New diterpenes of the pseudopterane class from two closely related Pseudopterogorgia species: Isolation, structural elucidation, and biological evaluation

ORGN 405

Jeffrey Marrero, arodrig@cnnet.upr.edu1, Claudia A. Ospina, clospina69@hotmail.com1, Abimael D. Rodrígiuez, arodrig@cnnet.upr.edu1, Raphael G. Raptis, raphael@adam.uprr.pr1, Peter Baran1, Scott G. Franzblau, sgf@uic.edu2, and Eduardo Ortega-Barria3. (1) Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346, (2) Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL 60612, (3) Cell and Molecular Biology of Pathogens Unit, Institute for Tropical Medicine and Health Sciences, Florida State University-Panamá, La Boca 1034, Balboa, Ancón, Panama
Parallel chemical investigations of the hexane and chloroform extracts of the sea plumes Pseudopterogorgia bipinnata and Pseudopterogorgia kallos have led to the discovery of seven new diterpenoids of the pseudopterane class, namely, kallolide D, kallolide D acetate, kallolide E, kallolide F, kallolide G, kallolide H, and kallolide I, in addition to ten previously described compounds of the pseudopterane and gersolane families of diterpenes. The chemical structures of the new metabolites were established by 1D- and 2D-NMR, IR, UV, HRMS, and, in some instances, by single-crystal X-ray crystallographic analyses. Biological screening of these metabolites revealed significant anti-parasitic activity but marginal anti-tubercular activity.

 

New Reactions and Methodology, Bioorganic Chemistry, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006