Gracilosulfates A–G, Monosulfated Polyoxygenated Steroids from the Marine Sponge Haliclona gracilis
Larisa K. Shubina, Tatyana N. Makarieva, В. А. Денисенко, Roman S. Popov, Sergey A. Dyshlovoy, Boris B. Grebnev, Pavel S. Dmitrenok, Gunhild von Amsberg, Valentin A. Stonik
Abstract
Seven new polyoxygenated steroids belonging to a new structural group of sponge steroids, gracilosulfates A–G (1–7), possessing 3β-O-sulfonato, 5β,6β epoxy (or 5(6)-dehydro), and 4β,23-dihydroxy substitution patterns as a common structural motif, were isolated from the marine sponge Haliclona gracilis. Their structures were determined by NMR and MS methods. The compounds 1, 2, 4, 6, and 7 inhibited the expression of prostate-specific antigen (PSA) in 22Rv1 tumor cells.
Topics & Concepts
SpongeStereochemistryChemistryBiologyBotanyMarine Sponges and Natural ProductsSynthetic Organic Chemistry MethodsTraditional and Medicinal Uses of Annonaceae