title: Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted Streptomyces sp.
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.
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California , San Diego, La Jolla, California 92093-0204, United States.
authors.forename: Sang-Jip
authors.initials: SJ
authors.lastname: Nam
authors.forename: Christopher A
authors.initials: CA
authors.lastname: Kauffman
authors.forename: Lauren A
authors.initials: LA
authors.lastname: Paul
authors.forename: Paul R
authors.initials: PR
authors.lastname: Jensen
authors.forename: William
authors.initials: W
authors.lastname: Fenical
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity*; D045325:HCT116 Cells; D006801:Humans; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry*
chemical_list: D004224:Diterpenes; D013729:Terpenes; C587941:actinoranone