Hellebrin

Specifications / Handling

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Product Details
Synonyms	3β-(O4-β-D-Glucopyranosyl-α-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14-β-bufa-20,22-dienolide; NSC93134
Product Type	Chemical
Properties
Formula	C₃₆H₅₂O₁₅
MW	724.8
CAS	13289-18-4
Source/Host Chemicals	Isolated from Helleborus purpurascens.
Purity Chemicals	≥99% (HPLC and UV Absorbance)
Appearance	White to off-white solid.
Solubility	Soluble in water (~4mg/ml).
InChi Key	DCSLTSSPIJWEJN-YRFFWODSSA-N
Smiles	[H]C(=O)[C@]12CC[C@@H](C[C@@]1(O)CCC1C2CC[C@]2(C)[C@H](CC[C@]12O)C1=COC(=O)C=C1)O[C@@H]1OC(C)[C@H](O[C@@H]2OC(CO)[C@@H](O)[C@@H](O)C2O)[C@H](O)C1O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light and moisture. Aqueous solutions should not be stored for longer than one day.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Highly potent Na⁺/K⁺-ATPase inhibitor, blocking the active efflux of Na⁺ and reuptake of K⁺.
Water soluble cardiotonic glycoside from the class of bufadienolides (with 2-pyrone ring).
Inhibits cancer cell growth in vitro. Shown to induce caspase-dependent apoptosis, reducing MDR resistance and the rate of mitochondrial oxidative phosphorylation in cancer cells.
Inotropic by increasing the intracellular Ca²⁺ concentration.
Immunosuppressive and anti-inflammatory agent that inhibits allogeneic T cell activation with much higher potency than cortisol or cyclosporin A.
Anti-seizure activity in pentylenetetrazole (PTZ)-induced epileptical seizures.

Product References

Ueber Hellebrin, ein krystallisiertes Glykosid aus Radix Hellebori nigri: W. Karrer; Helv. Chim. Acta 26, 1353 (1943)
The structure of hellebrin: P. Muhr, et al.; Liebigs Ann. Org. Bioorg. Chem. 2, 443 (1995)
In search of ideal inotropic steroids: recent progress: K.R. Repke, et al.; Prog. Drug Res. 47, 9 (1996)
Exquisitely small amounts of nonglucocorticoid natural steroids suppress the human allogeneic T-cell response: P. Terness, et al.; Transplant Proc. 33, 547 (2001)
The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity: P. Terness, et al.; Int. Immunopharmacol. 1, 119 (2001)
Apoptosis-mediated selective killing of malignant cells by cardiac steroids: maintenance of cytotoxicity and loss of cardiac activity of chemically modified derivatives: D. Daniel, et al.; Int. Immunopharmacol. 3, 1791 (2003)
Anti-cancer natural product library from traditional chinese medicine: V.B. Konkimalla & T. Efferth; Comb. Chem. High Throughput Screen. 11, 7 (2008)
FTIR spectral signature of the effect of cardiotonic steroids with antitumoral properties on a prostate cancer cell line: R. Gasper, et al.; Biochim. Biophys. Acta 1802, 1087 (2010)
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: L. Moreno Y. Banuls, et al.; Mol. Cancer 12, 33 (2013)
Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells: L. Moreno Y. Banuls, et al.; J. Nat. Prod. 76, 1078 (2013)
Natural compounds with important medical potential found in Helleborus sp.: M.C. Maior & C. Dobrota; Cent. Eur. J. Biol. 8, 272 (2013) (Review)
Studies on the constituents of Helleborus purpurascens: analysis and biological activity of the aqueous and organic extracts: M. H. Franz, et al.; Amino Acids 50, 163 (2018)
Antiseizure potential of the ancient Greek medicinal plant Helleborus odorus subsp. cyclophyllus and identification of its main active principles: J. Ethnopharm. 259, 112954 (2020)

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