(−)-Sweroside | CAS#14215-86-2 | Diverse iridoid glycoside

MedKoo Cat#: 464184 | Name: (−)-Sweroside

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Description:

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

(−)-Sweroside is an iridoid glycoside that has been found in L. japonica and has diverse biological activities, including anti-inflammatory, antiproliferative, and anti-obesity properties. It inhibits LPS-induced production of prostaglandin E2 and reactive oxygen species (ROS) in mouse RAW 264.7 macrophages when used at a concentration of 40 µM. (−)-Sweroside inhibits the growth of U937 lymphoma and HL-60 leukemia cells (IC50s = 67.92 and 62.58 µM, respectively) but not non-cancerous human peripheral blood mononuclear cells (PBMCs) or mouse bone marrow cells (BMCs). It reduces tumor growth in an HL-60 mouse xenograft model when administered at a dose of 50 mg/kg. (−)-Sweroside (120 mg/kg) reduces weight gain and serum total cholesterol, triglyceride, LDL cholesterol (LDL-C), and free fatty acid (FFA) levels in a mouse model of obesity induced by a high-fat diet (HFD).

Chemical Structure

(−)-Sweroside

CAS#14215-86-2

Theoretical Analysis

MedKoo Cat#: 464184

Name: (−)-Sweroside

CAS#: 14215-86-2

Chemical Formula: C16H22O9

Exact Mass: 358.1264

Molecular Weight: 358.34

Elemental Analysis: C, 53.63; H, 6.19; O, 40.18

Price and Availability

Size	Price	Availability
5mg	USD 250.00	2 Weeks
10mg	USD 400.00	2 Weeks
25mg	USD 800.00	2 Weeks
50mg	USD 1,100.00	2 Weeks

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Synonym

(−)-Sweroside; (−) Sweroside; 1,9-trans-9,5-cis-Sweroside;

IUPAC/Chemical Name

(4aS,5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one

InChi Key

VSJGJMKGNMDJCI-ZASXJUAOSA-N

InChi Code

InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1

SMILES Code

C=C[C@@H]1[C@]2(C(C(OCC2)=O)=CO[C@H]1O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[H]

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

to be determined

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	To be determined	0.0	100.00

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 358.34 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

1: 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 Aug 21;178:106189. doi: 10.1016/j.fitote.2024.106189. Epub ahead of print. PMID: 39154852. 2: Li H, Tang S, Xu Y, Sun Y, Li P, Li X, Zhang H, Hattori M, Wang Z. In vivo detection of the epimer metabolites of sweroside via ultra-performance liquid chromatography time-of-flight mass spectrometry combined with DNPH derivatization. Biomed Chromatogr. 2024 Jul 17:e5966. doi: 10.1002/bmc.5966. Epub ahead of print. PMID: 39021259. 3: Zhang X, Yu X, Sun X, Meng X, Fan J, Zhang F, Zhang Y. Comparative study on chemical constituents of different medicinal parts of Lonicera japonica Thunb. Based on LC-MS combined with multivariate statistical analysis. Heliyon. 2024 May 29;10(12):e31722. doi: 10.1016/j.heliyon.2024.e31722. PMID: 38975169; PMCID: PMC11225679. 4: Xia T, Su S, Wang L, Tang Z, Huo J, Song H. Exploring bitter characteristics of blue honeysuckle (Lonicera caerulea L.) berries by sensory-guided analysis: Key bitter compounds and varietal differences. Food Chem. 2024 Nov 1;457:140150. doi: 10.1016/j.foodchem.2024.140150. Epub 2024 Jun 18. PMID: 38905837. 5: Wang D, Yu X, Gao K, Li F, Li X, Pu H, Zhang P, Guo S, Wang W. Sweroside alleviates pressure overload-induced heart failure through targeting CaMKⅡδ to inhibit ROS-mediated NF-κB/NLRP3 in cardiomyocytes. Redox Biol. 2024 Aug;74:103223. doi: 10.1016/j.redox.2024.103223. Epub 2024 Jun 4. PMID: 38851078; PMCID: PMC11219961. 6: Adepiti AO, Nyamboki DK, Kibrom GB, Elujoba AA, Spiteller M, Matasyoh JC. Secondary metabolites from the stem bark of Alstonia boonei and the seeds of Picralima nitida with antibacterial activities. Nat Prod Res. 2024 Apr 29:1-6. doi: 10.1080/14786419.2024.2349254. Epub ahead of print. PMID: 38684042. 7: Szumny D, Kucharska AZ, Czajor K, Bernacka K, Ziółkowska S, Krzyżanowska- Berkowska P, Magdalan J, Misiuk-Hojło M, Sozański T, Szeląg A. Extract from Aronia melanocarpa, Lonicera caerulea, and Vaccinium myrtillus Improves near Visual Acuity in People with Presbyopia. Nutrients. 2024 Mar 23;16(7):926. doi: 10.3390/nu16070926. PMID: 38612968; PMCID: PMC11013737. 8: 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. 9: Tang X, Huang Y, Fang X, Tong X, Yu Q, Zheng W, Fu F. Cornus officinalis: a potential herb for treatment of osteoporosis. Front Med (Lausanne). 2023 Dec 4;10:1289144. doi: 10.3389/fmed.2023.1289144. PMID: 38111697; PMCID: PMC10725965. 10: Ma X, Guo Z, Zhao W, Chen L. Sweroside plays a role in mitigating high glucose-induced damage in human renal tubular epithelial HK-2 cells by regulating the SIRT1/NF-κB signaling pathway. Korean J Physiol Pharmacol. 2023 Nov 1;27(6):533-540. doi: 10.4196/kjpp.2023.27.6.533. PMID: 37884285; PMCID: PMC10613573. 11: Liu K, Jin Y, Gu L, Li M, Wang P, Yin G, Wang S, Wang T, Wang L, Wang B. Classification and Authentication of Lonicerae Japonicae Flos and Lonicerae Flos by Using 1H-NMR Spectroscopy and Chemical Pattern Recognition Analysis. Molecules. 2023 Sep 28;28(19):6860. doi: 10.3390/molecules28196860. PMID: 37836702; PMCID: PMC10574709. 12: Huang M, Yang Y, Chen Y, Li Y, Qin S, Xiao L, Long X, Hu K, Li Y, Ying H, Ding Y. Sweroside attenuates podocyte injury and proteinuria in part by activating Akt/BAD signaling in mice. J Cell Biochem. 2023 Nov;124(11):1749-1763. doi: 10.1002/jcb.30484. Epub 2023 Oct 5. PMID: 37796169. 13: Wang Z, Shi X, Jiang S, Sun J, Borjigin G, Li Q, Mu Y, Yang C, Wang Z, Kuang H. Simultaneous Determination of Five Iridoids of Picrorhiza scrophulariiflora in Rat Plasma Using UHPLC-ESI-MS/MS. Molecules. 2023 Aug 7;28(15):5925. doi: 10.3390/molecules28155925. PMID: 37570895; PMCID: PMC10421376. 14: Wang J, Ma X, Si X, Han W. Sweroside functionalized with Mesenchymal Stem cells derived exosomes attenuates sepsis-induced myocardial injury by modulating oxidative stress and apoptosis in rats. J Biomater Appl. 2023 Sep;38(3):381-391. doi: 10.1177/08853282231194317. Epub 2023 Aug 10. PMID: 37563958. 15: Popović Z, Vidaković V, Mijalković T, Krstić-Milošević D. Population-Related Variability in Qualitative and Quantitative Secondary Metabolite Profile of Gentianella austriaca (A. & J. Kern.) Holub. Plants (Basel). 2023 Jun 23;12(13):2434. doi: 10.3390/plants12132434. PMID: 37446995; PMCID: PMC10346188. 16: Dai LL, Cho SB, Li HF, A LS, Ji XP, Pan S, Bao ML, Bai L, Ba GN, Fu MH. Lomatogonium rotatum extract alleviates diabetes mellitus induced by a high-fat, high-sugar diet and streptozotocin in rats. World J Diabetes. 2023 Jun 15;14(6):846-861. doi: 10.4239/wjd.v14.i6.846. PMID: 37383587; PMCID: PMC10294064. 17: Ding Y, Chen Y, Hu K, Yang Q, Li Y, Huang M. Sweroside alleviates hepatic steatosis in part by activating AMPK/mTOR-mediated autophagy in mice. J Cell Biochem. 2023 Jul;124(7):1012-1022. doi: 10.1002/jcb.30428. Epub 2023 Jun 3. PMID: 37269482. 18: Wu P, Chang C, Zhu G, Zhai L, Zhang X, Huan Q, Gao Z, Deng H, Liang Y, Xiao H. Network Pharmacology Study of Bioactive Components and Molecular Mechanisms of the Glycoside Fraction from Picrorhiza scrophulariiflora Against Experimental Colitis. Drug Des Devel Ther. 2023 May 23;17:1531-1546. doi: 10.2147/DDDT.S407339. PMID: 37249930; PMCID: PMC10224697. 19: Wang J, Cao L, Gao X, Gao H, Chen X, Wang Z, Xiao W. Discovery of the material basis of Jiuwei Xifeng granules using pharmaco-chemistry and pharmacokinetics. J Ethnopharmacol. 2023 Sep 15;313:116504. doi: 10.1016/j.jep.2023.116504. Epub 2023 Apr 20. PMID: 37084988. 20: Yang C, Zhang N, Wu S, Jiang C, Xie L, Yang F, Yu Z. A Comparative Analysis of the Chloroplast Genomes of Three Lonicera Medicinal Plants. Genes (Basel). 2023 Feb 22;14(3):548. doi: 10.3390/genes14030548. PMID: 36980821; PMCID: PMC10048777.