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

doi:10.1021/np900047p

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 journal › Article › peer-review

21 Scopus citations

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.

Original language	English
Pages (from-to)	1385-1389
Number of pages	5
Journal	Journal of Natural Products
Volume	72
Issue number	8
DOIs	https://doi.org/10.1021/np900047p
State	Published - 28 Aug 2009
Externally published	Yes

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title = "Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone",

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.",

author = "Marrero, {Joaqu{\'i}n G.} and Laila Moujir and Andr{\'e}s, {Luc{\'i}a S.} and Monta{\~n}o, {Nayely P.} and Liliana Araujo and Luis, {Javier G.}",

year = "2009",

month = aug,

day = "28",

doi = "10.1021/np900047p",

language = "Ingl{\'e}s",

volume = "72",

pages = "1385--1389",

journal = "Journal of Natural Products",

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T1 - Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone

AU - Marrero, Joaquín G.

AU - Moujir, Laila

AU - Andrés, Lucía S.

AU - Montaño, Nayely P.

AU - Araujo, Liliana

AU - Luis, Javier G.

PY - 2009/8/28

Y1 - 2009/8/28

N2 - 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.

AB - 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.

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DO - 10.1021/np900047p

M3 - Artículo

C2 - 19711987

SN - 0163-3864

VL - 72

SP - 1385

EP - 1389

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 8

ER -

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

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