Antidiabeticin vitroandin vivoevaluation of cyclodipeptides isolated fromPseudomonas fluorescensIB-MR-66e

Lozano-González, Mariana; Ovalle-Magallanes, Berenice; Rangel‐Grimaldo, Manuel; Torre-Zavala, Susana De la; Noriega, Lilia G.; Tovar‐Palacio, Claudia; Tovar, Armando R.; Mata, Rachel

doi:10.1039/c9nj00645a

Cited by 7 publications

(11 citation statements)

References 26 publications

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“…Blood glucose concentrations were determined at 30, 60, 90, and 120 min postadministration of the carbohydrate load. The percentage of glycemic variation (%) was determined with respect to the basal level as follows: where G i is the basal glycemia and G t is the different glycemia values after treatment administration. , …”

Section: Methodsmentioning

confidence: 99%

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α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitors from Malbranchea circinata

et al. 2020

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During a search for new α-glucosidase and protein tyrosine phosphatase 1B inhibitors from fungal sources, eight new secondary metabolites, including two anthranilic acid-derived peptides (1 and 2), four glycosylated anthraquinones (3−6), 4-isoprenylravenelin (7), and a dimer of 5,8-dihydroxy-4-methoxy-α-tetralone (8), along with four known compounds (9−12), were isolated from solid ricebased cultures of Malbranchea circinata. The structural elucidation of these metabolites was performed using 1D and 2D NMR techniques and DFT-calculated chemical shifts. Compounds 1−3, 9, and 10 showed inhibitory activity to yeast α-glucosidase (αGHY), with IC 50 values ranging from 57.4 to 261.3 μM (IC 50 acarbose = 585.8 μM). The effect of 10 (10.0 mg/kg) was corroborated in vivo using a sucrose tolerance test in normoglucemic mice. The most active compounds against PTP-1B were 8−10, with IC 50 values from 10.9 to 15.3 μM (IC 50 ursolic acid = 27.8 μM). Docking analysis of the active compounds into the crystal structures of αGHY and PTP-1B predicted that all compounds bind to the catalytic domains of the enzymes. Together, these results showed that M. circinata is a potential source of antidiabetic drug leads.

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Section: Methodsmentioning

confidence: 99%

“…where G i is the basal glycemia and G t is the different glycemia values after treatment administration. 10,47 Docking Studies. The minimized structures for docking simulations were prepared using Autodock Tools package v1.5.4 (ADT, http://mgltools.scripps.edu/).…”

Section: Methodsmentioning

confidence: 99%

α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitors from Malbranchea circinata

et al. 2020

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“…The insulin secretion was expressed as the percentage of insulin secreted into the media with respect to the sum of the secreted and total insulin content. 44 − 46 …”

Section: Experimental Sectionmentioning

confidence: 99%

“…Oligomycin (2 μM), FCCP (0.5 μM), and a mixture of rotenone plus antimycin A (0.5 μM) were added sequentially, and three measurements were performed after the addition of each concentration of the compounds. 44 − 46 …”

Section: Experimental Sectionmentioning

confidence: 99%

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Antidiabetic Sterols from Peniocereus greggii Roots

et al. 2022

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The roots of the cactus Peniocereus greggii , which grows in Northern Mexico and in the south of Arizona, are highly valued by the Pima to treat diabetes and other illnesses, such as breast pain and common cold. As part of our chemical and pharmacological investigation on medicinal plants used for treating diabetes, herein we report the hypoglycemic and antihyperglycemic action of a decoction prepared from the roots of the plant. The active compounds were a series of cholestane steroids, namely, peniocerol ( 2 ), desoxyviperidone ( 3 ), viperidone ( 4 ), and viperidinone ( 5 ). Also, a new chemical entity was obtained from an alkalinized chloroform extract (CE1), which was characterized as 3,6-dihydroxycholesta-5,8(9),14-trien-7-one ( 6 ) by spectroscopic means. Desoxyviperidone ( 3 ) showed an antihyperglycemic action during an oral glucose tolerance test. Compound 3 was also able to decrease blood glucose levels during an intraperitoneal insulin tolerance test in hyperglycemic mice only in combination with insulin, thus behaving as an insulin sensitizer agent. Nevertheless, mitochondrial bioenergetic experiments revealed that compounds 3 and 6 increased basal respiration and proton leak, without affecting the respiration associated with ATP production in C2C12 myotubes. Finally, an ultraefficiency liquid chromatographic method for quantifying desoxyviperidone ( 3 ) and viperidone ( 4 ) in the crude drug was developed and validated. Altogether, our results demonstrate that Peniocereus greggii decoction possesses a hypoglycemic and antihyperglycemic action in vivo, that sterols 2 and 6 promotes insulin secretion in vitro, and that desoxyviperidone ( 3 ) physiologically behaves as an insulin sensitizer agent by a mechanism that may involve mitochondrial proton leak.

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Antidiabetic Potential of a Trimeric Anthranilic Acid Peptide Isolated from Malbranchea flocciformis

Rebollar‐Ramos,

Ovalle‐Magallanes,

Raja

et al. 2024

Chemistry & Biodiversity

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Compound 3, a trimeric anthranilic acid peptide, and another three metabolites were isolated from an organic extract from the culture medium of Malbranchea flocciformis ATCC 34530. The chemical structure proposed previously for 3 was unequivocally assigned via synthesis and X‐ray diffraction analysis. Tripeptide 3 showed insulinotropic properties by decreasing the postprandial peak in healthy and hyperglycemic mice. It also increased glucose‐induced insulin secretion in INS‐1E at 5µM, specifically at higher glucose concentrations. These results revealed that 3 might act as an insulin sensitizer and a non‐classical insulin secretagogue. Altogether, these findings are in harmony with the in vivo oral glucose tolerance test and acute oral hypoglycemic assay. Finally, the chemical composition of the extract was established by the Global Natural Products Social Molecular Network platform. Phylogenetic analysis using the internal transcribed spacer region revealed that M. flocciformis ATCC 34530 is related to the Malbrancheaceae.

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Antidiabeticin vitroandin vivoevaluation of cyclodipeptides isolated fromPseudomonas fluorescensIB-MR-66e

Abstract: Cyclodipeptides cyclo(l-Pro-l-Leu), 1; cyclo(l-Pro-l-Val), 2; and cyclo (l-Pro-l-Phe), 3 from Pseudomonas fluorescens IB-MR-66e showed α-glucosidase inhibitory activity.

Cited by 7 publications

References 26 publications

α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitors from Malbranchea circinata

α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitors from Malbranchea circinata

Antidiabetic Sterols from Peniocereus greggii Roots

Antidiabetic Potential of a Trimeric Anthranilic Acid Peptide Isolated from Malbranchea flocciformis

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