GOMISIN N Chemical Properties

alpha 

-22～-32°(D/20℃)(c=0.25,CH3CN)

storage temp. 

4°C, protect from light

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

color 

White to off-white

InChI

InChI=1/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/s3

InChIKey

RTZKSTLPRTWFEV-JNEKIBDFNA-N

SMILES

O1C2=C(OC)C3C4=C(OC)C(OC)=C(OC)C=C4C[C@@H](C)[C@@H](C)CC=3C=C2OC1 |&1:19,21,r|

LogP

6.460 (est)

GOMISIN N Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Schisandra chinensis.

Uses

Gomisin N, isolated from Schisandra chinensis. Gomisin N has the potential for use in the treatment of allergy. Gomisin N is an anti-cancer agent candidate capable of inhibiting the proliferation and inducing the apoptosis in cancer[1][2][3].

Definition

ChEBI: (+)-schisandrin B is an organic heterotetracyclic compound that is found in Fructus Schisandrae and Schisandra chinensis. It has a role as a nephroprotective agent, an apoptosis inhibitor, a plant metabolite, an anti-asthmatic agent, an antioxidant, an anti-inflammatory agent, a neuroprotective agent, a hepatoprotective agent and an antilipemic drug. It is an organic heterotetracyclic compound, an aromatic ether, an oxacycle and a cyclic acetal.

References

[1] Inoue H, et al. Gomisin N enhances TRAIL-induced apoptosis via reactive oxygen species-mediated up-regulation of death receptors 4 and 5. Int J Oncol. 2012 Apr;40(4):1058-65.
[2] Jung DY, et al. Antidiabetic effect of gomisin N via activation of AMP-activated protein kinase. Biochem Biophys Res Commun. 2017 Dec 16;494(3-4):587-593.
[3] Oh SY, et al. Anti-inflammatory effects of gomisin N, gomisin J, and schisandrin C isolated from the fruit of Schisandra chinensis. Biosci Biotechnol Biochem. 2010;74(2):285-91.
[4] Jang MK, et al. Gomisin N inhibits adipogenesis and prevents high-fat diet-induced obesity. Sci Rep. 2017 Jan 9;7:40345.
[5] Zhu PL, et al. Gomisin N Exerts Anti-liver Cancer Effects and Regulates PI3K-Akt and mTOR-ULK1 Pathways in Vitro. Biol Pharm Bull. 2020;43(8):1267-1271.
[6] Yim SY, et al. Gomisin N isolated from Schisandra chinensis significantly induces anti-proliferative and pro-apoptotic effects in hepatic carcinoma. Mol Med Rep. 2009 Sep-Oct;2(5):725-32. DOI:10.3892/mmr_00000163
[7] Takimoto Y, et al. Gomisin N in the herbal drug gomishi (Schisandra chinensis) suppresses inducible nitric oxide synthase gene via C/EBPβ and NF-κB in rat hepatocytes. Nitric Oxide. 2013 Jan 15;28:47-56.
[8] Jang MK, et al. Protective Effect of Gomisin N against Endoplasmic Reticulum Stress-Induced Hepatic Steatosis. Biol Pharm Bull. 2016 May 1;39(5):832-8.
[9] Chae JK, et al. Gomisin N Inhibits Melanogenesis through Regulating the PI3K/Akt and MAPK/ERK Signaling Pathways in Melanocytes. Int J Mol Sci. 2017 Feb 22;18(2):471.
[10] Song M, et al. Gomisin N rescues cognitive impairment of Alzheimer's disease by targeting GSK3β and activating Nrf2 signaling pathway. Phytomedicine. 2024 Sep;132:155811.

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