Verticillane derivatives from Bursera suntui and Bursera kerberi

• Published in: Journal of natural products (Washington, D.C.) Vol. 68; no. 11; pp. 1598 - 1602
• Main Authors: Hernandez-Hernandez, J.D, Roman-Marin, L.U, Cerda-Garcia-Rojas, C.M, Joseph-Nathan, P
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.2005; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; Bursera; Bursera - chemistry; Bursera kerberi; Bursera suntui; Burseraceae; chemical constituents of plants; chemical structure; Chemistry, Medicinal; Diterpenes - chemistry; Diterpenes - isolation & purification; diterpenoids; General pharmacology; Life Sciences & Biomedicine; Medical sciences; medicinal plants; Mexico; Molecular Conformation; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; plant biochemistry; plant products; Plant Sciences; Plant Stems - chemistry; Science & Technology; spectral analysis; Stereoisomerism; traditional medicine; verticillane; verticillene; verticillol; Mexico; Central America; America; BICYCLIC TAXANE DITERPENOIDS; NEEDLES; CANADENSIS; CHINESE YEW; JACKIELLA-JAVANICA; EVOLUTIONARY TRENDS; YEW TAXUS-CUSPIDATA; CHINENSIS VAR. MAIREI; MEDICINAL-PLANTS; TERPENOIDS; Monte Carlo method; Terpenoid; Diol; Pharmacognosy; Overhauser effect; NMR spectrometry; Burseraceae; Modeling; Stem; Medicinal plant; Racemic; Dicotyledones; Taxane derivatives; Angiospermae; Absolute configuration; Force field method; Plant origin; Diterpene; Isolation; Spermatophyta; Chemical synthesis; Structural analysis; Conformation; Optical rotatory dispersion
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050323e

The stems of Bursera suntui afforded two new verticillane derivatives, (1S,3Z,7E,11S,12S)-(+)-verticilla-3,7-dien-12,20-diol (1) and (1S,3Z,7E,11S,12S)-(+)-verticilla-3,7-dien-12,20-dio1 20-acetate (2), together with (1S,3E,7E,11-R)-(+)-verticilla-3,7,12(18)-triene (3), (1-R,3E,7E,11-R,12Z)-(+)-verticilla-3,7,12-triene (4), (1-R,7E,11Z)-(-)-verticilla-4(20),7,11-triene (5), and (1S,3E,7E,11S,12S)-(+)-verticilla-3,7-dien-12-ol (6). Compounds 3 and 4 are new enantiomericilly pure natural products whose racemic mixtures, derived from synthetic approaches toward the taxane skeleton, were obtained previously. The stems of Bursera kerberi afforded the new (1S,3E,7E,11S,12R)-(+)-verticilla-3,7-dien-12-ol (7) together with 3-5. This is the first time that verticillane derivatives have been isolated from the genus Bursera. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY, HSQC, and HMBC experiments, while the absolute configuration was determined by comparison of the optical rotatory dispersion data with that of recently revised (1S,3E, 7E, 1 1S, 12S)-(+)-verticilla-3,7-dien- 12-ol (6), obtained from Sciadopitys verticillata, and those of (1-R,3E,7E,11-R,12R)-(-)-verticilla-3,7-dien-12-o1 (8) and (1R,3E,7E,11R,12S)-(-)-verticilla-3,7-dien-12-ol (9), isolated from the liverwort Jackiella javanica. The conformational preferences of 1-7 were studied by molecular mechanics modeling employing the Monte Carlo protocol.