Gentianine

Gentianine
Names
	IUPAC name 5-Ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
	Other names Erythricine
Identifiers
CAS Number	439-89-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	137011
ChEBI	CHEBI:28981;
ChEMBL	ChEMBL4753058;
ChemSpider	314782;
KEGG	C06525;
PubChem CID	354616;
UNII	C2PD310UXB;
CompTox Dashboard (EPA)	DTXSID00963141 ;
	InChI 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;
	SMILES C=CC1=CN=CC2=C1CCOC2=O;
Properties
Chemical formula	C10H9NO2
Molar mass	175.187 g·mol−1
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 [77 °F], 100 kPa). Infobox references

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.

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[Merck-1] Merck Index (11th ed.). 4284 Gentianine.

[2] Proskurnina (1944), J. Gen. Chem. USSR, 14, 1148.

[kwak-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.

[pubchem-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.

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