1. Pentacyclic triterpene carboxylic acids derivatives integrated piperazine-amino acid complexes for α-glucosidase inhibition in vitro.
- Author
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Huang J, Zang X, Yang W, Yin X, Huang J, Wu S, and Hong Y
- Subjects
- Amino Acids chemistry, Carboxylic Acids chemical synthesis, Carboxylic Acids chemistry, Dose-Response Relationship, Drug, Glycoside Hydrolase Inhibitors chemical synthesis, Glycoside Hydrolase Inhibitors chemistry, Humans, Molecular Structure, Pentacyclic Triterpenes chemical synthesis, Pentacyclic Triterpenes chemistry, Piperazine chemistry, Structure-Activity Relationship, Amino Acids pharmacology, Carboxylic Acids pharmacology, Glycoside Hydrolase Inhibitors pharmacology, Pentacyclic Triterpenes pharmacology, Piperazine pharmacology, alpha-Glucosidases metabolism
- Abstract
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 activities of the pristine derivatives were evaluated in vitro. The results indicated that the inhibitory activity of some compounds (15e IC
50 = 591 μM, 16e IC50 = 423 μM) was closed to that of the reference acarbose (IC50 = 347 μM) in ethanol-water system. In addition, compound 16e (IC50 = 380 μM) showed superior inhibitory activity than acarbose (IC50 = 493 μM) in the measurement system with DMSO as solvent. The comparison of two different solvent systems showed that the derivatives had better α-glucosidase inhibitory activity in the DMSO system than that of in ethanol-water system. Regrettably, all of the as-synthesized derivatives exhibited inferior α-glucosidase inhibitory activities than those of the parent compounds in both test solvent systems. Furthermore, the result of enzyme kinetics demonstrated that the inhibition mechanism of compound 16e was noncompetitive inhibition with the inhibition constant Ki = 552 μM., (Copyright © 2021 Elsevier Inc. All rights reserved.)- Published
- 2021
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