Gracilosulfates A-G, Monosulfated Polyoxygenated Steroids from the Marine Sponge Haliclona gracilis

Mar Drugs. 2020 Aug 30;18(9):454. doi: 10.3390/md18090454.

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.

Keywords: Haliclona gracilis; anticancer activity; polyoxygenated steroids; sponge.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Haliclona / metabolism*
  • Humans
  • Kallikreins / metabolism
  • Male
  • Prostate-Specific Antigen / metabolism
  • Prostatic Neoplasms / drug therapy*
  • Prostatic Neoplasms / metabolism
  • Prostatic Neoplasms / pathology
  • Steroids / chemistry
  • Steroids / isolation & purification
  • Steroids / pharmacology*

Substances

  • Antineoplastic Agents
  • Steroids
  • KLK3 protein, human
  • Kallikreins
  • Prostate-Specific Antigen