Structure Determination and Biosynthesis of Dapalides A-C, Glycosylated Kahalalide F Analogues from the Marine Cyanobacterium <i>Dapis</i> sp.

ABSTRACT: Kahalalides were originally isolated from the marine mollusk Elysia rufescens and its green algal diet Bryopsis sp., but the true producer was revealed as the obligate bacterial symbiont Candidatus Endobryopsis kahalalidefaciens, residing within Bryopsis sp. The most notable is kahalalide F, a broad-spectrum antitumor depsipeptide that entered the clinic but failed from lack of efficacy. We have isolated three new glycosylated analogues of kahalalide F, termed dapalides A-C (1-3), from a marine cyanobacterium, Dapis sp., collected from Guam. The planar structures were determined by extensive NMR coupled with mass spectrometry. Acid hydrolysis of 1 using amino acid analysis revealed the absolute configuration of singlet and a mixture o

SUBMITTER: Ellis EK 

PROVIDER: S-EPMC12481561 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature