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Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.

Abstract
A new butenylflavanone, (2S)-5-hydroxy-7-methoxy-8-[(E)-3-oxo-1-butenyl]flavanone (1), and a new rotenoid, 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (2), as well as three active flavonoids of previously known structure, isoliquiritigenin (3), genistein (4), and chrysoeriol (5), along with nine known inactive compounds, alpha-toxicarol (6), sumatrol, 6a,12a-dehydro-alpha-toxicarol, 11-hydroxytephrosin, obovatin, marmesin, lupenone, benzyl benzoate, and benzyl trans-cinnamate, were isolated from an ethyl acetate-soluble extract of the stems of Tephrosia toxicaria, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structures of compounds 1 and 2 were elucidated by spectroscopic data interpretation. All isolates were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction. Selected compounds were tested in a mouse mammary organ culture assay to evaluate the inhibition of 7,12-dimethylbenz[a]anthracene (DMBA)-induced preneoplastic lesions.
AuthorsDae Sik Jang, Eun Jung Park, Young-Hwa Kang, Michael E Hawthorne, Jose Schunke Vigo, James G Graham, Fernando Cabieses, Harry H S Fong, Rajendra G Mehta, John M Pezzuto, A Douglas Kinghorn
JournalJournal of natural products (J Nat Prod) Vol. 66 Issue 9 Pg. 1166-70 (Sep 2003) ISSN: 0163-3864 [Print] United States
PMID14510590 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • (2S)-5-hydroxy-7-methoxy-8-((E)-3-oxo-1-butenyl)flavanone
  • 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin
  • Anticarcinogenic Agents
  • Chromones
  • Flavonoids
  • Heterocyclic Compounds, 4 or More Rings
  • NAD(P)H Dehydrogenase (Quinone)
Topics
  • Animals
  • Anticarcinogenic Agents (chemistry, isolation & purification, pharmacology)
  • Carcinoma, Hepatocellular
  • Chromones (chemistry, isolation & purification, pharmacology)
  • Flavonoids (chemistry, isolation & purification, pharmacology)
  • Heterocyclic Compounds, 4 or More Rings (chemistry, isolation & purification, pharmacology)
  • Mammary Neoplasms, Experimental
  • Mice
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) (metabolism)
  • Peru
  • Plant Stems (chemistry)
  • Plants, Medicinal (chemistry)
  • Stereoisomerism
  • Tephrosia (chemistry)
  • Tumor Cells, Cultured (drug effects)

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