Novel terpenoids from the West Indian sea whip Pseudopterogorgia elisabethae (Bayer). Elisapterosins A and B: rearranged diterpenes possessing an unprecedented cagelike framework.
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.
Rodríguez
A D
AD
Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan, Puerto Rico 00931-3346, USA. arodrig@goliath.cnnet.clu.edu
Ramírez
C
C
Rodríguez
I I
II
Barnes
C L
CL
D000818:Animals; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000737:chemistry; D003063:Cnidaria / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D011083:Polycyclic Compounds / Q000737:chemistry; D014407:Tumor Cells, Cultured; D014900:West Indies
D000995:Antitubercular Agents; D001952:Bridged-Ring Compounds; D004224:Diterpenes; D011083:Polycyclic Compounds; C414525:elisabethin D; C414523:elisapterosin A; C414524:elisapterosin B