Gomisin J | CAS# 66280-25-9 | Lignan

MedKoo Cat#: 574308 | Name: Gomisin J

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gomisin J is a lignan that inhibits HIV-1 IIIB replication in H9 T cells and decreases LPS-induced increases in nitric oxide (NO) production and p38, ERK, and JNK phosphorylation in RAW 264.7 cells. It induces relaxation of isolated, precontracted endothelium-intact rat aortic rings. Gomisin J is cytotoxic to 13 cancer cell lines, including breast, colon, and cervical cancer cells, when used at a concentration of 30 µg/ml.

Chemical Structure

Gomisin J

CAS#66280-25-9

Theoretical Analysis

MedKoo Cat#: 574308

Name: Gomisin J

CAS#: 66280-25-9

Chemical Formula: C22H28O6

Exact Mass: 388.1886

Molecular Weight: 388.46

Elemental Analysis: C, 68.02; H, 7.27; O, 24.71

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 750.00	2 Weeks

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Synonym

Gomisin J; Gomisin-J; GomisinJ; (-)-Gomisin J

IUPAC/Chemical Name

(6R,7S)-1,2,11,12-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene-3,10-diol

InChi Key

PICOUNAPKDEPCA-TXEJJXNPSA-N

InChi Code

InChI=1S/C22H28O6/c1-11-7-13-9-15(23)19(25-3)21(27-5)17(13)18-14(8-12(11)2)10-16(24)20(26-4)22(18)28-6/h9-12,23-24H,7-8H2,1-6H3/t11-,12+

SMILES Code

C[C@@H]1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3C[C@@H]1C)O)OC)OC)OC)OC)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gomisin J suppresses lipid accumulation by regulating the expression of lipogenic and lipolytic enzymes and inflammatory molecules through activation of AMPK, LKB1 and Ca2+/calmodulin-dependent protein kinase II and inhibition of fetuin-A in HepG2 cells.

In vitro activity:

Gomisin J attenuated lipid accumulation in OA-induced HepG2 cells. It also suppressed the expression of lipogenic enzymes and inflammatory mediators and increased the expression of lipolytic enzymes in OA-induced HepG2 cells. Reference: J Agric Food Chem. 2015 Nov 11;63(44):9729-39. https://pubmed.ncbi.nlm.nih.gov/26455261/

In vivo activity:

Furthermore, this study found that 80 mg/kg GJ (Gomisin J) treatment decreased the infarct volume in I/R rats at 6 h, 12 h, and 48 h of reperfusion. Altogether, these suggest that GJ relieves neuronal injury in I/R rats. Reference: Bioengineered. 2022 Mar;13(3):6908-6918. https://pubmed.ncbi.nlm.nih.gov/35235758/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	77.23
	DMSO	65.0	167.33
	Ethanol	30.0	77.23
	Ethanol:PBS (pH 7.2) (1:5)	0.2	0.41

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 388.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kim M, Lim SJ, Lee HJ, Kim SY, Nho CW. Gomisin J Inhibits Oleic Acid-Induced Hepatic Lipogenesis by Activation of the AMPK-Dependent Pathway and Inhibition of the Hepatokine Fetuin-A in HepG2 Cells. J Agric Food Chem. 2015 Nov 11;63(44):9729-39. doi: 10.1021/acs.jafc.5b04089. Epub 2015 Oct 28. PMID: 26455261. 2. Peng HL, Chen DF, Lan HX, Zhang XM, Gu Z, Jiang MH. Anti-lipid peroxidation of gomisin J on liver mitochondria and cultured myocardial cells. Zhongguo Yao Li Xue Bao. 1996 Nov;17(6):538-41. PMID: 9863151. 3. Min X, Zhao L, Shi Y, Wang J, Lv H, Song X, Zhao Q, Zhao Q, Jing R, Hu J. Gomisin J attenuates cerebral ischemia/reperfusion injury by inducing anti-apoptotic, anti-inflammatory, and antioxidant effects in rats. Bioengineered. 2022 Mar;13(3):6908-6918. doi: 10.1080/21655979.2022.2026709. PMID: 35235758; PMCID: PMC8973623. 4. Ye BH, Lee SJ, Choi YW, Park SY, Kim CD. Preventive effect of gomisin J from Schisandra chinensis on angiotensin II-induced hypertension via an increased nitric oxide bioavailability. Hypertens Res. 2015 Mar;38(3):169-77. doi: 10.1038/hr.2014.162. Epub 2014 Nov 27. PMID: 25427681.

In vitro protocol:

In vivo protocol:

1. Min X, Zhao L, Shi Y, Wang J, Lv H, Song X, Zhao Q, Zhao Q, Jing R, Hu J. Gomisin J attenuates cerebral ischemia/reperfusion injury by inducing anti-apoptotic, anti-inflammatory, and antioxidant effects in rats. Bioengineered. 2022 Mar;13(3):6908-6918. doi: 10.1080/21655979.2022.2026709. PMID: 35235758; PMCID: PMC8973623. 2. Ye BH, Lee SJ, Choi YW, Park SY, Kim CD. Preventive effect of gomisin J from Schisandra chinensis on angiotensin II-induced hypertension via an increased nitric oxide bioavailability. Hypertens Res. 2015 Mar;38(3):169-77. doi: 10.1038/hr.2014.162. Epub 2014 Nov 27. PMID: 25427681.

1. Chen, D.-F., Zhang, S.-X., Xie, J.-X., et al. Anti-AIDS agents—XXVI. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues. Bioorg. Med. Chem. 5(8), 1715-1723 (1997). 2. Oh, S.-Y., Kim, Y.H., Bae, D.S., et al. Anti-inflammatory effects of gomisin J, and Schisandrin C isolated from the fruit of Schisandra chinensis. Biosci. Biotechnol. Biochem. 74(2), 285-291 (2010). 3. Park, J.Y., Hoi, Y.W., Yun, J.W., et al. Gomisin J from Schisandra chinensis induces vascular relaxation via activation of endothelial nitric oxide synthase. Vascul. Pharmacol. 57(2-4), 124-130 (2012). 4. Jung, S., Moon, H.-I., Kim, S., et al. Anticancer activity of gomisin J from Schisandra chinensis fruit. Oncol. Rep. 41(1), 711-717 (2019).