Identification of Digestive Enzyme Inhibitors from Ludwigia octovalvis (Jacq.) P.H.Raven

Abstract

Current antiobesity and antidiabetic tools have been insufficient to curb these diseases and frequently cause side effects; therefore, new pancreatic lipase and α–glucosidase inhibitors could be excellent aids for the prevention and treatment of these diseases. The aim of this study was to identify, quantify, and characterize the chemical compounds with the highest degree of inhibitory activity of these enzymes, contained in a Ludwigia octovalvis hydroalcoholic extract. Chemical purification was performed by liquid–liquid separation and column chromatography. Inhibitory activities were measured in vitro, employing acarbose, orlistat, and a Camellia sinensis hydroalcoholic extract as references. For structural elucidation, Nuclear Magnetic Resonance was carried out, and High Performance Liquid Chromatography was used to quantify the compounds. For α–glucosidases, L. octovalvis hydroalcoholic extract and its ethyl acetate fraction showed half–maximal Inhibitory Concentration (IC50) values of 700 and 250 μg/mL, for lipase, 480 and 718 μg/mL, while C. sinensis showed 260 and 587 μg/mL. The most active compounds were identified as ethyl gallate (1, IC50 832 μM) and gallic acid (2, IC50 969 μM); both displayed competitive inhibition of α–glucosidases and isoorientin (3, IC50 201 μM), which displayed uncompetitive inhibition of lipase. These data could be useful in the development of a novel phytopharmaceutical drug.

New anti-α-Glucosidase and Antioxidant Ingredients from Winery Byproducts: Contribution of Alkyl Gallates

“…49 This activity could be due to the enzymatic inhibition developed by gallic acid and galloyl derivatives by competing directly with the substrate for the active binding site of the enzyme. 50 The hypoglycemic effect, could be also due to the inhibition of starch digestion by gallic acid and alkyl gallates as has previously been reported in the literature. 8 This inhibitory ability decreased in a reverse form with the alkyl chain length, as demonstrated by assessing how medium alkyl chain gallates (butyl and octyl gallates) were more efficient in inhibiting the enzymatic digestion of starch.…”

“…Altogether, these findings would reveal that the presence of the gallate group in the chemical structure is key for an efficient inhibition of α-glucosidase . This activity could be due to the enzymatic inhibition developed by gallic acid and galloyl derivatives by competing directly with the substrate for the active binding site of the enzyme …”

Chemical Characterization, Antilipidemic Effect and Anti-Obesity Activity of Ludwigia octovalvis in a Murine Model of Metabolic Syndrome

“…LSF8A: Pale-yellow powder NMR data were compared to literature descriptions of gallic acid [19], corilagin [20], ellagic acid [21] and ethyl gallate [22]. All of the isolated compounds had been previously identified in L. octovalvis [17,23], except for corilagin, which was, to our knowledge, isolated here for the first time in the genus Ludwigia.…”

“…In addition, this species had one of the strongest α-glucosidase and pancreatic lipase inhibitory activities among twenty three Mexican medicinal plants in a screening study [10]. The biological effect of L. octovalvis on α-glucosidase inhibition has been attributed to bioactive compounds such as gallic acid and ethyl gallate, while isoorientin has the strongest inhibitory activity for pancreatic lipase [17]. Regarding its toxicity, there were no adverse effects with oral administration of up to 5000 mg/kg of the methanolic extract in an acute toxicity model or of up to 800 mg/kg in a subacute toxicity model [18].…”

Acute toxicity study of hydroalcoholic extract of two Indian medicinal plants Alternanthera ficoidea and Ludwigia octovalvis

“…Toxicological information aids in determining whether or not an unknown herbal medication is harmless for clinical use. diseases, leucorrhoea, orchitis, hypertension, headache, and nephritis (8,9,10,11) . It is generally drunk as a health beverage (6).…”