Synthesis of water soluble pentacyclic dihydroxyterpene carboxylic acid derivatives coupled amino acids and their inhibition activities on α-glucosidase
Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with L-amino acids at C-28 position. The α-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better α-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50 = 382 μm and 10f: IC50 = 364 μm, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50 = 484 μm). Unfortunately, all of the derivatives possess lower inhibitory properties of α-glucosidase than those of the parent compounds in the measurement system of DMSO solution, even if the derivatives exhibit better water solubility than that of the parent compounds.
Semi-synthesis of C28-modified triterpene acid derivatives from maslinic acid or corosolic acid as potential α-glucosidase inhibitors
Combining two bioactive moieties by covalent bond into a novel single hybrid biological entity in view of the principle of active splicing, twenty-two C28-modified derivatives of pentacyclic dihydroxytriterpene carboxylic acids with saturated nitrogen heterocycle segments (i.e. 1-deoxynojirimycin or piperazines) have been synthesized. The inhibitory activities of all final target compounds on α-glucosidase were evaluated in vitro. The results of α-glucosidase inhibition assay indicate that some derivatives (e.g. 4b: IC50 = 1468.4 μM; 12b: IC50 = 499.6 μM 12c: IC50 = 768.5 μM, 13c: IC50 = 819.2 μM) show superior inhibitory activity in α-glucosidase than that of the precursor maslinic acid (IC50 = 2540.6 μM) or corosolic acid (IC50 = 1363.7 μM), in which compound 12b (IC50 = 499.6 μM) possesses stronger inhibitory activity than that of acarbose (IC50 = 606 μM). In addition, the result of enzyme kinetics study reveals that the inhibitory mechanism of the compound 12b is non-competitive inhibition and the inhibition constant Ki is 570 μM. The binding interaction between compounds with α-glucosidase are predicted by molecular docking simulation.
A new ursane triterpene from Monochaetum vulcanicum that inhibits DNA polymerase β lyase
Bioassay-directed fractionation of a butanone extract of Monochaetum vulcanicum resulted in the isolation of a new triterpene (1) and four known compounds, ursolic acid (2), 2α-hydroxyursolic acid (3), 3-(p-coumaroyl)ursolic acid (4), and β-sitosteryl-β-D-galactoside (5). The structure of the new compound 1 was established as 3β-acetoxy-2α -hydroxyurs-12-en-28-oic acid on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. Compounds 1-3 and 5 exhibited polymerase β lyase activity.
Chaturvedula, V. S. Prakash,Gao, Zhijie,Jones, Shannon H.,Feng, Xizhi,Hecht, Sidney M.,Kingston, David G. I.
Pentacyclic triterpene carboxylic acids derivatives integrated piperazine-amino acid complexes for α-glucosidase inhibition in vitro
Eighteen derivatives of pentacyclic triterpene carboxylic acids (Maslinic acid, Corosolic acid and Asiatic acid) have been prepared by coupling the piperazine complex of L-amino acids at the C-28 site of the parent compounds. The α-glucosidase inhibitory
Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases
The synthesis and biological evaluation of corosolic acid derivatives and related compounds as inhibitors of rabbit muscle glycogen phosphorylase a is described. Within this series of compounds, 8 (IC50 = 7.31 μM), 12d (IC50 = 3.26 μM), and 12e (IC50 = 5.1 μM) exhibited more potent activities than the parent compound 1 (IC50 = 20 μM). SAR of these compounds is also discussed.
NOVEL STRUCTURAL ANALOGS OF COROSOLIC ACID HAVING ANTI-DIABETIC AND ANTI-INFLAMMATORY PROPERTIES
This invention relates to novel corosolic acid analogs of the formula I, wherein R1, R2, R3, R4 and R5 are as indicated below in each of said analogs: 1. R1 = COCH3, R2/sub
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Triterpenoids from Bignonia unguiscati roots
One new triterpenoid named acetylbignonic acid 1 along with 2α-hydroxyursolic acid 2 have been isolated from the roots of Bignonia unguiscati. On the basis of chemical and spectral evidence, the structure of 1 has been established as 3β-acetoxy-19α-hydroxyurs-12-en-29β-oic acid.
The invention provides an early insulin secretion stimulator comprising corosolic acid, etc. The early insulin secretion stimulator of the invention is capable of rapidly inducing secretion of insulin immediately after meals without inducing secretion of insulin in the absence of blood glucose increase.
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