Orient

Structural formula
General
Surname	Orient
other names	2- (3,4-Dihydroxyphenyl) -5,7-dihydroxy-8 - [(2 S , 3 R , 4 R , 5 S , 6 R ) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydro -2 H -pyran-2-yl] -4 H -chromen-4-one ( IUPAC ) ; Lutexin; Luteolin 8-C-glucoside;
Molecular formula	C 21 H 20 O 11
Brief description	white to yellow odorless solid
External identifiers / databases
EC number	608-227-2
ECHA InfoCard	100.110.907
PubChem	5281675
ChemSpider	4444994
Wikidata	Q421676
properties
Molar mass	448.383 g mol −1
Physical state	firmly
Melting point	265-267 ° C
solubility	partially soluble in water; soluble in 1 M sodium hydroxide solution;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Orientin is a naturally occurring, glycated flavonoid , more precisely a glycated flavone . As an isolated substance, it is in the form of a yellow solid.

Occurrence

Blue passion flower

Orientin is found in many different plants, including the passion flower , rooibos , some types of bamboo and the Japanese iris .

Biological importance

Orientin has an antioxidant effect . In animal studies also it acts anti-inflammatory .

Isomers

The regioisomer isoorientin is also present as a natural product in various plants, including bamboo and passion fruit .

Individual evidence

↑ ^a ^b ^c Carl Roth: Safety data sheet Orientin (PDF; 40 kB)
^ ^A ^b V. C. da Silva, PT de Sousa Jr., EL Dall'oglio, GE Matiz, MG de Carvalho: Anti-inflammatory activities of flavonoids from Luxemburgia octandra flowers . In: Chemistry of Natural Compounds . tape 46 , no. 6 , 2011, p. 961-963 , doi : 10.1007 / s10600-011-9796-5 .
↑ ^a ^b ^c N. I. Pryakhina, KF Blinova: Luteolin C-glycosides from Iris ensata . In: Chemistry of Natural Compounds . tape 20 , no. 1 , 1084, ISSN 0009-3130 , p. 107 .
↑ ^a ^b ^c ^d Orientin data sheet at Sigma-Aldrich , accessed on December 23, 2019 ( PDF ).

↑ ER Pastene, G. Bocaz, I. Peric, M. Montes, V. Silva, E. Riffo: Separation by capillary electrophoresis of C-glycosylflavonoids in Passiflora sp. extracts . In: Boletín de la Sociedad Chilena de Química . tape 45 , no. 3 , 2000, pp. 461-467 , doi : 10.4067 / S0366-16442000000300017 .

↑ Astrid von Gadow, Elizabeth Joubert, Chris F. Hansmann: Comparison of the Antioxidant Activity of Aspalathin with That of Other Plant Phenols of Rooibos Tea (Aspalathus linearis), α-Tocopherol, BHT, and BHA . In: Journal of Agricultural and Food Chemistry . tape 45 , no. 3 , 1997, p. 632-638 , doi : 10.1021 / jf960281n .

↑ Yu Zhanga, Jingjing Jiaoa, Chengmei Liub, Xiaoqin Wua, Ying Zhang: Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography . In: Food Chemistry . tape 107 , no. 3 , 2008, p. 1326-1336 , doi : 10.1016 / j.foodchem.2007.09.037 .

↑ ^a ^b Wang, Jin; Tang, Feng; Yue, Yongde; Guo, Xuefeng; Yao, Xi: Development and validation of an HPTLC method for simultaneous quantitation of isoorientin, isovitexin, orientin, and vitexin in bamboo-leaf flavonoids . In: Journal of AOAC International . tape 93 , no. 5 , 2010, p. 1376-1383 ( ingentaconnect.com ).

↑ Nan Wu, Kuang Fu, Yu-Jie Fu, Yuan-Gang Zu, Fang-Rong Chang, Yung-Husan Chen, Xiao-Lei Liu, Yu Kong, Wei Liu, Cheng-Bo Gu: Antioxidant Activities of Extracts and Main Components of Pigeonpea [Cajanus cajan (L.) Millsp.] Leaves . In: Molecules . tape 14 , no. 3 , 2009, p. 1032-1043 , doi : 10.3390 / molecules14031032 .

↑ ML Zeraik, JH Yariwake: Quantification of isoorientin and total flavonoids in Passiflora edulis fruit pulp by HPLC-UV / DAD . In: Microchemical Journal . tape 96 , no. 1 , 2010, p. 86-91 , doi : 10.1016 / j.microc.2010.02.003 .

[carlroth-1] Carl Roth: Safety data sheet Orientin (PDF; 40 kB)

[Silva-2] A ^b V. C. da Silva, PT de Sousa Jr., EL Dall'oglio, GE Matiz, MG de Carvalho: Anti-inflammatory activities of flavonoids from Luxemburgia octandra flowers . In: Chemistry of Natural Compounds . tape 46 , no. 6 , 2011, p. 961-963 , doi : 10.1007 / s10600-011-9796-5 .

[Pryakhina-3] N. I. Pryakhina, KF Blinova: Luteolin C-glycosides from Iris ensata . In: Chemistry of Natural Compounds . tape 20 , no. 1 , 1084, ISSN 0009-3130 , p. 107 .

[Sigma-4] Orientin data sheet at Sigma-Aldrich , accessed on December 23, 2019 ( PDF ).

[5] ER Pastene, G. Bocaz, I. Peric, M. Montes, V. Silva, E. Riffo: Separation by capillary electrophoresis of C-glycosylflavonoids in Passiflora sp. extracts . In: Boletín de la Sociedad Chilena de Química . tape 45 , no. 3 , 2000, pp. 461-467 , doi : 10.4067 / S0366-16442000000300017 .

[6] Astrid von Gadow, Elizabeth Joubert, Chris F. Hansmann: Comparison of the Antioxidant Activity of Aspalathin with That of Other Plant Phenols of Rooibos Tea (Aspalathus linearis), α-Tocopherol, BHT, and BHA . In: Journal of Agricultural and Food Chemistry . tape 45 , no. 3 , 1997, p. 632-638 , doi : 10.1021 / jf960281n .

[7] Yu Zhanga, Jingjing Jiaoa, Chengmei Liub, Xiaoqin Wua, Ying Zhang: Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography . In: Food Chemistry . tape 107 , no. 3 , 2008, p. 1326-1336 , doi : 10.1016 / j.foodchem.2007.09.037 .

[Wang-8] Wang, Jin; Tang, Feng; Yue, Yongde; Guo, Xuefeng; Yao, Xi: Development and validation of an HPTLC method for simultaneous quantitation of isoorientin, isovitexin, orientin, and vitexin in bamboo-leaf flavonoids . In: Journal of AOAC International . tape 93 , no. 5 , 2010, p. 1376-1383 ( ingentaconnect.com ).

[9] Nan Wu, Kuang Fu, Yu-Jie Fu, Yuan-Gang Zu, Fang-Rong Chang, Yung-Husan Chen, Xiao-Lei Liu, Yu Kong, Wei Liu, Cheng-Bo Gu: Antioxidant Activities of Extracts and Main Components of Pigeonpea [Cajanus cajan (L.) Millsp.] Leaves . In: Molecules . tape 14 , no. 3 , 2009, p. 1032-1043 , doi : 10.3390 / molecules14031032 .

[10] ML Zeraik, JH Yariwake: Quantification of isoorientin and total flavonoids in Passiflora edulis fruit pulp by HPLC-UV / DAD . In: Microchemical Journal . tape 96 , no. 1 , 2010, p. 86-91 , doi : 10.1016 / j.microc.2010.02.003 .