Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

Abstract

The title compound, C21H28O, was isolated from the cytotoxic lipid extract of the Fidjian soft coral Nephthea sp. The steroid showed inhibitory activity to human colon adenocarcinoma SW480 cells (IC50 = 2.5 µg ml−1). The mol­ecular structure indicates that the A ring is almost planar (r.m.s. deviation = 0.032 Å), the B and C rings adopt chair conformations and the five-membered D ring is a half-chair. The B/C and C/D ring junctions are trans-fused.

Chemical Constituents and Biological Properties of the Marine Soft Coral <em>Nephthea</em>: A Review (Part 2)

“…[45]. A steroid, Pregna-1,4,20-trien-3-one (102), was identified which was found to exhibit inhibitory activity against human colon adenocarcinoma SW480 cells (IC 50 = 2.5 μg/ml) [46]. Furthermore two known alkaloids, nephoxaloid and caulerpin, have also been reported [47].…”

Chemical and Biological Diversity in Nephthea Soft Corals in the Current Decade: A Review

“…Tabot et al, isolated compound; pregna-1, 4, 20-trien-3one (40) from the DCM fraction of Nephthea sp. It showed inhibitory activity against human colon adenocarcinoma SW-480 cells (IC50 = 2.4 μg/ml)[25]. Here, we compile the steroids isolated from the genus Nephthea in the current decade as shown in table {1} and figures {1-3}.…”

“…Figure 2. Chemical structures of compounds(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29) …”