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Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on ?-Amylase and ?-Glucosidase.

ABSTRACT: Inhibition of ?-amylase and ?-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[b]furan scaffold (compounds 2a-f), with a substituted isatin (compounds 3a-c) and heterocyclic amino acids (compounds 4a,b). The target spiroindolone analogues 5a-r were evaluated for their potential inhibitory activities against the enzymes ?-amylase and ?-glucosidase. Preliminary results indicated that some of the target compounds exhibit promising ?-amylase and ?-glucosidase inhibitory activity. Among the tested spiroindolone analogues, the cycloadduct 5r was found to be the most active (IC50 = 22.61 ± 0.54 ?M and 14.05 ± 1.03 ?M) as ?-amylase and ?-glucosidase inhibitors, with selectivity indexes of 0.62 and 1.60, respectively. Docking studies were carried out to confirm the binding interaction between the enzyme active site and the spiroindolone analogues.

SUBMITTER: Altowyan MS

PROVIDER: S-EPMC6630796 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase.

Altowyan Mezna Saleh MS Barakat Assem A Al-Majid Abdullah Mohammed AM Al-Ghulikah H A HA

Molecules (Basel, Switzerland) 20190625 12

Inhibition of α-amylase and α-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[<i>b</i>]furan scaffold (compo ...[more]

PMID: 31242688

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Project description:The fruits of Canarium tramdenum are commonly used as foods and cooking ingredients in Vietnam, Laos, and the southeast region of China, whilst the leaves are traditionally used for treating diarrhea and rheumatism. This study was conducted to investigate the potential use of this plant bark as antioxidants, and ?-amylase and ?-glucosidase inhibitors. Five different extracts of C. tramdenum bark (TDB) consisting of the extract (TDBS) and factional extracts hexane (TDBH), ethyl acetate (TDBE), butanol (TDBB), and water (TDBW) were evaluated. The TDBS extract contained the highest amount of total phenolic (112.14 mg gallic acid equivalent per g dry weight), while the TDBB extract had the most effective antioxidant capacity compared to other extracts. Its IC50 values were 12.33, 47.87, 33.25, and 103.74 µg/mL in 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis (ABTS), reducing power (RP), and nitric oxide (NO) assays, respectively. Meanwhile, the lipid peroxidation inhibition of the four above extracts was proximate to that of butylated hydroxytoluene (BHT) as a standard antioxidant. The result of porcine pancreatic ?-amylase inhibition showed that TDB extracts have promising effects which are in line with the commercial diabetic inhibitor acarbose. Interestingly, the inhibitory ability on ?-glucosidase of all the extracts was higher than that of acarbose. Among the extracts, the TDBB extract expressed the strongest activity on the enzymatic reaction (IC50 = 18.93 µg/mL) followed by the TDBW extract (IC50 = 25.27 µg/mL), TDBS (IC50 = 28.17 µg/mL), and TDBE extract (IC50 = 141.37 µg/mL). The phytochemical constituents of the TDB extract were identified by gas chromatography?mass spectrometry (GC-MS). The principal constituents included nine phenolics, eight terpenoids, two steroids, and five compounds belonging to other chemical classes, which were the first reported in this plant. Among them, the presence of ?- and ?-amyrins were identified by GC-MS and appeared as the most dominant constituents in TDB extracts (1.52 mg/g). The results of this study revealed that C. tramdenum bark possessed rich phenolics and terpenoids, which might confer on reducing risks from diabetes. A high quantity of ?- and ?-amyrins highlighted the potentials of anti-inflammatory, anti-ulcer, anti-hyperlipidemic, anti-tumor, and hepatoprotective properties of C. tramdenum bark.

Dataset Information

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on ?-Amylase and ?-Glucosidase.

Publications

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase.

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