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

35 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

Access to Document

10.1021/ol402080s

Cite this

@article{03bd56a896744e6d9fd900cdec0b84f5,

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.",

author = "Nam, {Sang Jip} and Kauffman, {Christopher A.} and Paul, {Lauren A.} and Jensen, {Paul R.} and William Fenical",

year = "2013",

month = nov,

day = "1",

doi = "10.1021/ol402080s",

language = "English",

volume = "15",

pages = "5400--5403",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted streptomyces sp.

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 - http://www.scopus.com/inward/record.url?scp=84887075797&partnerID=8YFLogxK

U2 - 10.1021/ol402080s

DO - 10.1021/ol402080s

M3 - Article

C2 - 24152065

AN - SCOPUS:84887075797

SN - 1523-7060

VL - 15

SP - 5400

EP - 5403

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

Access to Document

Fingerprint

Cite this