Semi-synthesis, α-amylase inhibition, and kinetic and molecular docking studies of arylidene-based sesquiterpene coumarins isolated from Ferula tunetana Pomel ex Batt

被引:8
作者
Baccari, Wiem [1 ]
Saidi, Ilyes [1 ]
Filali, Insaf [2 ]
Znati, Mansour [1 ]
Lazrag, Houda [3 ]
Tounsi, Moncef [4 ]
Marchal, Axel [5 ,6 ]
Waffo-Teguo, Pierre [5 ,6 ]
Ben Jannet, Hichem [1 ]
机构
[1] Univ Monastir, Fac Sci Monastir, Lab Heterocycl Chem Nat Prod & React LR11ES39, Team Med Chem & Nat Prod, Ave Environm, Monastir 5019, Tunisia
[2] Prince Sattam Bin Abdulaziz Univ, Coll Sci & Humanities Al Kharj, Dept Chem, Al Kharj 11942, Saudi Arabia
[3] Univ Monastir, Higher Inst Biotechnol Monastir, Lab Genet Biodivers & Bioresources Valuat LR11S41, Monastir 5019, Tunisia
[4] Prince Sattam Bin Abdulaziz Univ, Basic Sci Dept, Preparatory Year Deanship, Alkharj 11942, Saudi Arabia
[5] Univ Bordeaux, Inst Sci Vigne & Vin, Unite Rech Enol Chemin Leysotte 210, EA 4577, CS50008, F-33882 Villenave Dornon, France
[6] Univ Bordeaux, Bordeaux INP, Bordeaux Sci Agro, UMR OENOL 1366,ISVV, F-33140 Villenave Dornon, France
关键词
GLUCOSIDASE; CHALCONE;
D O I
10.1039/d3ra07540k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite all the significant progresses made to enhance the efficacy of the existing bank of drugs used to manage and cure type II diabetes mellitus, there is still a need to search and develop novel bioactive compounds with superior efficacy and minimal adverse effects. This study describes the valorization of the natural bioactive sesquiterpene coumarin via the semi-synthesis of new analogs and the study of their alpha-amylase inhibition activity. The sesquiterpene coumarin named coladonin (1) was quantitatively isolated from the chloroform extract of endemic Ferula tunetana roots. Subsequently, the oxidation of 1 via the Jones oxidation reaction, used as a key reaction, afforded precursor 2. The condensation of oxidized coladonin (2) with various aryl aldehydes provided a series of new arylidene-based sesquiterpene coumarin derivatives (3a-m), which were characterized by NMR and ESI-HRMS experiments. All derivatives evaluated in vitro for their alpha-amylase inhibitory potential showed interesting alpha-amylase inhibition with IC50 values ranging from 7.24 to 28.98 mu M. Notably, compounds 3k and 3m exhibited lower IC50 values (7.24 mu M and 8.38 mu M, respectively) compared to the standard (acarbose: IC50 = 9.83 mu M). In addition, the structure-activity relationship (SAR) for all the compounds was studied. The most active compounds were found to be mixed-type inhibitors, which was revealed by kinetic studies. Furthermore, molecular in silico docking studies were established for all synthesized analogs with the binding site for the alpha-amylase enzyme.
引用
收藏
页码:4654 / 4665
页数:12
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