First seco-C oleananes from nature.
[structure: see text] The triterpenes 8,14-seco-oleana-8(26),13-dien-3beta-ol (1) and its acetyl derivative 2 were isolated from Stevia viscida and Stevia eupatoria, respectively. Their structures were elucidated by 2D NMR, including carbon-carbon connectivity experiments, and confirmed by X-ray diffraction analysis of ketone 3. The absolute configuration was determined by NMR analysis of the Mosher esters of 1. The biogenetic implications of the new substances are discussed.
Román
Luisa U
LU
Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Apartado 137, Morelia, Michoacán, 58000 Mexico. lroman@zeus.umich.mx
Guerra-Ramírez
Diana
D
Morán
Gerardo
G
Martínez
Iván
I
Hernández
Juan D
JD
Cerda-García-Rojas
Carlos M
CM
Torres-Valencia
J Martín
JM
Joseph-Nathan
Pedro
P
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D036625:Stevia / Q000737:chemistry*; D014315:Triterpenes
C496878:8,14-seco-oleana-8(26),13-dien-3-one; C496876:8,14-seco-oleana-8(26),13-dien-3beta-ol; D014315:Triterpenes; D009828:Oleanolic Acid