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Verrucosamide, a Cytotoxic 1,4-Thiazepane-Containing Thiodepsipeptide from a Marine-Derived Actinomycete.


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.

SUBMITTER: Nair V 

PROVIDER: S-EPMC7694325 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Verrucosamide, a Cytotoxic 1,4-Thiazepane-Containing Thiodepsipeptide from a Marine-Derived Actinomycete.

Nair Vimal V   Kim Min Cheol MC   Golen James A JA   Rheingold Arnold L AL   Castro Gabriel A GA   Jensen Paul R PR   Fenical William W  

Marine drugs 20201105 11


A new cytotoxic thiodepsipeptide, verrucosamide (<b>1</b>), was isolated along with the known, related cyclic peptide thiocoraline, from the extract of a marine-derived actinomycete, a <i>Verrucosispora</i> 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 (<b>1</b>) showed moderate cytotoxi  ...[more]

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