A steroid sapogenin with diverse biological activities
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Hecogenin

Item No. 21372

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,25R)-3-hydroxy-spirostan-12-one
CAS Number
467-55-0
Synonyms
  • (+)-Hecogenin
  • NSC 115921
Molecular Formula
C27H42O4
Formula Weight
430.6
Purity
≥80%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
λmax
238 nm
SMILES
O=C1[C@@]2(C)[C@](C[C@@]3([H])[C@]2([H])[C@H](C)[C@]4(OC[C@H](C)CC4)O3)([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])C1
InChi Code
InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1
InChi Key
QOLRLLFJMZLYQJ-LOBDNJQFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $49

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    1 g

    $213

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    Product Description

    Hecogenin is a natural steroid sapogenin with diverse biological activities that was originally isolated from A. sisalana and has been used in the synthesis of steroids.1 It has antioxidant, anti-inflammatory, antiproliferative, and neuroprotective properties.2,3,4,5 Hecogenin (10 μM) decreases superoxide anion formation induced by N-Formyl-Met-Leu-Phe (fMLP; Item No. 21495) in rat neutrophils by 23.6%.2 It also inhibits myeloperoxidase (MPO) release from human neutrophils activated by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) when used at a concentration of 1 μg/ml.3 Hecogenin inhibits proliferation of the breast cancer cell lines MDA-MB-231, MDA-MB-468, MCF-10A, MCF-7, T47D, BT474, and SK-BR-3 (IC50s = 28.7-38.2 μM).4 It decreases the number of glutamate-induced TUNEL-positive primary rat spinal motor neurons by 11% when used at a concentration of 1 μM.5 In vivo, hecogenin (15 mg/kg) decreases the mucosal lesion area of ethanol-induced gastric ulceration in mice.3 It also decreases tumor volume in an MDA-MB-231 human breast cancer mouse xenograft model when administered at a dose of 10 mg/kg three times per week.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cripps, A.L., and Blunden, G. A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalana. Steroids 31(5), 661-669 (1978).

    2. Tsai, P.L., Wang, J.P., Chang, C.W., et al. Constituents and bioactive principles of Polygonum chinensis. Phytochemistry 49(6), 1663-1666 (1998).

    3. Santos Cerqueira, G., dos Santos e Silva, G., Rios Vasconcelos, E., et al. Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in mice. Eur. J. Pharmacol. 683(1-3), 260-269 (2012).

    4. Elsayed, H.E., Ebrahim, H.Y., Haggag, E.G., et al. Rationally designed hecogenin thiosemicarbazone analogs as novel MEK inhibitors for the control of breast malignancies. Bioorg. Med. Chem. 25(24), 6297-6312 (2017).

    5. Vincent, A.M., Backus, C., Taubman, A.A., et al. Identification of candidate drugs for the treatment of ALS. Amyotroph. Lateral Scler. Other Motor Neuron Disord. 6(1), 29-36 (2005).