Harpagide | CAS#6926-08-5 | Neuroprotective agent

MedKoo Cat#: 464284 | Name: Harpagide

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Description:

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

Harpagide is a neuroprotective agent. It can protect acute cerebral ischemia in mice. Its therapeutical effects are approached to protecting the activity of brain mitochondria and decreasing protein expression level of caspase-3. Harpagide also has a potential for prevention of bone loss in ovariectomized (OVX) mice by regulating the stimulation of osteoblast differentiation and the suppression of osteoclast formation. Harpagide may have anti-inflammatory efficacy.

Chemical Structure

Harpagide

CAS#6926-08-5

Theoretical Analysis

MedKoo Cat#: 464284

Name: Harpagide

CAS#: 6926-08-5

Chemical Formula: C15H24O10

Exact Mass: 364.1369

Molecular Weight: 364.35

Elemental Analysis: C, 49.45; H, 6.64; O, 43.91

Price and Availability

Size	Price	Availability
10mg	USD 250.00	2 Weeks
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

No Data

Synonym

Harpagide; myoporoside

IUPAC/Chemical Name

(1S,4aS,5R,7S,7aR)-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5,6,7,7a-tetrahydrocyclopenta[c]pyran-4a,5,7(1H)-triol

InChi Key

XUWSHXDEJOOIND-YYDKPPGPSA-N

InChi Code

InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11-,12+,13+,14+,15-/m1/s1

SMILES Code

C[C@@]1(C[C@H]([C@@]2(C=CO[C@H]([C@H]12)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)O)O)O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 364.35 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: Erukainure OL, Atolani O, Muhammad A, Katsayal SB, Ebhuoma OO, Ibeji CU, Mesaik MA. Targeting the initiation and termination codons of SARS-CoV-2 spike protein as possible therapy against COVID-19: the role of novel harpagide 5-O-β- D-glucopyranoside from Clerodendrum volubile P Beauv. (Labiatae). J Biomol Struct Dyn. 2020 Nov 3:1-14. doi: 10.1080/07391102.2020.1840439. Epub ahead of print. PMID: 33140706; PMCID: PMC7651195. 2: Frezza C, de Vita D, Toniolo C, Ventrone A, Tomassini L, Foddai S, Nicoletti M, Guiso M, Bianco A, Serafini M. Harpagide: Occurrence in plants and biological activities - A review. Fitoterapia. 2020 Nov;147:104764. doi: 10.1016/j.fitote.2020.104764. Epub 2020 Oct 26. PMID: 33122133. 3: Gao D, Le Ba V, Rustam R, Cho CW, Yang SY, Su XD, Kim YH, Kang JS. Isolation of bioactive components with soluble epoxide hydrolase inhibitory activity from Stachys sieboldii MiQ. by ultrasonic-assisted extraction optimized using response surface methodology. Prep Biochem Biotechnol. 2020 Sep 17:1-10. doi: 10.1080/10826068.2020.1821217. Epub ahead of print. PMID: 32940554. 4: Yu X, Jiao Q, Jiang Y, Guo S, Zhang W, Liu B. Study on the Plasma Protein Binding Rate and Compatibility Regularity of the Constituents Migrating to Blood of Simiao Yong'an Decoction. Curr Drug Metab. 2020;21(12):979-993. doi: 10.2174/1567201817666200731170731. PMID: 32735517. 5: Xie G, Jiang Y, Huang M, Zhu Y, Wu G, Qin M. Dynamic analysis of secondary metabolites in various parts of Scrophularia ningpoensis by liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2020 Jul 15;186:113307. doi: 10.1016/j.jpba.2020.113307. Epub 2020 Apr 18. PMID: 32375107. 6: Wang K, Lou Y, Xu H, Zhong X, Huang Z. Harpagide from Scrophularia protects rat cortical neurons from oxygen-glucose deprivation and reoxygenation-induced injury by decreasing endoplasmic reticulum stress. J Ethnopharmacol. 2020 May 10;253:112614. doi: 10.1016/j.jep.2020.112614. Epub 2020 Jan 31. PMID: 32007630. 7: Shen ZY, Zhu B, Zhang QL, Qin LP. [Isolation and identification of endophytic fungi producing harpagoside and harpagide from Scrophularia ningpoensis]. Zhongguo Zhong Yao Za Zhi. 2019 May;44(10):2046-2050. Chinese. doi: 10.19540/j.cnki.cjcmm.20190301.008. PMID: 31355559. 8: Shi J, Shen L, Deng Z, Wang SH, Cui WJ, Zhang J, Liu A. [Grades evaluation of Scrophulariae Radix pieces based on quality constant]. Zhongguo Zhong Yao Za Zhi. 2019 May;44(9):1744-1749. Chinese. doi: 10.19540/j.cnki.cjcmm.20190326.303. PMID: 31342696. 9: Menghini L, Recinella L, Leone S, Chiavaroli A, Cicala C, Brunetti L, Vladimir-Knežević S, Orlando G, Ferrante C. Devil's claw (Harpagophytum procumbens) and chronic inflammatory diseases: A concise overview on preclinical and clinical data. Phytother Res. 2019 Sep;33(9):2152-2162. doi: 10.1002/ptr.6395. Epub 2019 Jul 4. PMID: 31273865. 10: Avato P, Argentieri MP. Quality Assessment of Commercial Spagyric Tinctures of Harpagophytum procumbens and Their Antioxidant Properties. Molecules. 2019 Jun 17;24(12):2251. doi: 10.3390/molecules24122251. PMID: 31212908; PMCID: PMC6630815. 11: Rong Y, Liu W, Zhou Z, Gong F, Bai J, Fan J, Li L, Luo Y, Zhou Z, Cai W. Harpagide inhibits neuronal apoptosis and promotes axonal regeneration after spinal cord injury in rats by activating the Wnt/β-catenin signaling pathway. Brain Res Bull. 2019 May;148:91-99. doi: 10.1016/j.brainresbull.2019.03.014. Epub 2019 Mar 30. PMID: 30940474. 12: Hannemann L, Lucaciu CR, Sharma S, Rattei T, Mayer KFX, Gierl A, Frey M. A promiscuous beta-glucosidase is involved in benzoxazinoid deglycosylation in Lamium galeobdolon. Phytochemistry. 2018 Dec;156:224-233. doi: 10.1016/j.phytochem.2018.10.012. Epub 2018 Oct 15. PMID: 30336442. 13: Skrzypczak-Pietraszek E, Reiss K, Żmudzki P, Pietraszek J. Enhanced accumulation of harpagide and 8-O-acetyl-harpagide in Melittis melissophyllum L. agitated shoot cultures analyzed by UPLC-MS/MS. PLoS One. 2018 Aug 22;13(8):e0202556. doi: 10.1371/journal.pone.0202556. PMID: 30133513; PMCID: PMC6104996. 14: Liu Z, Kuang W, Xu X, Li D, Zhu W, Lan Z, Zhang X. Putative identification of components in Zengye Decoction and their effects on glucose consumption and lipogenesis in insulin-induced insulin-resistant HepG2 cells. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jan 15;1073:145-153. doi: 10.1016/j.jchromb.2017.12.019. Epub 2017 Dec 12. PMID: 29272757. 15: Liu Y, Chi S, Wang W, Su L, Liu B. Simultaneous Determination of Seven Components in Rat Plasma by the UPLC-MS/MS Method and Application of Pharmacokinetic Studies to SimiaoYong'an Decoction. Molecules. 2017 Nov 9;22(11):1937. doi: 10.3390/molecules22111937. PMID: 29120359; PMCID: PMC6150365. 16: Kwon EB, Yang HJ, Kim YS, Li W, Choi JG. 8-O-(E-p-methoxycinnamoyl)harpagide Inhibits Influenza A Virus Infection by Suppressing Intracellular Calcium. Molecules. 2021 Feb 15;26(4):1029. doi: 10.3390/molecules26041029. PMID: 33672072; PMCID: PMC7919648.