Solving the Confusion of Gnaphaliin Structure: Gnaphaliin A and Gnaphaliin B Identified as Active Principles of Gnaphalium liebmannii with Tracheal Smooth Muscle Relaxant Properties

Inflorescences of Gnaphalium liebmannii, commonly known as “Gordolobo”, is the most important remedy in Mexican traditional medicine to treat respiratory diseases, including asthma. By a bioguided fractionation of the n-hexane extract of this plant, following the relaxant effect on guinea pig trache...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2009-06, Vol.72 (6), p.1061-1064
Main Authors: Rodríguez-Ramos, Fernando, Navarrete, Andrés
Format: Article
Language:English
Subjects:
Aminophylline - pharmacology
Animals
asthma
Biological and medical sciences
chemical structure
Disease Models, Animal
flavones
Flavonoids - chemistry
Flavonoids - isolation & purification
Flavonoids - pharmacology
fractionation
General pharmacology
gnaphaliin
Gnaphalium
Gnaphalium - chemistry
Gnaphalium liebmannii
Guinea Pigs
inflorescences
mass spectrometry
Medical sciences
medicinal plants
medicinal properties
Molecular Structure
muscle relaxants
Muscle Relaxation - drug effects
Muscle, Smooth - drug effects
nuclear magnetic resonance spectroscopy
Parasympatholytics - chemistry
Parasympatholytics - isolation & purification
Parasympatholytics - pharmacology
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
plant extracts
Plants, Medicinal - chemistry
Respiratory system
smooth muscle
Trachea - drug effects
X-ray diffraction
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Summary:Inflorescences of Gnaphalium liebmannii, commonly known as “Gordolobo”, is the most important remedy in Mexican traditional medicine to treat respiratory diseases, including asthma. By a bioguided fractionation of the n-hexane extract of this plant, following the relaxant effect on guinea pig tracheal smooth muscle, the flavones 5,7-dihydroxy-3,8-dimethoxyflavone (1) and 3,5-dihydroxy-7,8-dimethoxyflavone (2) were identified as the active relaxant compounds. Compounds 1 and 2 showed more potent relaxant properties than aminophylline in this model. Both 1 and 2 have been described as gnaphaliin in the past; here EIMS data, NMR experiments for both compounds, and X-ray diffraction analysis for 1 provided structural information to suggest that 1 and 2 should be named gnaphaliins A and B, respectively.
ISSN:0163-3864
1520-6025
DOI:10.1021/np800746j