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

HIDE SMILES / InChI

Molecular Formula	C16H14O5
Molecular Weight	286.2794
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Separation of some chiral flavanones by micellar electrokinetic chromatography.	2003 Aug	12900864
In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae).	2004 Sep	15324490
Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.	2004 Sep	15261964
Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE.	2008 Nov	18924103
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.	2008 Sep	18830449
A validated reverse-phase HPLC analytical method for the quantification of phenolic compounds in Baccharis dracunculifolia.	2009 Jan-Feb	18752260
From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine.	2009 Jul 22	19624827
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
Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.	2010 Apr 28	20302370
Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis.	2010 Nov 2	20850110

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:39:40 GMT 2023` Edited by `admin` on `Fri Dec 15 19:39:40 GMT 2023`
Record UNII	U02X7TF8UA
Record Status	`Validated (UNII)`
Record Version

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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