14813-27-5Relevant articles and documents
A flavonoid and indole alkaloid from flowers of Murraya paniculata
Wu Tain Shung,Chan Yu Yi,Leu Yann Lii,Huang
, p. 287 - 288 (1994)
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Myricetin 5,7,3',4',5'-pentamethyl ether and other methylated flavonoids from Murraya paniculata
Kinoshita, Takeshi,Firman, Kurnia
, p. 179 - 181 (1997)
Seven flavonoids, including one new flavonol, were isolated from the leaves of Murraya paniculata (Rutaceae). Four were identified as previously known constituents of M. paniculata or allied species, namely, 5,7,3',4',5'- pentamethoxyflavone, 5,7,8,3',4',5'-hexamethoxyflavone, 3,5,7,3',4',5'- hexamethoxyflavone and 3,5,7,8,3',4',5'-heptamethoxyflavone. The structure of the new flavonol was elucidated as 3-hydroxy-5,7,3',4',5'-pentamethoxyflavone on the basis of spectroscopic studies. Two other flavonoids, a methylated flavanone and its corresponding chalcone isomer were identified as 2-(S)- 5,7,3',4',5'-pentamethoxyflavanone and 2'-hydroxy-3,4,5,4',6'- pentamethoxychalcone, respectively.
Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity
Boutefnouchet, Sabrina,Bouzidi, Chouaha,Cojean, Sandrine,Figadère, Bruno,Grougnet, Rapha?l,Maciuk, Alexandre,Michel, Sylvie,Ortiz, Sergio,Vásquez-Ocmín, Pedro G.
, (2020/09/16)
A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.
Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity
Matsuda, Hisashi,Morikawa, Toshio,Toguchida, Iwao,Yoshikawa, Masayuki
, p. 788 - 795 (2007/10/03)
The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).