Absolute configuration of cembrane diterpenoids from Bursera multijuga.
The stems of Bursera multijuga afforded (-)-(1S,3E,7R,8R,11E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.
Juan D
JD
Hernández-Hernández
Hugo A
HA
García-Gutiérrez
Luisa U
LU
Román-Marín
Yunuen I
YI
Torres-Blanco
Carlos M
CM
Cerda-García-Rojas
Pedro
P
Joseph-Nathan
D031233:Bursera / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D015394:Molecular Structure; D053147:Plant Exudates / Q000737:chemistry*; D014961:X-Ray Diffraction
D004224:Diterpenes; D053147:Plant Exudates