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Structure elucidation and theoretical investigation of key steps in the biogenetic pathway of schisanartane
Wei-Lie Xiao1, Chun Lei, Jie Ren
1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650204, Yunnan, China.
Abstract:
Rubrifloradilactone C (4), a novel bioactive nortriterpenoid, along with four other nortriterpenoids (1-3, 5) were isolated from Schisandra rubriflora. The structure of 4 was determined by extensive NMR spectral analysis, computational evidence by using the GIAO method at the B3LYP/6-311++G(2d,p)//B3LYP/6-31G(d) levels, and X-ray analysis. DFT at the B3LYP/6-311+G(d,p) level was selected to clarify the key mechanistic steps in the formation of 1 and 4 through transition-state (TS) investigations. The effect of enzymes on the TS barriers was considered by using the polarized continuum model. Other possible products based on the new mechanism were predicted.
