Name | Isosteviol |
Synonyms | CCRIS 6121 Nsc 231875 NSC 231875 ISOSTEVIOL Ccris 6121 Isosteviol Isosteviol (NSC 231875) 16-oxobeyeran-18-oic acid (4α,8β,13β)-13--Methyl-16-oxo-17-norkauran-18-oic acid 13-beta-kauran-18-oicacid,13-methyl-16-oxo-17-nor-8-bet 17-Nor-8-beta,13-beta-kauran-18-oic acid, 13-methyl-16-oxo- (4-alpha,8-beta,13-beta)-13-methyl-16-oxo-17-norkauran-18-oicacid (4-alpha,8-beta,13-beta)-13-Methyl-16-oxo-17-norkauran-18-oic acid 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4-alpha,8-beta,13-beta)- 17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4-ALPHA,8-BETA,13-BETA)- |
CAS | 27975-19-5 |
InChI | InChI=1/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) |
Molecular Formula | C20H30O3 |
Molar Mass | 318.45 |
Density | 1.15±0.1 g/cm3(Predicted) |
Melting Point | 228.0 to 232.0 °C |
Boling Point | 455.6±38.0 °C(Predicted) |
Flash Point | 243.5°C |
Solubility | DMSO : ≥ 100 mg/mL (314.02 mM) |
Vapor Presure | 1.44E-09mmHg at 25°C |
Appearance | White crystal |
Color | White to Almost white |
pKa | 4.69±0.60(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.551 |
MDL | MFCD28411514 |
Physical and Chemical Properties | White crystals, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Stevia rebaudana Bertoni, also known as Stevia, Sweet Grass. |
In vitro study | Isosteviol ((-)-Isosteviol) dose-dependently relaxed the vasopressin (10 -8 M)-induced vasoconstriction in isolated aortic rings with or without endothelium. However, in the presence of potassium chloride (3×10 -2 M), the vasodilator effect of isosteviol on arterial strips disappeared. Only the inhibitors specific for the ATP-sensitive potassium (KATP) channel or small conductance calcium-activated potassium (SKCa) channel inhibited the vasodilator effect of isosteviol in isolated aortic rings contracted with 10 -8 M vasopressin. The attenuation by isosteviol of the vasopressin- and phenylephrine-induced increase in [Ca 2+ ]i was inhibited by glibenclamide, apamin and 4-aminopyridine but not by charybdotoxin. Furthermore, the inhibitory action of isosteviol on [Ca 2+ ]i was blocked when A7r5 cells co-treated with glibenclamide and apamin in conjunction with 4-aminopyridine were present. Isosteviol (1-100 micromol/l) inhibits angiotensin-II-induced DNA synthesis and endothelin-1 secretion. Measurements of 2'7'-dichlorofluorescin diacetate, a redox-sensitive fluorescent dye, showed an isosteviol-mediated inhibition of intracellular reactive oxygen species generated by the effects of angiotensin II. |
WGK Germany | 3 |
Reference Show more | 1. [IF=3.738] Selma Houchi et al."Investigation of common chemical components and inhibitory effect on GES-type β-lactamase (GES22) in methanolic extracts of Algerian seaweeds."Microb Pathogenesis. 2019 Jan;126:56 |
Plant source: | Stevia rebaudiana |
Biological activity | Isosteviol ((-)-Isosteviol) is a stevioside derivative, which is produced by acid-catalyzed hydrolysis of stevioside. Isosteviol inhibits DNA polymerase and DNA topoisomerase and has antibacterial, anticancer and antituberculosis effects. |
use | isesteviol has the effects of anti-hypertension, lowering blood sugar and inhibiting cancer cells. used for content determination/identification/pharmacological experiment, etc. |