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Kaempferitrin

IUPAC Name
5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]chromen-4-one

Synonyms
3,7-Bis[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 3,7-Bis[(6-deoxy-α-L-mannopyranosyl)oxy]-4',5-dihydroxyflavone; kaempferol3-O-α-L-rhamnopyranosyl-7-O-α-L-rhamnopyranoside

Description
Kaempferitrin is a flavonoid glycoside that has been found in B. pinnatum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 8.73 μg/ml) and is active against the bacteria S. aureus, P. aeruginosa, and S. typhi, as well as the fungi C. albicans, C. parapsilosis, and C. neoformans (MICs = 16-32 μg/ml). Kaempferitrin inhibits LPS-and IFN-γ-induced nitric oxide (NO) production in isolated mouse macrophages (IC50 = 40 μM). It decreases blood glucose levels in a rat model of alloxan-induced diabetes when administered at a dose of 100 mg/kg.

SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O

InChI
InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9-,10-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1

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