Profiles of Potentially Antiallergic Flavonoids in 27 Kinds of Health

Tea and Green Tea Infusions

Masatake Toyoda,*
,
Kei ko Tanaka,

Kaori Hoshi no,

Hi roshi Aki yama,

Aki o Tani mura,

and
Yuki o Sai to

Di vi si on of Foods, Nati onal I nsti tute of Heal th Sci ences, 1-18-1 Kami yoga, Setagaya-ku, Tokyo 158, Japan,
and Showa Womans Uni versi ty, 1-7 Tai shi do, Setagaya-ku, Tokyo 154, Japan
Seven fl avonoi d profi l es, some of whi ch were reported to show anti al l ergi c acti vi ty in vitro, were
surveyed i n 28 ki nds of tea. Fl avonoi ds were extracted wi th hot water, hydrol yzed to agl ycons, and
determi ned by HPLC. The hydrol ysi s ti me needed to obtai n the maxi mum for each agl ycon was
exami ned. Fl avonol s querceti n and kaempferol were found i n 17 ki nds of tea i nfusi ons, as wel l as
Japanese green tea i nfusi ons. Myri ceti n was found i n jasmi ne and pu-erh tea i nfusi ons. A fl avon,
l uteol i n, was found i n 5 ki nds of tea i nfusi ons i ncl udi ng great pl antai n tea. Api geni n was found i n
4 ki nds of tea i nfusi ons i ncl udi ng peri l l a l eaf tea, and scutel l arei n was found i n 3 ki nds of tea
i nfusi ons. Scutel l arei n, whi ch i s a potent anti al l ergi c and l ow cytotoxi c fl avonoi d, i s found i n great
pl antai n tea and was detected i n peri l l a l eaf and saffl ower tea i nfusi ons at concentrati ons of
approxi matel y 2 mg/g and 0.3 mg/g i n dri ed whol e tea l eaves, respecti vel y. The presence of
scutel l arei n i n both sampl es was confi rmed by LC/MS.
Keywords: Tea; green tea; flavonoids; quercetin; kaempferol; scutellarein
I NTRODUCTI ON
I n Japan, the demand for vari ous dri ed tea l eaves or
fl ower or treated seed such as green tea and other teas
i ncl udi ng ool ong tea, the i nfusi ons of whi ch are drunk
to keep good heal th (these are cal l ed heal th teas i n
Japan), i s growi ng. The nutri ti onal and therapeuti c
val ues of green tea have been revi ewed (Hara, 1995a).
I t was found that green tea had a benefi ci al effect on
cardi ovascul ar and cerebrovascul ar di seases, a hypoc-
hol esterol emi c effect, anti tumor properti es, and anti -
oxi dant, anti genotoxi c, and anti cari ous acti vi ti es; i t al so
si gni fi cantl y decreased bl ood chol esterol l evel s.
Parti cul ar emphasi s has been pl aced on a group of
pol yphenol i c compounds, because pol yphenol s and thei r
products are responsi bl e for the above-menti oned uni que
characteri sti cs of teas (Hara, 1995a; El l i ott, 1994) such
as anti -i nfl ammatory properti es and anti bacteri al prop-
erti es. The pol yphenol s i n tea are mai nl y fl avanol s,
fl avonol s, fl avonol gl ycosi des, fl avons, and depsi des.
Fourteen fl avonol s and fl avonol gl ycosi des and 19 fl a-
vons and fl avon gl ycosi des have been detected i n green
tea (Hara, 1995b).
The i nhi bi tory effects of hot water tea extracts on
hi stami ne rel ease from rat peri toneal mast cel l s and
thei r hyal uroni dase acti vi ty has been exami ned, and tea
extracts were shown to have anti al l ergi c effects (Maeda,
1989, 1990). Furthermore, structure-acti vi ty studi es
of fl avonoi ds as i nhi bi tors of hyal uroni dase showed that
l uteol i n, api geni n, kaempferol , and si l ybi n have anti -
al l ergi c acti vi ty in vitro(Kuppusamy, 1990). Hi stami ne
rel ease tests usi ng rat basophi l i c l eukemi a (RBL-2H3)
cel l s showed that scutel l arei n potentl y i nhi bi ts hi sta-
mi ne rel ease and has l ow cytotoxi ci ty (Kawasaki , 1994).
However, there are not many data i n the l i terature
on the content of the above-menti oned fl avonoi ds i n teas
except i n wi del y and commonl y consumed bl ack tea and
green tea. Our objecti ve i s to know the content of those
seven wel l -known fl avonoi ds i n heal th tea that i s bei ng
sol d i n Japan. Hertog et al . (1993) exami ned the
contents of three ki nds of fl avonoi ds i n three ki nds of
tea i ncl udi ng Japanese green tea. Engel hardt et al .
(1993) exami ned the api geni n and l uteol i n gl ycosi de
contents i n three ki nds of tea.
As fi ve wi despread fl avonoi d agl ycons were success-
ful l y determi ned by hi gh-performance l i qui d chroma-
tography (HPLC) (Hasl er and Sti cher, 1990), we used
HPLC to determi ne the amounts of the three major
fl avonol s, querceti n, kaempferol , and myri ceti n, and the
four major fl avons, scutel l arei n, api geni n, bai cal ei n, and
l uteol i n. After the most sui tabl e hydrol ysi s ti me had
been deci ded for each tea, we compared thei r l evel s i n
28 ki nds of tea i nfusi ons.
MATERI ALS AND METHODS
Materials. The fol l owi ng teas were used: (1) Angelica
keiskei l eaf tea (ashi tabacha i s the Japanese name); (2)
Gynostemma pentaphyllum tea (amachazurucha); (3) gi ngko
l eaf (Gingkobiloba) tea (i choucha); (4) great pl antai n (Plantago
major) tea (oobakocha/shazensou); (5) ground i vy (Glechoma
hederacea) tea (kaki doushi cha); (6) Japanese persi mmon (Di-
ospyros kaki) l eaf tea (kaki nohacha); (7) Chrysanthemum
fl ower (Chrysanthemum morifolium) tea (ki kubanacha); (8)
Gymnema sylvestre Schult. tea (gi munemacha); (9) guava
(Psidiumguajava L.) tea (guavacha); (10) Chi nese matri mony
vi ne (Lycium chinense Mi l l .) tea (kukocha); (11) l ow stri ped
bamboo l eaf (Sasa albo-marginata) tea (kumazasacha); (12)
mul berry l eaf (MorusbombycisKoi dz.) tea (kuwanohacha); (13)
peri l l a (Perilla frutescens) l eaf tea (shi sonohacha); (14) jasmi ne
(J asminumsambac) fl ower tea (jasumi ncha); (15) fi el d horse-
tai l (Equisetum arvense) tea (sugi nacha); (16) Rubus suavis-
simus tea (Chi nese tencha); (17) Houttuynia cordata tea
(dokudami cha); (18) gutta-perca tree (Eucommiaulmoides) l eaf
tea (tochucha); (19) East I ndi an l otus (Nelumbo nucifera) tea
(hasucha); (20) adl al y (Coixlachrymajobi) tea (hatomugi cha);
(21) banava (Legerstroemia speciosa) tea (banavacha); (22)
Japanese medl ar (Eriobotrya japonica) l eaf tea (bi wanohacha);
(23) pu-erh (Camellia sinensis, Chi nese mi crobi al -fermented
* Author to whom correspondence shoul d be ad-
dressed [e-mai l toyoda@ni hs.go.jp; fax +81(3)3707 6950].

Nati onal I nsti tute of Heal th Sci ences.

Showa Womans Uni versi ty.

2561 J. Agric. Food Chem. 1997, 45, 25612564
S0021-8561(97)00024-1 CCC: $14.00 1997 American Chemical Society
dark tea) tea (puarcha); (24) saffl ower (Carthamus tinetorius)
tea (beni banacha); (25) mugwort (Artemisia princeps) tea
(yomogi cha); (26) eucal yptus (Eucalyptus globulus) tea (yuukar-
i cha); (27) rooi bos (Aspalathus linearis) tea (rui bosucha); (28)
Japanese green tea (Camellia sinensis) (ryokucha).
Al l tea sampl es were purchased at retai l shops i n Tokyo and
Yokohama between August and December 1995.
HPLC grade api geni n, querceti n di hydrate, kaempferol ,
myri ceti n, l uteol i n, and bai cal ei n were purchased from Funa-
koshi Co. Ltd. (Tokyo), and scutel l arei n was ki ndl y suppl i ed
by Dr. Kawasaki , Foods and Drugs Safety Center (1988).
Methodsof Analysis. After l arge tea l eaves were cut i nto
smal l pi eces, the tea l eaf or powder (5.0 g) was extracted wi th
200 mL of boi l i ng di sti l l ed water at more than 95 C, gentl y
sti rred for 5 mi n, fi l tered through gl ass fi l ter No. 17-G 3
(Maeda Ltd. Co., pore si ze 40-100 m, thi ckness 5 mm,
di ameter 70 mm), transferred i nto a 200 mL measuri ng fl ask,
and made up to 200 mL wi th water. Then 100 mL of thi s was
concentrated to approxi matel y 10 mL usi ng a rotary evapora-
tor and made up to 10 mL wi th water, and 10 mL of methanol
was added. One mi l l i l i ter of the mi xture was transferred to a
15 mL reacti on test tube wi th a stopper, 0.25 mL of 6 N HCl
was added, and the mi xture was kept at 90 C for between 5
mi n and 7 h. After cool i ng i n an i ce bath, the mi xture was
made up to 10 mL wi th water and extracted twi ce wi th 40
and 30 mL of ethyl acetate. The organi c l ayer was washed
wi th a smal l amount of water and dri ed on anhydrous Na2-
SO4, then i t was concentrated and dri ed usi ng a rotary
evaporator and di ssol ved i n 500 L of methanol .
HPLC Analysis. The resul ti ng agl ycons were quanti fi ed
by RP-HPLC i n a precol umn of I nertsi l ODS-3 (C18, 4.0 10
mm, parti cl e si ze 5 m) and i n a separati ve col umn of I nertsi l
ODS-3 (C18, 4 5 250 mm, parti cl e si ze 5 m) usi ng 0.5% H3-
PO4/methanol (1/1, v/v) as the mobi l e phase, i njecti on vol ume
of 20 L, fl ow rate of 1 mL/mi n, oven temperature of 40 C,
and UV detecti on at 349 nm wi th the reference at 550 nm.
The threshol d was 1.0 mAU, and peak wi dth was 0.1 mi n.
Peak i denti ty was confi rmed usi ng a photodi ode array detector
to record the UV spectra of the fl avonoi ds i n the sampl es on-
l i ne between wavel engths of 190 and 500 nm. A Hewl ett-
Packard HP9000A hi gh-performance l i qui d chromatograph
was used. Al l determi nati ons were carri ed out i n tri pl i cate,
and each fl avonoi d was i denti fi ed by compari son wi th a
standard absorpti on curve. The detecti on l i mi t for fl avonoi ds
was approxi matel y 0.01 mg/g, but the confi rmati on l i mi t of
the UV curve was between 0.03 and 0.05 mg/g dependi ng on
the tea.
Thermospray Mass Spectrometry. Scutel l arei n was
anal yzed i n posi ti ve mode by an atomi c pressure thermospray
i nterface (Fi nni gan APCI ) l i nked to a mass spectrometer
(Fi nni gan 4600 quadrupol e). Anal ysi s was performed at 150
C of capi l l ary temperature, 500 C of vapori zed temperature,
and 1000 V of i on mul ti vol tage i n 65:35 methanol /water (v/v)
usi ng TSK gel ODS-80Ts (4.6 150 mm) col umn. Both
protonated and methanol adducted i ons were obtai ned.
RESULTS AND DI SCUSSI ON
Under our chromatographi c condi ti ons, seven ki nds
of fl avonoi ds were cl earl y separated as shown i n Fi gure
1. A detecti on wavel ength of 349 nm was sel ected
because rather hi gh responses of kaempferol , api geni n,
and bai cal ei n were obtai ned dependi ng on the mol ar
coeffi ci ent of absorpti on at thi s wavel ength. Two ex-
tracti on procedures for fl avonoi ds from tea were com-
pared. The contents of three ki nds of fl avonoi d, scutel -
l arei n, l uteol i n, and api geni n, i n the extract were
compared usi ng methanol , hot water, and great pl antai n
(shazensou) tea l eaves (4), as thi s tea i s known to
contai n these fl avonoi ds (Mi yai chi , 1989; Ni shi be, 1995).
Methanol extracti on yi el ded 3.2, 0.34, and 0.21 mg/g of
these fl avonoi ds from these dri ed tea l eaves, respec-
ti vel y, and 2.5, 0.35, and 0.23 mg/g when extracted wi th
hot water. Both methods gave si mi l ar resul ts except
the amount of scutel l arei n was a l i ttl e hi gher i n the
methanol extract. Accordi ngl y, we used the hot water
extracti on method as i t may provi de l evel s si mi l ar to
the actual di etary l evel s of fl avonoi ds taken i n from tea.
As the compl eteness of hydrol ysi s l argel y depends on
the type of gl ycosi de, we determi ned the opti mum
hydrol ysi s condi ti ons for the teas, as descri bed by
Hertog et al . (1993). That i s, after the hydrol ysi s of each
tea i nfusi on for 5, 10, 15, 30, and 60 mi n, and 2, 3, 4, 5,
6, and 7 h, seven ki nds of fl avonoi ds were determi ned
by HPLC, the ti me course of fl avonoi d peaks appearance
on chromatograms were recorded, and the ti me needed
to reach maxi mum concentrati on was deci ded. Tabl e 1
shows the opti mum hydrol ysi s ti mes for each fl avonoi d
observed i n 24 ki nds of tea. I n the case of ashi tabacha
(1) and 11 other teas, a hydrol ysi s ti me of 15 or 30 mi n
was suffi ci ent to obtai n the correspondi ng fl avonoi ds,
but the teas contai ni ng scutel l arei n gl ycosi de needed
l onger hydrol ysi s ti mes to obtai n the correspondi ng
agl ycon fl avonoi ds, the reason for whi ch i s apparentl y
due to the di fference of sugar bi ndi ng si tes i n these
fl avonoi d agl ycons. The recovery of querceti n, kaempfer-
ol , scutel l arei n, l uteol i n, and api geni n from great pl an-
tai n l eaf tea i nfusi ons spi ked at 1.0 mg/g was >90%.
Tabl e 2 shows the amount of 6 fl avonoi ds i n 27 ki nds
of heal th tea and Japanese green tea. Numbers i n the
same sampl es represent sampl es purchased from di f-
ferent compani es. No bai cal ei n was found i n any of the
teas. No fl avonoi d peaks tested were detected i n mug-
wort tea (26) and adl ay tea (20) i nfusi ons, al though the
Figure 1. Chromatogram of seven ki nds of standard fl a-
vonoi ds moni tored by UV detector. Peaks: (a) myri ceti n, (b)
scutel l arei n, (c) querceti n, (d) l uteol i n, (e) kaempferol , (f)
api geni n, and (g) bai cal ei n. HPLC condi ti ons: precol umn,
I nertsi l ODS-3 (C18); col umn, I nertsi l ODS-3 (C18); mobi l e
phase, 0.5% H3PO4/MeOH (1/1,v/v); col umn temperature, 40
C; i njecti on vol ume, 20 L; detecti on wavel ength, 349 nm; fl ow
rate, 1 mL/mi n.
Table 1. OptimumHydrolysis Time (Hours) for Each of
the Aglycon Flavonoids in Tea Infusions
fl avonoi ds
a
tea no. Myr Que Kae Scu Lut Api
1, 2, 3, 8, 17 0.25 0.25
9, 12, 14, 18, 19, 21, 22, 23, 28 0.5 0.5 0.5
26 1.0
16 1.0 0.5
6, 7, 10, 15 1.0 1.0 1.0 1.0
27 1.0 2.0
24 0.5 5.0
4 3.0 3.0 3.0
5 5.0
11 5.0 5.0 5.0 5.0
13 5.0 6.0 6.0
a
Myr, myri ceti n; Que, querceti n; Kae, kaempferol ; Scu, scutel -
l arei n; Lut, l uteol i n; Api , api geni n.
2562 J. Agric. Food Chem., Vol. 45, No. 7, 1997 Toyoda et al.
reason was not cl ear, and smal l amounts of myri ceti n,
querceti n, kaempferol , and l uteol i n were detected i n one
sampl e of l ow stri ped bamboo l eaf tea (11) i nfusi ons.
Japanese green tea i nfusi ons showed both querceti n and
kaempferol . Nakazawa (1995) summari zed studi es on
the functi on of gutta-perca tea (18) and reported the
presence of querceti n and kaempferol . Our resul ts
concurred wi th thi s. Shi moi et al . (1996) reported the
presence of l uteol i n as an anti oxi dati ve pl ant fl avonoi d
i n rooi bos tea (27) i nfusi ons; however, i t was not found
i n our sampl es. Rabe et al . (1994) reported the presence
of l uteol i n, querceti n, and i soqueci tri n as phenol i c
metabol i tes i n rooi bos tea (27) l eaves and stems. Sny-
ckers and Sal emi (1974) reported that the anti al l ergi c
effect of rooi bos tea was mai nl y due to the fl avonol
querceti n. We found that the mai n fl avonol s were
querceti n and kaempferol i n rooi bos tea i nfusi ons.
The most preval ent fl avonol s, querceti n and kaempfer-
ol , were found i n 17 ki nds of tea i nfusi ons i ncl udi ng
Japanese green tea as descri bed above. Myri ceti n,
found i n green tea i nfusi ons, was found i n onl y jasmi ne
tea and pu-erh teas. The fl avon l uteol i n, whi ch was not
confi rmed i n our green tea i nfusi ons because of the trace
content, was found i n ground i vy l eaves tea (5), chry-
santhemum fl ower tea (7), and peri l l a l eaf tea (13)
i nfusi ons, api geni n was found i n great pl antai n tea (4),
peri l l a l eaf tea (13), and fi el d horsetai l tea (sugi nacha)
(15) i nfusi ons, and scutel l arei n was found i n great
pl antai n tea (oobakocha) (4), peri l l a l eaf tea (shi socha)
(13), and saffl ower fl ower (beni bana) tea (24) i nfusi ons.
Scutel l arei n, whi ch was reported to be the strongest
anti al l ergi c fl avonoi d in vitro among the many fl a-
vonoi ds tested by Kawasaki (1994), i s one of the mai n
components i n great pl antai n (oobako) tea (4) (Mi yai chi ,
1989; Ni shi be, 1995). I t was al so detected i n peri l l a l eaf
tea (13) and saffl ower tea (24) at concentrati ons of 2 and
0.3 mg/g i n whol e dri ed tea l eaves, respecti vel y. Typi cal
chromatogram of peri l l a l eaf tea i nfusi ons i s shown i n
Fi gure 2. The presence of scutel l arei n i n the peri l l a l eaf
Table 2. Amount (Milligrams per Gram) of 6 Flavonoids in 27 Kinds of Health Tea and Green Tea
fl avonol s
a,b
fl avons
a,b
tea Myr Que Kae Scu Lut Api
Angelica keiskei l eaves (ashi tabacha) 0.03 ( 0.04
c
Gynostemma pentaphylluml eaves (amachazurucha) 1.80 ( 0.31 0.90 ( 0.17
gi ngko l eaves (i choucha) 0.18 ( 0.03 0.17 ( 0.01
great pl antai n l eaves (oobakocha) 0.02 ( 0 2.08 ( 0.11
ground i vy l eaves (kaki doushi cha) 0.08 ( 0
Japanese persi mmon l eaves (kaki nohacha) 1 1.05 ( 0.12 1.27 ( 0.13
2 0.60 ( 0.04 0.56 ( 0.08
chrysanthemum fl ower (ki kubanacha) 2.51 ( 0.67
gymnema (gi munemacha) 1 1.79 ( 0.21 1.45 ( 0.27
2 1.73 ( 0.22 0.72 ( 0.09
3 3.23 ( 0.12 1.52 ( 0.08
guava (guabacha) 1.09 ( 0.08 0.04 ( 0.03
Chi nese matri mony vi ne (kukocha) 1.41 ( 0.08 0.62 ( 0.01
l ow stri ped bamboo l eaves (kumazasacha) 1
2 0.03 ( 0.04 0.03 ( 0.01 0.03 ( 0.01 0.02 ( 0.01
mul berry l eaves (kuwanohacha) 2.67 ( 0.12 0.76 ( 0.04
peri l l a l eaves (shi sonohacha) 1 2.25 ( 0.49 1.08 ( 0.08 1.17 ( 0.16
2 2.22 ( 0.99 1.35 ( 0.57 0.39 ( 0.10
jasmi ne (jasumi ncha) 0.72 ( 0.12 1.15 ( 0.22 0.95 ( 0.22
fi el d horsetai l l eaves (sugi nacha) 1.05 ( 0 0.76 ( 0.04
Rubus suavissimus (Chi nese tenncha) 1 1.64 ( 0.19 0.46 ( 0.04
2 1.06 ( 0.01 0.38 ( 0.03
Houttuynia cordata (dokudami cha) 1 3.81 ( 0.63 0.08 ( 0.01
2 3.01 ( 0.40 0.06 ( 0.01
gutta-percha (tochucha) 1 1.43 ( 0.20 0.23 ( 0.04
2 1.19 ( 0.12 0.16 ( 0.01
3 0.28 ( 0.04 0.05 ( 0
East I ndi an l otus (hasucha) 6.00 ( 0.21 0.12 ( 0.04 0.08 ( 0.03
adl ay (hatomugi cha)
banava (banavacha) 1 0.96 ( 0.12 0.34 ( 0.05
2 1.03 ( 0.07 0.30 ( 0.03
Japanese medl ar (bi wanohacha) 1 0.39 ( 0.05 0.13 ( 0.01
2 0.09 ( 0.02 0.04 ( 0.02 0.08 ( 0.03 0.18 ( 0.10
pu-erh (puarcha) 0.40 ( 0.22 0.52 ( 0.18 0.23 ( 0.09 0.05 ( 0.09
saffl ower (beni banacha) 0.38 ( 0.03 0.29 ( 0.04
eucal yptus (yukari cha) 0.22 ( 0.03
mugwort (yomogi cha)
rooi bos (rui boscha) 0.92 ( 0.10 0.16 ( 0.32
Japanese green (sencha) 1.31 ( 0.14 1.56 ( 0.18 1.49 ( 0.17
a
Myr, myri ceti n; Que, querceti n; Kae, kaempferol ; Scu, scutel l arei n; Lut, l uteol i n; Api , api geni n.
b
Mi l l i grams of fl avonoi ds per gram
of dri ed tea.
c
Means of tri pl i cate determi nati on and the standard devi ati ons.
Figure 2. Typi cal chromatogram of a peri l l a tea extract.
Peaks: (a) scutel l arei n, (b) l uteol i n, and (c) api geni n. HPLC
condi ti ons were the same as shown i n the l egend of Fi gure 1
except the rati o of mobi l e phase i s 5.5:4.5 (v/v).
Profiles of Potentially Antiallergic Flavonoids in Tea Infusions J. Agric. Food Chem., Vol. 45, No. 7, 1997 2563
tea i nfusi ons and saffl ower tea i nfusi ons was confi rmed
by compari ng the mass spectrum peaks of scutel l arei n
standard peak (m/z 287 [M + H]
+
, m/z 319 [M + CH
3
-
OH + H]
+
)wi th those of an extract from peri l l a l eaf tea
and an extract from saffl ower tea.
Scutel l arei n i s usual l y contai ned i n and i s a functi onal
component of great pl antai n (oobako). I t has been used
si nce anci ent ti mes as a di ureti c and as an anti -
i nfl ammatory and anti asthmati c drug i n Chi na and
Japan (Mi tsuhashi , 1988). We confi rmed that i t i s al so
contai ned i n peri l l a l eaves, whi ch are a very popul ar
food i n Japan, and i n saffl ower, whi ch i s eaten sal ted
wi th vi negar i n a l ocal area of Japan.
ACKNOWLEDGMENT
We thank Dr. Masaru Kawasaki (Foods and Drugs
Safety Center, Hadano-shi , Japan) for a sampl e of
scutel l arei n and val uabl e suggesti ons and Dr. Yuki hi ro
Goda (Nati onal I nsti tute of Heal th Sci ences, Tokyo,
Japan) for ki nd hel p for our study.
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Recei ved for revi ew January 10, 1997. Revi sed manuscri pt
recei ved Apri l 18, 1997. Accepted Apri l 28, 1997.
X
Thi s project
i s fi nanci al l y supported by the Human Heal th Sci ences
Foundati on.
JF970024Y
X
Abstract publ i shed i n AdvanceACS Abstracts, June
15, 1997.
2564 J. Agric. Food Chem., Vol. 45, No. 7, 1997 Toyoda et al.