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Cytotoxic Phyllactone Analogs from the Marine Sponge Phyllospongia papyrecea.


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.

SUBMITTER: Zhang H 

PROVIDER: S-EPMC5384874 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Cytotoxic Phyllactone Analogs from the Marine Sponge Phyllospongia papyrecea.

Zhang Huawei H   Crews Phillip P   Tenney Karen K   Valeriote Frederick A FA  

Medicinal chemistry (Shariqah (United Arab Emirates)) 20170101 3


<h4>Background</h4>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.<h4>Methods</h4>Bioassay-guided fractionation was carried out on its dichloromethane extract. And nine compounds were purified and isol  ...[more]

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