KAEMPFERIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O6
Molecular Weight	300.2629
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=SQFSKOYWJBQGKQ-UHFFFAOYSA-N

InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28928604 | https://www.ncbi.nlm.nih.gov/pubmed/26345098 | https://www.ncbi.nlm.nih.gov/pubmed/23869536 | https://www.ncbi.nlm.nih.gov/pubmed/23355380 | http://pubs.rsc.org/-/content/articlelanding/2015/ra/c5ra19199h/unauth#!divAbstract

Kaempferide (3,5,7-trihydroxy-4′-methoxyflavone, Kae) is a naturally occurring flavonoid that is isolated from the roots of Alpinia officinarum (lesser galangal). Like other flavonoids, Kae also has a very good antioxidant properties and Kae can effectively reduce 1,1- diphenyl-2-picrylhydrazyl (DPPH). Studies have shown that Kae has anticancer and antihypertension effects. Kaempferide protects against myocardial Ischemia/reperfusion Injury through activation of the PI3K/Akt/GSK-3β pathway. Kaempferide inhibited potent antioxidant activity. Kaempferide is one of the candidates for active compound in propolis. Kaempferide, the most active among the four flavonoids isolated and characterized from Chromolaena odorata, induces apoptosis in cervical cancer cells while being pharmacologically safe.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine--tRNA ligase 1 Target ID: P0AGJ9 Gene ID: 948855.0 Gene Symbol: tyrS Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487455	Inhibitor 8297
TRAIL receptor-1 1 Target ID: CHEMBL3551 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25580686	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23869536 \| https://www.ncbi.nlm.nih.gov/pubmed/23840273	Inhibitor 8297
Hypoxia-inducible factor 1 alpha 17 Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21865046	Inhibitor 8297
Tyrosinase 41 Target ID: CHEMBL5346 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615910	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cardiovascular diseases 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28928604 https://www.ncbi.nlm.nih.gov/pubmed/21865046	Primary	Preclinical	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28588226	Primary	Basic research	Unknown Approved Use Unknown
Hyperpigmentation 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615910	Primary	Basic research	Unknown Approved Use Unknown
Cervical cancer 40 Sources: http://pubs.rsc.org/-/content/articlelanding/2015/ra/c5ra19199h/unauth#!divAbstract	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
Kaempferide triglycoside: a possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi.	2001 Apr	11314958
Phenolic compounds of propolis from Central Chilean matorral.	2001 Mar-Apr	11371020
Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9.	2002 Feb	11792676
Flavonol glycosides of Warburgia ugandensis leaves.	2003 Oct	14559287
Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.	2004 Sep	15261964
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005 Oct 4	16202168
Flavonoids from Echinops echinatus.	2006 Apr-May	16864424
In vitro antimalarial activity of flavonoid derivatives dehydrosilybin and 8-(1;1)-DMA-kaempferide.	2006 Jan	16256062
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.	2007 Nov	17709371
[Studies on chemical constituents of Salacia prinoides].	2008 Sep	19180955
Brazilian propolis: correlation between chemical composition and antimicrobial activity.	2008 Sep	18830454
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.	2008 Sep	18830449
Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.	2009 Aug 15	19615910
From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine.	2009 Jul 22	19624827
Reversing β-lactam antibiotic resistance of Staphylococcus aureus with galangin from Alpinia officinarum Hance and synergism with ceftazidime.	2010 Dec 15	21036573
Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes.	2010 Jan 1	19942440
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012 Jun	22445328

Patents

Sample Use Guides

In Vivo Use Guide

Rats were randomly divided into 7 groups: (1) sham group, rats underwent sham surgery; (2) I/R group, rats were subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (3) L-Kae (Kaempferide) + I/R group, rats were injected with a low dose of Kae (L-Kae; 0.1 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (4) M-Kae + I/R group, rats were injected with a moderate dose of Kae (M-Kae; 0.3 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (5) H-Kae + I/R group, rats were injected with a high dose of Kae (H-Kae; 1 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion;

Route of Administration: Intravenous

In Vitro Use Guide

Kaempferide inhibited melanogenesis (81.2% inhibition) in theophylline-stimulated mouse B16-4A5 cells at 30 uM after 72 hrs

Name

Type

Language

KAEMPFERIDE

Common Name

English

3,5,7-TRIHYDROXY-2-(4-METHOXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

4'-METHYLKAEMPFEROL

Common Name

English

NSC-407294

Code

English

KAEMPFEROL 4'-METHYL ETHER

Common Name

English

4'-O-METHYLKAEMPFEROL

Common Name

English

Code System Code Type Description

CHEBI

58925