- Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae)
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A series of 16 flavonoids were isolated and prepared from bud exudate of Gardenia urvillei and Gardenia oudiepe, endemic to New Caledonia. Most of them are rare polymethoxylated flavones. Some of these compounds showed noticeable activity against Leishmania (Leishmania) amazonensis, Plasmodium falciparum and Trypanosoma brucei gambiense, in addition to tubulin polymerization inhibition at low micromolar concentration. We also provide a full set of NMR data as some of the flavones were incompletely described.
- Mai, Linh H.,Chabot, Guy G.,Grellier, Philippe,Quentin, Lionel,Dumontet, Vincent,Poulain, Cyril,Espindola, Laila S.,Michel, Sylvie,Vo, Hue T.B.,Deguin, Brigitte,Grougnet, Rapha?l
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supporting information
p. 93 - 100
(2015/03/05)
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- Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates
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A strategy for selective mono-, di- and tri-O-methylation of kaempferol, predominantly on the basis of selective benzylation and controllable deacetylation of kaempferol acetates, was developed. From the selective deacetylation and benzylation of kaempferol tetraacetate (1), 3,4′,5,-tri-O-acetylkaempferol (2) and 7-O-benzyl-3,4′5,-tri-O-acetylkaempferol (8) were obtained, respectively. By controllable deacetylation and followed selective or direct methylation of these two intermediates, eight O-methylated kaempferols were prepared with 51-77% total yields from kaempferol.
- Mei, Qinggang,Wang, Chun,Yuan, Weicheng,Zhang, Guolin
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p. 288 - 293
(2015/03/31)
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- 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
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4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
- De Meyer,Haemers,Mishra,Pandey,Pieters,Vanden Berghe,Vlietinck
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p. 736 - 746
(2007/10/02)
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- 3-Alkoxyflavone antiviral agents
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Antiviral compositions containing 3-alkoxyflavone compounds as their active ingredients are disclosed.
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