Asarinin | CAS# 133-04-0 | Δ5-desaturase inhibitor

MedKoo Cat#: 574112 | Name: Asarinin

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Description:

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

Asarinin, also known as (–)-Asarinin, is a noncompetitive inhibitor of Δ5-desaturase. It is selective for Δ5-desaturase over Δ6- and Δ9-desaturase. Asarinin is cytotoxic to A2780 and SKOV3 ovarian cancer cells but not immortalized ovarian surface epithelial cells. It induces apoptosis and activates caspase-3, -8, and -9 in A2780 and SKOV3 cells.

Chemical Structure

Asarinin

CAS#133-04-0

Theoretical Analysis

MedKoo Cat#: 574112

Name: Asarinin

CAS#: 133-04-0

Chemical Formula: C20H18O6

Exact Mass: 354.1103

Molecular Weight: 354.36

Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 950.00	2 Weeks
100mg	USD 1,450.00	2 Weeks

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Synonym

(–)-Asarinin, (–)-Episesamin, Asarinin, Desgeranyloxyarmatumin, L-Asarinin

IUPAC/Chemical Name

5,5'-[(1R,3aS,4S,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis-1,3-benzodioxole

InChi Key

PEYUIKBAABKQKQ-FQZPYLGXSA-N

InChi Code

InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19-,20+/m1/s1

SMILES Code

[H][C@]1([C@@H](C2=CC(OCO3)=C3C=C2)OC4)[C@]4([H])[C@H](C5=CC(OCO6)=C6C=C5)OC1

Appearance

Solid

Purity

>95% (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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

(-)-Asarinin is a extract lignan from Zanthoxylum armatum, mainly produced in roots of this herb.

In vitro activity:

To examine whether (−)-asarinin (1)-induced cell death is mediated by the induction of apoptosis, two ovarian cancer cells A2780 and SKOV3 cells were treated with (−)-asarinin (1) and subsequently co-stained with PI and Annexin V-FITC. Treatment with (−)-asarinin increased the percentage of Annexin V-FITC positive/PI negative cells by up to 43% in A2780 cells and 48% in SKOV3 cells (Figure 2C,D). These results suggest that the (−)-asarinin (1)-induced cell death is associated with the induction of apoptosis in human ovarian cancer cells. Reference: Molecules. 2018 Aug; 23(8): 1849. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222791/

In vivo activity:

In order to further clarify the Th1/Th2/Treg cells in collagen induced arthritis after the treatment of asarinin, mRNA of Th1/Th2/Treg cells related cytokines was extracted from synovial tissue and patellar cartilage on day 81. Cytokine and transcription factor mRNA expression were determined by RT-PCR (Fig. 3a) and quantitative RT-PCR (Fig. 3b) as shown in Fig. 3. TNF-α, IL-12 and IL-18 were significantly reduced in asarinin-treated mice compared to the control group. Increased IL-10 and TGF-β mRNA levels were even more impressive (Figs. 3a, 3b). The expression of Foxp3 was up-regulated after asarinin treatment. A series of intracellular transcription factors is activated, resulting in helper T-cell activation and the differentiation of Th1/Th2, so GATA-3 and T-bet in the synovium were tested. GATA-3 mRNA expression was not different between the two groups (data not shown). However, T-bet mRNA expression was significantly lower in the asarinin-treated mice than in the control group (Figs. 3a, 3b). Reference: Biol Pharm Bull. 2019 Jul 1;42(7):1172-1178. https://pubmed.ncbi.nlm.nih.gov/31019160/

	Solvent	mg/mL	mM
Solubility
	DMSO	60.0	169.32
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.56
	DMF	20.0	56.44

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 354.36 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. Jeong M, Kim HM, Lee JS, Choi JH, Jang DS. (-)-Asarinin from the Roots of Asarum sieboldii Induces Apoptotic Cell Death via Caspase Activation in Human Ovarian Cancer Cells. Molecules. 2018 Jul 25;23(8):1849. doi: 10.3390/molecules23081849. PMID: 30044423; PMCID: PMC6222791. 2. Park HJ, Lee KS, Zhao TT, Lee KE, Lee MK. Effects of asarinin on dopamine biosynthesis and 6-hydroxydopamine-induced cytotoxicity in PC12 cells. Arch Pharm Res. 2017 May;40(5):631-639. doi: 10.1007/s12272-017-0908-z. Epub 2017 Apr 10. PMID: 28397192. 3. Hou Y, Hu T, Wei D, Gao J, Che D, Wang X, Wang C, He H. (-)-Asarinin inhibits mast cells activation as a Src family kinase inhibitor. Int J Biochem Cell Biol. 2020 Apr;121:105701. doi: 10.1016/j.biocel.2020.105701. Epub 2020 Jan 31. PMID: 32007602. 4. Dai Q, Wang M, Li Y, Li J. Amelioration of CIA by Asarinin Is Associated to a Downregulation of TLR9/NF-κB and Regulation of Th1/Th2/Treg Expression. Biol Pharm Bull. 2019 Jul 1;42(7):1172-1178. doi: 10.1248/bpb.b19-00083. Epub 2019 Apr 23. PMID: 31019160.

In vitro protocol:

In vivo protocol:

1. Hou Y, Hu T, Wei D, Gao J, Che D, Wang X, Wang C, He H. (-)-Asarinin inhibits mast cells activation as a Src family kinase inhibitor. Int J Biochem Cell Biol. 2020 Apr;121:105701. doi: 10.1016/j.biocel.2020.105701. Epub 2020 Jan 31. PMID: 32007602. 2. Dai Q, Wang M, Li Y, Li J. Amelioration of CIA by Asarinin Is Associated to a Downregulation of TLR9/NF-κB and Regulation of Th1/Th2/Treg Expression. Biol Pharm Bull. 2019 Jul 1;42(7):1172-1178. doi: 10.1248/bpb.b19-00083. Epub 2019 Apr 23. PMID: 31019160.

1: Negi DS, Negi N, Kumar A, Matsunami K, Schulz S, Jones PG. (±)-Asarinin. Acta Crystallogr C. 2013 Jan;69(Pt 1):87-9. doi: 10.1107/S0108270112049657. Epub 2012 Dec 13. PMID: 23282922. 2: Hou Y, Hu T, Wei D, Gao J, Che D, Wang X, Wang C, He H. (-)-Asarinin inhibits mast cells activation as a Src family kinase inhibitor. Int J Biochem Cell Biol. 2020 Apr;121:105701. doi: 10.1016/j.biocel.2020.105701. Epub 2020 Jan 31. PMID: 32007602. 3: Yu Q, Wang XD, Liu HM, Ma YX. Preparation and Characterization of Solid Acid Catalysts for the Conversion of Sesamin into Asarinin in Sesame Oil. Foods. 2022 Apr 24;11(9):1225. doi: 10.3390/foods11091225. PMID: 35563949; PMCID: PMC9102778. 4: Park HJ, Lee KS, Zhao TT, Lee KE, Lee MK. Effects of asarinin on dopamine biosynthesis and 6-hydroxydopamine-induced cytotoxicity in PC12 cells. Arch Pharm Res. 2017 May;40(5):631-639. doi: 10.1007/s12272-017-0908-z. Epub 2017 Apr 10. PMID: 28397192. 5: Jeong M, Kim HM, Lee JS, Choi JH, Jang DS. (-)-Asarinin from the Roots of Asarum sieboldii Induces Apoptotic Cell Death via Caspase Activation in Human Ovarian Cancer Cells. Molecules. 2018 Jul 25;23(8):1849. doi: 10.3390/molecules23081849. PMID: 30044423; PMCID: PMC6222791. 6: Dai Q, Wang M, Li Y, Li J. Amelioration of CIA by Asarinin Is Associated to a Downregulation of TLR9/NF-κB and Regulation of Th1/Th2/Treg Expression. Biol Pharm Bull. 2019 Jul 1;42(7):1172-1178. doi: 10.1248/bpb.b19-00083. Epub 2019 Apr 23. PMID: 31019160. 7: Yu Q, Cai XS, Leveneur S, Wang XD, Liu HM, Zhang CX, Ma YX. Kinetic modeling of the sesamin conversion into asarinin in the presence of citric acid loading on Hβ. Front Nutr. 2022 Aug 10;9:983843. doi: 10.3389/fnut.2022.983843. PMID: 36034908; PMCID: PMC9399800. 8: Jeong SH, Jang JH, Cho HY, Lee YB. Simultaneous determination of asarinin, β-eudesmol, and wogonin in rats using ultraperformance liquid chromatography- tandem mass spectrometry and its application to pharmacokinetic studies following administration of standards and Gumiganghwal-tang. Biomed Chromatogr. 2021 Apr;35(4):e5021. doi: 10.1002/bmc.5021. Epub 2020 Nov 30. PMID: 33169364. 9: Andargie M, Vinas M, Rathgeb A, Möller E, Karlovsky P. Lignans of Sesame (Sesamum indicum L.): A Comprehensive Review. Molecules. 2021 Feb 7;26(4):883. doi: 10.3390/molecules26040883. PMID: 33562414; PMCID: PMC7914952. 10: Gu J, Zhang L, Wang Z, Chen Y, Zhang G, Zhang D, Wang X, Bai X, Li X, Lili Z. The effect of Asarinin on Toll-like pathway in rats after cardiac allograft implantation. Transplant Proc. 2015 Mar;47(2):545-8. doi: 10.1016/j.transproceed.2014.12.019. PMID: 25769604. 11: Dai Q, Li Y, Wang M, Li Y, Li J. TlR2 and TlR4 are involved in the treatment of rheumatoid arthritis synovial fibroblasts with a medicated serum of asarinin through inhibition of Th1/Th17 cytokines. Exp Ther Med. 2020 Apr;19(4):3009-3016. doi: 10.3892/etm.2020.8557. Epub 2020 Feb 26. PMID: 32256787; PMCID: PMC7086207. 12: Chen C, Shi X, Zhou T, Li W, Li S, Bai G. Full-length transcriptome analysis and identification of genes involved in asarinin and aristolochic acid biosynthesis in medicinal plant Asarum sieboldii. Genome. 2021 Jun;64(6):639-653. doi: 10.1139/gen-2020-0095. Epub 2020 Dec 15. PMID: 33320770. 13: Bai X, Gou X, Cai P, Xu C, Cao L, Zhao Z, Huang M, Jin J. Sesamin Enhances Nrf2-Mediated Protective Defense against Oxidative Stress and Inflammation in Colitis via AKT and ERK Activation. Oxid Med Cell Longev. 2019 Aug 26;2019:2432416. doi: 10.1155/2019/2432416. PMID: 31534619; PMCID: PMC6732632. 14: Li CY, Chow TJ, Wu TS. The epimerization of sesamin and asarinin. J Nat Prod. 2005 Nov;68(11):1622-4. doi: 10.1021/np050106d. PMID: 16309310. 15: Li K, Yang DS, Gu XF, Di B. Absolute configuration determination of asarinin by synchrotron radiation with crystalline sponge method. Fitoterapia. 2019 Apr;134:135-140. doi: 10.1016/j.fitote.2019.02.010. Epub 2019 Feb 13. PMID: 30771464. 16: Bai Q, Wang Z, Piao Y, Zhou X, Piao Q, Jiang J, Liu H, Piao H, Li L, Song Y, Yan G. Sesamin Alleviates Asthma Airway Inflammation by Regulating Mitophagy and Mitochondrial Apoptosis. J Agric Food Chem. 2022 Apr 27;70(16):4921-4933. doi: 10.1021/acs.jafc.1c07877. Epub 2022 Apr 14. PMID: 35420033. 17: He H, Yang T, Li F, Zhang L, Ling X. A novel study on the immunomodulatory effect of umbilical cord derived mesenchymal stem cells pretreated with traditional Chinese medicine Asarinin. Int Immunopharmacol. 2021 Nov;100:108054. doi: 10.1016/j.intimp.2021.108054. Epub 2021 Sep 3. PMID: 34492537. 18: Ren JY, Yin BW, Li X, Zhu SQ, Deng JL, Sun YT, Zhang ZA, Guo ZH, Pei HT, Zhang F, Li RQ, Chen FG, Ma YX. Sesamin attenuates PM2.5-induced cardiovascular injury by inhibiting ferroptosis in rats. Food Funct. 2021 Dec 13;12(24):12671-12682. doi: 10.1039/d1fo02913d. PMID: 34825691. 19: Zhang LL, Lu SF, Zhang S, Nie HG, Guan ZZ, Yang BF. [Effect of asarinin on the acute heart transplantation rejection and the expression of adhesion molecule]. Zhongguo Zhong Yao Za Zhi. 2006 Mar;31(6):494-7. Chinese. PMID: 16722383. 20: Wang Y, Wen J, Almoiliqy M, Wang Y, Liu Z, Yang X, Lu X, Meng Q, Peng J, Lin Y, Sun P. Sesamin Protects against and Ameliorates Rat Intestinal Ischemia/Reperfusion Injury with Involvement of Activating Nrf2/HO-1/NQO1 Signaling Pathway. Oxid Med Cell Longev. 2021 Sep 29;2021:5147069. doi: 10.1155/2021/5147069. PMID: 34630849; PMCID: PMC8494576.

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

View History

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