Novel Cytotoxic Oxygenated C29 Sterols from the Colombian Marine Sponge Polymastia tenax

Santafé, Gílmar; Paz, Vanessa; Rodrı́guez, Jaime; Jiménez, Carlos

doi:10.1021/np0200459

Cited by 40 publications

(24 citation statements)

References 9 publications

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“…Phyllanthin, a lignan compound, is a known principal constituent of P. niruri and there have been no data reported on its cytotoxic effect. Sterol glucoside was also been detected in PPWH-7 and sterols isolated from various marine organisms and alga was reported to possess cytotoxic activity [58]–[60].…”

Section: Discussionmentioning

confidence: 99%

Growth Inhibition of Human Gynecologic and Colon Cancer Cells by Phyllanthus watsonii through Apoptosis Induction

et al. 2012

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Phyllanthus watsonii Airy Shaw is an endemic plant found in Peninsular Malaysia. Although there are numerous reports on the anti cancer properties of other Phyllanthus species, published information on the cytotoxicity of P. watsonii are very limited. The present study was carried out with bioassay-guided fractionation approach to evaluate the cytotoxicity and apoptosis induction capability of the P. watsonii extracts and fractions on human gynecologic (SKOV-3 and Ca Ski) and colon (HT-29) cancer cells. P. watsonii extracts exhibited strong cytotoxicity on all the cancer cells studied with IC50 values of ≤ 20.0 µg/mL. Hexane extract of P. watsonii was further subjected to bioassay-guided fractionation and yielded 10 fractions (PW-1→PW-10). PW-4→PW-8 portrayed stronger cytotoxic activity and was further subjected to bioassay-guided fractionation and resulted with 8 sub-fractions (PPWH-1→PPWH-8). PPWH-7 possessed greatest cytotoxicity (IC50 values ranged from 0.66 – 0.83 µg/mL) and was selective on the cancer cells studied. LC-MS/MS analysis of PPWH-7 revealed the presence of ellagic acid, geranic acid, glochidone, betulin, phyllanthin and sterol glucoside. Marked morphological changes, ladder-like appearance of DNA and increment in caspase-3 activity indicating apoptosis were clearly observed in both human gynecologic and colon cancer cells treated with P. watsonii especially with PPWH-7. The study also indicated that P. watsonii extracts arrested cell cycle at different growth phases in SKOV-3, Ca Ski and HT-29 cells. Cytotoxic and apoptotic potential of the endemic P. watsonii was investigated for the first time by bioassay-guided approach. These results demonstrated that P. watsonii selectively inhibits the growth of SKOV-3, Ca Ski and HT-29 cells through apoptosis induction and cell cycle modulation. Hence, P. watsonii has the potential to be further exploited for the discovery and development of new anti cancer drugs.

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Section: Discussionmentioning

confidence: 99%

Growth Inhibition of Human Gynecologic and Colon Cancer Cells by Phyllanthus watsonii through Apoptosis Induction

et al. 2012

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“…One oxygenated methine carbon resonated at d 71.8 (C-3), one oxygenated quaternary carbon at d 82.5 (C-17), and two trisubstituted double bond carbon atoms C-5 and C-6 at d 140. 6 19), and four methyl doublets at d 0.79 (J ¼ 6.5 Hz, Me-26), 0.81 (J ¼ 6.5 Hz, Me-29), 0.85 (J ¼ 6.9 Hz, Me-27), and 0.90 (J ¼ 6.9 Hz, Me-21). The characteristic H-6 of steroid 5,6-enes was noticed at d 5.33 as a doublet (J ¼ 5.5 Hz).…”

Section: Resultsmentioning

confidence: 99%

New cytotoxic steroids from the fruits ofSyzygium siamense

Chumkaew¹,

Kato²,

Chantrapromma³

2010

Journal of Asian Natural Products Research

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A new sterol, stigmast-5-ene-3beta,17alpha-diol (1), together with six known compounds, stigmast-5-ene-3beta-yl formate (2), stigmast-5-ene-3beta,7alpha-diol (3), stigmast-5-ene-7alpha-methoxy-3beta-ol (4), stigmast-5-ene-3-one (5), 3beta-sitostanol (6), and 3beta-sitosterol (7), was isolated from the fruits of Syzygium siamense, of which compound 2 is reported for the first time from a natural source. Their structures were elucidated by spectroscopic methods. The isolated compounds (1-7) were evaluated for their cytotoxic activities against human oral epidermoid carcinoma cancer (KB), human breast cancer (BC), and human small cell lung cancer (NCI-H187) cell lines.

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“…However, little information is known about this species, and the only detected classes of compounds already described for the genus Polymastia are sterols and tetrahydroxyamide [40,41]. These compounds exhibited significant cytotoxic activity toward human lung carcinoma (A-549), human colon carcinomas (HT-29 and H-116), mice endothelial (MS-1), and human prostate carcinoma (PC-3) cell lines in the range of 0.5-10 μg/mL, but the mechanisms underlying these properties were not reported.…”

Section: Discussionmentioning

confidence: 99%

Extracts of marine sponge Polymastia janeirensis induce oxidative cell death through a caspase-9 apoptotic pathway in human U138MG glioma cell line

Frota¹,

Braganhol²,

Cañedo³

et al. 2008

Invest New Drugs

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We have studied the apoptotic pathway activated in response to marine sponge extracts of Polymastia janeirensis. The effect on intracellular ROS production was also examined. Exposure of U138MG glioma cell line to doses higher than 5 microg/mL has decreased glioma cell viability, with an IC(50) <15 microg/mL for both aqueous and organic extracts. However, extracts at higher doses (50 and 100 microg/mL) have stronger cytotoxic effects, decreasing more than 90% of glioma cell viability. The antioxidant Trolox (100 microM) reversed the cell death percentage induced by extracts at 10 and 25 microg/mL. The type of cell death induced by such high doses was predominantly necrosis, while a high percentage of apoptotic glioma cells was found at 10 microg/mL. Moreover, inhibition of caspase-8 with Z-IETD (a caspase-8 inhibitor) had no effect on the amount of apoptosis induced by 10 microg/mL, but inhibition of caspase-9 with Z-LEHD (a caspase-9 inhibitor) decreased apoptosis. We also observed a dose-dependent increase in ROS production, and similarly to effects observed on viability of glioma cells, and on cell death, higher doses also had more severe effects. Co-treatment with Trolox significantly reduced ROS production by extracts at doses lower than 50 microg/mL. This is a first report demonstrating that marine sponge extracts of P. janeirensis induce oxidative cell death through a caspase-9 apoptotic pathway.

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Novel Cytotoxic Oxygenated C29 Sterols from the Colombian Marine Sponge Polymastia tenax

Cited by 40 publications

References 9 publications

Growth Inhibition of Human Gynecologic and Colon Cancer Cells by Phyllanthus watsonii through Apoptosis Induction

Growth Inhibition of Human Gynecologic and Colon Cancer Cells by Phyllanthus watsonii through Apoptosis Induction

New cytotoxic steroids from the fruits ofSyzygium siamense

Extracts of marine sponge Polymastia janeirensis induce oxidative cell death through a caspase-9 apoptotic pathway in human U138MG glioma cell line

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