Gentianine

Last updated
Gentianine
Gentianine.svg
Names
IUPAC name
5-Ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
Other names
Erythricine
Identifiers
3D model (JSmol)
137011
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
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
  • C=CC1=CN=CC2=C1CCOC2=O
Properties
C10H9NO2
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).

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

  1. 1 2 3 4 Merck Index (11th ed.). 4284 Gentianine.
  2. ↑ Proskurnina (1944), J. Gen. Chem. USSR, 14, 1148.
  3. 1 2 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. 1 2 "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.
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