Kinsenoside | CAS#151870-74-5 | glycoside

MedKoo Cat#: 558529 | Name: Kinsenoside

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Description:

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

Kinsenoside is a glycoside with antihyperlipidemic, immunosuppressive, and anti-inflammatory properties. It raises lipolysis mediated by adipose triglyceride lipase and increases hydrolysis of triglycerides in C3H10T1/2 adipocytes.

Chemical Structure

Kinsenoside

CAS#151870-74-5

Theoretical Analysis

MedKoo Cat#: 558529

Name: Kinsenoside

CAS#: 151870-74-5

Chemical Formula: C10H16O8

Exact Mass: 264.0845

Molecular Weight: 264.23

Elemental Analysis: C, 45.46; H, 6.10; O, 48.44

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 385.00	2 Weeks
10mg	USD 700.00	2 Weeks

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Related CAS #

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Synonym

Kinsenoside;

IUPAC/Chemical Name

2(3H)-Furanone, 4-(.beta.-D-glucopyranosyloxy)dihydro-, (R)-

InChi Key

MQEPWBMWFIVRPS-ZGSHZZHUSA-N

InChi Code

InChI=1S/C10H16O8/c11-2-5-7(13)8(14)9(15)10(18-5)17-4-1-6(12)16-3-4/h4-5,7-11,13-15H,1-3H2/t4-,5-,7-,8+,9-,10-/m1/s1

SMILES Code

O=C1OC[C@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)C1

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

Certificate of Analysis

View CoA: current batch, Lot#C20M07C28

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Kinsenoside rescues the nucleus pulposus cells (NPCs) viability under oxidative stress and protects against apoptosis, senescence and mitochondrial dysfunction in a Nrf2-dependent way.

In vitro activity:

Kinsenoside increased both adipose triglyceride lipase (ATGL)-mediated lipolysis, which was upregulated by AMP-activated protein kinase (AMPK) activation, and the hydrolysis of triglycerides to glycerol and fatty acids that require transportation into mitochondria for further β-oxidation. The results suggested that the mechanism underlying the catabolic effects of kinsenoside on lipolysis and increased CPT1 induction was mediated through an AMPK-dependent pathway. Reference: Phytomedicine. 2015 Jun 1;22(6):641-7. https://pubmed.ncbi.nlm.nih.gov/26055129/

In vivo activity:

Compared with model group, kinsenoside significantly inhibited paw edema and decreased the arthritis score and disease incidence. Histopathological examination demonstrated that kinsenoside effectively protected bone and cartilage of knee joint from erosion, lesion and deformation versus those from the CIA group. Reference: BMC Complement Altern Med. 2016 Feb 25;16:80. https://pubmed.ncbi.nlm.nih.gov/26916550/

	Solvent	mg/mL	mM
Solubility
	DMF	14.0	52.98
	DMSO	33.0	124.89
	PBS (pH 7.2)	10.0	37.85

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 264.23 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. Wang Y, Zuo R, Wang Z, Luo L, Wu J, Zhang C, Liu M, Shi C, Zhou Y. Kinsenoside ameliorates intervertebral disc degeneration through the activation of AKT-ERK1/2-Nrf2 signaling pathway. Aging (Albany NY). 2019 Sep 23;11(18):7961-7977. doi: 10.18632/aging.102302. Epub 2019 Sep 23. PMID: 31546235; PMCID: PMC6781981. 2. Cheng KT, Wang YS, Chou HC, Chang CC, Lee CK, Juan SH. Kinsenoside-mediated lipolysis through an AMPK-dependent pathway in C3H10T1/2 adipocytes: Roles of AMPK and PPARα in the lipolytic effect of kinsenoside. Phytomedicine. 2015 Jun 1;22(6):641-7. doi: 10.1016/j.phymed.2015.04.001. Epub 2015 Apr 28. PMID: 26055129. 3. Xiang M, Liu T, Tan W, Ren H, Li H, Liu J, Cao H, Cheng Q, Liu X, Zhu H, Tuo Y, Wang J, Zhang Y. Effects of kinsenoside, a potential immunosuppressive drug for autoimmune hepatitis, on dendritic cells/CD8+ T cells communication in mice. Hepatology. 2016 Dec;64(6):2135-2150. doi: 10.1002/hep.28825. Epub 2016 Oct 28. PMID: 27639182. 4. Hsiao HB, Hsieh CC, Wu JB, Lin H, Lin WC. Kinsenoside inhibits the inflammatory mediator release in a type-II collagen induced arthritis mouse model by regulating the T cells responses. BMC Complement Altern Med. 2016 Feb 25;16:80. doi: 10.1186/s12906-016-1054-8. PMID: 26916550; PMCID: PMC4766613.

In vitro protocol:

In vivo protocol:

1. Xiang M, Liu T, Tan W, Ren H, Li H, Liu J, Cao H, Cheng Q, Liu X, Zhu H, Tuo Y, Wang J, Zhang Y. Effects of kinsenoside, a potential immunosuppressive drug for autoimmune hepatitis, on dendritic cells/CD8+ T cells communication in mice. Hepatology. 2016 Dec;64(6):2135-2150. doi: 10.1002/hep.28825. Epub 2016 Oct 28. PMID: 27639182. 2. Hsiao HB, Hsieh CC, Wu JB, Lin H, Lin WC. Kinsenoside inhibits the inflammatory mediator release in a type-II collagen induced arthritis mouse model by regulating the T cells responses. BMC Complement Altern Med. 2016 Feb 25;16:80. doi: 10.1186/s12906-016-1054-8. PMID: 26916550; PMCID: PMC4766613.

1: Hsiao HB, Lin H, Wu JB, Lin WC. Kinsenoside prevents ovariectomy-induced bone loss and suppresses osteoclastogenesis by regulating classical NF-κB pathways. Osteoporos Int. 2013 May;24(5):1663-76. doi: 10.1007/s00198-012-2199-z. Epub 2012 Nov 10. PubMed PMID: 23143538; PubMed Central PMCID: PMC3627854. 2: Cheng KT, Wang YS, Chou HC, Chang CC, Lee CK, Juan SH. Kinsenoside-mediated lipolysis through an AMPK-dependent pathway in C3H10T1/2 adipocytes: Roles of AMPK and PPARα in the lipolytic effect of kinsenoside. Phytomedicine. 2015 Jun 1;22(6):641-7. doi: 10.1016/j.phymed.2015.04.001. Epub 2015 Apr 28. PubMed PMID: 26055129. 3: Hsiao HB, Hsieh CC, Wu JB, Lin H, Lin WC. Kinsenoside inhibits the inflammatory mediator release in a type-II collagen induced arthritis mouse model by regulating the T cells responses. BMC Complement Altern Med. 2016 Feb 25;16:80. doi: 10.1186/s12906-016-1054-8. PubMed PMID: 26916550; PubMed Central PMCID: PMC4766613. 4: Liu Q, Qiao AM, Yi LT, Liu ZL, Sheng SM. Protection of kinsenoside against AGEs-induced endothelial dysfunction in human umbilical vein endothelial cells. Life Sci. 2016 Oct 1;162:102-7. doi: 10.1016/j.lfs.2016.08.022. Epub 2016 Aug 25. PubMed PMID: 27567684. 5: Zhang Y, Xia Y, Lai Y, Tang F, Luo Z, Xue Y, Yao G, Zhang Y, Zhang J. Efficient synthesis of kinsenoside and goodyeroside a by a chemo-enzymatic approach. Molecules. 2014 Oct 22;19(10):16950-8. doi: 10.3390/molecules191016950. PubMed PMID: 25340300. 6: Rehman SU, Choi MS, Kim IS, Luo Z, Xue Y, Yao G, Zhang Y, Yoo HH. In Vitro Assessment of CYP-Mediated Drug Interactions for Kinsenoside, an Antihyperlipidemic Candidate. Molecules. 2016 Jun 18;21(6). pii: E800. doi: 10.3390/molecules21060800. PubMed PMID: 27322236. 7: Liu ZL, Liu Q, Xiao B, Zhou J, Zhang JG, Li Y. The vascular protective properties of kinsenoside isolated from Anoectochilus roxburghii under high glucose condition. Fitoterapia. 2013 Apr;86:163-70. doi: 10.1016/j.fitote.2013.03.006. Epub 2013 Mar 15. PubMed PMID: 23500382. 8: Hsiao HB, Wu JB, Lin H, Lin WC. Kinsenoside isolated from Anoectochilus formosanus suppresses LPS-stimulated inflammatory reactions in macrophages and endotoxin shock in mice. Shock. 2011 Feb;35(2):184-90. doi: 10.1097/SHK.0b013e3181f0e7a3. PubMed PMID: 20661184. 9: Hsieh WT, Tsai CT, Wu JB, Hsiao HB, Yang LC, Lin WC. Kinsenoside, a high yielding constituent from Anoectochilus formosanus, inhibits carbon tetrachloride induced Kupffer cells mediated liver damage. J Ethnopharmacol. 2011 May 17;135(2):440-9. doi: 10.1016/j.jep.2011.03.040. Epub 2011 Apr 4. PubMed PMID: 21470577. 10: Xiang M, Liu T, Tan W, Ren H, Li H, Liu J, Cao H, Cheng Q, Liu X, Zhu H, Tuo Y, Wang J, Zhang Y. Effects of kinsenoside, a potential immunosuppressive drug for autoimmune hepatitis, on dendritic cells/CD8(+) T cells communication in mice. Hepatology. 2016 Dec;64(6):2135-2150. doi: 10.1002/hep.28825. Epub 2016 Oct 28. PubMed PMID: 27639182. 11: Rehman SU, Kim IS, Choi MS, Luo Z, Yao G, Xue Y, Zhang Y, Yoo HH. Development of a hydrophilic interaction liquid chromatography-tandem mass spectrometric method for the determination of kinsenoside, an antihyperlipidemic candidate, in rat plasma and its application to pharmacokinetic studies. J Pharm Biomed Anal. 2016 Feb 20;120:19-24. doi: 10.1016/j.jpba.2015.12.003. Epub 2015 Dec 4. PubMed PMID: 26686829. 12: Liu Q, Liu ZL, Tian J, Shi W, Liu YQ. The semisynthetic spin-labelled derivatives of 3-hydroxybutanolide as potential oxidative stress inhibitors. Nat Prod Res. 2014;28(14):1037-44. doi: 10.1080/14786419.2014.903477. Epub 2014 Apr 4. PubMed PMID: 24697680. 13: Du X, Sun N, Tamura T, Mohri A, Sugiura M, Yoshizawa T, Irino N, Hayashi J, Shoyama Y. Higher yielding isolation of kinsenoside in Anoectochilus and its antihyperliposis effect. Biol Pharm Bull. 2001 Jan;24(1):65-9. PubMed PMID: 11201248. 14: Zhang X, Huang HH, Chen QH. A novel total synthesis of kinsenoside and goodyeroside A relying on the efficient reaction of the chiral 2(5H)-furanones. J Asian Nat Prod Res. 2005 Oct;7(5):711-21. PubMed PMID: 16176903. 15: Wu JB, Lin WL, Hsieh CC, Ho HY, Tsay HS, Lin WC. The hepatoprotective activity of kinsenoside from Anoectochilus formosanus. Phytother Res. 2007 Jan;21(1):58-61. PubMed PMID: 17078107. 16: Han Q, Bing W, Di Y, Hua L, Shi-He L, Yu-Hua Z, Xiu-Guo H, Yu-Gang W, Qi-Ming F, Shih-Mo Y, Ting-Ting T. Kinsenoside screening with a microfluidic chip attenuates gouty arthritis through inactivating NF-κB signaling in macrophages and protecting endothelial cells. Cell Death Dis. 2016 Sep 1;7(9):e2350. doi: 10.1038/cddis.2016.255. PubMed PMID: 27584788; PubMed Central PMCID: PMC5059859. 17: Zhang Y, Cai J, Ruan H, Pi H, Wu J. Antihyperglycemic activity of kinsenoside, a high yielding constituent from Anoectochilus roxburghii in streptozotocin diabetic rats. J Ethnopharmacol. 2007 Nov 1;114(2):141-5. Epub 2007 Jun 3. PubMed PMID: 17869039. 18: Righi V, Parenti F, Tugnoli V, Schenetti L, Mucci A. Crocus sativus Petals: Waste or Valuable Resource? The Answer of High-Resolution and High-Resolution Magic Angle Spinning Nuclear Magnetic Resonance. J Agric Food Chem. 2015 Sep 30;63(38):8439-44. doi: 10.1021/acs.jafc.5b03284. Epub 2015 Sep 22. PubMed PMID: 26367873. 19: Du XM, Irino N, Furusho N, Hayashi J, Shoyama Y. Pharmacologically active compounds in the Anoectochilus and Goodyera species. J Nat Med. 2008 Apr;62(2):132-48. doi: 10.1007/s11418-007-0169-0. Epub 2008 Jan 18. Review. PubMed PMID: 18404313. 20: Zhang FS, Lv YL, Zhao Y, Guo SX. Promoting role of an endophyte on the growth and contents of kinsenosides and flavonoids of Anoectochilus formosanus Hayata, a rare and threatened medicinal Orchidaceae plant. J Zhejiang Univ Sci B. 2013 Sep;14(9):785-92. doi: 10.1631/jzus.B1300056. PubMed PMID: 24009198; PubMed Central PMCID: PMC3773549.