Novel terpenoids from the West Indian sea whip Pseudopterogorgia elisabethae (Bayer). Elisapterosins A and B: rearranged diterpenes possessing an unprecedented cagelike framework.

Abstract

Four diterpenes and a nor-diterpenoid, all of which possess unusual carbocyclic skeletons, were isolated from the hexane solubles of the West Indian gorgonian Pseudopterogorgia elisabethae. The structures and relative configurations of novel metabolites elisabethin D (2), elisabethin D acetate (3), 3-epi-elisabanolide (5), elisapterosin A (6), and elisapterosin B (7) were elucidated by interpretation of overall spectral data, which included 2D NMR correlation methods, IR, UV, and accurate mass measurements (HREI-MS and HRFAB-MS), chemical reactions, and X-ray diffraction analyses. The tetracyclic carbon skeleton of the elisapterosins is undescribed and constitutes a new class of C(20) rearranged diterpenes. Elisapterosin B displays strong in vitro anti-tuberculosis activity.

• Authors: A D Rodríguez, C Ramírez, I I Rodríguez, C L Barnes
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 65 Issue 5 Pg. 1390-8 (Mar 10 2000) ISSN: 0022-3263 [Print] United States
• PMID: 10814100 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antitubercular Agents
• Bridged-Ring Compounds
• Diterpenes
• Polycyclic Compounds
• elisabethin D
• elisapterosin A
• elisapterosin B

Topics

• Animals
• Antitubercular Agents (chemistry, isolation & purification, metabolism, pharmacology)
• Bridged-Ring Compounds (chemistry)
• Cnidaria (chemistry)
• Crystallography, X-Ray
• Diterpenes (chemistry, isolation & purification, metabolism, pharmacology)
• Humans
• Magnetic Resonance Spectroscopy
• Models, Molecular
• Molecular Conformation
• Molecular Structure
• Mycobacterium tuberculosis (drug effects)
• Polycyclic Compounds (chemistry)
• Tumor Cells, Cultured
• West Indies