11/2019 Profiles of Potentially Antiallergic Flavonoids in 27 Kinds of Health Tea & Green Tea Infusions

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Profiles of Potentially Antiallergic Flavonoids in 27 Kinds of HealthTea and Green Tea Infusions

Masatake Toyoda,*, Keiko Tan a ka, Kaori Hoshino, Hiroshi Akiyama, Akio Tanimura, a n dYu kio S a i to

Division of Foods, Na tional Instit ute of H ealth Sciences, 1-18-1 Ka miyoga, Seta ga ya -ku, Tokyo 158, J apa n,an d S howa Womans U niversity, 1-7 Taishido, S eta gay a-ku, Tokyo 154, J apa n

Seven flavonoid profiles, some of w hich were reported to show an tiallergic act ivity i n v i t r o , we resurveyed in 28 kinds of tea. Flavonoids were extra cted w ith hot w at er, hydrolyzed to aglycons, an ddetermined by HP LC. The hydrolysis t ime needed to obtain t he maximum for each aglycon w asexamined. Flavonols quercetin a nd ka empferol were found in 17 kinds of tea infusions, as well asJ apa nese green tea infusions. Myricetin wa s found in jasmine a nd pu-erh tea infusions. A flavon,luteolin, was found in 5 kinds of tea infusions including great planta in tea. Apigenin wa s found in4 kinds of tea infusions including perilla leaf tea, and scutellarein was found in 3 kinds of teainfusions. Scutella rein, which is a potent a ntia llergic an d low cytotoxic flavonoid, is found in greatp la n t a in t e a a n d wa s de t ect e d in p eri l la lea f a n d s a f f lowe r t e a in fu s ion s a t con ce n t ra t ion s ofapproximat ely 2 mg/g and 0.3 mg/g in dried w hole t ea leaves, respectively. The presence ofscutellarein in both sa mples wa s confirmed by L C/MS.

Keywords: Tea; green tea; fl avonoid s; querceti n; kaem pferol; scutellar ein

INTRODUCTION

In J apan , the deman d for various dried tea leaves orflower or trea ted seed such as green tea a nd other teasincluding oolong tea, the infusions of which are drunkt o k e e p g o o d h e a l t h ( t h e s e a re c a l le d h e a l t h t e a s inJ a p a n ) , is g rowin g . Th e n u t r i t ion a l a n d t h e ra p eu t icvalues of green tea have been reviewed (Hara, 1995a).I t was found that green tea had a beneficial effect oncardiovascular and cerebrovascular diseases, a hypoc-holesterolemic effect , ant itumor propert ies, and anti-oxidant , ant igenotoxic, and a nticarious activities; it a lso

significa ntly decreased blood cholesterol levels.P a rt icu la r e mph a s is h a s be e n p la ce d o n a g rou p o fpolyphenolic compounds , because polyphenols an d t heirproducts ar e responsible for th e a bove-mentioned uniquechara cteristics of teas (Ha ra , 1995a; Elliott, 1994) suchas anti-inflammatory properties and antibacterial prop-ert ies. The polyphenols in t ea a re ma inly f lavan ols,f lavonols, f lavonol glycosides, f la vons, an d depsides.Fourteen flavonols a nd flavonol glycosides a nd 19 fla-vons and flavon glycosides ha ve been detected in gr eentea (Hara, 1995b).

The inhibitory effects of hot wa ter t ea extra cts onh is t a min e re le a s e f rom ra t p eri t on e a l ma s t ce lls a n dtheir hya luronidase a ctivity ha s been examined, and teaextracts w ere shown to have a ntia llergic effects (Maeda,

1989, 1990). Fur therm ore, str ucture-act ivity st udiesof flavonoids as inh ibitors of hya luronidase showed tha tluteolin, apigenin, kaempferol, and silybin have anti-allergic activity i n v i t r o (Kuppusamy, 1990). Hista minerelease tests using rat basophilic leukemia (RBL-2H3)cells showed that scutellarein potently inhibits hista-mine release a nd h a s low cytotoxicity (Ka wa sa ki, 1994).

H o we ve r , t h ere a re n o t ma n y da t a in t h e l i t era t u reon the content of the above-mentioned flavonoids in teas

except in widely a nd commonly consumed bla ck tea a ndgreen tea. Our objective is to know th e content of thoseseven well-known flavonoids in health tea that is beings ol d i n J a p a n . H e r t og e t a l . (1993) e xa m i n ed t h econtents of three kinds of f la vonoids in three kinds oft e a in clu din g J a p a n e s e g re en t e a . E n g e lh a rdt e t a l .(1993) examined the apigenin and luteolin glycosidecontents in th ree kinds of tea.

As five widespread flavonoid aglycons were success-fully determined by high-performa nce liquid chroma -tography (HP LC) (Ha sler an d St icher, 1990), w e usedH P L C t o de t e rmin e t h e a mo u n t s o f t h e t h re e ma j o r

flavonols, quercetin, ka empferol, and m yricetin, a nd t hefour major flavons, scutellarein, apigenin, baicalein, andluteolin. After the most suitable hydrolysis t ime ha dbeen decided for each tea, we compared their levels in28 kinds of tea infusions.

MATERIALS AND METHODS

Materials. The foll ow i ng t e as w e r e use d : (1) Angelicakeiskei l e a f t e a (a s h i t a b a ch a i s t h e J a p a n e se n a m e ); (2 )Gynost emm a pent aphyl l um t ea (ama chazurucha); (3) gingkoleaf (Gingko bil oba) tea (ichoucha); (4) great plant ain (P l ant agomaj or ) tea (oobakocha/sha zensou); (5) ground ivy (Glechomahederacea) tea (ka kidoushicha); (6) J a pan ese persimmon (D i -ospyros kaki ) l e af t e a (kaki nohac ha); (7) C h r y sant he m um

flower (C h r y s a n t h e m u m m o r i f o l i u m ) tea (kikubanacha); (8)Gymnema syl vest re S chul t . tea (gimunemacha ); (9) guava(P si di um guaj avaL.) tea (guava cha); (10) Chinese ma trimonyvine (Lyci um chi nense Mill.) tea (kukocha); (11) low stripedbamboo leaf (S asa al bo-margi nat a) tea (kumazasacha); (12)mulberry leaf (M orus bombycisKoidz.)t ea (kuwa nohacha ); (13)perilla (Perilla frutescens) leaf tea (shisonohacha ); (14) jasmine(J a s m i n u m sa m b a c ) flower tea (ja sumincha ); (15) field h orse-t a i l (Equisetum arvense) tea (suginacha); (16) Rubus suavi s- s i m u s tea (Chinese tencha); (17) H o u t t u y n i a cor d a t a t ea(dokuda micha ); (18) gut ta -perca tree (Eucommia ulmoides)leaftea (tochucha ); (19) Ea st Indian lotus (Nel umbo nu ci f era) tea(ha sucha ); (20) a dlaly (Coi x l achrymaj obi ) tea (hatomugicha);(21) b ana va (L egerstr oemi a speciosa) t e a (b anava c ha); (22)J apa nese medlar (Eriobotrya japonica) leaf tea (biwan ohacha );(23) pu-erh (Camel l i a si nensi s, Chinese microbial-fermented

* Au t h or t o wh o m corre sp on de n ce s h ou ld be a d-dressed [e-mail [email protected]; fax +81(3)3707 6950].

Nat ional Inst itut e of Health Sciences. Showa Womans U niversity.

2561J. Agric. Food Chem. 1997, 45, 25612564

S0021-8561(97)00024-1 CCC: $14.00 1997 American Chemical Society


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dark tea) tea (puarcha); (24) safflower (C a r t h a m u s t i n et or i u s )t e a (b eni bana c ha); (25) m ug w or t (A rt emi si a pr i nceps) t e a(yomogicha); (26) eucalyptus (Eucalyptus globulu s) tea (yuukar-icha ); (27) rooibos (A spal at hus l i neari s) tea (ruibosucha ); (28)J apa nese green t ea (Camel l i a si nensi s) (ryokucha).

All tea sa mples were purcha sed at reta il shops in Tokyo a ndYokohama between August a nd December 1995.

H P L C g r ad e api g eni n, q ue r ce t i n d i hy dr at e , kae m pfer ol,myricetin, luteolin, and baicalein w ere purchased from Funa -koshi Co. Ltd. (Tokyo), and scutellarein was kindly suppliedby Dr. Kawasaki, Foods and Drugs Safety Center (1988).

Methods of Analysis. After large tea leaves were cut intosmall pieces, the tea leaf or powder (5.0 g) was extracted with200 mL of boil ing disti l led water at more than 95 C, gentlyst i r r ed for 5 m i n, f i lt e r ed t hr ough g l ass f il t e r No. 17-G 3(M ae d a L t d . C o., por e si ze 40-100 m , t h i ck n es s 5 m m ,diameter 70 mm), tra nsferred into a 200 mL measuring flask,an d made up to 200 mL with w at er. Then 100 mL of this wa sconcentra ted to a pproximately 10 mL using a rotary evapora-tor and ma de up to 10 mL with w at er, and 10 mL of methanolwa s added. One mill i li ter of the mixture wa s tra nsferred to a15 mL reaction t est tube w ith a stopper, 0.25 mL of 6 N HClw a s ad d e d , and t he m i xt ur e w as ke pt a t 90 C for b e t w e en 5m i n and 7 h. Aft e r cool ing i n a n i c e bat h, t he m i xt ur e w asm ad e up t o 10 m L w i t h w at e r and e xt r ac t e d t w i c e w i t h 40and 30 m L of e t hy l ac et at e . The or gani c l ay e r w as w a she dw i t h a sm al l am ount of w at e r and d r i e d on anhy d r ous Na 2-S O4, t h en i t w a s con cen t r a t ed a n d d ri ed u si ng a r ot a r y

evaporator a nd dissolved in 500 L of methanol.HPLC Analysis. The resulting a glycons were q uan tified

by RP -HP LC in a precolumn of Inertsi l ODS-3 (C 18, 4.0 10mm, particle size 5m) and in a separat ive column of Inertsi lODS -3 (C 18, 4 5 250 mm, part icle size 5m) using 0.5%H 3-P O4/met ha nol (1/1, v/v) a s t he m obile pha se, in jection volum eof 20 L, flow ra te of 1 mL/min, oven temperature of 40 C,and UV d e t e ct i on at 349 nm w i t h t he r e fer e nce a t 550 nm .T he t hr e shol d w as 1. 0 m AU, and pe ak w i d t h w as 0. 1 m i n.Peak identity was confirmed using a photodiode array detectorto record t he U V spectra of the flavonoids in t he sa mples on-l ine b e t w e en w a ve le ng t hs of 190 and 500 nm . A H e w l et t -Packard HP9000A high-performance l iquid chromatographwa s used. All determinat ions were carried out in triplicat e,a n d e a ch f la v o noi d w a s i de nt i fi ed b y co mp a r is on w i t h asta nda rd absorpt ion curve. The detection limit for flavonoids

wa s a pproximately 0.01 mg/g, but the confirmat ion l imit ofthe U V curve wa s betw een 0.03 a nd 0.05 mg/g depending ont he t e a.

Thermospray Mass Spectrometry. S c ut e ll ar e in w a sana lyzed in positive mode by a n a tomic pressure thermosprayi nt er fac e (Finni g an AP C I ) l i nked t o a m ass spec t r om e t er(Finnigan 4600 quadrupole). Ana lysis wa s performed at 150 C of capillary t empera ture, 500 C of vaporized temperat ure,an d 1000 V of ion mult ivoltage in 65:35 metha nol/wa ter (v/v)using TSK gel ODS-80Ts (4.6 150 m m ) colum n. B ot hprotonated and methanol adducted ions were obtained.

R E S UL T S AND DI S C US S I O N

Under our chromatographic conditions, seven kinds

of flavonoids were clearly separated as shown in Figure1. A de t ect ion wa v elen g t h of 349 n m wa s s elect e dbeca use ra ther high responses of kaempferol, apigenin,a n d ba ica le in we re o bt a in e d de pe n din g on t h e mo la rcoefficient of absorption a t this w avelength. Two ex-traction procedures for flavonoids from tea were com-pared. The content s of three kinds of flavonoid, scutel-l a r ei n , l ut e ol in , a n d a p ig en i n, i n t h e e xt r a c t w e r ecompared using methanol, hot w at er, and great planta in(s h a ze n sou ) t e a lea v e s ( 4), a s t h is t e a is k n o wn t ocontain these flavonoids (Miyaichi, 1989; Nishibe, 1995).Meth a nol extr a ction yielded 3.2, 0.34, and 0.21 mg/g ofthese flavonoids from these dried tea leaves, respec-tively, a nd 2.5, 0.35, an d 0.23 mg/g w hen extr a cted w ithh ot wa t e r . B o t h me t h o ds g a v e s imila r re su lt s e xce pt

t h e a mo u n t o f s c u t e l la re in wa s a l i t t le h ig h e r in t h e

methan ol extract . Accordingly, we used the hot w at erextract ion method as it may provide levels similar tothe a ctual dieta ry levels of flavonoids ta ken in from tea .

As t he completeness of hydrolysis la rgely depends ont h e t y p e o f g ly cos ide , w e de t ermin ed t h e op t imumh y droly s is con dit ion s f or t h e t e a s , a s de scribed byHertog et al. (1993). That is, after the hydrolysis of eachtea infusion for 5, 10, 15, 30, and 60 min, and 2, 3, 4, 5,6, and 7 h, seven kinds of f lavonoids w ere determinedby H PL C, t he time course of flavonoid peaks a ppeara nceon chromatograms were recorded, and the time neededto reach ma ximum concentra tion wa s decided. Table 1shows the optimum hydrolysis times for each flavonoidobserved in 24 kinds of tea. In th e case of ashita bacha(1) an d 11 other tea s, a hydr olysis time of 15 or 30 minwa s sufficient to obtain the corresponding flavonoids,but the teas containing scutellarein glycoside neededlonger h ydrolysis t imes to obta in the correspondingaglycon flavonoids, the reason for w hich is a ppar entlydu e t o t h e di f f e re n c e o f s u g a r bin din g s i t e s in t h e s efla vonoid a glycons. The recovery of quercetin, kaempfer-ol, scutellarein, luteolin, and apigenin from great plan-ta in leaf t ea infusions spiked at 1.0 mg/g w as >90%.

Ta ble 2 shows t he a mount of 6 fla vonoids in 27 kindsof health tea and J apa nese green tea. Numbers in thesame samples represent samples purchased from dif-ferent companies. No baica lein wa s found in any of theteas. No flavonoid peaks t ested were detected in mug-wort tea (26) and adlay tea (20) infusions, although the

Figure 1. C hr om at og r am of se ve n ki nd s of s t and ar d f l a-vonoids monitored by UV detector. Pea ks: (a) myricetin, (b)scutellarein, (c) qu ercetin, (d) luteolin, (e) ka empferol , (f)api g eni n, and (g ) b ai c al ei n. H P L C cond it i ons: pr ec ol um n,Inertsi l ODS-3 (C 18); column, Inertsi l ODS-3 (C 18); mobilephase, 0.5%H 3P O4/MeOH (1/1,v/v); colum n t emper a tu re, 40C; injection volume, 20L; detection wavelength, 349 nm; flowra te, 1 mL /min.

Table 1. Optimum Hydrolysis Time (Hours) for Each ofthe Aglycon Flavonoids in Tea Infusions

flavonoids a

t ea n o. My r Que K a e S cu L ut Api

1, 2, 3, 8, 17 0.25 0.259, 12, 14, 18, 19, 21, 22, 23, 28 0.5 0.5 0.526 1.016 1.0 0.56, 7, 10, 15 1.0 1.0 1.0 1.027 1.0 2.024 0.5 5.04 3.0 3.0 3.05 5.011 5.0 5.0 5.0 5.013 5.0 6.0 6.0

a Myr, myricetin; Que, quercetin; Kae, kaempferol; Scu, scutel-larein; L ut , luteolin; Api, a pigenin.

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reason was not clear, and small amounts of myricetin,quercetin, kaempferol, and luteolin were detected in onesample of low striped bamboo leaf tea (11) infusions.J apanese green tea infusions showed both quercetin andkaempferol. Naka zaw a (1995) summa rized studies onthe function of gutta-perca tea (18) and reported thep res en ce of q u e rce t in a n d k a e mpf erol . O u r re su lt sconcurred with this. Shimoi et al. (1996) reported thepresence of luteolin as an antioxidative plant flavonoidin rooibos tea (27) infusions; however, it w a s not foundin our samples. Rabe et al. (1994) reported the presenceof lu t eol in , q u e rce t in , a n d is oq u e ci t r in a s p h en olicmeta bolites in rooibos tea (27) leaves and st ems. Sn y-ckers a nd Sa lemi (1974) reported tha t the a ntiallergic

e ff ect of rooibos t e a wa s ma in ly du e t o t h e f la v o n olq u er ce t in . We f ou n d t h a t t h e m a i n f la v on ol s w e r equercetin and kaempferol in rooibos tea infusions.

The most prevalent flavonols, quercetin a nd ka empfer-ol, were found in 17 kinds of tea infusions includingJ a p a n e s e g ree n t e a a s de scribed a bo ve . M y rice t in ,found in green tea infusions, was found in only jasminetea a nd pu-erh teas. The flavon luteolin, which wa s notconfirmed in our green tea infusions because of the tracecontent , was found in ground ivy leaves tea (5), chry-s a n t h e mu m f lowe r t e a (7), a n d p eri lla lea f t e a (13)infusions, apigenin was found in great plantain tea (4),perilla leaf tea (13), and field horsetail tea (suginacha)(15) in f u sion s , a n d s cu t e lla re in wa s f ou n d in g re a tplant a in t ea (ooba kocha ) (4), perilla lea f tea (shisocha )

(13), and safflower flower (benibana) tea (24) infusions.Sc ut e l la re in , w h ich wa s re port e d t o be t h e s t ron g es tantiallergic f lavonoid i n v i tr o a m o n g t h e m a n y f l a -vonoids tested by Kawasaki (1994), is one of the maincomponents in grea t pla nt a in (oobako) tea (4) (Miya ichi,1989; Nishibe, 1995). It w a s also detected in perilla lea ftea (13) and safflower tea (24) at concentrations of 2 and0.3 mg/g in w hole dried tea leaves, respectively. Typicalchroma togram of perilla leaf tea infusions is shown inFigur e 2. The presence of scutellar ein in the perilla lea f

Table 2. Amount (Milligrams per Gram) of 6 Flavonoids in 27 Kinds of Health Tea and Green Tea

flavonols a,b f lavonsa,b

t ea My r Que K a e S cu L ut Api

Angeli ca keiskei lea ves (a shit a ba ch a ) 0.03 ( 0.04c

Gynostemma pentaphyllum lea ves (a ma ch a zur uch a ) 1.80 ( 0 .3 1 0 .9 0 ( 0.17gin gko lea ves (ich ouch a ) 0.18 ( 0 .0 3 0 .1 7 ( 0.01gr ea t pla n t a in lea ves (ooba koch a ) 0.02 ( 0 2.08 ( 0.11gr oun d ivy lea ves (ka kidoush ich a ) 0.08 ( 0J a pa nese per sim mon lea ves (ka kin oh a ch a ) 1 1.05 ( 0 .1 2 1 .2 7 ( 0.13

2 0.60 ( 0 .0 4 0 .5 6 ( 0.08ch r y sa n t h em um flow er (kikuba n a ch a ) 2.51 ( 0.67

gym n em a (gim un em a cha ) 1 1.79 ( 0 .2 1 1 .4 5 ( 0.272 1.73 ( 0 .2 2 0 .7 2 ( 0.093 3.23 ( 0 .1 2 1 .5 2 ( 0.08

gua va (gua ba ch a ) 1.09 ( 0 .0 8 0 .0 4 ( 0.03C h in ese m a t r im on y vin e (kukoch a ) 1.41 ( 0 .0 8 0 .6 2 ( 0.01low striped bamboo leaves (kumaza sacha) 1

2 0.03 ( 0 .0 4 0 .0 3 ( 0 .0 1 0 .0 3 ( 0.01 0.02 ( 0.01m ulber r y lea ves (kuw a n oh a ch a ) 2.67 ( 0 .1 2 0 .7 6 ( 0.04per illa lea ves (sh ison oh a ch a ) 1 2.25 ( 0 .4 9 1 .0 8 ( 0 .0 8 1 .1 7 ( 0.16

2 2.22 ( 0 .9 9 1 .3 5 ( 0 .5 7 0 .3 9 ( 0.10ja sm in e (ja sum inch a ) 0.72 ( 0 .1 2 1 .1 5 ( 0 .2 2 0 .9 5 ( 0.22field h or set a il lea ves (sugin a ch a ) 1.05 ( 0 0.76 ( 0.04Rubus suavissimus(C h in ese t en n ch a ) 1 1.64 ( 0 .1 9 0 .4 6 ( 0.04

2 1.06 ( 0 .0 1 0 .3 8 ( 0.03H ou t t u y n i a cor d a t a (dokuda m ich a ) 1 3.81 ( 0 .6 3 0 .0 8 ( 0.01

2 3.01 ( 0 .4 0 0 .0 6 ( 0.01gut t a -per ch a (t och uch a ) 1 1.43 ( 0 .2 0 0 .2 3 ( 0.04

2 1.19 ( 0 .1 2 0 .1 6 ( 0.013 0.28 ( 0 .0 4 0 .0 5 ( 0

E a st I ndia n lot us (h a such a ) 6.00 ( 0 .2 1 0 .1 2 ( 0.04 0.08 ( 0.03adlay (hatomugicha)ba n a va (ba n a va ch a ) 1 0.96 ( 0 .1 2 0 .3 4 ( 0.05

2 1.03 ( 0 .0 7 0 .3 0 ( 0.03J a pa n ese m edla r (biw a n oh a ch a ) 1 0.39 ( 0 .0 5 0 .1 3 ( 0.01

2 0.09 ( 0 .0 2 0 .0 4 ( 0.02 0.08 ( 0 .0 3 0 .1 8 ( 0.10pu-er h (pua r ch a ) 0.40 ( 0 .2 2 0 .5 2 ( 0 .1 8 0 .2 3 ( 0.09 0.05 ( 0.09sa fflow er (ben iba n a ch a ) 0.38 ( 0 .0 3 0 .2 9 ( 0.04euca lypt us (y uka r ich a ) 0.22 ( 0.03mugwort (yomogicha)r ooibos (r uibosch a ) 0.92 ( 0 .1 0 0 .1 6 ( 0.32J a pa n ese gr een (sen ch a ) 1.31 ( 0 .1 4 1 .5 6 ( 0 .1 8 1 .4 9 ( 0.17

a Myr, myricet in; Que, quercet in; Ka e, kaempferol; Scu, scutellarein; Lut , luteolin; Api, a pigenin. b Milligram s of f lavonoids per gra mof dried tea . c Means of t riplicate determinat ion and the standard deviat ions.

Figure 2. Ty pic al c hr om at og r am of a per i ll a t e a e xt r ac t .Pea ks: (a) scutellarein, (b) luteolin, and (c) apigenin. HP LCconditions were the same as shown in the legend of Figure 1except the ra tio of mobile phas e is 5.5:4.5 (v/v).

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tea infusions and safflower tea infusions was confirmedby comparing the mass spectrum peaks of scutellareins t a n da rd p e a k (m/z287 [M + H ]+, m/z319 [M + C H 3-OH + H ]+)with those of an extract from perilla leaf teaand an extract from safflower tea.

Scutellar ein is usually contained in an d is a functionalcomponent of great plant ain (oobako). It h a s been useds in ce a n ci en t t im es a s a d iu r et i c a n d a s a n a n t i-i nf la m m a t o r y a n d a n t i a s t h m a t i c dr u g i n C h i na a n dJ a pan (Mitsuha shi, 1988). We confirmed tha t it is a lsocontained in perilla leaves, which are a very popularfood in J apan, and in safflower, which is eaten saltedwith vinegar in a local area of J apan.

ACKNOWLEDGMENT

W e t h a n k D r. M a s a ru K a wa s a k i ( F o o ds a n d D ru g sS a f e t y C e nt e r, H a d a n o -s h i, J a p a n ) f o r a s a m p le ofscutellarein and valuable suggestions and Dr. YukihiroGoda (Nat ional Inst itute of Healt h Sciences, Tokyo,J apa n) for kind help for our st udy.

LITERATURE CITED

Elliott , M., J r . ; Chitha n, K . The impact of plant flavonoids onmamm alian biology: implicat ions for immunity, inflamma -

tion and cancer. In The Flavonoids, Advances in Researchsince 1986;Harborne, J . B. , Ed.; Cha pman & Ha ll: London,1994; Chapter 15.

E n g el h a r dt , U . H . ; F i n ge r, A. ; K u h r , S . D e t er m in a t i on o fflavone C-glycosides in tea. Z. Lebensm. Unt ers. F orsch.1993, 19 7, 239-244.

Fa ng, Z.; Zeng, X. Isolat ion and identificat ion of flavonoids andorganic a cid from Gynostemma pentaphyllum Makino. Zhong-guo Z hongyao Z azhi 1989, 14, 676-678.

Hara, Y.; Luo, S.-J . ; Wickremasinghe, R. L. ; Yamanishi , T.Use s and b e ne fi t s of t e a . F ood Rev. I nt . 1995a, 11 , 527-542.

Hara, Y.; Luo, S.-J . ; Wickremasinghe, R. L. ; Yamanishi , T.Chemical composition of tea .Food Rev. In t. 1995b, 1 1, 435-456.

Hasler, A.; Sticher, O. High-performance l iquid chromato-

graphic determination of five widespread flavonoid agly-cones. J . C h r o m a t o gr . 1990, 50 8, 236-240.H e r t o g , M . G . L . ; H o l l m a n , P . C . H . ; P u t t e , B . C o n t e n t o f

potential ly an ticarcinogenic flavonoids of t ea infusions,w i ne s, and fr uit jui ce s. J . A g r i c . F ood C h em . 1993, 41,1242-1246.

Kaw asa ki, M.; Ha yashi, T.; Arisawa , M.; Morita, N.; B erganza,L. H. 8-Hydroxytricetin 7-glucuronide, a -glucuronidaseinhibitor from S copari a dul ci s. P h yt ochemi st ry 1988, 27,3709-3711.

Ka wa saki, M.; Toyoda, M.; Teshima, R.; Saw ada , J . ; Hay ash i,T.; Arisawa, M.; Shimizu, M.; Morita, N.; Inoue, S. ; Saito,

Y. In vitro antial lergic activity of flavonoids in histaminerelease a ssa y using ra t ba sophilic leukemia(RBL-2H3) cells.Jpn. J. F ood Hyg. S ci . 1994, 35, 497-503.

Kuppusamy, U . R.; Khoo, H. E.; Da s, N. P. St ructure-activitystudies of flavonoids as inhibitors of hyaluronidase. B i o- chem. P harm acol . 1990, 40, 397-401.

Maeda, Y.; Yamamoto, Y.; Masui, T.; Sugiyama, K.; Yokota,M . ; Nakag om i, K . ; Tana ka, H . ; Takaha shi , I . ; K ob ay ashi ,T. Inh ibitory effect of tea extr acts on hista mine release frommast cells (Studies on anti-allergic activity in tea I). J p n .J. F ood H yg. Sci .1989, 30, 295-299.

Maeda, Y.; Yamamoto, Y.; Masui, T.; Sugiyama, K.; Yokota,

M . ; Nakag om i, K . ; Tana ka, H . ; Takaha shi , I . ; K ob ay ashi ,T.; Kobayash i, E. Inh ibitory effect of tea extra cts on hya lu-ronidase (Studies on anti-allergic activity in tea II). J p n . J .F ood H yg. S ci . 1990, 31, 233-237.

Maurice, J . C-Glycosylflavonoids. In TheFlavonoids, Advancesin Research since 1986; H a r b or ne , J . B . , E d . ; C hapm an &Ha ll : London, 1994; Cha pter 3.

M i t suhashi , H . I l l u s t r a t ed M ed i c a l P l a n t s o f t h e W o r l d i n Colour; H okuryukan, J apa n, 1988; p 443.

Miya ichi, Y.; Kizu, H.; Tomimori, T.; Lin, C .-C. S tudies on theconsti tuents of Scutellaria species. XI. On t he flavonoidc onst i t ue nt s of t he ae r i al par t s of S c u t e l l a r i a i n d i c a L .C h em . P h a r m . B u l l . 1989, 37, 794-797.

N a k a z a w a , Y . C u r r en t s t a t u s a n d ov er v ie w on s t u d ie s o nfunction of tochu-cha. Gekkan F udo K emi k aru1995, 1 1, 72-78.

Nishibe, S.; Murai, M.; Tamayama, Y. Studies on constituentsof Plantaginis Herba 7 Flavonoids from P l an t ago asi at i caa nd P . host i f ol i a. N at . M ed. 1995, 49, 340-342.

P a r k, J . C . ; C ho, Y. S . ; P a r k, S . K . ; P ar k, J . R . ; C hun, S . S . ;Ok, K. D.; Choi, J . W. Isolation of flavone-7-O-glycosidesfrom the aerial parts of An geli ca keiskei and antihyperlipi-demic effects. Saengyak H akh oechi 1995, 26, 337-343.

R ab e , C . ; S t e e nkam p, J . A. ; J oub er t , E . ; B ur g e r , J . F . W. ;Ferreira, D . P henolic metabolites from rooibos tea (A spal - at hus l i neari s). P hyt ochemi st ry1994, 35, 1559-1565.

S hi m oi , K . ; M asud a, S . ; S he n, B . ; Fur ug or i , M . ; K i nae , N.Radioprotective effects of antioxidative plant flavonoids inmice. M ut at . Res. 1996, 35 0, 153-161.

Snyckers, F. O.; Salemi, G. S outh African medicina l plants I .Qeurcetin as the major in vitro active component of rooibost e a . J . S . A f r . C h em . I n s t .1974, 27, 5-7.

Received for review J an uary 10, 1997. Revised ma nuscriptreceived April 18, 1997. Accepted April 28, 1997.X This projecti s f in a n c ia l ly s u pp or t ed b y t h e H u m a n H e a l t h S ci en ce sFoundation.

J F970024Y

X Abstract published in Advan ce ACS Abstracts,J une15, 1997.

2564 J. Agric. Food Chem.,Vol. 45, No. 7, 1997 Toyoda et al.

profiles of potentially antiallergic flavonoids in 27 kinds of health tea & green tea infusions

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