Bioactive sesterterpenoids from a Korean sponge Monanchora sp

J Nat Prod. 2013 Feb 22;76(2):170-7. doi: 10.1021/np300573m. Epub 2013 Jan 29.

Abstract

Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Furans / isolation & purification
  • Humans
  • Korea
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification*
  • Sesterterpenes / pharmacology*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Furans
  • Sesterterpenes
  • Spiro Compounds
  • spiroketal