Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.
The new aromatic diterpenes 7beta-O-benzylrosmanol (3), 7beta-O-benzyl-11,12-di-O-methylrosmanol (4), and 7alpha-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), 7beta-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.
Marrero
Joaquín G
JG
Instituto Universitario de Bio-Organica "Antonio Gonzalez", Departamento de Quimica Organica, Universidad de La Laguna, Avenida Astrofisico Francisco Sanchez 2, 38206 La Laguna, Tenerife, Canary Islands, Spain.
Moujir
Laila
L
Andrés
Lucía S
LS
Montaño
Nayely P
NP
Araujo
Liliana
L
Luis
Javier G
JG
D045784:Abietanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002522:Chlorocebus aethiops; D004224:Diterpenes / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D027544:Salvia / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014709:Vero Cells
D045784:Abietanes; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D011809:Quinones; C505171:rosmaquinone A; C068623:carnosol