title: Palhicerines A-F, Lycopodium alkaloids from the club moss Palhinhaea cernua.
abstract: Four fawcettimine-type (palhicerines A-D, resp.) and two lycopodine-type (palhicerines E and F) Lycopodium alkaloids together with twenty known ones were isolated from the whole plant of Palhinhaea cernua. The structures and absolute configurations of the palhicerines A-F were determined by extensive spectroscopic methods, single-crystal X-ray diffraction analyses, chemical transformation, and electronic circular dichroism (ECD) calculations or induced electronic circular dichroism (IECD) spectra. Among the isolates, the new C/D-ring of the palhicerines A-C (trans-fused fawcettimine-type alkaloids) are rare, and each possesses a β-oriented C-16 methyl group and a distinctive tertiary methoxy group at C-13. Chemotaxonomy for differentiating species in the genus Palhinhaea is briefly discussed.
authors: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China.
authors: Yu
authors: Y
authors: Tang
authors: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China. Electronic address: jxiong@fudan.edu.cn.
authors: Juan
authors: J
authors: Xiong
authors: Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA, 19104-6323, USA.
authors: Yike
authors: Y
authors: Zou
authors: State Key Laboratory of Drug Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, No. 555 Zuchongzhi Road, Shanghai, 201203, PR China.
authors: Hai-Yan
authors: HY
authors: Zhang
authors: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China. Electronic address: jfhu@fudan.edu.cn.
authors: Jin-Feng
authors: JF
authors: Hu
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D029542:Lycopodiaceae / Q000737:chemistry* / Q000235:genetics; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011807:Quinolizines / Q000737:chemistry
chemical_list: D000470:Alkaloids; D011807:Quinolizines; C524731:fawcettimine; C000614682:palhicerine A; C000614514:palhicerine E; C016542:lycopodine
keywords: Lycopodiaceae; Lycopodium alkaloids; Palhicerines; Palhinhaea cernua