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Morphinane alkaloids with cell protective effects from Sinomenium acutum.
Guan-Hu Bao1, Guo-Wei Qin, Rui Wang
1Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
Journal of Natural Products
|July 26, 2005
Summary
Researchers identified new morphinane alkaloids from Sinomenium acutum. Some compounds, including N-demethylsinomenine, demonstrated protective effects against cell damage.
Area of Science:
- Natural Product Chemistry
- Pharmacology
- Medicinal Chemistry
Background:
- The stems of Sinomenium acutum are a source of bioactive alkaloids.
- Understanding the chemical constituents and their biological activities is crucial for potential therapeutic applications.
Purpose of the Study:
- To isolate and characterize novel and known morphinane alkaloids from Sinomenium acutum stems.
- To evaluate the protective effects of the isolated compounds against hydrogen peroxide-induced cell injury.
Main Methods:
- Isolation of alkaloids using chromatographic techniques.
- Structure elucidation through spectroscopic analysis (e.g., NMR, MS) and chemical methods.
- In vitro assessment of cytoprotective activity against oxidative stress.
Main Results:
- One new morphinane alkaloid, sinomenine N-oxide (1), and one new natural occurring morphinane alkaloid, N-demethylsinomenine (2), were identified.
- Six known alkaloids were also isolated: 7,8-didehydro-4-hydroxy-3,7-dimethoxymorphinan-6-ol (3), sinomenine (4), sinoacutine (5), N-norsinoacutine, acutumine, and acutumidine.
- Compounds 2 (N-demethylsinomenine), 3, and 5 (sinoacutine) exhibited protective effects against hydrogen peroxide-induced cell injury.
Conclusions:
- The chemical investigation of Sinomenium acutum yielded novel and known morphinane alkaloids.
- N-demethylsinomenine, 7,8-didehydro-4-hydroxy-3,7-dimethoxymorphinan-6-ol, and sinoacutine show potential as cytoprotective agents against oxidative stress.