ISOSAKURANETIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14O5
Molecular Weight	286.2794
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=HMUJXQRRKBLVOO-AWEZNQCLSA-N

InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 | https://www.ncbi.nlm.nih.gov/pubmed/24006495 | https://www.ncbi.nlm.nih.gov/pubmed/28715803 | https://www.ncbi.nlm.nih.gov/pubmed/28013186

Isosakuranetin is a citrus fruit flavanone. It is a TRPM3 channel blocker and CYP1 enzyme isoforms inhibitor. It is a strong candidate, as chemopreventive food ingredient against CYP1B1-related carcinogenesis. Isosakuranetin may be useful in treating neuropathic pain without body temperature increase. Isosakuranetin attenuated ethanol-induced gastritis by inhibiting the infiltration of immune cells, including neutrophils, via the regulation of CXCL4 (or IL-8) secretion and the activation NF-κB.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
transient receptor potential cation channel, subfamily M, member 3 1 Target ID: 226025.0 Gene Symbol: Trpm3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24006495 \| https://www.ncbi.nlm.nih.gov/pubmed/28720517	Blocker 537	50.0 nM [IC50]
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	2.2 µM [IC50]
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	3.1 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	1.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24006495 https://www.ncbi.nlm.nih.gov/pubmed/28715803	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Preventing	Basic research	Unknown Approved Use Unknown
Hemorrhagic gastritis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28013186	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antioxidative bioavailability of artepillin C in Brazilian propolis.	2004 Apr 15	15047190
Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE.	2008 Nov	18924103
Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats.	2009 Jul	19571393
Modulation of Akt, JNK, and p38 activation is involved in citrus flavonoid-mediated cytoprotection of PC12 cells challenged by hydrogen peroxide.	2009 Mar 25	19222219

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 2 or 10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Isosakuranetin blocked the inward TRPM3 currents at -113 mV slightly more potently (IC50 = 80 nM) compared with the outward TRPM currents measured at -87 mV (IC50 = 120 nM). Both currents were isosakuranetin sensitive and almost completely blocked at a concentration of 3 uM.

Name

Type

Language

ISOSAKURANETIN

Common Name

English

4'-METHYLNARINGENIN

Common Name

English

(2S)-5,7-DIHYDROXY-2-(4-METHOXYPHENYL)-2,3-DIHYDROCHROMEN-4-ONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60963980