alpha-Hederin
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MedKoo CAT#: 592366

CAS#: 27013-91-8

Description: alpha-Hederin is derived from beta-amyrin. It induces apoptosis in hepatocellular carcinoma cells.


Chemical Structure

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alpha-Hederin
CAS# 27013-91-8

Theoretical Analysis

MedKoo Cat#: 592366
Name: alpha-Hederin
CAS#: 27013-91-8
Chemical Formula: C41H66O12
Exact Mass: 750.4554
Molecular Weight: 750.97
Elemental Analysis: C, 65.58; H, 8.86; O, 25.57

Price and Availability

Size Price Availability Quantity
1.0mg USD 210.0 2 Weeks
5.0mg USD 425.0 2 Weeks
10.0mg USD 685.0 2 Weeks
25.0mg USD 1200.0 2 Weeks
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Synonym: alpha-Hederin

IUPAC/Chemical Name: (4alpha)-3beta-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid

InChi Key: KEOITPILCOILGM-LLJOFIFVSA-N

InChi Code: InChI=1S/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23-,24-,25+,26+,27-,28-,29-,30+,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1

SMILES Code: C[C@@]1(CO)[C@@H](O[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)CC[C@]4(C)[C@@]5([H])CC=C6[C@]7([H])CC(C)(C)CC[C@@](C(O)=O)7CC[C@](C)6[C@@](C)5CC[C@@]14[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: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 750.97 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.

Recalculate based on batch purity %
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

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1: Li J, Wu DD, Zhang JX, Wang J, Ma JJ, Hu X, Dong WG. Mitochondrial pathway mediated by reactive oxygen species involvement in α-hederin-induced apoptosis in hepatocellular carcinoma cells. World J Gastroenterol. 2018 May 7;24(17):1901-1910. doi: 10.3748/wjg.v24.i17.1901. PubMed PMID: 29740205; PubMed Central PMCID: PMC5937207.

2: Tabassum H, Ahmad A, Ahmad IZ. Nigella sativa L. and Its Bioactive Constituents as Hepatoprotectant: A Review. Curr Pharm Biotechnol. 2018;19(1):43-67. doi: 10.2174/1389201019666180427110007. PubMed PMID: 29701149.

3: Sun D, Shen W, Zhang F, Fan H, Xu C, Li L, Tan J, Miao Y, Zhang H, Yang Y, Cheng H. α-Hederin inhibits interleukin 6-induced epithelial-to-mesenchymal transition associated with disruption of JAK2/STAT3 signaling in colon cancer cells. Biomed Pharmacother. 2018 May;101:107-114. doi: 10.1016/j.biopha.2018.02.062. Epub 2018 Feb 23. PubMed PMID: 29477470.

4: Xu L, Cheng G, Lu Y, Wang S. An active molecule from Pulsatilla chinensis, Pulsatilla saponin A, induces apoptosis and inhibits tumor growth of human colon cancer cells without or with 5-FU. Oncol Lett. 2017 May;13(5):3799-3802. doi: 10.3892/ol.2017.5884. Epub 2017 Mar 21. PubMed PMID: 28529594; PubMed Central PMCID: PMC5431750.

5: Wu AG, Zeng W, Wong VK, Zhu YZ, Lo AC, Liu L, Law BY. Hederagenin and α-hederin promote degradation of proteins in neurodegenerative diseases and improve motor deficits in MPTP-mice. Pharmacol Res. 2017 Jan;115:25-44. doi: 10.1016/j.phrs.2016.11.002. Epub 2016 Nov 9. PubMed PMID: 27838509.

6: Lorent JH, Léonard C, Abouzi M, Akabi F, Quetin-Leclercq J, Mingeot-Leclercq MP. α-Hederin Induces Apoptosis, Membrane Permeabilization and Morphologic Changes in Two Cancer Cell Lines Through a Cholesterol-Dependent Mechanism. Planta Med. 2016 Dec;82(18):1532-1539. Epub 2016 Aug 30. PubMed PMID: 27574896.

6: Ebrahimi H, Fallahi M, Khamaneh AM, Ebrahimi Saadatlou MA, Saadat S, Keyhanmanesh R. Effect of α-Hederin on IL-2 and IL-17 mRNA and miRNA-133a Levels in Lungs of Ovalbumin-Sensitized Male Rats. Drug Dev Res. 2016 Mar;77(2):87-93. doi: 10.1002/ddr.21292. Epub 2016 Feb 10. PubMed PMID: 26865286.

7: Zhu R, Zhang CG, Liu Y, Yuan ZQ, Chen WL, Yang SD, Li JZ, Zhu WJ, Zhou XF, You BG, Zhang XN. CD147 monoclonal antibody mediated by chitosan nanoparticles loaded with α-hederin enhances antineoplastic activity and cellular uptake in liver cancer cells. Sci Rep. 2015 Dec 7;5:17904. doi: 10.1038/srep17904. PubMed PMID: 26639052; PubMed Central PMCID: PMC4671144.

8: Keyhanmanesh R, Saadat S, Mohammadi M, Shahbazfar AA, Fallahi M. The Protective Effect of α-Hederin, the Active Constituent of Nigella sativa, on Lung Inflammation and Blood Cytokines in Ovalbumin Sensitized Guinea Pigs. Phytother Res. 2015 Nov;29(11):1761-7. doi: 10.1002/ptr.5429. Epub 2015 Aug 21. PubMed PMID: 26292851.