Four alkaloids, lucidine B, oxolucidine A, lucidine A, and lucidulinone from Lycopodium lucidulum.
The structures of four alkaloids extracted from Lycopodium lucidulum (Lycopodiaceae) were established by X-ray and 2D NMR spectroscopic analyses. The dihydro-derivative of oxolucidine A, which was obtained by NaBH4 reduction of oxolucidine A, was treated with p-bromobenzoyl chloride to afford crystals, whose X-ray crystallographic analysis established the stereostructure, including the absolute configuration. The 2D NMR spectra of tetrahydrodeoxylucidine B were fully analyzed to establish the full structure of lucidine B, and the hitherto unknown stereochemistry at the C-14 position was established as beta-H. The structure of a new alkaloid, lucidulinone, was determined by spectroscopic analysis to be luciduline lactam.
Tori
M
M
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan. tori@ph.bunri-u.ac.jp
Shimoji
T
T
Shimura
S E
SE
Takaoka
S
S
Nakashima
K
K
Sono
M
M
Ayer
W A
WA
D000470:Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D010936:Plant Extracts; D011804:Quinolines; C410968:lucidine A; C410967:lucidulinone; C410969:oxolucidine A; C027890:serratanine