American Chemical Society
ol503230s_si_002.pdf (12.91 MB)

Unraveling the Metabolic Pathway in Leucosceptrum canum by Isolation of New Defensive Leucosceptroid Degradation Products and Biomimetic Model Synthesis

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journal contribution
posted on 2014-12-19, 00:00 authored by Shi-Hong Luo, Cedric L. Hugelshofer, Juan Hua, Shu-Xi Jing, Chun-Huan Li, Yan Liu, Xiao-Nian Li, Xu Zhao, Thomas Magauer, Sheng-Hong Li
Seven new leucosceptroid degradation products possessing a C20, C21, or C25 framework, norleucosceptroids D–H (15), leucosceptroids P (6), and Q (7), have been isolated from Leucosceptrum canum. Their structures were determined by comprehensive NMR, MS, and single-crystal X-ray diffraction analyses. Discovery of these key intermediates, together with the biomimetic oxidation of a model system, supports the hypothesis that two biosynthetic pathways are operative. Antifeedant activity was observed for compounds 13.