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- Title
Verrucosamide, a Cytotoxic 1,4-Thiazepane-Containing Thiodepsipeptide from a Marine-Derived Actinomycete.
- Authors
Nair, Vimal; Kim, Min Cheol; Golen, James A.; Rheingold, Arnold L.; Castro, Gabriel A.; Jensen, Paul R.; Fenical, William
- Abstract
A new cytotoxic thiodepsipeptide, verrucosamide (1), was isolated along with the known, related cyclic peptide thiocoraline, from the extract of a marine-derived actinomycete, a Verrucosispora sp., our strain CNX-026. The new peptide, which is composed of two rare seven-membered 1,4-thiazepane rings, was elucidated by a combination of spectral methods and the absolute configuration was determined by a single X-ray diffraction study. Verrucosamide (1) showed moderate cytotoxicity and selectivity in the NCI 60 cell line bioassay. The most susceptible cell lines were MDA-MB-468 breast carcinoma with an LD50 of 1.26 µM, and COLO 205 colon adenocarcinoma with an LD50 of 1.4 µM. Also isolated along with verrucosamide were three small 3-hydroxy(alkoxy)-quinaldic acid derivatives that appear to be products of the same biosynthetic pathway.
- Subjects
CELL lines; COLON (Anatomy); X-ray diffraction; ACID derivatives; BIOLOGICAL assay
- Publication
Marine Drugs, 2020, Vol 18, Issue 11, p549
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md18110549