Epigallocatechin
gallate (EGCG), also known as epigallocatechin
3-gallate, is the ester of epigallocatechin
and gallic acid, and is a type of catechin.
Molecular
formula C22H18O11
Molar
mass 458.37 g mol-1
Food
Sources: Carob flour is the best source
of epigallocatechin gallate but nuts,
fruits and green tea are also very good
sources. The dominant and most important
catechin in green tea is (-) Epigallocatechin
Gallate.
Epigallocatechin
gallate (EGCG), also known as epigallocatechin 3-gallate,
is the ester of epigallocatechin and gallic
acid, and is a type of catechin.
EGCG
is the most abundant catechin in tea and
is a potent antioxidant that may have
therapeutic applications in the treatment
of many disorders (e.g. cancer). It is
found in green - but not black - tea,
as EGCG is converted into thearubigins
in black teas. In a high temperature environment,
an epimerization change is more likely
to occur; however as exposure to boiling
water for 30 straight minutes only leads
to a 12.4% reduction in the total amount
of EGCG, the amount lost in a brief exposure
is insignificant. In fact, even when special
conditions were used to create temperatures
well over that of boiling water, the amount
lost scaled up only slightly.[3]
EGCG
can be found in many supplements.
EGCG
and HIV
There
has been research investigating the benefit
of EGCG from green tea in the treatment
of HIV infection, where EGCG has been
shown to reduce plaques related to AIDS-related
dementia in the laboratory, as well as
block gp120.[4][5][6] However, these
effects have yet to be confirmed in live
human trials, and it does not imply that
green tea will cure or block HIV infection,
but it may help regulate viral load as
long as it is not involved in adverse
drug reactions. The concentrations of
EGCG used in the studies could not be
reached by drinking green tea. More study
into EGCG and HIV is currently underway.[7]
EGCG
and Cancer
There
is increasing evidence to show that EGCG
along with other flavonoids can be beneficial
in treating brain,[8] prostate,[9][10] cervical[11] and bladder[12] cancers. EGCG has been shown to bind and
inhibit the anti-apoptotic protein Bcl-xl,[13] which has been implicated
in both cancer cell and normal cell survival.[14]
EGCG
and endometriosis
Xu
et al. found that antiangiogenic effects
of EGCG inhibits the growth of blood vessels
and thus reduces lesion size in experimental
endometriosis (mouse model).[16]
Drug
Interactions
A
recent study using mouse models at the
University of Southern California showed
that, in contrast to the myriad benefits
commonly associated with green tea and
green tea extract (GTE), EGCG binds with
the anti-cancer drug Velcade, significantly
reducing its bioavailability and thereby
rendering it therapeutically useless.[17] Dr. Schönthal, who headed the study,
suggests that consumption of green tea
and GTE products be strongly contraindicated
for patients undergoing treatment for
multiple myeloma and mantle cell lymphoma.[17] EGCG has a slight stimulatory
effect due to it increasing adrenaline
levels.[18][unreliable
source?]Epigallocatechin-3-gallate,
may reduce the bioavaialbilty of the drug
sunitinib when they are taken together.[19]
Possible
carcinogenic potential
EGCG
was, among other tea polyphenols, found
to be a strong topoisomerase inhibitor,
similar to some chemotherapeutic anticancer
drugs, for example, etoposide and doxorubicin. [20] [21] [22] [23][24] This property may be responsible for anticarcinogenic
however also a carcinogenic potential
of the substance. High intake of polyphenolic
compounds during pregnancy is suspected
to increase risk of neonatal leukemia.
Bioflavonoid supplements should not be
used by pregnant women.[25][26][27] A strong association between high intake
of tea during pregnancy and elevated risk
of childhood malignant central nervous
system (CNS) tumours was found.[28]
References
- http://chemicalland21.com/lifescience/-EPIGALLOCATECHINGALLATE.htm
- http://www.caymanchem.com/pdfs/70935.pdf
- . doi:10.1021/jf0730338.
- Williamson
MP, McCormick TG, Nance CL, Shearer
WT (December 2006). "Epigallocatechin
gallate, the main polyphenol in green
tea, binds to the T-cell receptor,
CD4: Potential for HIV-1 therapy". The Journal of Allergy and Clinical
Immunology 118 (6): 1369–74. doi:10.1016/j.jaci.2006.08.016.
- Hamza
A, Zhan CG (February 2006). "How can
(-)-epigallocatechin gallate from
green tea prevent HIV-1 infection?
Mechanistic insights from computational
modeling and the implication for rational
design of anti-HIV-1 entry inhibitors". The Journal of Physical Chemistry.
B 110 (6): 2910-7. doi:10.1021/jp0550762.
- Yamaguchi
K, Honda M, Ikigai H, Hara Y, Shimamura
T (January 2002). "Inhibitory effects
of (-)-epigallocatechin gallate on
the life cycle of human immunodeficiency
virus type 1 (HIV-1)". Antiviral
Research 53 (1): 19-34. doi:10.1016/S0166-3542(01)00189-9.
- Nance
CL, Shearer WT (November 2003). "Is
green tea good for HIV-1 infection?". The Journal of Allergy and Clinical
Immunology 112 (5): 851–3. doi:10.1016/j.jaci.2003.08.048.
- Das
A, Banik NL, Ray SK (November 2009).
"Flavonoids activated caspases for
apoptosis in human glioblastoma T98G
and U87MG cells but not in human normal
astrocytes". Cancer 116 (1): NA. doi:10.1002/cncr.24699.
- Hsieh
TC, Wu JM (October 2009). "Targeting CWR22Rv1 prostate cancer cell proliferation and gene
expression by combinations of the
phytochemicals EGCG, genistein, and
quercetin". Anticancer Research 29 (10): 4025–32. PMID 19846946. http://ar.iiarjournals.org/cgi/pmidlookup?view=long&pmid=19846946.
- Bettuzzi
S, Brausi M, Rizzi F, Peracchia G,
Corti A (January 2006). "Chemoprevention of Human Prostate Cancer by Oral Administration
of green Tea Catechins in Volunteers
with High-Grade Prostate Intraepithelial
Neoplasia: A Preliminary Report from
a One-Year Proof-of-Principle Study". American Associaation for Cancer
Research 66 (2): 1234-1240. http://cancerres.aacrjournals.org/cgi/reprint/66/2/1234.pdf.
- Qiao
Y, Cao J, Xie L, Shi X (September
2009). "Cell growth inhibition and
gene expression regulation by (-)-epigallocatechin-3-gallate
in human cervical cancer cells". Archives
of Pharmacal Research 32 (9): 1309-15. doi:10.1007/s12272-009-1917-3. PMID 19784588.
- Philips
BJ, Coyle CH, Morrisroe SN, Chancellor
MB, Yoshimura N (August 2009). "Induction
of apoptosis in human bladder cancer
cells by green tea catechins". Biomedical
Research 30 (4): 207–15. doi:10.2220/biomedres.30.207. PMID 19729851.
- Leone
M, Zhai D, Sareth S, Kitada S, Reed
JC, Pellecchia M (December 2003). "Cancer prevention by tea polyphenols is linked to their direct
inhibition of antiapoptotic Bcl-2-family
proteins". Cancer Research 63 (23): 8118–21. PMID 14678963. http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=14678963.
- Cherbonnel-Lasserre
C, Dosanjh MK (October 1997). "Suppression
of apoptosis by overexpression of
Bcl-2 or Bcl-xL promotes survival
and mutagenesis after oxidative damage". Biochimie 79 (9-10):
613-7. doi:10.1016/S0300-9084(97)82011-1.
- dead link
- doi:10.1016/j.fertnstert.2011.07.008
- Neith,
Katie. "Green tea
blocks benefits of cancer drug, study
finds". http://www.usc.edu/uscnews/stories/16226.html. Retrieved 2009-02-04.
- "Examine.com: Green Tea Catechins". http://examine.com/supplements/Green+Tea+Catechins/.
- Ge J, Tan BX, Chen Y, Yang L, Peng
XC, Li HZ, Lin HJ, Zhao Y, Wei M,
Cheng K, Li LH, Dong H, Gao F, He
JP, Wu Y, Qiu M, Zhao YL, Su JM, Hou
JM, Liu JY.,"Interaction of green
tea polyphenol epigallocatechin-3-gallate
with sunitinib: potential risk of
diminished sunitinib bioavailability",
J Mol Med (Berl). 2011 Jun;89(6):595-602
- Neukam,
K.; Pastor, N.; Cortés, F. (Jun 2008).
"Tea flavanols inhibit cell growth
and DNA topoisomerase II activity
and induce endoreduplication in cultured
Chinese hamster cells". Mutat Res 654 (1): 8-12. doi:10.1016/j.mrgentox.2008.03.013.
- DM.;
Mukhtar, H. (Oct 2001). "Green tea
constituent (-)-epigallocatechin-3-gallate
inhibits topoisomerase I activity
in human colon carcinoma cells". Biochem
Biophys Res Commun 288 (1): 101-5. doi:10.1006/bbrc.2001.5736.
- Suzuki,
K.; Yahara, S.; Hashimoto, F.; Uyeda,
M. (Sep 2001). "Inhibitory activities
of (-)-epigallocatechin-3-O-gallate
against topoisomerases I and II". Biol Pharm Bull 24 (9):
1088-90.
- Bandele,
OJ.; Osheroff, N. (Apr 2008). "(-)-Epigallocatechin gallate, a major constituent of green tea,
poisons human type II topoisomerases". Chem Res Toxicol 21 (4): 936–43. doi:10.1021/tx700434v. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2893035.
- Bandele,
OJ.; Osheroff, N. (May 2007). "Bioflavonoids as poisons of human topoisomerase II alpha and II
beta". Biochemistry 46 (20): 6097–108. doi:10.1021/bi7000664. PMC 2893030. PMID 17458941. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2893030.
- Paolini,
M.; Sapone, A.; Valgimigli, L. (Jun
2003). "Avoidance of bioflavonoid
supplements during pregnancy: a pathway
to infant leukemia?". Mutat Res 527 (1–2): 99-101. PMID 12787918.
- Strick,
R.; Strissel, PL.; Borgers, S.; Smith,
SL.; Rowley, JD. (Apr 2000). "Dietary bioflavonoids induce cleavage in the MLL gene and may
contribute to infant leukemia". Proc Natl Acad Sci U S A 97 (9): 4790-5. doi:10.1073/pnas.070061297. PMC 18311. PMID 10758153. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=18311.
- Ross,
JA. (Apr 2000). "Dietary flavonoids and the MLL gene: A pathway to infant leukemia?". Proc Natl Acad Sci U S A 97 (9): 4411-3. doi:10.1073/pnas.97.9.4411. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=34309.
- Plichart,
M.; Menegaux, F.; Lacour, B.; Hartmann,
O.; Frappaz, D.; Doz, F.; Bertozzi,
AI.; Defaschelles, AS. et al. (Aug
2008). "Parental smoking, maternal alcohol, coffee and tea consumption
during pregnancy and childhood malignant
central nervous system tumours: the
ESCALE study (SFCE)". Eur J
Cancer Prev 17 (4): 376-83. doi:10.1097/CEJ.0b013e3282f75e6f. PMC 2746823. PMID 18562965. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2746823.
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