Aromatase Inhibitors from Broussonetia papyrifera

Autor: Dongho Lee, Krishna P. L. Bhat, Harry H. S. Fong, Norman R. Farnsworth, John M. Pezzuto, A. Douglas Kinghorn
Rok vydání: 2001
Předmět:
Magnetic Resonance Spectroscopy
Spectrophotometry
Infrared
Placenta
Flavonoid
Pharmaceutical Science
Pharmacognosy
Moraceae
Mass Spectrometry
Analytical Chemistry
Chalcone
Chalcones
Pregnancy
Drug Discovery
Enzyme Inhibitors
Aromatase
chemistry.chemical_classification
Molecular Structure
biology
Aromatase Inhibitors
Chemistry
Circular Dichroism
Biological activity
Biochemistry
Enzyme inhibitor
Flavanones
Molecular Medicine
Female
Algorithms
Inhibitory Concentration 50
Structure-Activity Relationship
Microsomes
medicine
Anticarcinogenic Agents
Humans
Benzofurans
Flavonoids
Pharmacology
Plants
Medicinal
Terpenes
Organic Chemistry
Cancer
Broussonetia
medicine.disease
biology.organism_classification
Complementary and alternative medicine
Polyphenol
biology.protein
Spectrophotometry
Ultraviolet
Illinois
Zdroj: Journal of Natural Products. 64:1286-1293
ISSN: 1520-6025
0163-3864
DOI: 10.1021/np010288l
Popis: Bioassay-guided fractionation of an ethyl acetate-soluble extract from the whole plants of Broussonetia papyrifera, using an in vitro aromatase inhibition assay, led to the isolation of five new active compounds, 5,7,2',4'-tetrahydroxy-3-geranylflavone (1), isogemichalcone C (8), 3'-[gamma-hydroxymethyl-(E)-gamma-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate (9), demethylmoracin I (10), and (2S)-2',4'-dihydroxy-2' '-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone (11), and 10 known (12-21) compounds which were also found to be active. Of these compounds, the most potent were 9 (IC(50) 0.5 microM), 11 (IC(50) 0.1 microM), isolicoflavonol (12, IC(50) 0.1 microM), and (2S)-abyssinone II (13, IC(50) 0.4 microM). Additionally, six new compounds, 5,7,3',4'-tetrahydroxy-6-geranylflavonol (2), 5,7,3',4'-tetrahydroxy-3-methoxy-6-geranylflavone (3), (2S)-7,4'-dihydroxy-3'-prenylflavan (4), 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane (5), 1-(2,4-dihydroxy-3-prenylphenyl)-3-(4-hydroxyphenyl)propane (6), and 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxy-3-prenylphenyl)propane (7), were isolated and characterized, but proved to be inactive as aromatase inhibitors, as were an additional 21 known compounds. The structures of the new compounds (1-11) were elucidated by spectroscopic methods. Structure-activity relationships in the aromatase assay were determined for the benzofurans, biphenylpropanoids, coumarins, and various types of flavonoids (chalcones, flavans, flavanones, and flavones) obtained among a total of 42 constituents of B. papyrifera.
Databáze: OpenAIRE
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