Topsensterols A-C, Cytotoxic Polyhydroxylated Sterol Derivatives from a Marine Sponge Topsentia sp.

Min Chen,Xu-Dong Wu,Qing Zhao,Chang-Yun Wang

doi:10.3390/md14080146

Min Chen, Xu-Dong Wu + Show 2 more

Open Access

https://doi.org/10.3390/md14080146

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Journal: Marine Drugs	Publication Date: Aug 1, 2016
Citations: 23	License type: CC BY 4.0

Affiliation: Ocean University of China, Yangzhou University

Abstract

Three new polyhydroxylated sterol derivatives topsensterols A–C (1–3) have been isolated from a marine sponge Topsentia sp. collected from the South China Sea. Their structures were elucidated by detailed analysis of the spectroscopic data, especially the NOESY spectra. Topsensterols A–C (l–3) possess novel 2β,3α,4β,6α-tetrahydroxy-14α-methyl Δ9(11) steroidal nuclei with unusual side chains. Compound 2 exhibited cytotoxicity against human gastric carcinoma cell line SGC-7901 with an IC50 value of 8.0 μM. Compound 3 displayed cytotoxicity against human erythroleukemia cell line K562 with an IC50 value of 6.0 μM.

Highlights

Most marine invertebrates are soft bodied and have a sedentary life style, resulting in the formation of distinctive chemical protection strategy [1,2]
The frozen sample sampleofofsponge spongeTopsentia at room temperature, and the solution was evaporated under with 95% EtOH (8 L 5 times) at room temperature, and the EtOH solution was evaporated under reduced pressure pressure to to give give the the crude crude extract
This extract was subjected to a silica gel column chromatograph (CC) and the fractions were purified octadecylsilyl silica gelgel andand semi-preparative to obtain compounds by octadecylsilyl silica semi-preparative to obtain compounds was obtained as a white amorphous powder

Summary

Introduction

Most marine invertebrates are soft bodied and have a sedentary life style, resulting in the formation of distinctive chemical protection strategy [1,2]. Marine invertebrates represent a rich source of structurally novel and mechanistically unique secondary metabolites for the discovery of new drug leads [3]. Sponges (Porifera) including the genus of Topsentia have been recognized as outstanding producers of sterols possessing novel side chains with unique alkylation and dealkylation patterns and displaying a variety of biological activities [4,5,6,7]. In our continuing efforts to discover new bioactive substances from marine invertebrates, a chemical investigation of a sponge of Topsentia sp. Three new polyhydroxylated steroids, topsensterols A–C (1–3) (Figure 1), were isolated from its n-butanol extract.

Discussion

2, Supplementary

General Experimental Procedures

Animal Material

Extraction and Isolation

Conclusions