Hellebrigenin

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

MedKoo CAT#: 584295

CAS#: 465-90-7

Description: Hellebrigenin triggers DNA damage, mitochondria collapse, cell cycle arrest and apoptosis which may indicate efficacy against hepatocellular carcinomas.


Chemical Structure

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Hellebrigenin
CAS# 465-90-7

Theoretical Analysis

MedKoo Cat#: 584295
Name: Hellebrigenin
CAS#: 465-90-7
Chemical Formula: C24H32O6
Exact Mass: 416.2199
Molecular Weight: 416.514
Elemental Analysis: C, 69.21; H, 7.74; O, 23.05

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Hellebrigenin

IUPAC/Chemical Name: 5-beta-Bufa-20,22-dienolide, 3-beta,5,14-trihydroxy-19-oxo-

InChi Key: TVKPTWJPKVSGJB-XHCIOXAKSA-N

InChi Code: InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1

SMILES Code: O=C(C=C1)OC=C1[C@H]2CC[C@]3(O)[C@]4([H])CC[C@]5(O)C[C@@H](O)CC[C@]5(C=O)[C@@]4([H])CC[C@]23C

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 416.514 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: Yu T, Tian HY, Yuan XF, Hu SZ, Jiang RW. 14,15-Didehydro-hellebrigenin. Acta Crystallogr Sect E Struct Rep Online. 2012 Jun 1;68(Pt 6):o1614-5. doi: 10.1107/S1600536812018570. Epub 2012 May 5. PubMed PMID: 22719419; PubMed Central PMCID: PMC3379221.

2: Moreno Y Banuls L, Urban E, Gelbcke M, Dufrasne F, Kopp B, Kiss R, Zehl M. Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells. J Nat Prod. 2013 Jun 28;76(6):1078-84. doi: 10.1021/np400034d. Epub 2013 May 24. PubMed PMID: 23706005.

3: Yuan XF, Tian HY, Li JH, Yu T, Jiang RW. Secohellebrigeninamide. Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o682. doi: 10.1107/S160053681200520X. Epub 2012 Feb 10. PubMed PMID: 22412577; PubMed Central PMCID: PMC3295466.

4: Zhang PW, Jiang RW, Ye WC, Tian HY. [Bufadienolides from venom of Bufo bufo gargarizans]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(5):841-5. Chinese. PubMed PMID: 25204176.

5: Moreno Y Banuls L, Katz A, Miklos W, Cimmino A, Tal DM, Ainbinder E, Zehl M, Urban E, Evidente A, Kopp B, Berger W, Feron O, Karlish S, Kiss R. Hellebrin and its aglycone form hellebrigenin display similar in vitro growth inhibitory effects in cancer cells and binding profiles to the alpha subunits of the Na+/K+-ATPase. Mol Cancer. 2013 Apr 26;12:33. doi: 10.1186/1476-4598-12-33. PubMed PMID: 23621895; PubMed Central PMCID: PMC3722118.

6: Tempone AG, Pimenta DC, Lebrun I, Sartorelli P, Taniwaki NN, de Andrade HF Jr, Antoniazzi MM, Jared C. Antileishmanial and antitrypanosomal activity of bufadienolides isolated from the toad Rhinella jimi parotoid macrogland secretion. Toxicon. 2008 Jul;52(1):13-21. doi: 10.1016/j.toxicon.2008.05.008. Epub 2008 Jul 15. PubMed PMID: 18588907.

7: Herzig S, Lüllmann H, Mohr K, Seemann B. Acrihellin, a cardioactive steroid escaping from the organ-bath. Naunyn Schmiedebergs Arch Pharmacol. 1987 Mar;335(3):326-30. PubMed PMID: 3587374.

8: Deng LJ, Hu LP, Peng QL, Yang XL, Bai LL, Yiu A, Li Y, Tian HY, Ye WC, Zhang DM. Hellebrigenin induces cell cycle arrest and apoptosis in human hepatocellular carcinoma HepG2 cells through inhibition of Akt. Chem Biol Interact. 2014 Aug 5;219:184-94. doi: 10.1016/j.cbi.2014.06.003. Epub 2014 Jun 20. PubMed PMID: 24954031.

9: Cunha-Filho GA, Resck IS, Cavalcanti BC, Pessoa CO, Moraes MO, Ferreira JR, Rodrigues FA, Dos Santos ML. Cytotoxic profile of natural and some modified bufadienolides from toad Rhinella schneideri parotoid gland secretion. Toxicon. 2010 Sep 1;56(3):339-48. doi: 10.1016/j.toxicon.2010.03.021. Epub 2010 Apr 8. PubMed PMID: 20381513.

10: Engel J, Isaac O, Posselt K, Thiemer K, Uthemann H. Synthesis of orally active cardiosteroid derivatives. Arzneimittelforschung. 1983;33(9):1215-8. PubMed PMID: 6685501.

11: Yang J, Zhang YH, Miao F, Zhou L, Sun W. Two new bufadienolides from the rhizomes of Helleborus thibetanus Franch. Fitoterapia. 2010 Sep;81(6):636-9. doi: 10.1016/j.fitote.2010.03.009. Epub 2010 Mar 15. PubMed PMID: 20230875.

12: Tschesche R, Scholten H, Peters M. [Biogenesis of steroid derivatives in the plant kingdom. 14. Hydroxylation in the 5-position during the biogenesis of hellebrigenin]. Z Naturforsch B. 1969 Nov;24(11):1492. German. PubMed PMID: 4391385.

13: Qiao L, Huang YF, Cao JQ, Zhou YZ, Qi XL, Pei YH. One new bufadienolide from Chinese drug "Chan'Su". J Asian Nat Prod Res. 2008 Mar-Apr;10(3-4):233-7. doi: 10.1080/10286020701604839. PubMed PMID: 18335338.

14: Yoda A, Hokin LE. Studies on the characterization of the sodium-potassium transport adenosine triphosphatase. 8. Effects of ligands on fluorescence due to interaction of the enzyme with a fluorescent derivative of hellebrigenin. Mol Pharmacol. 1972 Jan;8(1):30-40. PubMed PMID: 4258647.

15: Kupchan SM, Hemingway RJ, Hemingway JC. Tumor inhibitors. XLIV. The isolation and characterization of hellebrigenin 3-acetate and hellebrigenin 3,5-diacetate, bufadienolide tumor inhibitors from Bersama abyssinica. J Org Chem. 1969 Dec;34(12):3894-8. PubMed PMID: 5357531.

16: Stroman F, Jakovlev V, Metzenauer P, Roth E, Thiemer K. [The pharmacology of a new cardiosteroid, a partially synthetic derivative of the aglycone hellebrigenin (acrihellin)]. Arzneimittelforschung. 1984;34(7):769-79. German. PubMed PMID: 6541912.

17: Ruoho AE, Hokin LE, Hemingway RJ, Kupchan SM. Hellebrigenin 3-haloacetates: potent site-directed alkylators of transport adenosinetriphosphatase. Science. 1968 Mar 22;159(3821):1354-5. PubMed PMID: 4230690.

18: Bassarello C, Muzashvili T, Skhirtladze A, Kemertelidze E, Pizza C, Piacente S. Steroidal glycosides from the underground parts of Helleborus caucasicus. Phytochemistry. 2008 Mar;69(5):1227-33. doi: 10.1016/j.phytochem.2007.11.007. Epub 2008 Jan 28. PubMed PMID: 18226823.

19: Han L, Wang H, Si N, Ren W, Gao B, Li Y, Yang J, Xu M, Zhao H, Bian B. Metabolites profiling of 10 bufadienolides in human liver microsomes and their cytotoxicity variation in HepG2 cell. Anal Bioanal Chem. 2016 Apr;408(10):2485-95. doi: 10.1007/s00216-016-9345-y. Epub 2016 Feb 11. PubMed PMID: 26869342.

20: Schmeda-Hirschmann G, Quispe C, Arana GV, Theoduloz C, Urra FA, Cárdenas C. Antiproliferative activity and chemical composition of the venom from the Amazonian toad Rhinella marina (Anura: Bufonidae). Toxicon. 2016 Oct;121:119-129. doi: 10.1016/j.toxicon.2016.09.004. Epub 2016 Sep 8. PubMed PMID: 27616454.