Sterols from Thai Marine Sponge Petrosia (Strongylophora) sp. and Their Cytotoxicity

Abstract

Eight new sterols (1–5 and 11–13), together with eight known compounds (6–10 and 14–16) were isolated from marine sponge Petrosia sp. The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis. The cytotoxicity of some compounds against a panel of human cancer cell lines is also reported.

Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

“…Structure 1 with relative stereochemistry as shown was thus assigned to erectusolide B, which contained fused cyclohexene and cyclobutane rings. It could derive from luffariolide A (Figure 1) [11], through a biogenetic pathway involving a 2 + 2 cycloaddition of double bonds at C-4/C-5 and C-10/C-11 as suggested by Lin, H.W. and co-workers [4].…”

“…Marine organisms have always been an attractive source of natural products with novel and exotic structures and useful biological activities [1,2,3,4,5,6,7,8,9,10,11]. Marine sponges of the genus Hyrtios (order Dictyoceratida family Thorectidae) have yielded scalarane [6,8,12,13,14] and manoalide [12] types sesterterpenes, which are important groups of active secondary metabolites.…”

“…Marine sponges of the genus Hyrtios (order Dictyoceratida family Thorectidae) have yielded scalarane [6,8,12,13,14] and manoalide [12] types sesterterpenes, which are important groups of active secondary metabolites. They have been reported to possess many biological activities, such as cytotoxic [3,6,15,16], antibacterial [9,11], antibiotic [17] activities, inhibition of the DNA-relaxing activity of mouse DNA topoisomerase I [12], and enhancement nerve growth factor synthesis in cultured astroglial cells [13]. As a part of our ongoing research program focused on the discovery of cytotoxic compounds from Thai marine sponges [18,19,20], drawing from the previous report, one sesterterpene, erectusolide A, six phenolic alkenes, erectuseneols A–F, together with nine known compounds, were isolated from the EtOAc soluble extract of Hyrtios erectus (Chulabhorn Research Institute (CRI) 588) [3].…”

Marine natural products

“…The absolute conguration of these compounds was established by comparison of calculated and experimental ECD spectra. 468 A number of steroid 1178-1187, 469 were isolated from sponges of the genera Crella, Dysidea, Petrosia and Poecillastra. A Korean specimen of Clathria gombawuiensis was the source of gombasterol A-F 1197-1202, heavily oxygenated sterols with four congeners having the unusual C/D cis ring fusion, yielding new members of the H-14b family of marine sterols.…”

Microbial Sterolomics as a Chemical Biology Tool

“…Some of these compounds, other known analogues, and seven new analogues have also been extracted from the marine sponge Petrosia ( Strongylophora ) sp. Compounds 130 , 131 , 134 – 141 , and 143 – 147 ( Figure 15 ) displayed micromolar inhibition across various human cancer cell lines tested, with the ketal 139 showing weaker activity [ 99 ]. Representatives from this class of steroids from Xestospongia spp.…”