Two New Polymethoxylated Flavones, a Class of Compounds with Potential Anticancer Activity, Isolated from Cold Pressed Dancy Tangerine Peel Oil Solids

Ten polymethoxylated flavonoids were isolated and characterized from cold pressed tangerine oil solids; they are 5,6,7,3‘,4‘-pentamethoxyflavone (sinensetin) (I); 7-hydroxy-3,5,6,3‘,4‘-pentamethoxyflavone (II); 5-hydroxy-6,7,8,3‘,4‘-pentamethoxyflavone (III); 5,6,7,8,3‘,4‘-hexamethoxyflavone (nobile...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1997-02, Vol.45 (2), p.364-368
Main Authors: Chen, Jie, Montanari, Antonio M, Widmer, Wilbur W
Format: Article
Language:English
Subjects:
ACEITES VEGETALES
AGENTES ANTINEOPLASTICOS
Biological and medical sciences
DECHET AGRICOLE
DESECHOS AGRICOLAS
ESPECTROMETRIA
FLAVONOIDE
FLAVONOIDES
General pharmacology
HUILE VEGETALE
MANDARINA
MANDARINE
Medical sciences
MEDICAMENT CYTOSTATIQUE
PELURE
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
PIEL (VEGETAL)
SPECTROMETRIE
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Summary:Ten polymethoxylated flavonoids were isolated and characterized from cold pressed tangerine oil solids; they are 5,6,7,3‘,4‘-pentamethoxyflavone (sinensetin) (I); 7-hydroxy-3,5,6,3‘,4‘-pentamethoxyflavone (II); 5-hydroxy-6,7,8,3‘,4‘-pentamethoxyflavone (III); 5,6,7,8,3‘,4‘-hexamethoxyflavone (nobiletin) (IV); 5,6,7,8,4‘-pentamethoxyflavone (tangeretin) (V); 5,7,8,4‘-tetramethoxyflavone (tetra-O-methylisoscutellarein) (VI); 7-hydroxy-3,5,6,8,3‘,4‘-hexamethoxyflavone (VII); 5,6,7,4‘-tetramethoxyflavone (tetra-O-methylisoscutellarein) (VIII); 3,5,6,7,8,3‘,4‘-heptamethoxyflavone (IX); and 5,7,8,3‘,4‘-pentamethoxyflavone (X). Structures of the compounds were elucidated on the basis of spectroscopic methods and chemical data. Compounds II and VII are novel natural products; compounds IV, V, and VIII have been reported with significant activity against various strains of carcinoma cells; and compounds I and IV decrease erythrocyte aggregation and sedimentation in vitro. A biological activity screen of other compounds is in progress. Keywords: Polymethoxylated flavones; antitumor activity; Citrus; tangerine oils; Dancy tangerine
ISSN:0021-8561
1520-5118
DOI:10.1021/jf960110i