Sesamolin | CAS#526-07-8 | inhibits cell proliferation

MedKoo Cat#: 592119 | Name: Sesamolin

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Description:

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

Sesamolin inhibits proliferation of human lymphocytic leukemia cells in culture. Targeting MYH14 by sesamolin, a cytotoxicity-based approach, can be applied synergistically with chemotherapy and endocrine therapy to eventually mitigate EC development.

Chemical Structure

Sesamolin

CAS#526-07-8

Theoretical Analysis

MedKoo Cat#: 592119

Name: Sesamolin

CAS#: 526-07-8

Chemical Formula: C20H18O7

Exact Mass: 370.1053

Molecular Weight: 370.36

Elemental Analysis: C, 64.86; H, 4.90; O, 30.24

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00

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Related CAS #

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Synonym

Sesamolin; AI3-20978; AI3 20978; AI320978

IUPAC/Chemical Name

1,3-Benzodioxole, 5-(4-(1,3-benzodioxol-5-yloxy)tetrahydro-1H,3H-furo(3,4-c)furan-1-yl)-, (1S-(1alpha,3a alpha,4alpha,6a alpha))-

InChi Key

ZZMNWJVJUKMZJY-NSMLZSOPSA-N

InChi Code

InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m1/s1

SMILES Code

[H][C@]12[C@](CO[C@H]2OC3=CC=C(OCO4)C4=C3)([H])[C@H](C5=CC=C(OCO6)C6=C5)OC1

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sesaminol potently inhibits MAPK cascades by preventing phosphorylation of JNK, p38 MAPKs, and caspase-3 but not ERK-MAPK expression.

In vitro activity:

This study describes the role of sesamolin in activating natural killer (NK) cells by modulating the differentiation and activation of DCs. Sesamolin enhances the cytolytic activity and migration of NK cells by influencing dendritic cells (DCs). Co-culturing NK cells with sesamolin-treated mature dendritic cells (mDCs) showed improved cytolytic activity compared to other combinations. Additionally, NK cell migration towards mDCs was enhanced, especially after sesamolin activation of mDCs. Reference: Arch Pharm Res. 2020 Apr;43(4):462-474. https://pubmed.ncbi.nlm.nih.gov/32279231/

In vivo activity:

Sesamolin may be a potential compound for obesity-associated nonalcoholic fatty liver disease (NAFLD) treatment. In mice with NAFLD, sesamolin effectively suppressed obesity-associated metabolic disorder, attenuated hepatic steatosis and the infiltration of inflammatory cells, and decreased levels of hepatic proinflammatory cytokines. Sesamolin also altered the composition of gut microbiota associated with NAFLD at the genus level. Reference: Int J Mol Sci. 2022 Nov 10;23(22):13853. https://pubmed.ncbi.nlm.nih.gov/36430326/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	81.00
	DMSO	12.0	32.40
	Ethanol	0.5	1.35

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 370.36 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. Lee JK. Sesamolin promotes cytolysis and migration activity of natural killer cells via dendritic cells. Arch Pharm Res. 2020 Apr;43(4):462-474. doi: 10.1007/s12272-020-01229-y. Epub 2020 Apr 11. PMID: 32279231. 2. Wu D, Wang XP, Zhang W. Sesamolin exerts anti-proliferative and apoptotic effect on human colorectal cancer cells via inhibition of JAK2/STAT3 signaling pathway. Cell Mol Biol (Noisy-le-grand). 2019 Jul 31;65(6):96-100. PMID: 31472054. 3. Yu J, Sun H, Yang Y, Yan Y. Sesamolin Alleviates Nonalcoholic Fatty Liver Disease through Modulating Gut Microbiota and Metabolites in High-Fat and High-Fructose Diet-Fed Mice. Int J Mol Sci. 2022 Nov 10;23(22):13853. doi: 10.3390/ijms232213853. PMID: 36430326; PMCID: PMC9694049. 4. Kitipaspallop W, Sillapaprayoon S, Phuwapraisirisan P, Kim WK, Chanchao C, Pimtong W. Developmental effects of sesamolin on zebrafish (Danio rerio) embryos. Comp Biochem Physiol C Toxicol Pharmacol. 2022 Jun;256:109319. doi: 10.1016/j.cbpc.2022.109319. Epub 2022 Feb 25. PMID: 35227877.

In vitro protocol:

In vivo protocol:

1. Yu J, Sun H, Yang Y, Yan Y. Sesamolin Alleviates Nonalcoholic Fatty Liver Disease through Modulating Gut Microbiota and Metabolites in High-Fat and High-Fructose Diet-Fed Mice. Int J Mol Sci. 2022 Nov 10;23(22):13853. doi: 10.3390/ijms232213853. PMID: 36430326; PMCID: PMC9694049. 2. Kitipaspallop W, Sillapaprayoon S, Phuwapraisirisan P, Kim WK, Chanchao C, Pimtong W. Developmental effects of sesamolin on zebrafish (Danio rerio) embryos. Comp Biochem Physiol C Toxicol Pharmacol. 2022 Jun;256:109319. doi: 10.1016/j.cbpc.2022.109319. Epub 2022 Feb 25. PMID: 35227877.

1: Kim DY, Oh S, Ko HS, Park S, Jeon YJ, Kim J, Yang DK, Park KW. Sesamolin suppresses adipocyte differentiation through Keap1-dependent Nrf2 activation in adipocytes. Nutr Res. 2024 Aug;128:14-23. doi: 10.1016/j.nutres.2024.05.005. Epub 2024 May 29. PMID: 39002358. 2: Yin WT, Yang CJ, Yang HJ, Hu BB, Zhang F, Wang XD, Liu HM, Miao HM. Sesame lignans modulate aroma formation in sesame oil through the Maillard reaction and lipid oxidation in model systems. Food Chem. 2024 Nov 1;457:140079. doi: 10.1016/j.foodchem.2024.140079. Epub 2024 Jun 11. PMID: 38901343. 3: Rosalina R, Kamwilaisak K, Sutthanut K, Srisongkram T, Weerapreeyakul N. Probing the stability and quality of the cellulose-based Pickering emulsion containing sesamolin-enriched sesame oil by chemometrics-assisted ATR-FTIR spectroscopy. Food Chem. 2024 Sep 15;452:139555. doi: 10.1016/j.foodchem.2024.139555. Epub 2024 May 6. PMID: 38728896. 4: Lin Y, Chen X, Lin L, Xu B, Zhu X, Lin X. Sesamolin serves as an MYH14 inhibitor to sensitize endometrial cancer to chemotherapy and endocrine therapy via suppressing MYH9/GSK3β/β-catenin signaling. Cell Mol Biol Lett. 2024 May 2;29(1):63. doi: 10.1186/s11658-024-00583-9. PMID: 38698330; PMCID: PMC11067147. 5: Hoyos BE, Johnson JB, Mani JS, Batley RJ, Trotter T, Bhattarai SP, Naiker M. The Effect of Water Stress on Bioactive Compounds in Australian-Grown Black Sesame. Plants (Basel). 2024 Mar 11;13(6):793. doi: 10.3390/plants13060793. PMID: 38592794; PMCID: PMC10974145. 6: Nouska C, Irakli M, Palakas P, Lytou AE, Bouloumpasi E, Biliaderis CG, Lazaridou A. Influence of sesame cake on physicochemical, antioxidant and sensorial characteristics of fortified wheat breads. Food Res Int. 2024 Feb;178:113980. doi: 10.1016/j.foodres.2024.113980. Epub 2024 Jan 4. PMID: 38309883. 7: Gina NNT, Kuo JL, Wu ML, Chuang SM. Sesamin and sesamolin potentially inhibit adipogenesis through downregulating the peroxisome proliferator-activated receptor γ protein expression and activity in 3T3-L1 cells. Nutr Res. 2024 Mar;123:4-17. doi: 10.1016/j.nutres.2023.12.011. Epub 2023 Dec 25. PMID: 38228077. 8: Kim S, Lee E, Lee J, An YJ, Oh E, Kim JI, Kim SW, Kim MY, Lee MH, Cho KS. Identification of QTLs and allelic effect controlling lignan content in sesame (Sesamum indicum L.) using QTL-seq approach. Front Genet. 2023 Dec 11;14:1289793. doi: 10.3389/fgene.2023.1289793. PMID: 38148976; PMCID: PMC10750367. 9: Comini E, Rubiales D, Reveglia P. Variability of Fatty Acid Composition and Lignan Content in Sesame Germplasm, and Effect of Roasting. ACS Food Sci Technol. 2023 Oct 2;3(10):1747-1758. doi: 10.1021/acsfoodscitech.3c00304. PMID: 37881444; PMCID: PMC10594645. 10: Ramazani E, Ebrahimpour F, Emami SA, Shakeri A, Javadi B, Sahebkar A, Tayarani-Najaran Z. Neuroprotective Effects of Sesamum indicum, Sesamin and Sesamolin Against 6-OHDA-induced Apoptosis in PC12 Cells. Recent Adv Food Nutr Agric. 2023;14(2):126-133. doi: 10.2174/2772574X14666230804151124. PMID: 37539928. 11: Hadipour E, Emami SA, Tayarani-Najaran N, Tayarani-Najaran Z. Effects of sesame (Sesamum indicum L.) and bioactive compounds (sesamin and sesamolin) on inflammation and atherosclerosis: A review. Food Sci Nutr. 2023 May 22;11(7):3729-3757. doi: 10.1002/fsn3.3407. PMID: 37457142; PMCID: PMC10345702. 12: Zhang Y, Wang J, Tan H, Lu X, Wang D, Wei Q. Evaluation of Steaming and Drying of Black Sesame Seeds for Nine Cycles Using Grey-Correlation Analysis Based on Variation-Coefficient Weight. Molecules. 2023 Jul 7;28(13):5266. doi: 10.3390/molecules28135266. PMID: 37446935; PMCID: PMC10343377. 13: Chi Y, He HW, Chen CY, Zhao SY, Zhou H, Xu D, Liu X, Xu G. Furofuran Lignans for Plant Protection: Discovery of Sesamolin and Its Derivatives as Novel Anti- Tobacco Mosaic Virus and Antibacterial Agents. J Agric Food Chem. 2023 Jul 19;71(28):10798-10808. doi: 10.1021/acs.jafc.3c03257. Epub 2023 Jul 7. PMID: 37418668. 14: Oboulbiga EB, Douamba Z, Compaoré-Sérémé D, Semporé JN, Dabo R, Semde Z, Tapsoba FW, Hama-Ba F, Songré-Ouattara LT, Parkouda C, Dicko MH. Physicochemical, potential nutritional, antioxidant and health properties of sesame seed oil: a review. Front Nutr. 2023 Jun 1;10:1127926. doi: 10.3389/fnut.2023.1127926. PMID: 37377483; PMCID: PMC10292629. 15: Wan Y, Zhou Q, Zhao M, Hou T. Byproducts of Sesame Oil Extraction: Composition, Function, and Comprehensive Utilization. Foods. 2023 Jun 15;12(12):2383. doi: 10.3390/foods12122383. PMID: 37372594; PMCID: PMC10297287. 16: Arooj A, Rabail R, Naeem M, Goksen G, Xu B, Aadil RM. A comprehensive review of the bioactive components of sesame seeds and their impact on bone health issues in postmenopausal women. Food Funct. 2023 Jun 6;14(11):4966-4980. doi: 10.1039/d3fo00531c. PMID: 37212033. 17: Nair AB, Dalal P, Kadian V, Kumar S, Garg M, Rao R, Almuqbil RM, Alnaim AS, Aldhubiab B, Alqattan F. Formulation Strategies for Enhancing Pharmaceutical and Nutraceutical Potential of Sesamol: A Natural Phenolic Bioactive. Plants (Basel). 2023 Mar 3;12(5):1168. doi: 10.3390/plants12051168. PMID: 36904028; PMCID: PMC10005287. 18: Dossou SSK, Song S, Liu A, Li D, Zhou R, Berhe M, Zhang Y, Sheng C, Wang Z, You J, Wang L. Resequencing of 410 Sesame Accessions Identifies SINST1 as the Major Underlying Gene for Lignans Variation. Int J Mol Sci. 2023 Jan 5;24(2):1055. doi: 10.3390/ijms24021055. PMID: 36674569; PMCID: PMC9860558. 19: Yang Y, Yu J, Huo J, Yan Y. Sesamolin Attenuates Kidney Injury, Intestinal Barrier Dysfunction, and Gut Microbiota Imbalance in High-Fat and High-Fructose Diet-Fed Mice. J Agric Food Chem. 2023 Jan 25;71(3):1562-1576. doi: 10.1021/acs.jafc.2c07084. Epub 2023 Jan 11. PMID: 36630317. 20: Du J, Chen X, Zhao Y, Zhao T, Wang D, Chen Z, Wang C, Meng Q, Yao J, Sun H, Liu K, Wu J. Characterization of three naturally occurring lignans, sesamol, sesamolin, and sesamin, as potent inhibitors of human cytochrome P450 46A1: Implications for treating excitatory neurotoxicity. Front Pharmacol. 2022 Nov 22;13:1046814. doi: 10.3389/fphar.2022.1046814. PMID: 36483743; PMCID: PMC9722955.