Nematicidal Stemona Alkaloids from Stemona parviflora

Eight new alkaloids, 3β-n-butylstemonamine (1), 8-oxo-3β-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N 4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Ste...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-10, Vol.79 (10), p.2599-2605
Main Authors: Huang, Sheng-Zhuo, Kong, Fan-Dong, Ma, Qing-Yun, Guo, Zhi-Kai, Zhou, Li-Man, Wang, Qi, Dai, Hao-Fu, Zhao, You-Xing
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Antinematodal Agents - chemistry
Antinematodal Agents - isolation & purification
Antinematodal Agents - pharmacology
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - isolation & purification
Drugs, Chinese Herbal - pharmacology
Heterocyclic Compounds, 4 or More Rings
Inhibitory Concentration 50
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots - chemistry
Stemonaceae - chemistry
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Summary:Eight new alkaloids, 3β-n-butylstemonamine (1), 8-oxo-3β-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N 4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1–4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 μM, respectively.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00528