4.7 Article

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

Journal

MARINE DRUGS
Volume 12, Issue 3, Pages 1569-1579

Publisher

MDPI AG
DOI: 10.3390/md12031569

Keywords

Anthogorgia ochracea; antiproliferative effect; guaiazulene-based analogue; zebrafish embryo; gorgonian

Funding

  1. National Natural Science Foundation of China [41176121, 41130858, 41322037, 81172977]
  2. National High Technology Research and Development Program of China (863 Program) [2013AA093001]
  3. Program for New Century Excellent Talents in University, Ministry of Education of China [NCET-11-0472]

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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 C-16 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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