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Kaempferitrin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-K1001

  • Specification : 98%

  • CAS number : 482-38-2

  • Formula : C27H30O14

  • Molecular Weight : 578.52

  • PUBCHEM ID : 5486199

  • Volume : 20mg

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Catalogue Number

BF-K1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

578.52

Appearance

Yellow crystal

Botanical Source

Siraitia grosvenorii,Eleutherococcus sessiliflorus,Dicliptera chinensis,Eurycorymbus cavaleriei,Heritiera littoralis

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O

Synonyms

kaempferol 3-O-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside/4H-1-Benzopyran-4-one, 3,7-bis[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-/3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy-α-L-mannopyranoside/kaempferol 3,7-di-O-α-L-rhamnoside/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/Kaempferol 3,7-L-dirhamnoside/Kaemferitrin/Kaempferol 3,7-dirhamnoside/lespenefril/kaempferol-3,7-O-α-L-dirhamnoside/Lespenephryl/Kaempferol-3,7-O-bis-α-L-rhamnoside/Kaempferitrin/Kaempferol 3,7-bisrhamnoside/Lespedin

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

Density

1.7±0.1 g/cm3

Solubility

Methanol

Flash Point

302.8±27.8 °C

Boiling Point

908.6±65.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

PUPKKEQDLNREIM-QNSQPKOQSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:482-38-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31456483

Abstract

Context: Kaempferitrinis (KF) is a bioactive flavonoid and possesses numerous pharmacological activities. However, whether KF affects the activity of human liver cytochrome P450 (CYP) enzymes remains unclear. Objective: This study investigates the effects of KF on eight major CYP isoforms in human liver microsomes (HLMs). Materials and methods: In vitro, HLMs were used to investigate the inhibitory effects of KF (100 μM) on the eight human liver CYP isoforms (i.e., 1A2, 3A4, 2A6, 2E1, 2D6, 2C9, 2C19, and 2C8), and corresponding probe substrates were used. Enzyme kinetic studies (0-50 μM of KF) were conducted to determine the inhibition mode of KF on CYP enzymes. Results: The results showed that KF inhibited the activity of CYP1A2, 3A4, and 2C9, with IC50 values of 20.56, 13.87, and 14.62 μM, respectively, but that other CYP isoforms were not affected. Enzyme kinetic studies showed that KF was not only a noncompetitive inhibitor of CYP3A4, but also a competitive inhibitor of CYP1A2 and 2C9, with Ki values of 7.11, 10.24, and 7.58 μM, respectively. In addition, KF is a time-dependent inhibitor for CYP3A4 with KI/Kinact value of 10.85/0.036 min/μM. Discussion: The in vitro studies of KF with CYP isoforms indicate that KF has the potential to cause pharmacokinetic drug interactions with other co-administered drugs metabolized by CYP1A2, 3A4, and 2C9. Conclusion: It is recommended that KF should not be used with other drugs metabolized by CYP1A2, 3A4, and 2C9. Further clinical studies are needed to evaluate the significance of this interaction.

KEYWORDS

CYP1A2; CYP2C9; CYP3A4; Herb-drug interaction

Title

In vitro inhibitory effects of kaempferitrin on human liver cytochrome P450 enzymes.

Author

Zhang N1, Liu J2, Chen Z3, Dou W4.

Publish date

2019 Dec

PMID

31351191

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:
Bauhinia forficata Link, commonly known as “cow’s paw”, is a native plant from South America. Its leaves are widely used in Brazilian folk medicine to treat diabetes and cardiovascular disorders. Although this species’ biological potential has been extensively proven as an antidiabetic, anti-inflammatory and antioxidant agent, there is a lack of studies to evidence its action on the cardiovascular system.

AIM OF THE STUDY:
This study was designed to investigate the vascular effects of B. forficata leaves preparations and its majority compound kaempferitrin, as well as its aglycone form kaempferol, in rat aortic rings of normotensive (NTR) and hypertensive (SHR) rats.

MATERIALS AND METHODS:
Aorta rings from NTR and SHR precontracted with phenylephrine were exposed to cumulative concentrations of B. forficata extract, fractions (1-50 μg/mL) and compounds (0.001-0.3 μg/mL). The mechanisms involved in the vasorelaxant effect of ethyl-acetate plus butanol fraction (EAButF) were also evaluated.

RESULTS:
Although kaempferitrin is the most abundant compound found in both methanolic extract and EAButF, 24 minor phenolic compounds were identified in B. forficata leaves, including kaempferol. EAButF was the only with endothelium-dependent and independent vasorelaxant properties in both NTR and SHR. The incubation with L-NAME or ODQ completely blocked EAButF-induced vasorelaxation. On the other hand, the incubation with propranolol, atropine, indomethacin, glibenclamide or barium chloride did not change the vasorelaxant activity of EAButF (50 μg/mL). Nevertheless, the incubation with tetraethylammonium and 4-aminopyridine significantly influenced the EAButF activity. It was also shown that Ca2+ influx or efflux is not related to EAButF vasorelaxation potential. Kaempferitrin and kaempferol were also able to relax the rat aortic rings in 34.70% and 40.54%, respectively.

CONCLUSIONS:
This study shows, for the first time, the vasorelaxant effect of EAButF from B. forficata leaves, an effect that may be attributed to the modulation of vascular tone through nitric oxide/soluble guanylate cyclase pathway, and potassium channels. The bioactive kaempferitrin and kaempferol seem to be important for the effects observed with the fraction. Finally, preparations obtained from the leaves of B. forficata may be interesting candidates for new or complementary strategies regarding cardiovascular diseases.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Flavonoids; Kaempferitrin; Kaempferol; Medicinal plants; Nitric oxide; Vasculature

Title

Bauhinia forficata link, a Brazilian medicinal plant traditionally used to treat cardiovascular disorders, exerts endothelium-dependent and independent vasorelaxation in thoracic aorta of normotensive and hypertensive rats.

Author

Cechinel-Zanchett CC1, da Silva RCMVAF1, Tenfen A1, Siebert DA2, Micke G2, Vitali L2, Cechinel-Filho V1, Faloni de Andrade S1, de Souza P3.

Publish date

2019 Oct 28

PMID

31155798

Abstract

Rheumatoid arthritis (RA) is a complex chronic inflammatory disease that is associated with the aberrant activation of fibroblast-like synoviocytes (FLS). Kaempferitrin is a natural flavonoid glycoside that possesses anti-inflammatory bioactivity. However, the effect of kaempferitrin on RA has not yet been revealed. The aim of the present study was to investigate the effect of kaempferitrin on human RA-FLS MH7A cell line. We found that kaempferitrin inhibited proliferation and induced apoptosis of MH7A cells. Kaempferitrin decreased the levels of interleukin (IL)-1β, IL-6, tumor necrosis factor (TNF)-α, matrix metalloproteinase (MMP)-1, and MMP-3 in MH7A cells. Moreover, kaempferitrin blocked the activation of nuclear factor-κB (NF-κB) and protein kinase B (Akt)/mammalian target of rapamycin (mTOR) pathways. Furthermore, treatment with kaempferitrin decreased paw thickness and arthritis scores, and reduced the serum levels of IL-1β, IL-6, and TNF-α in a collagen-induced arthritis mouse model. In conclusion, kaempferitrin inhibited cell proliferation, induced cell apoptosis, and ameliorated inflammation of RA-FLS by suppressing the NF-κB and Akt/mTOR pathways.

© 2019 John Wiley & Sons, Ltd.

Title

Kaempferitrin inhibits proliferation, induces apoptosis, and ameliorates inflammation in human rheumatoid arthritis fibroblast-like synoviocytes.

Author

Wang J1, Zhao Q1.

Publish date

2019 Jun


Description :

Antidiabetic activity of Sedum dendroideum: metabolic enzymes as putative targets for the bioactive flavonoid kaempferitrin. PUMID/DOI:24817132 IUBMB Life. 2014 May;66(5):361-70. First, the major flavonoids kaempferol 3,7-dirhamnoside or Kaempferitrin (1), kaempferol 3-glucoside-7-rhamnoside (2), and kaempferol 3-neohesperidoside-7-rhamnoside (3) were tested. Then, the monoglycosides kaempferol 7-rhamnoside (5) and kaempferol 3-rhamnoside (6) were assayed to establish their structure/activity relationship. The effect of 1 on PFK was evaluated in skeletal muscle, liver, and adipose tissue from treated mice. LJ (400 mg/kg), BF (40 mg/kg), and flavonoid 1 (4 mg/kg) reduced glycemia in diabetic mice (120 min) by 52, 53, and 61%, respectively. Flavonoids 2, 3, 5, and 6 were inactive or showed little activity, suggesting that the two rhamnosyl moieties in Kaempferitrin are important requirements. Kaempferitrin enhanced the PFK activity chiefly in hepatic tissue, suggesting that it is able to stimulate tissue glucose utilization. This result is confirmed testing Kaempferitrin on C2C12 cell line, where it enhanced glucose consumption, lactate production, and the key regulatory glycolytic enzymes. The hypoglycemic activity of Kaempferitrin depends on the presence of both rhamnosyl residues in the flavonoid structure when intraperitoneally administered. Our findings show for the first time that a flavonoid is capable of stimulating PFK in a model of diabetes and that Kaempferitrin stimulates glucose-metabolizing enzymes. This study contributes to the knowledge of the mechanisms by which this flavonoid exerts its hypoglycemic activity.