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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 of ORIENTIN

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

PubMed

TitleDatePubMed
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.
1994 Aug 3
Synthesis of 8-C-glucosylflavones.
2001 Aug 30
Characterization of the polyphenolic composition of purple loosestrife (Lythrum salicaria).
2001 Jan-Feb
Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L.
2001 Jul
Radiation protection of human lymphocyte chromosomes in vitro by orientin and vicenin.
2001 Nov 15
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
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
O-Galloyl-C-glycosylflavones from Pelargonium reniforme.
2002 Feb
Antioxidant constituents from Setaria viridis.
2002 Jun
A benzoquinone and flavonoids from Cyperus alopecuroides.
2002 Jun
Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge.
2002 Mar
Quantitative characterization of flavonoid compounds in Rooibos tea (Aspalathus linearis) by LC-UV/DAD.
2002 Sep 25
Flavonoids from Achillea nobilis L.
2003 Jan-Feb
Quantitative analysis of flavonoids in the flowers and leaves of Ficaria verna Huds.
2003 Sep-Oct
Protection against prenatal irradiation-induced genomic instability and its consequences in adult mice by Ocimum flavonoids, orientin and vicenin.
2004 Sep
An analysis of flavonoid compounds in leaves of Japonolirion (Petrosaviaceae).
2005 Feb
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
LC and UV determination of flavonoids from Passiflora alata medicinal extracts and leaves.
2005 Feb 23
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
Bioactivity guided isolation of antimicrobial compounds from Lythrum salicaria.
2005 Sep
Anti-apoptotic effect and the mechanism of orientin on ischaemic/reperfused myocardium.
2006 Apr-May
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
[Protective effects of orientin on myocardial ischemia and hypoxia in animal models].
2007 Aug
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.
2007 Jul 28
Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts.
2007 Nov 28
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.
2008
Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.
2008 Apr 15
Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system.
2008 Dec
Evaluation of Antioxidant and Wound Healing Effects of Alcoholic and Aqueous Extract of Ocimum sanctum Linn in Rats.
2008 Mar
[Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC].
2008 Oct
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
Phytoconstituents of Jatropha curcas L. leaves and their immunomodulatory activity on humoral and cell-mediated immune response in chicks.
2009 Jul-Aug
Neural cell protective compounds isolated from Phoenix hanceana var. formosana.
2009 Jun
Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves.
2009 Mar 4
Effect of heat on aspalathin, iso-orientin, and orientin contents and color of fermented rooibos (Aspalathus linearis) iced tea.
2009 May 27
Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.
2009 Sep
Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview.
2010 Jan
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
The compound isolated from the leaves of Phyllostachys nigra protects oxidative stress-induced retinal ganglion cells death.
2010 Jun
Vitexin, orientin and other flavonoids from Spirodela polyrhiza inhibit adipogenesis in 3T3-L1 cells.
2010 Oct
Antinociceptive properties of conocarpan and orientin obtained from Piper solmsianum C. DC. var. solmsianum (Piperaceae).
2010 Oct
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
  • Download
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
Created by admin on Sat Jun 26 05:45:39 UTC 2021 , Edited by admin on Sat Jun 26 05:45:39 UTC 2021
PRIMARY
WIKIPEDIA
Orientin
Created by admin on Sat Jun 26 05:45:39 UTC 2021 , Edited by admin on Sat Jun 26 05:45:39 UTC 2021
PRIMARY
PUBCHEM
5281675
Created by admin on Sat Jun 26 05:45:39 UTC 2021 , Edited by admin on Sat Jun 26 05:45:39 UTC 2021
PRIMARY
CAS
28608-75-5
Created by admin on Sat Jun 26 05:45:39 UTC 2021 , Edited by admin on Sat Jun 26 05:45:39 UTC 2021
PRIMARY
FDA UNII
IAX93XCW6C
Created by admin on Sat Jun 26 05:45:39 UTC 2021 , Edited by admin on Sat Jun 26 05:45:39 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
ORAC value expressed as umol TE/g for this compound was 1700 +/- 78.9. ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH.
PARENT -> CONSTITUENT ALWAYS PRESENT