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Planta Med 2006; 72(8): 735-739
DOI: 10.1055/s-2006-931584
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Calyculatine: a New Dolabellane Diterpenoid from the Marine Sponge Eunicea calyculata

Wei Xiang1 , 2 , Leng Chee Chang1
  • 1Department of Chemistry and Biochemistry, College of Science and Engineering, University of Minnesota Duluth, Duluth, MN, U.S.A.
  • 2Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan, P. R. China
Further Information

Publication History

Received: December 23, 2005

Accepted: February 16, 2006

Publication Date:
31 May 2006 (online)

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Abstract

A new dolabellane diterpenoid, 7(S)-hydroperoxy-13-keto-(1S,11R)-dolabella-3(E),8(17),12(18)-triene (1), and two known compounds, 7(S),8(S)epoxy-13-keto-1(S),11(R)-dolabella-3(E),12 (18)-diene (2) and 13-keto-1(S),11(R)-dolabella-3(E),7(E),12(18)-triene (3), were isolated from the marine sponge Eunicea calyculata. The structure of 1 was elucidated by 1D 1H- and 13C-NMR spectra and 2D HMQC, HMBC, and the relative stereochemistry was established by analysis of coupling constants and NOESY spectra. In addition, an X-ray crystallographic analysis on a single crystal of 2 was carried out. Compounds 1 and 2 were inactive in the hyphae formation inhibition assay (HFI) in Streptomyces 85E while compound 3 showed inhibitory activity at a concentration of 20 μg/20 μL in the HFI assay.

Key words

Eunicea calyculata - dolabellane diterpenoid - calyculatine - hyphae formation inhibition - Streptomyces 85E

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Dr. Leng Chee Chang

Department of Chemistry and Biochemistry

246 Chemistry Building

1039 University Drive

University of Minnesota Duluth

Duluth

Minnesota 55812-3020

U.S.A.

Phone: +1-218-726-7346

Fax: +1-218-726-7394

Email: lcchang@d.umn.edu