Gentianine
Gentianine
Names
IUPAC name
5-Ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
Other names
Erythricine
Identifiers
137011
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
Key: DFNZYFAJQPLJFI-UHFFFAOYSA-N
Properties
C 10 H 9 N O 2
Molar mass
175.187 g·mol−1
Melting point
82–83 °C (180–181 °F; 355–356 K)[ 1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Gentianine is a pyridine -derived alkaloid . Originally isolated in 1944 from Gentiana kirilowi ,[ 2] it has also been found in Gentiana macrophylla ,[ 3] fenugreek ,[ 4] Strychnos angolensis ,[ 5] Strychnos xantha ,[ 5] and other plants.[ 1]
Gentianine is a crystalline solid with a melting point of 82-83 °C.[ 1] It is a base that forms salts, such as the hydrochloride salt, upon treatment with acids.[ 1]
Gentianine has been studied for its potential anti-inflammatory properties.[ 3] [ 6] [ 7] [ 8]
References
^ a b c d Merck Index (11th ed.). 4284 Gentianine.
^ Proskurnina (1944), J. Gen. Chem. USSR , 14 , 1148.
^ a b Kwak, Wie-Jong; Kim, Joo-Hyon; Ryu, Keun-Ho; Cho, Yong-Baik; Jeon, Sun-Duck; Moon, Chang-Kiu (2005). "Effects of Gentianine on the Production of Pro-inflammatory Cytokines in Male Sprague-Dawley Rats Treated with Lipopolysaccharide (LPS)" . Biological and Pharmaceutical Bulletin . 28 (4): 750–753. doi :10.1248/bpb.28.750 . PMID 15802824 .
^ "Gentianine (FDB007359)" . FooDB . The Metabolomics Innovation Centre. Retrieved June 30, 2022 .
^ a b "Gentianine" . PubChem . Retrieved June 30, 2022 .
^ Wenjin, Chen; Jianwei, Wang (2017). "Protective Effect of Gentianine, a compound from du Huo Ji Sheng Tang, against Freund's Complete Adjuvant-Induced Arthritis in Rats". Inflammation . 40 (4): 1401–1408. doi :10.1007/s10753-017-0583-8 . PMID 28501981 . S2CID 4476482 .
^ Wang, Na; Liu, Yao; Jia, Caixia; Gao, Chengwen; Zheng, Ting; Wu, Mingxuan; Zhang, Qian; Zhao, Xiangzhong; Li, Zhiqiang; Chen, Jianxin; Wu, Chuanhong (2021). "Machine learning enables discovery of Gentianine targeting TLR4/NF-κB pathway to repair ischemic stroke injury". Pharmacological Research . 173 : 105913. doi :10.1016/j.phrs.2021.105913 . PMID 34563661 . S2CID 237942721 .
^ Mirzaee, Fatemeh; Hosseini, Amirsaeed; Jouybari, Hossein Bakhshi; Davoodi, Ali; Azadbakht, Mohammad (2017). "Medicinal, biological and phytochemical properties of Gentiana species" . Journal of Traditional and Complementary Medicine . 7 (4): 400–408. doi :10.1016/j.jtcme.2016.12.013 . PMC 5634738 . PMID 29034186 .