129314-37-0
Chemical Structure
Licorisoflavan A
Synonym(s): 7-O-Methyllicorisoflavan B
- CAS No.: 129314-37-0
- Formula:C27H34O5
- Molecular Weight:438.56
IUPAC Name: (R)-4-(5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)chroman-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
InChIKey: GDAAEAXMNLVRCZ-SFHVURJKSA-N
SMILES: COC1=C2C(OC[C@@H](C3=C(C(C/C=C(C)/C)=C(O)C=C3)O)C2)=CC(OC)=C1C/C=C(C)/C
Biological Activity: Licorisoflavan A (7-O-Methyllicorisoflavan B) is a isoflavan-quinone, that can be isolated from Glycyrrhiza uralensis[1]. Licorisoflavan A exhibits anti-inflammatory and antimicrobial properties[2][3]. It can inhibit the secretion of IL-6 and chemokines by LPS-stimulated macrophages in a concentration-dependent manner, and also suppress the secretion of MMP-7, MMP-8, and MMP-9 in macrophages[4]. Licorisoflavan A exertes potent antidepressant-like effects involving BDNF-TrkB pathway and AMPA receptors[5].
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Licorisoflavan A | Licorisoflavan A (7-O-Methyllicorisoflavan B) is a isoflavan-quinone, that can be isolated from Glycyrrhiza uralensis. Licorisoflavan A exhibits anti-inflammatory and antimicrobial properties. It can inhibit the secretion of IL-6 and chemokines by LPS-stimulated macrophages in a concentration-dependent manner, and also suppress the secretion of MMP-7, MMP-8, and MMP-9 in macrophages. Licorisoflavan A exertes potent antidepressant-like effects involving BDNF-TrkB pathway and AMPA receptors. | |||||||||||||||||||||
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References
- [1]. Gafner S, et al. Isoflavonoids and coumarins from Glycyrrhiza uralensis: antibacterial activity against oral pathogens and conversion of isoflavans into isoflavan-quinones during purification. J Nat Prod. 2011 Dec 27;74(12):2514-9. [Content Brief]
- [2]. Ahn SJ, Park SN, Lee YJ, Cho EJ, Lim YK, Li XM, Choi MH, Seo YW, Kook JK. In vitro antimicrobial activities of 1-methoxyficifolinol, licorisoflavan A, and 6,8-diprenylgenistein against Streptococcus mutans. Caries Res. 2015;49(1):78-89.
- [3]. Villinski JR, Bergeron C, Cannistra JC, Gloer JB, Coleman CM, Ferreira D, Azelmat J, Grenier D, Gafner S. Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis. J Nat Prod. 2014 Mar 28;77(3):521-6.
- [4]. La VD, Tanabe S, Bergeron C, Gafner S, Grenier D. Modulation of matrix metalloproteinase and cytokine production by licorice isolates licoricidin and licorisoflavan A: potential therapeutic approach for periodontitis. J Periodontol. 2011 Jan;82(1):122-8.
- [5]. Xiao D, Liu L, Li Y, Ruan J, Wang H. Licorisoflavan A Exerts Antidepressant-Like Effect in Mice: Involvement of BDNF-TrkB Pathway and AMPA Receptors. Neurochem Res. 2019 Sep;44(9):2044-2056.
