New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities.

Kseniya M Tabakmakher,Roman S Popov,Vladimir A Denisenko,Tatyana N Makarieva,Carsten Bokemeyer,Nguyen X Cuong,Sergey A Dyshlovoy,Boris B Grebnev,Pavel S Dmitrenok,Gunhild Von Amsberg

doi:10.3390/md17080445

Abstract

Seven new unusual polysulfated steroids—topsentiasterol sulfate G (1), topsentiasterol sulfate I (2), topsentiasterol sulfate H (3), bromotopsentiasterol sulfate D (4), dichlorotopsentiasterol sulfate D (8), bromochlorotopsentiasterol sulfate D (9), and 4β-hydroxyhalistanol sulfate C (10), as well as three previously described—topsentiasterol sulfate D (7), chlorotopsentiasterol sulfate D (5) and iodotopsentiasterol sulfate D (6) have been isolated from the marine sponge Halichondria vansoesti. Structures of these compounds were determined by detailed analysis of 1D- and 2D-NMR and HRESIMS data, as well as chemical transformations. The effects of the compounds on human prostate cancer cells PC-3 and 22Rv1 were investigated.

Highlights

Active trisulfated steroids are characteristic secondary metabolites found in some marine sponges
One more subgroup includes topsentiasterol sulfates A–E from the sponge Topsentia sp. [15], Sch 575867 from the deep-water sponge belonging to the family Astroscleridae [16], spheciosterol sulfates from the sponge Spheciospongia sp. [17], as well as chloro- and iodotopsentiasterol sulfates D, isolated from the
Ten polysulfated steroids 1–10 were isolated from the Vietnamese marine sponge Halichondria vansoesti

Summary

Introduction

Active trisulfated steroids are characteristic secondary metabolites found in some marine sponges. These polar steroids comprise several structural subgroups in the sponges. The first compound, bearing a common 2β,3α,6α-trisulfoxy steroid nucleus, halistanol sulfate, was isolated in 1981 from the Okinawan sponge Halichondria cf moorei [1] (Figure S1). The subgroup includes sokotrasterol sulfate from the sponge Halichondria sp. [13], and Petrosia strongilata [14] In their steroid nuclei, 2β,3α,6α-trisulfoxy functionality is combined with a C-9(11)-double bond and a methyl group at C-14. One more subgroup includes topsentiasterol sulfates A–E from the sponge Topsentia sp. One more subgroup includes topsentiasterol sulfates A–E from the sponge Topsentia sp. [15], Sch 575867 from the deep-water sponge belonging to the family Astroscleridae [16], spheciosterol sulfates from the sponge Spheciospongia sp. [17], as well as chloro- and iodotopsentiasterol sulfates D, isolated from the sponge Topsentia sp. in our laboratory [18]

Methods

Results

Conclusion