Cytotoxic Phyllactone Analogs from the Marine Sponge Phyllospongia papyrecea

Author(s): Huawei Zhang*, Phillip Crews, Karen Tenney, Frederick A. Valeriote.

Journal Name: Medicinal Chemistry

Volume 13 , Issue 3 , 2017

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Abstract:

Background: A growing evidence indicates that marine sponge Phyllospongia sp. is one of rich sources of 20, 24-bishomoscalarane sesterterpenes with potent biological activities. In order to search more bioactive 20, 24-bishomoscalarane sesterterpenes for new drug discovery, chemical investigation was carried out on an Indonesian marine sponge P. papyrecea.

Methods: Bioassay-guided fractionation was carried out on its dichloromethane extract. And nine compounds were purified and isolated using HPLC. Their chemical structures were determined by a combination of spectroscopic and spectrometric data, including 1D-, 2D-NMR and HRESI-MS. Their cytotoxic activities were performed on three human tumor cell lines A549, MCF-7 and HeLa using the CCK-8 method.

Results: One new 20, 24-bishomoscalarane sesterterpene, phyllactone H (9), was isolated and elucidated together with phyllactones A-B (1-2) and D-G (3-6), 12α, 24-dihydroxy-20, 24-dimethyl-15, 17- scalaradien-25, 24-olides (7-8). Compounds 1 and 2, 3 and 4, 5 and 6, 7 and 8 were C-24 anomers and inseparable mixtures, respectively. The 1H and 13C-NMR data for 7/8 were firstly reported in this paper.

Conclusion: Compounds 1-9 possessed in vitro moderate cytotoxicities against A549, MCF-7 and HeLa cells with IC50 values of less than 25 μM.

Keywords: Marine sponge, Phyllospongia papyrecea, sesterterpene, phyllactone, cytotoxic activity.

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Article Details

VOLUME: 13
ISSUE: 3
Year: 2017
Page: [295 - 300]
Pages: 6
DOI: 10.2174/1573406412666161007150828
Price: $65

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