Swertiamarin | CAS#17388-39-5 | antidiabetic

MedKoo Cat#: 561201 | Name: Swertiamarin

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Description:

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

Swertiamarin is an active compound isolated from Enicostemma littorale possesses antidiabetic activity and enhances β cell regeneration which causes reversal of diabetes. Swertiamarin possesses antihyperglycemic, antihyperlipidemic, cytoprotective, and immune reactivity and also a broad spectrum potential of treating diabetes and other complications related to diabetes.

Chemical Structure

Swertiamarin

CAS#17388-39-5

Theoretical Analysis

MedKoo Cat#: 561201

Name: Swertiamarin

CAS#: 17388-39-5

Chemical Formula: C16H22O10

Exact Mass: 374.1213

Molecular Weight: 374.34

Elemental Analysis: C, 51.34; H, 5.92; O, 42.74

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 285.00
50mg	USD 450.00

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Synonym

Swertiamarin; Swertiamaroside

IUPAC/Chemical Name

(3S,4R,4aR)-4-ethenyl-4a-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one

InChi Key

HEYZWPRKKUGDCR-QBXMEVCASA-N

InChi Code

InChI=1S/C16H22O10/c1-2-7-14(24-6-8-13(21)23-4-3-16(7,8)22)26-15-12(20)11(19)10(18)9(5-17)25-15/h2,6-7,9-12,14-15,17-20,22H,1,3-5H2/t7-,9+,10+,11-,12+,14-,15-,16+/m0/s1

SMILES Code

O=C1OCC[C@]2(O)C1=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2C=C

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

>2 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:

Swertiamarin's biological target involves its ability to modulate various pathways involved in inflammation and bone metabolism. Specifically, it targets the receptor activator of nuclear factor kappa-B ligand (RANKL), receptor activator of nuclear factor kappa-B (RANK), and osteoprotegerin (OPG) system, crucial in regulating osteoclast differentiation and bone resorption.

In vitro activity:

In this in vitro study, swertiamarin demonstrated neuroprotective potential against neuro-inflammation induced by LPS in BV-2 cells. Treatment with swertiamarin at varying concentrations significantly inhibited the secretion of pro-inflammatory cytokines such as IL-1β, IL-6, IL-18, and TNF-α, as confirmed by ELISA and western blot analyses. Proteomics analysis using TMT-LC-MS/MS highlighted potential biological processes regulated by swertiamarin related to cellular responses, RNA polymerase II transcription cofactor activity, and neurotransmitter receptor binding, suggesting its therapeutic promise in managing neuro-inflammatory diseases. Reference: Wang G, Quan J, Su N, Li P, Yu Q. Proteomic Analysis of Swertiamarin-treated BV-2 Cells and Possible Implications in Neuroinflammation. J Oleo Sci. 2022 Mar 2;71(3):395-400.

In vivo activity:

In this in vivo study, swertiamarin was evaluated for its potential as an antimalarial agent using Swiss albino mice infected with Plasmodium berghei. Administration of swertiamarin orally before infection delayed parasite development compared to untreated controls. The compound appeared to modulate IFN-γ and IL-10 levels, suggesting an immunomodulatory effect. However, its short half-life necessitated higher and more frequent dosing for sustained therapeutic benefit against malaria. Reference: Patel N, Zinzuvadia A, Prajapati M, Tyagi RK, Dalai S. Swertiamarin-mediated immune modulation/adaptation confers protection against Plasmodium berghei. Future Microbiol. 2022 Aug;17:931-941.

	Solvent	mg/mL	mM
Solubility
	DMSO	250.0	667.84

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 374.34 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:

Patel N, Zinzuvadia A, Prajapati M, Tyagi RK, Dalai S. Swertiamarin-mediated immune modulation/adaptation confers protection against Plasmodium berghei. Future Microbiol. 2022 Aug;17:931-941. doi: 10.2217/fmb-2021-0298. Epub 2022 Jun 15. PMID: 35704297. Xu L, Li D, Zhu Y, Cai S, Liang X, Tang Y, Jin S, Ding C. Swertiamarin supplementation prevents obesity-related chronic inflammation and insulin resistance in mice fed a high-fat diet. Adipocyte. 2021 Dec;10(1):160-173. Wang G, Quan J, Su N, Li P, Yu Q. Proteomic Analysis of Swertiamarin-treated BV-2 Cells and Possible Implications in Neuroinflammation. J Oleo Sci. 2022 Mar 2;71(3):395-400. doi: 10.5650/jos.ess21333. Epub 2022 Feb 11. PMID: 35153246. Hairul-Islam MI, Saravanan S, Thirugnanasambantham K, Chellappandian M, Simon Durai Raj C, Karikalan K, Gabriel Paulraj M, Ignacimuthu S. Swertiamarin, a natural steroid, prevent bone erosion by modulating RANKL/RANK/OPG signaling. Int Immunopharmacol. 2017 Dec;53:114-124. doi: 10.1016/j.intimp.2017.10.022. PMID: 29078090.

In vitro protocol:

Wang G, Quan J, Su N, Li P, Yu Q. Proteomic Analysis of Swertiamarin-treated BV-2 Cells and Possible Implications in Neuroinflammation. J Oleo Sci. 2022 Mar 2;71(3):395-400. doi: 10.5650/jos.ess21333. Epub 2022 Feb 11. PMID: 35153246. Hairul-Islam MI, Saravanan S, Thirugnanasambantham K, Chellappandian M, Simon Durai Raj C, Karikalan K, Gabriel Paulraj M, Ignacimuthu S. Swertiamarin, a natural steroid, prevent bone erosion by modulating RANKL/RANK/OPG signaling. Int Immunopharmacol. 2017 Dec;53:114-124. doi: 10.1016/j.intimp.2017.10.022. PMID: 29078090.

In vivo protocol:

1: Wang W, Tan Y, Mao J, Xiong W. Swertiamarin and sweroside are potential inhibitors of COVID-19 based on the silico analysis. Medicine (Baltimore). 2024 Nov 8;103(45):e40425. doi: 10.1097/MD.0000000000040425. PMID: 39533611; PMCID: PMC11556981. 2: Chen H, Liu P, Yu R, Mohammadtursun N, Aikemu A, Yang X. Swertiamarin ameliorates type 2 diabetes by activating ADRB3/UCP1 thermogenic signals in adipose tissue. Phytomedicine. 2024 Oct 30;135:156190. doi: 10.1016/j.phymed.2024.156190. Epub ahead of print. PMID: 39515102. 3: Xuan L, Xiao H, Zhao Z, Feng J, Ni L, Wu J. Integrated Transcriptomics and Metabolomics Reveal Key Insights into Iridoid Biosynthesis in Gentiana crassicaulis Seeds during Germination. Genes (Basel). 2024 Sep 26;15(10):1255. doi: 10.3390/genes15101255. PMID: 39457379; PMCID: PMC11507440. 4: Cao C, Hu B, Wang J, Li W, Guo L, Sheng J, Zhang C. Swertianin Promotes Anti- Tumor activity by facilitating Macrophage M1 polarization via STING signaling. Int Immunopharmacol. 2024 Dec 5;142(Pt B):113182. doi: 10.1016/j.intimp.2024.113182. Epub 2024 Sep 18. PMID: 39298821. 5: Liu S, Li J, Wu X. [Swertiamarin ameliorates 2, 4, 6-trinitrobenzenesulfonic acid-induced colitis in mice by inhibiting intestinal epithelial cell apoptosis]. Nan Fang Yi Ke Da Xue Xue Bao. 2024 Aug 20;44(8):1545-1552. Chinese. doi: 10.12122/j.issn.1673-4254.2024.08.13. PMID: 39276050; PMCID: PMC11378047. 6: Khamlich J, Douiyeh I, Saih A, Moussamih S, Regragui A, Kettani A, Safi A. Identification of small molecule glucokinase activators for the treatment of diabetes based on plants from the traditional Chinese medicine: In silico analysis. Microb Pathog. 2024 Oct;195:106851. doi: 10.1016/j.micpath.2024.106851. Epub 2024 Aug 26. PMID: 39197693. 7: Chang J, Zou S, Xiao Y, Zhu D. Correction: Identification and validation of targets of swertiamarin on idiopathic pulmonary fibrosis through bioinformatics and molecular docking-based approach. BMC Complement Med Ther. 2024 Aug 21;24(1):312. doi: 10.1186/s12906-024-04616-w. Erratum for: BMC Complement Med Ther. 2023 Oct 5;23(1):352. doi: 10.1186/s12906-023-04171-w. PMID: 39169345; PMCID: PMC11340049. 8: Li HM, Chen T, Qian LX, Wang S, Shen C, Li LC, Li YL. Therapeutic effect of iridoid and xanthone glycosides components extracted from Swertia Mussotti on calculous cholecystitis and its clinical complications by targeting COX2. Fitoterapia. 2024 Oct;178:106189. doi: 10.1016/j.fitote.2024.106189. Epub 2024 Aug 21. PMID: 39154852. 9: Li L, Xiao S, Dai X, Tang Z, Wang Y, Ali M, Ataya FS, Sahar I, Iqbal M, Wu Y, Li K. Multi-omics analysis and the remedial effects of Swertiamarin on hepatic injuries caused by CCl4. Ecotoxicol Environ Saf. 2024 Sep 1;282:116734. doi: 10.1016/j.ecoenv.2024.116734. Epub 2024 Jul 17. PMID: 39024951. 10: Valenta Šobot A, Drakulić D, Todorović A, Janić M, Božović A, Todorović L, Filipović Tričković J. Gentiopicroside and swertiamarin induce non-selective oxidative stress-mediated cytotoxic effects in human peripheral blood mononuclear cells. Chem Biol Interact. 2024 Aug 1;398:111103. doi: 10.1016/j.cbi.2024.111103. Epub 2024 Jun 7. PMID: 38852899. 11: Zhao Z, He D, Wang J, Xiao Y, Gong L, Tang C, Peng H, Qiu X, Liu R, Zhang T, Li J. Swertiamarin relieves radiation-induced intestinal injury by limiting DNA damage. Mol Cell Biochem. 2024 May 25. doi: 10.1007/s11010-024-05030-z. Epub ahead of print. PMID: 38795212. 12: Hao J, Zhou J, Lin P, Wu J. Quantitative comparison and evaluation between aerial and underground parts of Gentiana straminea through simultaneous determination of five major compounds by RP-HPLC. Heliyon. 2024 Apr 15;10(8):e29232. doi: 10.1016/j.heliyon.2024.e29232. PMID: 38660265; PMCID: PMC11040066. 13: Kumar S, Niguram P, Jairaj V, Chauhan N, Jinagal S, Sagar S, Sindhu RK, Chandra A. Exploring the potential of semi-synthetic Swertiamarin analogues for GLUT facilitation and insulin secretion in NIT-1 cell lines: a molecular docking and in-vitro study. Nat Prod Res. 2024 Apr 15:1-5. doi: 10.1080/14786419.2024.2342005. Epub ahead of print. PMID: 38619018. 14: Kolure R, Vinaitheerthan N, Thakur S, Godela R, Doli SB, Santhepete Nanjundaiah M. Protective effect of Enicostemma axillare - Swertiamarin on oxidative stress against nicotine-induced liver damage in SD rats. Ann Pharm Fr. 2024 Sep;82(5):792-799. doi: 10.1016/j.pharma.2024.03.009. Epub 2024 Apr 3. PMID: 38579927. 15: Wang J, Liu R, Zhang J, Su H, Yang Q, Wulu J, Li J, Zhang Z, Lv Z. Comparative analysis of phytochemical profile and antioxidant and anti- inflammatory activity of four Gentiana species from the Qinghai-Tibet Plateau. J Ethnopharmacol. 2024 May 23;326:117926. doi: 10.1016/j.jep.2024.117926. Epub 2024 Feb 17. PMID: 38369064. 16: Yin Y, Fu H, Mi F, Yang Y, Wang Y, Li Z, He Y, Yue Z. Genomic characterization of WRKY transcription factors related to secoiridoid biosynthesis in Gentiana macrophylla. BMC Plant Biol. 2024 Jan 23;24(1):66. doi: 10.1186/s12870-024-04727-z. PMID: 38262919; PMCID: PMC10804491. 17: Ma W, Long J, Dong L, Zhang J, Wang A, Zhang Y, Yan D. Uncovering the key pharmacodynamic material basis and possible molecular mechanism of Xiaoke formulation improve insulin resistant through a comprehensive investigation. J Ethnopharmacol. 2024 Apr 6;323:117752. doi: 10.1016/j.jep.2024.117752. Epub 2024 Jan 11. PMID: 38216099. 18: Chen YC, Chen JH, Tsai CF, Wu CT, Chang PC, Yeh WL. Inhibition of tumor migration and invasion by fenofibrate via suppressing epithelial-mesenchymal transition in breast cancers. Toxicol Appl Pharmacol. 2024 Feb;483:116818. doi: 10.1016/j.taap.2024.116818. Epub 2024 Jan 11. PMID: 38215994. 19: Chabane S, Boudjelal A, Bouaziz-Terrachet S, Spinozzi E, Maggi F, Petrelli R, Tail G. Analgesic effect of Centaurium erythraea and molecular docking investigation of the major component swertiamarin. Nat Prod Res. 2024 Dec;38(24):4511-4517. doi: 10.1080/14786419.2023.2278160. Epub 2023 Nov 10. PMID: 37948163. 20: Kou B, Jiang Y, Chen Y, Yang J, Sun J, Yan Y, Weng L, Xiao C. A Study of Gentianae Radix et Rhizoma Class Differences Based on Chemical Composition and Core Efficacy. Molecules. 2023 Oct 17;28(20):7132. doi: 10.3390/molecules28207132. PMID: 37894611; PMCID: PMC10609378.