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

Sang Jip Nam; Christopher A. Kauffman; Lauren A. Paul; Paul R. Jensen; William Fenical

doi:10.1021/ol402080s

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

Sang Jip Nam
, Christopher A. Kauffman
, Lauren A. Paul
, Paul R. Jensen
, William Fenical

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

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.

Original language	English
Pages (from-to)	5400-5403
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	21
DOIs	https://doi.org/10.1021/ol402080s
State	Published - 1 Nov 2013

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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.",

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year = "2013",

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AU - Nam, Sang Jip

AU - Kauffman, Christopher A.

AU - Paul, Lauren A.

AU - Jensen, Paul R.

AU - Fenical, William

PY - 2013/11/1

Y1 - 2013/11/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84887075797

U2 - 10.1021/ol402080s

DO - 10.1021/ol402080s

M3 - Article

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SP - 5400

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

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