title: Lycojaponicumins A-C, three alkaloids with an unprecedented skeleton from Lycopodium japonicum.
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.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050, China.
authors.forename: Xiao-Jing
authors.initials: XJ
authors.lastname: Wang
authors.forename: Gui-Jie
authors.initials: GJ
authors.lastname: Zhang
authors.forename: Peng-Yu
authors.initials: PY
authors.lastname: Zhuang
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Shi-Shan
authors.initials: SS
authors.lastname: Yu
authors.forename: Xiu-Qi
authors.initials: XQ
authors.lastname: Bao
authors.forename: Dan
authors.initials: D
authors.lastname: Zhang
authors.forename: Yu-He
authors.initials: YH
authors.lastname: Yuan
authors.forename: Nai-Hong
authors.initials: NH
authors.lastname: Chen
authors.forename: Shuang-gang
authors.initials: SG
authors.lastname: Ma
authors.forename: Jing
authors.initials: J
authors.lastname: Qu
authors.forename: Yong
authors.initials: Y
authors.lastname: Li
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D053961:Azabicyclo Compounds / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D032502:Lycopodium / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000470:Alkaloids; D053961:Azabicyclo Compounds; C587803:lycojaponicumin A; C587805:lycojaponicumin B; C587804:lycojaponicumin C