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Aromatase inhibitors from Broussonetia papyrifera.
- Source :
-
Journal of natural products [J Nat Prod] 2001 Oct; Vol. 64 (10), pp. 1286-93. - Publication Year :
- 2001
-
Abstract
- 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.
- Subjects :
- Algorithms
Anticarcinogenic Agents chemistry
Anticarcinogenic Agents pharmacology
Benzofurans chemistry
Benzofurans pharmacology
Chalcone analogs & derivatives
Chalcone chemistry
Chalcone pharmacology
Chalcones
Circular Dichroism
Enzyme Inhibitors chemistry
Enzyme Inhibitors pharmacology
Female
Flavonoids chemistry
Flavonoids pharmacology
Humans
Illinois
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Mass Spectrometry
Microsomes enzymology
Molecular Structure
Placenta enzymology
Plants, Medicinal chemistry
Pregnancy
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Structure-Activity Relationship
Terpenes chemistry
Terpenes pharmacology
Anticarcinogenic Agents isolation & purification
Aromatase
Aromatase Inhibitors
Benzofurans isolation & purification
Chalcone isolation & purification
Enzyme Inhibitors isolation & purification
Flavanones
Flavonoids isolation & purification
Moraceae chemistry
Terpenes isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 0163-3864
- Volume :
- 64
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 11678652
- Full Text :
- https://doi.org/10.1021/np010288l