Marine Drugs (Mar 2014)

Ochracenoids A and B, Guaiazulene-Based Analogues from Gorgonian Anthogorgia ochracea Collected from the South China Sea

  • Juan-Juan Zheng,
  • Chang-Lun Shao,
  • Min Chen,
  • Li-She Gan,
  • Yu-Chun Fang,
  • Xu-Hui Wang,
  • Chang-Yun Wang

DOI
https://doi.org/10.3390/md12031569
Journal volume & issue
Vol. 12, no. 3
pp. 1569 – 1579

Abstract

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Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3–6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C16 skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio.

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