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Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted Streptomyces sp.

Authors
  • Nam, Sang-Jip
  • Kauffman, Christopher A
  • Paul, Lauren A
  • Jensen, Paul R
  • Fenical, William
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Nov 01, 2013
Volume
15
Issue
21
Pages
5400–5403
Identifiers
DOI: 10.1021/ol402080s
PMID: 24152065
Source
Medline
License
Unknown

Abstract

The isolation and structure elucidation of a new meroterpenoid, actinoranone (1), produced by a marine bacterium closely related to the genus Streptomyces is reported. Actinoranone is composed of an unprecedented dihydronaphthalenone polyketide linked to a bicyclic diterpenoid. The stereochemistry of 1 was defined by application of the advanced Mosher's method and by interpretation of spectroscopic data. Actinoranone (1) is significantly cytotoxic to HCT-116 human colon cancer cells with an LD50 = 2.0 μg/mL.

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