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Org Lett. 2014 Jan 17;16(2):464-7. doi: 10.1021/ol403350e. Epub 2013 Dec 20.

Thelepamide: an unprecedented ketide-amino acid from Thelepus crispus, a marine annelid worm.

Author information

1
Departamento de Química Fundamental, Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA), Universidade da Coruña , 15071 A Coruña, Spain.

Abstract

Thelepamide (1) was characterized during a program to study cytotoxic substances from an unusual source, the tidal zone-derived annelid Thelephus crispus. Its structure contains a tetraketide and a tripeptide subunit and possesses striking atom diversity, consisting of 17 carbons and 8 heteroatoms. The relative configurations at four chiral sites were elucidated via ROESY, J-based configurational analysis, and DFT calculations. It was modestly active against leukemia cells (IC50 = 5 μg/mL) and inactive against solid tumor cell lines.

PMID:
24359301
PMCID:
PMC3932301
DOI:
10.1021/ol403350e
[Indexed for MEDLINE]
Free PMC Article

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