Hupercumines A and B, Lycopodium Alkaloids from Huperzia cunninghamioides, Inhibiting Acetylcholinesterase

Yusuke Hirasawa; Chiho Mitsui; Nahoko Uchiyama; Takashi Hakamatsuka; Hiroshi Morita

doi:10.1021/acs.orglett.8b00152

Hupercumines A and B, Lycopodium Alkaloids from Huperzia cunninghamioides, Inhibiting Acetylcholinesterase

Org Lett. 2018 Mar 2;20(5):1384-1387. doi: 10.1021/acs.orglett.8b00152. Epub 2018 Feb 12.

Authors

Yusuke Hirasawa¹, Chiho Mitsui¹, Nahoko Uchiyama², Takashi Hakamatsuka², Hiroshi Morita¹

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hoshi University , Ebara 2-4-41 Shinagawa-ku, Tokyo 142-8501, Japan.
² National Institute of Health Sciences , 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, Japan.

PMID: 29431448
DOI: 10.1021/acs.orglett.8b00152

Abstract

A novel class of C₃₈N₄ Lycopodium alkaloid, hupercumine A (1), consisting of two octahydroquinolines, a decahydroquinoline, and a piperidine, and a new C₂₇N₃-type alkaloid, hupercumine B (2), were isolated from Huperzia cunninghamioides (Hayata) Holub. The structures and absolute configurations of 1 and 2 were elucidated on the basis of spectroscopic data, chemical means, and biogenetic point of view. Hupercumines A (1) and B (2) showed moderate inhibitory activity against acetylcholinesterase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / chemistry
Alkaloids / chemistry*
Alkaloids / isolation & purification
Cholinesterase Inhibitors / chemistry*
Cholinesterase Inhibitors / isolation & purification
Huperzia / chemistry*
Lycopodium / chemistry*
Molecular Structure
Piperidines / chemistry*
Piperidines / isolation & purification
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Quinolines / chemistry*
Quinolines / isolation & purification
Stereoisomerism

Substances

Alkaloids
Cholinesterase Inhibitors
Piperidines
Plant Extracts
Quinolines
decahydroquinoline-5-carboxylic acid
Acetylcholinesterase