title: Arborisidine and Arbornamine, Two Monoterpenoid Indole Alkaloids with New Polycyclic Carbon-Nitrogen Skeletons Derived from a Common Pericine Precursor.
abstract: Two new monoterpene indole alkaloids, characterized by previously unencountered natural product skeletons, viz., arborisidine (1), incorporating indolizidine and cyclohexanone moieties fused to an indole unit, and arbornamine (2), incorporating an unprecedented 6/5/6/5/6 "arbornane" skeleton (distinct from the eburnan or tacaman skeleton), were isolated from a Malayan Kopsia arborea. The structures of the alkaloids were determined based on analysis of the NMR and MS data. Possible biogenetic pathways to these alkaloids from a common pericine precursor (3) are presented.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Suet-Pick
authors.initials: SP
authors.lastname: Wong
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Kam-Weng
authors.initials: KW
authors.lastname: Chong
authors.affiliation: School of Pharmacy, University of Nottingham Malaysia Campus , Jalan Broga, 43500 Semenyih, Selangor, Malaysia.
authors.forename: Kuan-Hon
authors.initials: KH
authors.lastname: Lim
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Siew-Huah
authors.initials: SH
authors.lastname: Lim
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Yun-Yee
authors.initials: YY
authors.lastname: Low
authors.affiliation: Department of Chemistry, Faculty of Science, University of Malaya , 50603 Kuala Lumpur, Malaysia.
authors.forename: Toh-Seok
authors.initials: TS
authors.lastname: Kam
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D046948:Secologanin Tryptamine Alkaloids; C000610009:arborisidine; C000610008:arbornamine; C037128:pericine; D002244:Carbon; D009584:Nitrogen