New Lycopodine-Type Alkaloids from <i>Lycopodium carinatum</i>

Abstract

The structures of new lycopodine-type alkaloids, lycopocarinamines A-F, which were isolated from Lycopodium carinatum, were elucidated by spectroscopic analysis and chemical conversions. The proposed structure of lycocarinatine A was revised.

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

“…The aforementioned structure required the presence of six oxygen atoms, while only five were present based on the molecular formula suggested by the HRESIMS data, necessitating the formation of an oxygen bridge between two of the three oxygenated carbons (C-7/C-11/C-12). In fact, lycopodine-type alkaloids have been frequently reported to possess a Δ 11(12) double bond, − which could be epoxidized. The chemical shifts of C-11 and C-12 were consistent with an 11,12-oxirane moiety.…”

Biomarkers identification of Lycopodiaceae and Huperziaceae species from peninsular Malaysia with HPLC chromatographic profiling and partial least square analysis

“…The chemical shift of sp 3 quaternary carbon attached to nitrogen was shifted downfield compared to sp 3 quaternary carbon attached to the hydrogen atom [43]. Similarly, the chemical shift of sp 2 quaternary carbon attached to nitrogen atom was shifted downfield compared to the sp 2 quaternary carbon [43,44] attached to the hydrogen atom. Partial structures of C-2-C-3, C-6-C-8, and C-11-C-10 were deduced from the 1 H-1 H COSY spectra (Supporting Information).…”

Frontiers in Medicinal Chemistry 2017 in Bern, Switzerland

“…Prof. Dr. H. Takayama (Chiba University), guest speaker of the Pharmaceutical Society of Japan (PSJ), presented remarkably efficient total syntheses of alkaloid natural products from the two genera of plants, Lycopodium and Gelsemium . The group achieved an eleven‐step synthesis of the Lycopodium products lycodine and flabellidine and of koumidine, koumine and gelseridone produced by plants of the Gelsemium genus . Prof. Dr. Anna K. H. Hirsch (University of Groningen, Figure ) was awarded the 2017 innovation prize for outstanding and innovative scientific achievements in the areas of medical and pharmaceutical chemistry, jointly awarded by the Medicinal Chemistry Division of the German Chemical Society (GDCh) and the Pharmaceutical/Medicinal Chemistry Division of the German Pharmaceutical Society (DPhG).…”

“…The group achieved an eleven-step synthesis of the Lycopodium productsl ycodine and flabellidine and of koumidine, kouminea nd gelseridone produced by plants of the Gelsemium genus. [38,39] Prof. Dr.A nna K. H. Hirsch (University of Groningen, Figure 2) was awarded the 2017 innovation prize for outstanding and innovative scientific achievements in the areas of medical and pharmaceutical chemistry,jointly awarded by the Medicinal Chemistry Division of the German Chemical Society( GDCh) and the Pharmaceutical/Medicinal Chemistry Division of the German Pharmaceutical Society (DPhG). She presented her research on exploring hit-identification strategies for energy-coupling factor transporters as an ovel antibiotic target.…”