Anti-AIDS agents, 10. Acacetin-7-O-beta-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids.
An active anti-HIV principle, acacetin-7-O-beta-D-galactopyranoside, has been isolated from Chrysanthemum morifolium. Seven additional flavonoids isolated from this plant, 13 known related flavonoids, and 14 synthetic flavonoids were also evaluated as inhibitors of HIV replication in H9 cells. A known flavone, chrysin, was found to be the most promising compound in this series. Flavonoids with hydroxy groups at C-5 and C-7 and with a C-2-C-3 double bond were more potent inhibitors of HIV growth. In general, the presence of substituents (hydroxyl and halogen) in the B-ring increased toxicity and/or decreased activity.
Hu
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CQ
Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599.
Chen
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Shi
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Kilkuskie
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Cheng
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YC
Lee
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KH
D000998:Antiviral Agents / Q000302:isolation & purification* / Q000494:pharmacology; D002478:Cells, Cultured; D005419:Flavonoids / Q000302:isolation & purification* / Q000494:pharmacology*; D005697:Galactosides / Q000302:isolation & purification* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D013058:Mass Spectrometry; D008516:Medicine, Chinese Traditional; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D014779:Virus Replication / Q000187:drug effects; D015215:Zidovudine / Q000494:pharmacology
D000998:Antiviral Agents; D005419:Flavonoids; D005697:Galactosides; C086771:acacetin-7-O-galactopyranoside; D015215:Zidovudine