Erythrolic acids A-E, meroterpenoids from a marine-derived erythrobacter sp.

Youcai Hu, Aaron G. Legako, Ana Paula D M Espindola, John B. MacMillan

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Erythrolic acids A-E (1-5) are five unusual meroterpenoids isolated from the bacterium Erythrobacter sp. derived from a marine sediment sample collected in Galveston, TX. The structures were elucidated by means of detailed spectroscopic analysis and chemical derivatization. The erythrolic acids contain a 4-hydroxybenzoic acid appended with a modified terpene side chain. The side-chain modifications include oxidation of a terminal methyl substituent and in the case of 1-4 addition of a two-carbon unit to give terpene side chains of unusual length: C22 for 1 and 2, C17 for 3, and C12 for 4. The relative and absolute configurations of the meroterpenoids were determined by coupling constant, NOE, and Mosher's analysis. In vitro cytotoxicity toward a number of nonsmall cell lung cancer (NSCLC) cell lines revealed only modest activity for erythrolic acid D (4) (2.5 μM against HCC44). The discovery of these unusual diterpenes, along with the previously reported erythrazoles, demonstrates the natural product potential of a previously unstudied group of bacteria for drug discovery. The unusual nature of the terpene side chain, we believe, involves an oxidation of a terminal methyl group to a carboxylic acid and subsequent Claisen condensation with acetyl-CoA.

Original languageEnglish (US)
Pages (from-to)3401-3407
Number of pages7
JournalJournal of Organic Chemistry
Volume77
Issue number7
DOIs
StatePublished - Apr 6 2012

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Terpenes
Acids
Bacteria
Cells
Oxidation
Acetyl Coenzyme A
Spectroscopic analysis
Diterpenes
Cytotoxicity
Carboxylic Acids
Biological Products
Condensation
Sediments
Carbon

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Erythrolic acids A-E, meroterpenoids from a marine-derived erythrobacter sp. / Hu, Youcai; Legako, Aaron G.; Espindola, Ana Paula D M; MacMillan, John B.

In: Journal of Organic Chemistry, Vol. 77, No. 7, 06.04.2012, p. 3401-3407.

Research output: Contribution to journalArticle

Hu, Youcai ; Legako, Aaron G. ; Espindola, Ana Paula D M ; MacMillan, John B. / Erythrolic acids A-E, meroterpenoids from a marine-derived erythrobacter sp. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 7. pp. 3401-3407.
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