ISOVITEXIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O10
Molecular Weight	432.3775
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=C(O)C3=C(OC(=CC3=O)C4=CC=C(O)C=C4)C=C2O

InChI

InChIKey=MYXNWGACZJSMBT-VJXVFPJBSA-N

InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H20O10
Molecular Weight	432.3775
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24291393 | https://www.ncbi.nlm.nih.gov/pubmed/15965085 | https://www.ncbi.nlm.nih.gov/pubmed/27693342 | https://www.ncbi.nlm.nih.gov/pubmed/28891090

Isovitexin (apigenin-6-C-glucoside), an isomer of vitexin, is found in plants such as pigeon pea, Passiflora, bamboo, mimosa, wheat leaves, rice hull of Oryza sativa and others. Isovitexin is poorly absorbed in the gastrointestinal tract. The highest level of intravenously administrated isovitexin was examined in kidney, liver, lung, and lowest in the brain. Isovitexin helps to stimulate apoptotic cell death and autophagy of various cancer cells through the upstream regulation of Bax, PARP, p-JNK, and MAPK and the downstream regulation of the caspases Bcl-2 and ERK1/2. Isovitexin has been proved to have various activities, such as anti-oxidant, anti-inflammatory, anti-Alzheimer's disease and others.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27693342	Inhibitor 8504
Apoptosis 156 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28891090	Activator 1447
Aldose reductase 45 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24291393	Inhibitor 8504	0.13 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28891090	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26385725 https://www.ncbi.nlm.nih.gov/pubmed/24291393 https://www.ncbi.nlm.nih.gov/pubmed/27693342	Preventing	Basic research	Unknown Approved Use Unknown
Neurocognitive disorders 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25096710	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Phenolic constituents of Phenax angustifolius.	2001 Jan	11170671
Characterization of the polyphenolic composition of purple loosestrife (Lythrum salicaria).	2001 Jan-Feb	11302202
Acylated flavone C-glycosides from Cucumis sativus.	2001 Sep	11524127
Phenolic constituents and antioxidant properties of Xanthosoma violaceum leaves.	2003 Oct 22	14558757
Distinction of the C-glycosylflavone isomer pairs orientin/isoorientin and vitexin/isovitexin using HPLC-MS exact mass measurement and in-source CID.	2005 Sep-Oct	16223084
[Studies on chemical constituents from stellaria media. I].	2007 Jun	17672340
Aromatic diglycosides from Cladogynos orientalis.	2007 Mar	17161443
Flavonoids from Acacia pennata and their cyclooxygenase (COX-1 and COX-2) inhibitory activities.	2007 Sep	17823873
Isovitexin-2'-O-beta-[6-O-E-p-coumaroylglucopyranoside] from UV-B irradiated leaves of rice, Oryza sativa L. inhibits fertility of Helicoverpa armigera.	2007 Sep-Oct	17880511
Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS.	2008 Feb	18196523
Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.	2009 Sep	19446614
Potential insulin secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats.	2010 Dec	20678557
Chemical composition of the SFE-CO extracts from Cajanus cajan (L.) Huth and their antimicrobial activity in vitro and in vivo.	2010 Dec 1	20576412
The constituents of Urtica cannabina used in Uighur medicine.	2010 May	20645802
Topical and systemic anti-inflammatory effects of Echinodorus macrophyllus (Kunth) Micheli (Alismataceae).	2010 Oct	20828306
Extracts from the Mongolian traditional medicinal plants Dianthus versicolorFisch. and Lilium pumilum Delile stimulate bile flow in an isolated perfused rat liver model.	2010 Oct 5	20656004
Comparative study of the flavonoids of some Verbena species cultivated in Egypt by using high-performance liquid chromatography coupled with ultraviolet spectroscopy and atmospheric pressure chemical ionization mass spectrometry.	2010 Oct 8	20817165

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 0.1 or 0.25 mg/kg

Route of Administration: Intragastric

In Vitro Use Guide

Isovitexin inhibited the release of TNF-alpha, a proinflammatory cytokine, upon LPS activation of RAW 264.7 macrophages with a 50% inhibitory concentration (IC50) of 78.6 uM. Isovitexin markedly reduced LPS-stimulated PGE2 production in a concentration-dependent manner, with an IC50 of 80.0 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:56:09 GMT 2025` Edited by `admin` on `Mon Mar 31 22:56:09 GMT 2025`
Record UNII	KTQ9R9MS0Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOVITEXIN

Common Name

English

6-C-.BETA.-D-GLUCOPYRANOSYLAPIGENIN

Preferred Name

English

4H-1-BENZOPYRAN-4-ONE, 6-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-

Systematic Name

English

Isovitexin [WHO-DD]

Common Name

English

AVROSIDE

Common Name

English

ISOVITEXIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]

Common Name

English

ISOAVROSIDE

Common Name

English

APIGENIN-6-C-GLUCOSIDE

Common Name

English

SAPONARETIN

Common Name

English

Classification Tree Code System Code

DSLD

4451 (Number of products:1)