Novel antimycobacterial benzoxazole alkaloids, from the west Indian Sea whip Pseudopterogorgia elisabethae.
[formula: see text] Our screening for marine natural products with anti-tuberculosis activity from the West Indian gorgonian coral Pseudopterogorgia elisabethae resulted in the isolation of two active diterpenoid alkaloids, pseudopteroxazole (1) and seco-pseudopteroxazole (2). Their structures were elucidated by NMR spectral analysis, including a variety of two-dimensional techniques. Compounds 1 and 2 are previously undescribed diterpenoids containing the uncommon benzoxazole moiety. Biological screening studies indicated that pseudopteroxazole (1) is a potent growth inhibitor of Mycobacterium tuberculosis H37Rv, while seco-pseudopteroxazole (2) shows moderate to strong inhibitorial activity.
Rodríguez
A D
AD
Department of Chemistry, University of Puerto Rico, San Juan, USA.
Ramírez
C
C
Rodríguez
I I
II
González
E
E
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001583:Benzoxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003063:Cnidaria / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000470:Alkaloids; D000995:Antitubercular Agents; D001583:Benzoxazoles; C410139:pseudoteroxazole; C410138:seco-pseudoteroxazole