Extending the Record of Meroditerpenes from Cacospongia Marine Sponges

Brent K. Rubio,† Rob W. M. van Soest,‡ and Phillip Crews*†
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California Santa Cruz, Santa Cruz, California 95064, and Zologisch Museum, University of Amsterdam, P.O. Box 94766, 1090 GT Amsterdam, The Netherlands
J. Nat. Prod., 2007, 70 (4), pp 628–631
DOI: 10.1021/np060633c
Publication Date (Web): March 9, 2007
Copyright © 2007 American Chemical Society and American Society of Pharmacognosy
†

 University of California, Santa Cruz.

,
‡

 University of Amsterdam.

,
*

 To whom correspondence should be addressed. E-mail:  phil@chemistry.ucsc.edu. Tel:  (831) 459-2603. Fax:  (831) 459-2935.

Abstract

Abstract Image

A new meroditerpene, (+)-isojaspic acid (1), along with two known meroditerpenes, cacospongin D (2) and jaspaquinol (3), have been isolated from a marine sponge Cacospongia. Comprehensive taxonomic identification distinguished this Cacospongia apart from morphologically similar Psammocinia. The absolute stereochemistry of 1 was elucidated on the basis of extensive 1D and 2D NMR techniques and analysis of the optical rotation versus (+)-zonarol (8), (+)-isozonarol (9), (−)-dactylosponol (10), and (+)-hyatellaquinone (11). Furthermore, bioactivity evaluation showed that the meroditerpenes isolated significantly inhibited Staphylococcus epidermidis.

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History

  • Published In Issue April 27, 2007
  • Received December 21, 2006

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