Structures of Cribochalines A and B, Branched-Chain Methoxylaminoalkyl Pyridines from the Micronesian Sponge, Cribochalina sp. Absolute Configuration and Enantiomeric Purity of Related O-Methyl Oximes

Two new 3-alkyl pyridines, cribochalines A (2) and B (3), were isolated from the North Pacific sponge Cribochalina sp. The known related oxime, ikimine A, was shown to be a 2.8:1 mixture of the (S)- and (R)-enantiomers. Cribochaline A exhibited antifungal activity against Candida albicans ATCC and Fluconazole-resistant strains C. albicans 96–489, C. krusei and C. glabrata.