Abstract

Oolong tea extract (OTE) and the purified polymeric polyphenols from OTE have been found to inhibit glucosyltransferase (GTase) of mutans streptococci. In view of the partial fermentation characteristic of oolong tea, we describe here an in vitro model reaction system to produce partially fermented products of d-(+)-catechin or green tea extract (GTE) using horseradish peroxidase. A dimeric catechin molecule was identified as dehydro-dicatechin A by instrumental analyses. The molecular size of some oligomeric catechins was estimated by the elution profile with HPLC. These catechin oligomers markedly inhibited GTase from Streptococcus sobrinus 6715. As the degree of polymerization of catechin or GTE increased, GTase was inhibited more effectively. These results suggest that polymeric polyphenols found in OTE are synthesized by partial fermentation due to oxidases/peroxidases present in tea leaves.

References

[1]
Hamada
S.
Slade
H.D.
(
1980
)
The biology, immunology, and cariogenicity of Streptococcus mutans
.
Microbiol. Rev.
 
44
,
331
384
.
[2]
Fujiwara
T.
Tamesada
M.
Bian
Z.
Kawabata
S.
Kimura
S.
Hamada
S.
(
1996
)
Deletion and reintroduction of glucosyltransferase genes of Streptococcus mutans and role of their gene products in sucrose dependent cellular adherence
.
Microb. Pathogen.
 
20
,
225
233
.
[3]
van Houte
J.
(
1994
)
Role of micro-organisms in caries etiology
.
J. Dent. Res.
 
73
,
672
681
.
[4]
Nakahara
K.
Kawabata
S.
Ono
H.
Ogura
K.
Tanaka
T.
Ooshima
T.
Hamada
S.
(
1993
)
Inhibitory effect of oolong tea polyphenols on glucosyltransferases of mutans streptococci
.
Appl. Environ. Microbiol.
 
59
,
968
973
.
[5]
Nakahara
K.
Kontani
M.
Ono
H.
Kodama
T.
Tanaka
T.
Ooshima
T.
Hamada
S.
(
1995
)
Glucosyltransferase from Streptococcus sobrinus catalyzes glucosylation of catechin
.
Appl. Environ. Microbiol.
 
61
,
2768
2770
.
[6]
Balentine
D.A.
(
1992
)
Manufacturing and chemistry of tea
. In:
Phenolic Compounds in Food and Their Effects on Health I. Analysis, occurrence, and Chemistry
  (
Ho
C.-T.
Lee
C.Y.
Huang
M.-T.
, Eds.), pp.
102
117
.
American Chemical Society
,
Washington, DC
.
[7]
Graham
H.N.
(
1992
)
Green tea composition, consumption, and polyphenol chemistry
.
Prevent. Med.
 
21
,
334
350
.
[8]
Furuta
T.
Koga
T.
Nisizawa
T.
Okahashi
N.
Hamada
S.
(
1985
)
Purification and characterization of glucosyl-transferases from Streptococcus mutans 6715
.
J. Gen. Microbiol.
 
131
,
285
293
.
[9]
Weinges
K.
Mattauch
H.
Wilkins
C.
Frost
D.
(
1971
)
Spektroskopische und chemische Konstitutionsaufklärung des Dehydro-dicatechins A
.
Liebigs Ann. Chem.
 
754
,
124
136
.
[10]
Ullah
M.R.
(
1991
)
Tea
. In:
Food Enzymology
  (
Fox
P.F.
, Ed.), pp.
163
187
.
Elsevier
,
London
.
[11]
Hammerschmidt
R.
Nuckles
E.M.
Kuc
J.A.
(
1982
)
Association of enhanced peroxidase activity with induced systemic resistance of cucumber to Colletotrichum lagenarium
.
Physiol. Plant Pathol.
 
20
,
73
82
.
[12]
Levine
A.
Tenhaken
R.
Dixon
R.
Lamb
C.
(
1994
)
H2O2 from the oxidative burst orchestrates the plant hypersensitive disease resistance response
.
Cell
 
79
,
583
593
.
[13]
Bradley
D.J.
Kjellbom
P.
Lamb
C.J.
(
1992
)
Elicitor- and wound-induced oxidative cross-linking of a proline-rich plant cell wall protein: a novel, rapid defense response
.
Cell
 
70
,
21
30
.
[14]
Kobayashi
A.
Koguchi
Y.
Kanzaki
H.
Kajiyama
S.
Kawazu
K.
(
1994
)
Production of a new type of bioactive phenolic compound
.
Biosci. Biotech. Biochem.
 
58
,
133
134
.
[15]
Kobayashi
A.
Koguchi
Y.
Kanzaki
H.
Kajiyama
S.
Kawazu
K.
(
1994
)
A new type of antimicrobial phenolics produced by plant peroxidase and its possible role in the chemical defense systems against plant pathogens
.
Z. Naturforsch.
 
49c
,
411
414
.
[16]
Mcevily
A.J.
Iyengar
R.
Gross
A.T.
(
1992
)
Inhibition of polyphenol oxidase by phenolic compound
. In:
Phenolic Compounds in Food and Their Effects on Health I. Analysis, Occurrence, and Chemistry
  (
Ho
C.-T.
Lee
C.Y.
Huang
M.-T.
, Eds.), pp.
318
325
.
American Chemical Society
,
Washington, DC
.
[17]
Ooshima
T.
Minami
T.
Aono
W.
Izumitani
A.
Sobue
S.
Fujiwara
T.
Kawabata
S.
Hamada
S.
(
1993
)
Oolong tea polyphenols inhibit experimental dental caries in SPF rats nfected with mutans streptococci
.
Caries Res.
 
27
,
124
129
.