LEUCOCIANIDOL

Details

Stereochemistry	EPIMERIC
Molecular Formula	C15H14O7
Molecular Weight	306.2675
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SBZWTSHAFILOTE-NOYMGPGASA-N

InChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H/t13?,14-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H14O7
Molecular Weight	306.2675
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.vidal.fr/substances/2079/leucocianidol/ | https://www.baliarda.com.ar/Adjuntos/PdfsProductos/ProctoIkatral.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2116628

Leucocianidol is a vasoprotector. It increases the resistance of vessels and decreases their permeability. Leucocianidol increases the tonicity of the veins. Leucocianidol is used in the management of capillary fragility, hemorrhoids, venolymphatic insufficiency. In combination with lidocaine and hydrocortisone, it is used in the symptomatic treatment of hemorrhoidal crisis. Leucocianidol inhibits 12-lipoxygenase.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
arachidonate 12-lipoxygenase activity 1 Target ID: GO:0004052 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2116628	Inhibitor 8297

PubMed

Title	Date	PubMed
[Action of leucocyanidol on blood serum in vitro].	1958 Jun 9	13546891
[Effect of leucocyanidol on auxin catabolism].	1967	5582432
[Synthesis of monomeric leucocyanidol].	1968 Nov 5	5701227
[Fungicidal activity of leucocyanidol in the presence of copper].	1971 Jul	5113897
[Leucocyanidol and circulatory pathology in contraception].	1976 Jun	981868
Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of non-enzymic lipid peroxidation.	1990 Aug 15	2386548
Superoxide scavenging properties of flavonoids in a non-enzymic system.	1990 Jan-Feb	2158783
Inhibition of sheep platelet arachidonate metabolism by flavonoids from Spanish and Indian medicinal herbs.	1990 Mar	2116628
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880
Reaction mechanism from leucoanthocyanidin to anthocyanidin 3-glucoside, a key reaction for coloring in anthocyanin biosynthesis.	2001 Jul 13	11316805
Expression of anthocyanins and proanthocyanidins after transformation of alfalfa with maize Lc.	2003 Jul	12857826
The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity.	2003 Nov 3	14552794
The Arabidopsis TDS4 gene encodes leucoanthocyanidin dioxygenase (LDOX) and is essential for proanthocyanidin synthesis and vacuole development.	2003 Sep	12940955
Molecular and biochemical analysis of two cDNA clones encoding dihydroflavonol-4-reductase from Medicago truncatula.	2004 Mar	14976232
Early steps in proanthocyanidin biosynthesis in the model legume Medicago truncatula.	2007 Nov	17885080
Structure and reaction mechanism of basil eugenol synthase.	2007 Oct 3	17912370
Molecular cloning and function analysis of an anthocyanidin synthase gene from Ginkgo biloba, and its expression in abiotic stress responses.	2008 Dec 31	18779661
Biotransformation of (+)-catechin into taxifolin by a two-step oxidation: primary stage of (+)-catechin metabolism by a novel (+)-catechin-degrading bacteria, Burkholderia sp. KTC-1, isolated from tropical peat.	2008 Feb 8	18068670
Arabidopsis R2R3-MYB transcription factor AtMYB60 functions as a transcriptional repressor of anthocyanin biosynthesis in lettuce (Lactuca sativa).	2008 Jun	18317777
Brassica orthologs from BANYULS belong to a small multigene family, which is involved in procyanidin accumulation in the seed.	2009 Nov	19760260
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010 Dec 13	21144003
Neighbour identity hardly affects litter-mixture effects on decomposition rates of New Zealand forest species.	2010 Feb	19756760
A potential of some medicinal plants as an antiulcer agents.	2010 Jul	22228953
Phytochemical investigation and antimicrobial activity of Psidium guajava L. leaves.	2010 Jul	20931082
Ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis tt7 mutant grown under nitrogen stress.	2010 Jun	20357139

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:15:13 GMT 2023` Edited by `admin` on `Fri Dec 15 16:15:13 GMT 2023`
Record UNII	RAP1D6110C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEUCOCIANIDOL

Official Name

English

leucocianidol [INN]

Common Name

English

2H-1-BENZOPYRAN-3,4,5,7-TETROL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3S)-

Systematic Name

English

Leucocianidol [WHO-DD]

Common Name

English

3,3',4,4',5,7-FLAVANHEXOL

Systematic Name

English

LEUCOCYANIDIN [MI]

Common Name

English

FLAVAN

Systematic Name

English

LEUCOCYANIDIN

Common Name

English

LEUCOCIANIDOL [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1745