• Archives of Pharmacal Research
• /
• v.24 no.5
• /
• pp.441-445
• /
• 2001

Resveratrol, a trihydroxystilbene found in grapes and several plants, has been shown to be active in inhibiting multistage carcinogenic process. Using resveratrol as the prototype, we synthesized several analogs and evaluated their growth inhibitory effect using cultured human cancer cells. In the present report we show that one of the resveratrol analogs, 3, 5,2',4'-tetramethoxy-trans-stilbene, potentiated the inhibition of cancer cell growth. Prompted by the strong growth Inhibitory activity of the compound ($IC_{50}$; $0.8{\mu}$ g/ml) compared to resveratrol ($IC_{50}$; $18{\mu}$ug/ml) in cultured human colon cancer cells (Col2), we performed an action mechanism study using the compound. The compound induced the accumulation of cellular DNA contents in the sub-CO phase DNA contents of the cell cycle by in a time-dependent manner. The morphological changes were also consistent with an apoptotic process. This result indicated that the compound induced apoptosis of cancer cells, and may be a candidate for use in the development of potential cancer chemotherapeutic or cancer chemopreventive agents.

• Journal of Applied Biological Chemistry
• /
• v.44 no.1
• /
• pp.20-22
• /
• 2001

We have attempted to synthesize polyhydroxy stilbene compounds through the benzyl thioether moiety. During synthesis, we unexpectedly observed that demethylation of the compound under $AlCl_3$ in ethanethiol resulted in a regioselective addition of thiol to the double bond as well as complete demethylation. We report on the regioselective short synthesis for general structure and its structural identification.

• Biomolecules & Therapeutics
• /
• v.15 no.2
• /
• pp.95-101
• /
• 2007

Resveratrol (3,5,4’-trihydroxy-trans-stilbene), a naturally occurring phytoallexin abundant in grapes and several plants, has been shown to be active in inhibiting proliferation and inducing apoptosis in several human cancer cell lines. On the line of the biological activity of resveratrol, a variety of resveratrol analogs were synthesized and evaluated for their growth inhibitory effects against several human cancer cell lines. In the present study, we found that one of the resveratrol analogs, 3,4,5-trimethoxy-4’-bromo-cis-stilbene, markedly suppressed human colon cancer cell proliferation (EC$_{50}$ = 0.01 ${\mu}$g/ml), and the inhibitory activity was superior to its corresponding trans-isomer (EC$_{50}$ = 1.6 ${\mu}$g/ml) and resveratrol (EC$_{50}$ = 18.7 ${\mu}$g/ml). Prompted by the strong growth inhibitory activity in cultured human colon cancer cells (Col2), we investigated its mechanism of action. 3,4,5-Trimethoxy-4’-bromo-cis-stilbene induced arrest of cell cycle progression at G2/M phase and increased at sub-G1 phase DNA contents of the cell cycle in a time- and dose-dependent manner. Colony formation was also inhibited in a dose-dependent manner, indicating the inhibitory activity of the compound on cell proliferation. Moreover, the morphological changes and condensation of the cellular DNA by the treatment of the compound were well correlated with the induction of apoptosis. These data suggest the potential of 3,4,5-trimethoxy-4’-bromo-cis-stilbene might serve as a cancer chemotherapeutic or chemopreventive agent by virtue of arresting the cell cycle and inducing apoptosis for the human colon cancer cells.

• Archives of Pharmacal Research
• /
• v.25 no.5
• /
• pp.636-639
• /
• 2002

The extract of the root of Polygonum multiflorum exhibited a significant antioxidant activity assessed by the DPPH radical scavenging activity in vitro. The bioassay-guided fractionation of the extract yielded a stilbene glucoside, (E)-2,3,5,4'-tetrahydroxystilbene-2-Ο-$\beta$-d-glucopyranoside (1) as an active constituent responsible for the antioxidant property. Compound 1 demonstrated a moderate DPPH radical scavenging activity ($IC_{50}$, 40 $\mu$M), while the corresponding deglucosylated stilbene 2 exhibited a much higher activity ($IC_{50}$, 0.38 $\mu$M).

• YAKHAK HOEJI
• /
• v.42 no.1
• /
• pp.1-4
• /
• 1998

In continued studies on cultivated Korean rhubarb rhizomes, three additional stilbene compounds were isolated from water extract by column chromatographic separation using Sepha dex LH-20, ODS-gel. Compound I, desoxyrhapontigenin(3,5-dihydroxy-4`-methoxystilbene), Compound II, rhapontigenin(3,3`,5-trihydroxy-4`-methoxystilbene), and compound III, piceatannol(3,3`,4`,5-tetrahydroxystilbene) were elucidated based on physico-chemical and spectroscopic evidences(UV, IR, $^1H$-NMR, $^13C$-NMR and Mass).

• YAKHAK HOEJI
• /
• v.51 no.2
• /
• pp.140-144
• /
• 2007

Polygonum cuspidatum has been used as treatments of dermatitis, gonorrhea, inflammation, and hyperlipidaemia in traditional medicine. We examined liver protective effect on CCl$_4$ inducing hepatotoxicity and anti-oxidative activity by TBA method. Phytochemical examination of Polygonum cuspidatum led to the isolation and characterization of emodin 8-O-${\beta}$-D-glucopyranoside (compound 1), and trans-resveratrol 3-O-${\beta}$-D-glucopyranoside (compound 2). Compounds 1 and 2 enhanced the inhibition of anti-lipid peroxidative effects in liver homogenate. In chemical parameters obtained from serum analysis, compounds 1 and 2 also revealed significant decrease in hepatotoxicity. These results suggested that the antraquinone and stilbene which were isolated from Polygonum cuspidatum might be used as therapeutic agent of hepatitis.

• Archives of Pharmacal Research
• /
• v.29 no.11
• /
• pp.946-951
• /
• 2006

One new stilbene glucoside (6), along with five known compounds (1-5), were isolated from the roots of Polygonum multiflorum Thumb., and their chemical structures established based on physicochemical and spectroscopic data. Of the compounds, compound 3 showed DNA topoisomerase I and II inhibitory activities.

• Proceedings of the PSK Conference
• /
• 2000.10a
• /
• pp.133.1-133.1
• /
• 2000

• Proceedings of the PSK Conference
• /
• 2002.04a
• /
• pp.107.1-107.1
• /
• 2002

• Natural Product Sciences
• /
• v.25 no.3
• /
• pp.244-247
• /
• 2019

A new isoprenylated stilbene, flavestinK (1) together with two known isoprenylated stilbenes, flavestin B (2), flavestin G (3), and two isoprenilated flavanones, 4-O-methyl-8-isoprenylnaringenin (4) and 8-isoprenyl-5,7-dihydroxyflavanone (5) were isolated from the leaves of Macaranga recurvata Gage. All of the structures have been determined based on HRESIMS, 1D and 2D NMR spectral data. All of the isolated compounds were evaluated for their cytotoxicity against three human cancer cells (HeLa, T47D and WiDr). Compound 1 showed higher activity than doxorubicin against HeLa cells with $IC_{50}$ value of $13.1{\mu}g/mL$.