Misplaced Pages

Gentianine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Gentianine
Names
IUPAC name 5-Ethenyl-3,4-dihydropyranopyridin-1-one
Other names Erythricine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 137011
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2Key: DFNZYFAJQPLJFI-UHFFFAOYSA-N
SMILES
  • C=CC1=CN=CC2=C1CCOC2=O
Properties
Chemical formula C10H9NO2
Molar mass 175.187 g·mol
Melting point 82–83 °C (180–181 °F; 355–356 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Gentianine is a pyridine-derived alkaloid. Originally isolated in 1944 from Gentiana kirilowi, it has also been found in Gentiana macrophylla, fenugreek, Strychnos angolensis, Strychnos xantha, and other plants.

Gentianine is a crystalline solid with a melting point of 82-83 °C. It is a base that forms salts, such as the hydrochloride salt, upon treatment with acids.

Gentianine has been studied for its potential anti-inflammatory properties.

References

  1. ^ Merck Index (11th ed.). 4284 Gentianine.
  2. Proskurnina (1944), J. Gen. Chem. USSR, 14, 1148.
  3. ^ 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.
  4. "Gentianine (FDB007359)". FooDB. The Metabolomics Innovation Centre. Retrieved June 30, 2022.
  5. ^ "Gentianine". PubChem. Retrieved June 30, 2022.
  6. 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.
  7. 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.
  8. 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.
Stub icon

This article about an alkaloid is a stub. You can help Misplaced Pages by expanding it.

Categories: