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. 2010 Sep 22;58(18):10016-9.
doi: 10.1021/jf102311t.

Anticancer and anti-inflammatory effects of cysteine metabolites of the green tea polyphenol, (-)-epigallocatechin-3-gallate

Joshua D Lambert  1 , Shengmin Sang, Jungil Hong, Chung S Yang
Affiliations

Anticancer and anti-inflammatory effects of cysteine metabolites of the green tea polyphenol, (-)-epigallocatechin-3-gallate

Joshua D Lambert et al. J Agric Food Chem. .

Abstract

(-)-Epigallocatechin-3-gallate (EGCG) has been shown to have cancer preventive activity in vitro and in vivo. We have previously shown that EGCG can undergo conjugation to cysteine to form 2'-cysteinyl-EGCG and 2''-cysteinyl-EGCG. Studies of thiol-conjugated metabolites of methamphetamine indicate that such metabolites are not detoxified but retain biological activity. Here, we examined the growth inhibitory, pro-oxidant, and anti-inflammatory activities of the cysteine metabolites of EGCG. Both compounds dose-dependently inhibited the growth of colon cancer and intestinal cell lines. Both metabolites prevented aberrant arachidonic acid release and nitric oxide production by lipopolysaccharide-stimulated RAW264.7 cells. Under cell culture conditions, 2''-cysteinyl-EGCG produced H2O2 at a faster rate than EGCG. The results of the present study show that cysteine conjugates of EGCG retain the growth inhibitory, anti-inflammatory, and pro-oxidant activities of EGCG in vitro and may play a role in disease prevention in vivo. These results remain to be confirmed in vivo.

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Figures

Figure 1
Figure 1
Structure of EGCG, 2′-cysteinyl-EGCG, and 2″-cysteinyl-EGCG.
Figure 2
Figure 2
Growth inhibitory effects of 2′-cysteinyl-EGCG (A) and 2″-cysteinyl-EGCG (B) against HT-29, HCT-116, IEC-6 and INT-407A cells. Cells were treated for 48 h and growth inhibition was determined by the MTT assay. Each point represents n = 12 – 18. Error bars represent the standard deviation.
Figure 3
Figure 3
Effect of 2′-cysteinyl-EGCG, and 2″-cysteinyl-EGCG on NO production (A) and aberrant arachidonic acid release (B) by LPS-stimulated RAW264.7 murine macrophage cells. Data represent the mean of n = 3. Error bars represent the standard deviation. ** = p < 0.01 compared to LPS-stimulated control.
Figure 4
Figure 4
H2O2 generation by EGCG and 2″-cysteinyl-EGCG under cell culture conditions. EGCG or 2″-cysteinyl-EGCG (50 μM) were incubated in serum-free cell culture medium at 37°C under 5% CO2 atmosphere. Each point represents the mean of n = 6. Error bars represent that standard deviation. ** = p < 0.01.
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