ORIENTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O11
Molecular Weight	448.3777
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(c(cc1-c2cc(=O)c3c(cc(c(c3o2)[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O)O)O)O

InChI

InChIKey=PLAPMLGJVGLZOV-VPRICQMDSA-N

InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H20O11
Molecular Weight	448.3777
Charge	0
Count

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

Approval Year

PubMed

Title	Date	PubMed
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994 Aug 3	7520698
Synthesis of 8-C-glucosylflavones.	2001 Aug 30	11513825
Characterization of the polyphenolic composition of purple loosestrife (Lythrum salicaria).	2001 Jan-Feb	11302202
Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L.	2001 Jul	11515721
Radiation protection of human lymphocyte chromosomes in vitro by orientin and vicenin.	2001 Nov 15	11673069
Flavonoid concentrations in three grass species and a sedge grown in the field and under controlled environment conditions in response to enhanced UV-B radiation.	2002 Feb	11849979
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.	2002 Feb	11849977
O-Galloyl-C-glycosylflavones from Pelargonium reniforme.	2002 Feb	11830160
Antioxidant constituents from Setaria viridis.	2002 Jun	12135101
A benzoquinone and flavonoids from Cyperus alopecuroides.	2002 Jun	12031430
Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge.	2002 Mar	11849843
Quantitative characterization of flavonoid compounds in Rooibos tea (Aspalathus linearis) by LC-UV/DAD.	2002 Sep 25	12236672
Flavonoids from Achillea nobilis L.	2003 Jan-Feb	12622219
Quantitative analysis of flavonoids in the flowers and leaves of Ficaria verna Huds.	2003 Sep-Oct	14577646
Protection against prenatal irradiation-induced genomic instability and its consequences in adult mice by Ocimum flavonoids, orientin and vicenin.	2004 Sep	15586885
An analysis of flavonoid compounds in leaves of Japonolirion (Petrosaviaceae).	2005 Feb	15703853
Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed-phase high-performance liquid chromatography with ultraviolet diode array detection.	2005 Feb 18	15782963
LC and UV determination of flavonoids from Passiflora alata medicinal extracts and leaves.	2005 Feb 23	15708685
Isolation and purification of flavonoid glycosides from Trollius ledebouri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.	2005 Oct 28	16199228
Bioactivity guided isolation of antimicrobial compounds from Lythrum salicaria.	2005 Sep	15975734
Anti-apoptotic effect and the mechanism of orientin on ischaemic/reperfused myocardium.	2006 Apr-May	16864433
A rapid ultra-performance liquid chromatography-electrospray ionization tandem mass spectrometric method for the qualitative and quantitative analysis of the constituents of the flower of Trollius ledibouri Reichb.	2006 Nov 24	17723770
[Protective effects of orientin on myocardial ischemia and hypoxia in animal models].	2007 Aug	17715018
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.	2007 Jul 28	17537670
Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts.	2007 Nov 28	17966982
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.	2008	19023787
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.	2008 Apr 15	18415863
Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system.	2008 Dec	19006051
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.	2008 Mar	18317555
[Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC].	2008 Oct	19166010
Screening and structural characterization of alpha-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MS(n) and SORI-CID FTICR MS.	2009 Aug	19443236
Phytoconstituents of Jatropha curcas L. leaves and their immunomodulatory activity on humoral and cell-mediated immune response in chicks.	2009 Jul-Aug	19791499
Neural cell protective compounds isolated from Phoenix hanceana var. formosana.	2009 Jun	19628235
Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves.	2009 Mar 4	19305357
Effect of heat on aspalathin, iso-orientin, and orientin contents and color of fermented rooibos (Aspalathus linearis) iced tea.	2009 May 27	21314198
Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.	2009 Sep	19446614
Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview.	2010 Jan	22228948
Antioxidant Activity and Lipid-Lowering Effect of Essential Oils Extracted from Ocimum sanctum L. Leaves in Rats Fed with a High Cholesterol Diet.	2010 Jan	20104265
The compound isolated from the leaves of Phyllostachys nigra protects oxidative stress-induced retinal ganglion cells death.	2010 Jun	20381571
Vitexin, orientin and other flavonoids from Spirodela polyrhiza inhibit adipogenesis in 3T3-L1 cells.	2010 Oct	20878708
Antinociceptive properties of conocarpan and orientin obtained from Piper solmsianum C. DC. var. solmsianum (Piperaceae).	2010 Oct	20473574

Patents

Substance Class	Chemical Created by `admin` on `Sat Jun 26 05:45:39 UTC 2021` Edited by `admin` on `Sat Jun 26 05:45:39 UTC 2021`
Record UNII	IAX93XCW6C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORIENTIN

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-8-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-

Systematic Name

English

ORIENTINE

Common Name

English

(1S)-1,5-ANHYDRO-1-(2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-CHROMEN-8-YL)-D-GLUCITOL

Systematic Name

English

D-GLUCITOL, 1,5-ANHYDRO-1-C-(2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-1-BENZOPYRAN-8-YL)-, (1S)-

Systematic Name

English

LUTEOLIN 8-C-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

C10114

Code

English

J17.734B

Code

English

MASSBANK PR020063

Code

English

LUTEOLIN 8-C-.BETA.-GLUCOPYRANOSIDE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-8-BETA-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-

Common Name

English

8-(.BETA.-D-GLUCOPYRANOSYL)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

LUTEOLIN-8-GLUCOSIDE

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-8-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

LUTEOLIN 8-GLUCOSIDE

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-8-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-4H-CHROMEN-4-ONE

Systematic Name

English

LUTEXIN

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-8-((2S,3R,4R,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)-4H-CHROMEN-4-ONE

Systematic Name

English

8-.BETA.-D-GLUCOPYRANOSYL-3',4',5,7-TETRAHYDROXYFLAVONE

Systematic Name

English

NIAID AIDS# 026706

Code

English

LUTEOLIN 8-C-GLUCOSIDE

Common Name

English

2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-8-(.BETA.-D-GLUCOPYRANOSYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

8-.BETA.-D-GLUCOSYLLUTEOLIN

Common Name

English

Code System Code Type Description

EPA CompTox

28608-75-5