Lycojaponicumins A–C, Three Alkaloids with an Unprecedented Skeleton from <i>Lycopodium japonicum</i>
Xiaojing Wang(Chinese Academy of Medical Sciences & Peking Union Medical College), Guijie Zhang(Chinese Academy of Medical Sciences & Peking Union Medical College), Peng‐Yu Zhuang(Chinese Academy of Medical Sciences & Peking Union Medical College), Yan Zhang(Chinese Academy of Medical Sciences & Peking Union Medical College), Shi‐Shan Yu(Chinese Academy of Medical Sciences & Peking Union Medical College), Xiu-Qi Bao(Chinese Academy of Medical Sciences & Peking Union Medical College), Dan Zhang(Chinese Academy of Medical Sciences & Peking Union Medical College), Yu‐He Yuan(Chinese Academy of Medical Sciences & Peking Union Medical College), Nai‐Hong Chen(Chinese Academy of Medical Sciences & Peking Union Medical College), Shuang‐Gang Ma(Chinese Academy of Medical Sciences & Peking Union Medical College), Jing Qu(Chinese Academy of Medical Sciences & Peking Union Medical College), Yong Li(Chinese Academy of Medical Sciences & Peking Union Medical College)
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Abstract
Lycojaponicumins A-C (1-3), three trace alkaloids isolated from Lycopodium japonicum, represent a unique heterocyclic skeleton formed by the new linkage C4-C9. Notably, lycojaponicumins A and B (1 and 2) are the first examples of natural products possessing a 5/5/5/5/6 pentacyclic ring system with a 1-aza-7-oxabicyclo[2.2.1]heptane moiety. These structures were elucidated by spectroscopic methods and X-ray diffraction analysis. A plausible biogenetic pathway was proposed.
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