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methyl brevifolincarboxylate

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methyl brevifolincarboxylate Basic information

Product Name:
methyl brevifolincarboxylate
Synonyms:
  • methyl brevifolincarboxylate
  • methyl 7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylate
  • Cyclopenta[c][2]benzopyran-1-carboxylic acid, 1,2,3,5-tetrahydro-7,8,9-trihydroxy-3,5-dioxo-, methyl ester
  • methyl brevifolincarboxylate USP/EP/BP
CAS:
154702-76-8
MF:
C14H10O8
MW:
306.22
Mol File:
154702-76-8.mol
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methyl brevifolincarboxylate Chemical Properties

storage temp. 
Store at -20°C
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methyl brevifolincarboxylate Usage And Synthesis

Uses

Methyl brevifolincarboxylate (Brevifolincarboxylic acid methyl ester) is a potent influenza virus PB2 cap-binding inhibitor. Methyl brevifolincarboxylate has anti-oxidant activity. Methyl brevifolincarboxylate also inhibits platelet aggregation, lipid metabolism and inflammation[1][2][4][5][6].

Definition

ChEBI: An organic heterotricyclic compound that is 1,2,3,5-tetrahydrocyclopenta[c]isochromene substituted by hydroxy groups at positions 7, 8 and 9, oxo groups at positions 3 and 5 and a methoxycarbonyl group at position 1. Isolated from Phyll nthus urinaria and Phyllanthus niruri, it exhibits vasorelaxant activity.

Synthesis

Extraction method of short-leaf hematoxylin methyl ester: take dry leaves under the beads of the whole grass, beaten into coarse powder, placed into the Sojitz extractor, first add petroleum ether degreasing, the dregs of the drug cool dry, and then fully extracted with methanol. Separate the methanol extract, concentrated methanol extract with reduced pressure distillation, to get methanol extract. This extract was mixed with appropriate amount of water, and then sequentially distributed with chloroform and n-butanol, n-butanol was taken out and concentrated under reduced pressure, and then mixed with silica gel and diatomaceous earth, silica gel low-pressure column chromatography, and then chloroform-methanol-water was used as the gradient elution, and the eluates were collected separately, and each portion of 250 ml was obtained as the 36th portion of the crude product of short-leafed Succinum sativum phenolic acid methyl ester. The crude product was then purified by silica gel column for the second time, and recrystallized with methanol-chloroform to obtain pure methyl short-leaf thujaplichenate.

References

[1] Wu QY, et al. Chromatographic fingerprint and the simultaneous determination of five bioactive components of geranium carolinianum L. water extract by high performance liquid chromatography. Int J Mol Sci. 2011;12(12):8740-8749. DOI:10.3390/ijms12128740
[2] Fang SH, et al. Anti-oxidant and inflammatory mediator's growth inhibitory effects of compounds isolated from Phyllanthus urinaria. J Ethnopharmacol. 2008;116(2):333-340. DOI:10.1016/j.jep.2007.11.040
[3] Iizuka T, et al. Vasorelaxant effects of methyl brevifolincarboxylate from the leaves of Phyllanthus niruri. Biol Pharm Bull. 2006 Jan;29(1):177-9. DOI:10.1248/bpb.29.177
[4] Iizuka T, et al. Inhibitory effects of methyl brevifolincarboxylate isolated from Phyllanthus niruri L. on platelet aggregation. Biol Pharm Bull. 2007 Feb;30(2):382-4. DOI:10.1248/bpb.30.382

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