Isosteviol

Isosteviol is a diterpenoid that has been found in P. tetraspermum and has diverse biological activities. It is also a hydrolysis product of the natural non-caloric sweetener stevioside (Cay-11902). Isosteviol scavenges hydroxyl and superoxide radicals in cell-free assays (IC50s = 76.92 and 91.7 µg/ml, respectively) and inhibits DNA polymerase alpha, beta, and lambda, as well as topoisomerase II (IC50s = 64, 177, 103, and 190 µM, respectively). It is active against various Gram-positive and Gram-negative bacteria, including several strains of methicillin-resistant S. aureus (MRSA, MICs = 8-250 µg/ml), and fungi, including C. albicans and T. mentagrophytes (MICs = 62.5-500 µg/ml). Isosteviol inhibits the proliferation of MOLT-4 leukemia cells in a concentration-dependent manner. It induces relaxation of isolated rat aortic strips precontracted with vasopressin, an effect that can be reversed by the potassium channel inhibitors glibenclamide (glyburide, Cay-15009) or apamin (Cay-17082) but not charybdotoxin (Cay-24115). Isosteviol (5 and 10 mg/kg) reduces plasma glucose levels in the intravenous glucose tolerance test in Zucker diabetic rats. It has been used in the synthesis of isosteviol glycosides with anticancer activity.Formal Name: (4alpha,8beta,13beta)-13-methyl-16-oxo-17-norkauran-18-oic acid. CAS Number: 27975-19-5. Synonyms: (-)-Isosteviol, Ketoisostevic acid, NSC 231875, iso-Steviol. Molecular Formula: C20H30O3. Formula Weight: 318.5. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Acetonitrile: Soluble, Chloroform: Soluble. SMILES: C[C@]1(CCC2)[C@@](CC3)([H])[C@@](CC[C@]1([H])[C@]2(C)C(O)=O)(CC4=O)C[C@]34C. InChi Code: InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1. InChi Key: KFVUFODCZDRVSS-XGBBNYNSSA-N. Origin: Plant/Stevia rebaudiana.