Hederagenin
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MedKoo CAT#: 329990

CAS#: 465-99-6

Description: Hederagenin, a triterpenoid saponin, is used to study the properties of triterpenoid saponins as biopesticides that prevent fungal growth, bacterial growth, and viral plant diseases. Hederagenin may be used as a reference in assays to detect it in biological fluids. Hederagenin Supplementation Alleviates the Pro-Inflammatory and Apoptotic Response to Alcohol in Rats.


Chemical Structure

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Hederagenin
CAS# 465-99-6

Theoretical Analysis

MedKoo Cat#: 329990
Name: Hederagenin
CAS#: 465-99-6
Chemical Formula: C30H48O4
Exact Mass: 472.3553
Molecular Weight: 472.71
Elemental Analysis: C, 76.23; H, 10.24; O, 13.54

Price and Availability

Size Price Availability Quantity
50.0mg USD 250.0 2 Weeks
200.0mg USD 650.0 2 Weeks
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Synonym: Hederagenin; Astrantiagenin E; Caulosapogenin; Hederagenol; NSC 24954.

IUPAC/Chemical Name: (4aS,6aR,6bS,8aR,9R,10S,12aS,12bR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

InChi Key: PGOYMURMZNDHNS-HKIRUCENSA-N

InChi Code: InChI=1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26+,27-,28-,29-,30-/m0/s1

SMILES Code: C1=2[C@@]([C@@]3([C@@H]([C@@]4(CC[C@@H]([C@]([C@@H]4CC3)(CO)C)O)C)CC2)C)(CC[C@@]2(C(=O)O)CCC(C[C@@H]12)(C)C)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

Preparing Stock Solutions

The following data is based on the product molecular weight 472.71 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: Han JY, Chun JH, O SA, Park SB, Hwang HS, Lee H, Choi YE. Transcriptomic analysis of Kalopanax septemlobus and characterization of KsBAS, CYP716A94, and CYP72A397 genes involved in hederagenin saponin biosynthesis. Plant Cell Physiol. 2017 Nov 24. doi: 10.1093/pcp/pcx188. [Epub ahead of print] PubMed PMID: 29186583.

2: Liu XX, Yang YT, Wang X, Wang KY, Liu JQ, Lei L, Luo XM, Zhai R, Fu FH, Wang HB, Bi Y. Design, synthesis and biological evaluation of novel α-hederagenin derivatives with anticancer activity. Eur J Med Chem. 2017 Dec 1;141:427-439. doi: 10.1016/j.ejmech.2017.09.016. Epub 2017 Oct 7. PubMed PMID: 29040953.

3: Rodríguez-Hernández D, Barbosa LCA, Demuner AJ, Nain-Perez A, Ferreira SR, Fujiwara RT, de Almeida RM, Heller L, Csuk R. Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives. Eur J Med Chem. 2017 Nov 10;140:624-635. doi: 10.1016/j.ejmech.2017.09.045. Epub 2017 Sep 22. PubMed PMID: 29024910.

4: Kim GJ, Song DH, Yoo HS, Chung KH, Lee KJ, An JH. Hederagenin Supplementation Alleviates the Pro-Inflammatory and Apoptotic Response to Alcohol in Rats. Nutrients. 2017 Jan 6;9(1). pii: E41. doi: 10.3390/nu9010041. PubMed PMID: 28067819; PubMed Central PMCID: PMC5295085.

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: Liu Z, Lu YH, Feng X, Zou YX, Diao Z, Chu ZY. Microbial transformation of hederagenin by Cunninghamella echinulate, Mucor subtilissimus, and Pseudomonas oleovorans. J Asian Nat Prod Res. 2017 Jul;19(7):712-718. doi: 10.1080/10286020.2016.1232252. Epub 2016 Sep 26. PubMed PMID: 27666872.

7: Rodríguez-Hernández D, Barbosa LCA, Demuner AJ, de Almeida RM, Fujiwara RT, Ferreira SR. Highly potent anti-leishmanial derivatives of hederagenin, a triperpenoid from Sapindus saponaria L. Eur J Med Chem. 2016 Nov 29;124:153-159. doi: 10.1016/j.ejmech.2016.08.030. Epub 2016 Aug 17. PubMed PMID: 27569196.

8: Zhang H, Jing F, Zhang Z. Development and validation of a quantification method for oleanolic acid and hederagenin in rat plasma: application to the pharmacokinetic study. Biomed Chromatogr. 2017 Feb;31(2). doi: 10.1002/bmc.3801. Epub 2016 Aug 21. PubMed PMID: 27465077.

9: Greatrex BW, Daines AM, Hook S, Lenz DH, McBurney W, Rades T, Rendle PM. Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives. ChemistryOpen. 2015 Sep 30;4(6):740-55. doi: 10.1002/open.201500149. eCollection 2015 Dec. PubMed PMID: 27308200; PubMed Central PMCID: PMC4906508.

10: Rodríguez-Hernández D, Demuner AJ, Barbosa LC, Heller L, Csuk R. Novel hederagenin-triazolyl derivatives as potential anti-cancer agents. Eur J Med Chem. 2016 Jun 10;115:257-67. doi: 10.1016/j.ejmech.2016.03.018. Epub 2016 Mar 9. PubMed PMID: 27017553.

11: Rezgui A, Mitaine-Offer AC, Miyamoto T, Tanaka C, Delemasure S, Dutartre P, Lacaille-Dubois MA. Oleanolic acid and hederagenin glycosides from Weigela stelzneri. Phytochemistry. 2016 Mar;123:40-7. doi: 10.1016/j.phytochem.2015.12.016. Epub 2016 Jan 19. PubMed PMID: 26805449.

12: Lu SH, Guan JH, Huang YL, Pan YW, Yang W, Lan H, Huang S, Hu J, Zhao GP. Experimental Study of Antiatherosclerosis Effects with Hederagenin in Rats. Evid Based Complement Alternat Med. 2015;2015:456354. doi: 10.1155/2015/456354. Epub 2015 Oct 19. PubMed PMID: 26557859; PubMed Central PMCID: PMC4629025.

13: Lee CW, Park SM, Zhao R, Lee C, Chun W, Son Y, Kim SH, Jung JY, Jegal KH, Cho IJ, Ku SK, Kim YW, Ju SA, Kim SC, An WG. Hederagenin, a major component of Clematis mandshurica Ruprecht root, attenuates inflammatory responses in RAW 264.7 cells and in mice. Int Immunopharmacol. 2015 Dec;29(2):528-537. doi: 10.1016/j.intimp.2015.10.002. Epub 2015 Oct 23. PubMed PMID: 26481049.

14: Rodríguez-Hernández D, Demuner AJ, Barbosa LC, Csuk R, Heller L. Hederagenin as a triterpene template for the development of new antitumor compounds. Eur J Med Chem. 2015 Nov 13;105:57-62. doi: 10.1016/j.ejmech.2015.10.006. Epub 2015 Oct 9. PubMed PMID: 26476750.

15: Gao Y, He C, Bi W, Wu G, Altman E. Bioassay Guided Fractionation Identified Hederagenin as a Major Cytotoxic Agent from Cyclocarya paliurus Leaves. Planta Med. 2016 Jan;82(1-2):171-9. doi: 10.1055/s-0035-1557900. Epub 2015 Sep 21. PubMed PMID: 26393939.

16: Liang BF, Huang F, Wang HT, Wang GH, Yuan X, Zhang MZ, Guo HB, Cheng YF, Xu JP. Involvement of norepinephrine and serotonin system in antidepressant-like effects of hederagenin in the rat model of unpredictable chronic mild stress-induced depression. Pharm Biol. 2015 Mar;53(3):368-77. doi: 10.3109/13880209.2014.922586. Epub 2014 Dec 4. PubMed PMID: 25471378.

17: Liu BX, Zhou JY, Li Y, Zou X, Wu J, Gu JF, Yuan JR, Zhao BJ, Feng L, Jia XB, Wang RP. Hederagenin from the leaves of ivy (Hedera helix L.) induces apoptosis in human LoVo colon cells through the mitochondrial pathway. BMC Complement Altern Med. 2014 Oct 24;14:412. doi: 10.1186/1472-6882-14-412. PubMed PMID: 25342273; PubMed Central PMCID: PMC4216349.

18: Zhang R, Zhu H, Ding L, Yang Z. Determination of asperosaponin VI and its active metabolite hederagenin in rat tissues by LC-MS/MS: application to a tissue distribution study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 May 15;959:22-6. doi: 10.1016/j.jchromb.2014.03.030. Epub 2014 Apr 2. PubMed PMID: 24747520.

19: Lorent J, Lins L, Domenech Ò, Quetin-Leclercq J, Brasseur R, Mingeot-Leclercq MP. Domain formation and permeabilization induced by the saponin α-hederin and its aglycone hederagenin in a cholesterol-containing bilayer. Langmuir. 2014 Apr 29;30(16):4556-69. doi: 10.1021/la4049902. Epub 2014 Apr 14. PubMed PMID: 24690040.

20: Liu EW, Wang JL, Han LF, Chang YX, Wang T, Huo Y, Wang L, Gao XM. Pharmacokinetics study of asperosaponin VI and its metabolites cauloside A, HN saponin F and hederagenin. J Nat Med. 2014 Jul;68(3):488-97. doi: 10.1007/s11418-014-0821-4. Epub 2014 Mar 11. PubMed PMID: 24615060.