Aromatase inhibitors from Broussonetia papyrifera

Dongho Lee, K. P L Bhat, H. H S Fong, N. R. Farnsworth, J. M. Pezzuto, A. D. Kinghorn

Research output: Contribution to journalArticle

130 Citations (Scopus)

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′-[y -hydroxymethyl-(E)-y-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 (IC50 0.5 μM), 11 (IC50 0.1 μM), isolicoflavonol (12,IC50 0.1 μM), and (2S)-abyssinone II (13, IC50 0.4 νM). Additionally, six new compounds, 5,7,3′,4′-tetrahydroxy-6-geranylflavone (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.

Original languageEnglish
Pages (from-to)1286-1293
Number of pages8
JournalJournal of Natural Products
Volume64
Issue number10
DOIs
Publication statusPublished - 2001 Nov 14
Externally publishedYes

Fingerprint

Broussonetia
Broussonetia papyrifera
Propane
Aromatase Inhibitors
propane
Inhibitory Concentration 50
inhibitory concentration 50
Aromatase
flavanones
Assays
Benzofurans
Flavanones
Chalcones
Flavones
Coumarins
Bioassay
Fractionation
benzofurans
chalcones
Flavonoids

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Lee, D., Bhat, K. P. L., Fong, H. H. S., Farnsworth, N. R., Pezzuto, J. M., & Kinghorn, A. D. (2001). Aromatase inhibitors from Broussonetia papyrifera. Journal of Natural Products, 64(10), 1286-1293. https://doi.org/10.1021/np010288l

Aromatase inhibitors from Broussonetia papyrifera. / Lee, Dongho; Bhat, K. P L; Fong, H. H S; Farnsworth, N. R.; Pezzuto, J. M.; Kinghorn, A. D.

In: Journal of Natural Products, Vol. 64, No. 10, 14.11.2001, p. 1286-1293.

Research output: Contribution to journalArticle

Lee, D, Bhat, KPL, Fong, HHS, Farnsworth, NR, Pezzuto, JM & Kinghorn, AD 2001, 'Aromatase inhibitors from Broussonetia papyrifera', Journal of Natural Products, vol. 64, no. 10, pp. 1286-1293. https://doi.org/10.1021/np010288l
Lee D, Bhat KPL, Fong HHS, Farnsworth NR, Pezzuto JM, Kinghorn AD. Aromatase inhibitors from Broussonetia papyrifera. Journal of Natural Products. 2001 Nov 14;64(10):1286-1293. https://doi.org/10.1021/np010288l
Lee, Dongho ; Bhat, K. P L ; Fong, H. H S ; Farnsworth, N. R. ; Pezzuto, J. M. ; Kinghorn, A. D. / Aromatase inhibitors from Broussonetia papyrifera. In: Journal of Natural Products. 2001 ; Vol. 64, No. 10. pp. 1286-1293.
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