Hecogenin

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. It has antioxidant, anti-inflammatory, antiproliferative, and neuroprotective properties. Hecogenin (10 µM) decreases superoxide anion formation induced by N-Formyl-Met-Leu-Phe (fMLP, Cay-21495) in rat neutrophils by 23.6%. It also inhibits myeloperoxidase (MPO) release from human neutrophils activated by phorbol 12-myristate 13-acetate (PMA, Cay-10008014) when used at a concentration of 1 µg/ml. 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). It decreases the number of glutamate-induced TUNEL-positive primary rat spinal motor neurons by 11% when used at a concentration of 1 µM. In vivo, hecogenin (15 mg/kg) decreases the mucosal lesion area of ethanol-induced gastric ulceration in mice. 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.Formal Name: (3beta,5alpha,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: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 30 mg/ml, Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml. lambdamax: 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.