Alkaloids from Stems and Leaves of Stemona japonica and Their Insecticidal Activities

Five new alkaloids, 6β-hydroxystemofoline (1), 16-hydroxystemofoline (2), neostemofoline (3), protostemodiol (4), and 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (5), along with 10 known alkaloids, were isolated from stems and leaves of Stemona japonica. Their structures were elucidated by 1D a...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2008-01, Vol.71 (1), p.112-116
Main Authors: Tang, Chun-Ping, Chen, Tong, Velten, Robert, Jeschke, Peter, Ebbinghaus-Kintscher, Ulrich, Geibel, Sven, Ye, Yang
Format: Article
Language:English
Subjects:
16-hydroxystemofoline
6β-hydroxystemofoline
alkaloids
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Animals
Aphids - drug effects
Biological and medical sciences
Brassica - drug effects
Chemical control
chemical structure
Control
dihydroprotostemonine
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - isolation & purification
Drugs, Chinese Herbal - pharmacology
Fundamental and applied biological sciences. Psychology
General pharmacology
insect pests
insecticidal properties
Insecticides - chemistry
Insecticides - isolation & purification
Insecticides - pharmacology
Medical sciences
medicinal plants
Molecular Structure
Myzus persicae
neostemofoline
Oriental traditional medicine
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Phytopathology. Animal pests. Plant and forest protection
Plant Leaves - chemistry
Plant Stems - chemistry
Plants, Medicinal - chemistry
protostemodiol
Protozoa. Invertebrates
spectral analysis
Spodoptera - drug effects
Spodoptera frugiperda
Stemona
Stemona japonica
Stemonaceae - chemistry
stereochemistry
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Description
Summary:Five new alkaloids, 6β-hydroxystemofoline (1), 16-hydroxystemofoline (2), neostemofoline (3), protostemodiol (4), and 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (5), along with 10 known alkaloids, were isolated from stems and leaves of Stemona japonica. Their structures were elucidated by 1D and 2D NMR and other spectroscopic studies. The insecticidal activity of the agonist 16-hydroxystemofoline (2) and antagonist 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (5) was demonstrated by electrophysiological in vitro tests on the insect nicotinic acetylcholine receptor and by in vivo screenings against relevant agricultural insect pests.
ISSN:0163-3864
1520-6025
DOI:10.1021/np070427k