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chrysosplenetin B

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chrysosplenetin B Basic information

Product Name:
chrysosplenetin B
Synonyms:
  • chrysosplenetin B
  • 3,6,7,3'-Tetramethylquercetagetin
  • 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one
  • EMD-20940
  • 4H-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-
  • 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxy-
  • chrgsosplenetin B
  • 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxychromen-4-one
CAS:
603-56-5
MF:
C19H18O8
MW:
374.34
Mol File:
603-56-5.mol
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chrysosplenetin B Chemical Properties

Melting point:
203-205 °C
Boiling point:
615.8±55.0 °C(Predicted)
Density 
1.44±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble; Methanol: soluble
form 
A crystalline solid
pka
6.13±0.40(Predicted)
color 
Light yellow to yellow
InChI
InChI=1S/C19H18O8/c1-23-11-7-9(5-6-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
InChIKey
NBVTYGIYKCPHQN-UHFFFAOYSA-N
SMILES
O=C1C(=C(C2C=CC(=C(C=2)OC)O)OC2=CC(=C(C(=C21)O)OC)OC)OC
LogP
3.037 (est)
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chrysosplenetin B Usage And Synthesis

Occurance

Chrysosplenetin B is a tetramethoxyflavone that is the 3,6,7,3'-tetramethyl ether derivative of quercetagetin. It has a role as an antiviral agent and a plant metabolite. It is a tetramethoxyflavone and a dihydroxyflavone. It derives from a quercetagetin.
Chrysosplenetin B is an O-methylated flavonol. It can be found in the root of Berneuxia thibetica and in Chamomilla recutita.

Chemical Properties

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Laggera pterodonta.

Uses

Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1].

Definition

ChEBI: A tetramethoxyflavone that is the 3,6,7,3'-tetramethyl ether derivative of quercetagetin.

IC 50

CYP3A

References

[1] Ma L, et al. Chrysosplenetin inhibits artemisinin efflux in P-gp-over-expressing Caco-2 cells and reverses P-gp/MDR1 mRNA up-regulated expression induced by artemisinin in mouse small intestine. Pharm Biol. 2017 Dec;55(1):374-380. DOI:10.1080/13880209.2016.1241810

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