Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone

Joaquín G. Marrero, Laila Moujir, Lucía S. Andrés, Nayely P. Montaño, Liliana Araujo, Javier G. Luis

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The new aromatic diterpenes 7β-O-benzylrosmanol (3), 7β-O-benzyl-11,12-di-O-methylrosmanol (4), and 7α-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The structures of these compounds were established from their physical and spectroscopic data. The known diterpenes sagequinone methide A (6), 7β-O-methylrosmanol (7), 7-O-methylrosmanol (8), and rosmaquinone B (9) were obtained from rosmanol (2). The spectroscopic data of these semisynthetic diterpenes were identical to data reported in the literature. In addition, the new semisynthetic isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities. © 2009 American Chemical Society and American Society of Pharmacognosy.
Original languageAmerican English
Pages (from-to)1385-1389
Number of pages1246
JournalJournal of Natural Products
DOIs
StatePublished - 28 Aug 2009
Externally publishedYes

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Abietane Diterpenes
Diterpenes
Salvia
Nuclear magnetic resonance spectroscopy
Protons
Magnetic Resonance Spectroscopy
Acids
rosmaquinone

Cite this

Marrero, Joaquín G. ; Moujir, Laila ; Andrés, Lucía S. ; Montaño, Nayely P. ; Araujo, Liliana ; Luis, Javier G. / Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone. In: Journal of Natural Products. 2009 ; pp. 1385-1389.
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Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone. / Marrero, Joaquín G.; Moujir, Laila; Andrés, Lucía S.; Montaño, Nayely P.; Araujo, Liliana; Luis, Javier G.

In: Journal of Natural Products, 28.08.2009, p. 1385-1389.

Research output: Contribution to journalArticle

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