Pachycladins A-E, prostate cancer invasion and migration inhibitory Eunicellin-based diterpenoids from the red sea soft coral Cladiella pachyclados

J Nat Prod. 2010 May 28;73(5):848-53. doi: 10.1021/np900787p.

Abstract

Alcyonaria species are among the important marine invertebrate classes that produce a wealth of chemically diverse bioactive diterpenes. Examples of these are the potent microtubule disruptor sarcodictyins and eleutherobin. The genus Cladiella has proven to be a rich source of cytotoxic eunicellin-based diterpenoids. Five new eunicellin diterpenes, pachycladins A-E (1-5), were isolated from the Red Sea soft coral Cladiella pachyclados. The known sclerophytin A Cladiellisin, 3-acetylcladiellisin, 3,6-diacetylcladiellisin, (+)-polyanthelin A, klysimplexin G, klysimplexin E, sclerophytin F methyl ether, (6Z)-cladiellin (cladiella-6Z,11(17)-dien-3-ol), sclerophytin B, and patagonicol were also identified. The structures of the isolated compounds were elucidated by extensive interpretation of their spectroscopic data. These compounds were evaluated for their ability to inhibit growth, proliferation, invasion, and migration of the prostate cancer cells PC-3. Some of the new metabolites exhibited significant anti-invasive activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Bridged-Ring Compounds / chemistry
  • Cell Movement / drug effects
  • Cell Proliferation / drug effects
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Humans
  • Indian Ocean
  • Male
  • Marine Biology
  • Molecular Structure
  • Prostatic Neoplasms / drug therapy*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Wound Healing / drug effects

Substances

  • Antineoplastic Agents
  • Bridged-Ring Compounds
  • Diterpenes
  • Furans
  • eleutherobin
  • eunicellin
  • sclerophytin F
  • patagonicol