Unraveling the Metabolic Pathway in Leucosceptrum canum by Isolation of New Defensive Leucosceptroid Degradation Products and Biomimetic Model Synthesis
- 4 December 2014
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 16 (24), 6416-6419
- https://doi.org/10.1021/ol503230s
Abstract
Seven new leucosceptroid degradation products possessing a C20, C21, or C25 framework, norleucosceptroids D–H (1–5), 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 1–3.Keywords
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