Alpha-glucosidase and amylase inhibitory effects of Eruca vesicaria subsp. longirostris essential oils: synthesis of new 1,2,4-triazole-thiol derivatives and 1,3,4-thiadiazole with potential inhibitory activity

Abstract

Context: The substantial increase in the number of diabetics has encouraged the search for new pharmacological strategies to face this problem. In this regard, triazole and its derivatives have attracted considerable attention for the past few decades due to their pharmacological significance. Objective: Evaluation of the inhibitory activity of α-glucosidase and α-amylase in essential oils extracted from plant Eruca vesicaria (L) Cav. subsp. longirostris (Brassicaceae) (EVL) and to verify whether the triazoles and thiadiazol bearing the lipophilic 4-methylthiobutyl group synthesized from the essential oil contribute to this activity. Materials and methods: The essential oils were extracted by hydrodistillation from leaf, stem, root, and fruit of EVL, and their chemical compositions were analyzed by gas chromatography and gas chromatography-mass spectrometry. We present here the synthesis of three new types of 1,2,4-triazole-thiol and 1,3,4-thiadiazol and the structures were confirmed by NMR, mass spectrometry. The α-glucosidase and α-amylase inhibitory activities were investigated in vitro . Results: The main compound in fruit, stem, and root was erucin (96.6, 85.3, and 83.7%, respectively). The three essential oils of the fruit, stem, and root have strong inhibitory activity on α-glucosidase and α-amylase; IC 50 values of roots were 0.81 ± 0.02 μg/mL and 0.13 ± 0.01 μg/mL, respectively. Derivatives 1 b , 2 b , 3 b, and 2c showed remarkable inhibitory activity against α-glucosidase with potencies better than that of acarbose with IC 50 values ranging between 0.49 and 1.43 μM. Conclusions: Current results indicate that ECL fruit essential oil can be used as a natural precursor for the synthesis of triazoles as potential hypoglycemic agents.

Optimization of cold press and enzymatic‐assisted aqueous oil extraction from tomato seed by response surface methodology: Effect on quality characteristics

“…α‐glucosidase (α‐glucosidase obtained by Saccharomyces cerevisiae ) and α‐amylase (α‐Amylase obtained by B. licheniformis ) inhibitory activities were determined as previously described by Hichri et al. (2019), with some modifications. Ten microliter of the α‐glucosidase and α‐amylase solutions in 25‐mM phosphate buffer (pH 6.86) reacted with 2.5‐mM p ‐nitrophenyl‐α‐ d ‐glucopyranoside (pNPG), separately.…”

“…The oil extracts were mixed with a FRAP reagent (10 mM of TPTZ solution in 40-mM HCl, 20-mM FeCl 3 , and 0.3-M acetate buffer at pH 3.6) followed by spectrophotometric measurement of the absorbance of the reaction mixture after incubation at 37°C for 30 min at 593 nm against the blank. The results were expressed as mM FeSO 4 per L oil sample.Determination of α-glucosidase and α-amylase inhibition activity α-glucosidase (α-glucosidase obtained by Saccharomyces cerevisiae) and α-amylase (α-Amylase obtained by B. licheniformis) inhibitory activities were determined as previously described byHichri et al (2019), with some modifications. Ten microliter of the α-glucosidase and αamylase solutions in 25-mM phosphate buffer (pH 6.86) reacted with 2.5-mM p-nitrophenylαd-glucopyranoside (pNPG), separately.…”

Modeling and simulation in medical sciences: an overview of specific applications based on research experience in EMRI (Endocrinology and Metabolism Research Institute of Tehran University of Medical Sciences)

“…This data could be of use for synthesizing more potent inhibitors. Recently, many natural extracts and synthetic new molecules have been investigated with regard to their alpha-amylase inhibitory properties [37][38][39][40][41][42][43][44][45][46][47][48] and this line of study seems to be promising with regard to finding effective anti-diabetic aids.…”

1,2,4-Triazoles as Important Antibacterial Agents

“…The 1,2,4-triazole core has been incorporated into a wide variety of therapeutically important agents available in clinical therapy, such as itraconazole, posaconazole, voriconazole (antifungal), ribavirin (antiviral), rizatriptan (antimigraine), alprazolam (anxiolytic), trazodone (antidepressant), letrozole and anastrozole (antitumoral) ( Figure 2 ). In the last few decades, scientists have been paying considerable attention to the synthesis of 1,2,4-triazole derivatives showing such comprehensive biological activities as an antifungal [ 6 , 7 ] antitubercular [ 8 ], antioxidant [ 9 ], anticancer [ 10 ], anti-inflammatory [ 11 ], analgesic [ 12 ], antidiabetic [ 13 ], anticonvulsant [ 14 ], and anxiolytic [ 15 ] activity. With regard to the antifungal activity, triazole-based pharmacophore has replaced the previously widely used imidazole pharmacophore in systemically active azoles, due to lower toxicity and higher bioavailability of triazole derivatives as well as an increased specificity for fungal cytochrome p450 and a lower impact on human sterol synthesis [ 16 ].…”