α-Amylase and α-glucosidase inhibitors from Zanthoxylum chalybeum Engl. root bark

Ochieng, Charles O.; Nyongesa, Daniel Wasiali; Yamo, Kevin O.; Onyango, Joab O.; Langat, Moses K.; Manguro, Lawrence A.O.

doi:10.1016/j.fitote.2020.104719

Cited by 13 publications

(9 citation statements)

References 18 publications

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“…Chaylbemides A-C, fagaramide, skimmianine, norchelerythrine, 6-acetonyldihydrochelerythrine, and 6-hydroxy-N-methyl decarine Ochieng et al (2020).…”

Section: Zanthoxylum Chalybeummentioning

confidence: 99%

Antidiabetic Medicinal Plants Used in Democratic Republic of Congo: A Critical Review of Ethnopharmacology and Bioactivity Data

et al. 2021

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Several studies have been conducted and published on medicinal plants used to manage Diabetes Mellitus worldwide. It is of great interest to review available studies from a country or a region to resort to similarities/discrepancies and data quality. Here, we examined data related to ethnopharmacology and bioactivity of antidiabetic plants used in the Democratic Republic of Congo. Data were extracted from Google Scholar, Medline/PubMed, Scopus, ScienceDirect, the Wiley Online Library, Web of Science, and other documents focusing on ethnopharmacology, pharmacology, and phytochemistry antidiabetic plants used in the Democratic Republic of Congo from 2005 to September 2021. The Kew Botanic Royal Garden and Plants of the World Online web databases were consulted to verify the taxonomic information. CAMARADES checklist was used to assess the quality of animal studies and Jadad scores for clinical trials. In total, 213 plant species belonging to 72 botanical families were reported. Only one plant, Droogmansia munamensis, is typically native to the DRC flora; 117 species are growing in the DRC and neighboring countries; 31 species are either introduced from other regions, and 64 are not specified. Alongside the treatment of Diabetes, about 78.13% of plants have multiple therapeutic uses, depending on the study sites. Experimental studies explored the antidiabetic activity of 133 plants, mainly in mice, rats, guinea pigs, and rabbits. Several chemical classes of antidiabetic compounds isolated from 67 plant species have been documented. Rare phase II clinical trials have been conducted. Critical issues included poor quality methodological protocols, author name incorrectly written (16.16%) or absent (14.25%) or confused with a synonym (4.69%), family name revised (17.26%) or missing (1.10%), voucher number not available 336(92.05%), ecological information not reported (49.59%). Most plant species have been identified and authenticated (89.32%). Hundreds of plants are used to treat Diabetes by traditional healers in DRC. However, most plants are not exclusively native to the local flora and have multiple therapeutic uses. The analysis showed the scarcity or absence of high-quality, in-depth pharmacological studies. There is a need to conduct further studies of locally specific species to fill the gap before their introduction into the national pharmacopeia.

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“…Chaylbemides A-C, fagaramide, skimmianine, norchelerythrine, 6-acetonyldihydrochelerythrine, and 6-hydroxy-N-methyl decarine Ochieng et al (2020).…”

Section: Zanthoxylum Chalybeummentioning

confidence: 99%

Antidiabetic Medicinal Plants Used in Democratic Republic of Congo: A Critical Review of Ethnopharmacology and Bioactivity Data

et al. 2021

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“…There are several reports on plant-derived triterpenes inhibitory activity against carbohydrate digestive enzymes (Nazaruk & Borzym-Kluczyk, 2015). Regarding lupane-type triterpenes in other studies, α-glucosidase and α-amylase inhibitory activities of lupenone possesses a carbonyl ketone at C-3 (IC 50 : 88.62 μM and 108.61 μM, respectively) were stronger than those of lupeol, which possesses a hydroxy group at C-3 (IC 50 : 90.86 μM and 116.19 μM, respectively), with acarbose IC 50 values of 44.88 μM and 42.67 μM, respectively (Ochieng et al, 2020). Our results agree with those of other studies, showing that the carbonyl ketone at C-3 is important for α-glucosidase and αamylase inhibitory activities (Yonemoto et al, 2014;Pujirahayu et al, 2019).…”

Section: Identification Of Four Compounds From Banana Peel By Nmr Analysismentioning

confidence: 81%

Major triterpenes, cycloeucalenone and 31‐norcyclolaudenone as inhibitors against both α‐glucosidase and α‐amylase in banana peel

Shang

Koyama

2021

Int J of Food Sci Tech

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The inhibitory activities of banana peel extract against carbohydrate digestive enzymes were investigated. Cycloeucalenone and 31-norcyclolaudenone were obtained by bioassay-guided fractionation as effective inhibitors of α-glucosidase and α-amylase. The structure-activity relationships of four triterpenes isolated from banana peel, cycloeucalenone, 31-norcyclolaudenone and cycloeucalenol and its isomer were investigated. The IC 50 values of cycloeucalenone and 31-norcyclolaudenone against α-glucosidase were 31.83 AE 2.46 μM and 38.85 AE 1.54 μM, respectively, and their IC 50 values against α-amylase were 20.33 AE 0.59 μM and 27.63 AE 0.83 μM, respectively. In contrast, cycloeucalenol and its isomer had insufficient inhibitory activity against either enzyme. The primary active sites of cycloeucalenone and 31-norcyclolaudenone are the carbonyl group at C-3 and the double bond in the side chain. Cycloeucalenone induced a parabolic mixed-type inhibition with a K i value of 73.86 μM in the α-glucosidase inhibitory assay. This study provides new evidence for the potential use of banana peel triterpenes as antidiabetic agents.

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“…The powdered root bark (0.8 kg) was exhaustively extracted with 95% aqueous methanol (4 × 1.5 L) and filtered to afford a 30 g crude sample. The crude sample was partitioned into total alkaloid extraction and nonalkaloid fraction, followed by a series of chromatographic procedures that led to the isolation of eleven pure compounds as described by Ochieng et al, 2020 [ 12 ]. Furthermore, the structures of the eleven compounds were elucidated following spectroscopic techniques as described by Ocheing et al, 2020 [ 12 ].…”

Section: Methodsmentioning

confidence: 99%

“…Subsequently, bioactivity-guided isolation resulted in the identification of some of the bioactive compounds including chaylbemide A ( 1 ), chalybemide B ( 2 ) and chalybemide C ( 3 ), fagaramide ( 4 ); skimmianine ( 5 ), norchelerythrine ( 6 ), 6-acetonyldihydrochelerythrine ( 7 ) and 6-hydroxy-N-methyldecarine ( 8 ), ailanthoidol ( 9 ), 2,3-epoxy-6,7-methylenedioxyconiferol ( 10 ) and sesamine ( 11 ) with the structures shown in Figure 1 . These compounds have been shown to inhibit the enzymes α-glycosidase and α-amylase with IC 50 values between 43.22 and 49.36 μM at comparable levels to ( p > 0.05) the positive control acarbose which has IC 50 values of 42.67 and 44.88 μM against α-amylase and α-glycosidase, respectively [ 12 ]. Such results established the ability of Z. chalybuem against DM; however, the study failed to establish the possible mechanism of interaction between the enzymes and the inhibitors (compounds), thus necessitating further investigation on the mode of actions via inhibition kinetics and molecular interaction studies.…”

Section: Introductionmentioning

confidence: 99%

Inhibition Kinetics and Theoretical Studies on Zanthoxylum chalybeum Engl. Dual Inhibitors of α-Glucosidase and α-Amylase

Kimani

Ochieng

Ogutu

et al. 2023

JoX

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Compounds from Zanthoxylum chalybeum Engl. were previously reported for inhibitory activities of amylase and glucosidase enzymatic action on starch as a preliminary study toward the establishment of a management strategy against postprandial hyperglycemia, however, the inhibitory kinetics and molecular interaction of these compounds were never established. A study was thus designed to establish the inhibitory kinetics and in silico molecular interaction of α-glucosidase and α-amylase with Z. chalybeum metabolites based on Lineweaver–Burk/Dixon plot analyses and using Molecular Operating Environment (MOE) software, respectively. Skimmianine (5), Norchelerythrine (6), 6-Acetonyldihydrochelerythrine (7), and 6-Hydroxy-N-methyldecarine (8) alkaloids showed mixed inhibition against both α-glucosidase and α-amylase with comparable Ki to the reference acarbose (p > 0.05) on amylase but significantly higher activity than acarbose on α-glucosidase. One phenolic 2,3-Epoxy-6,7-methylenedioxyconiferol (10) showed a competitive mode of inhibition both on amylase and glucosidase which were comparable (p > 0.05) to the activity of acarbose. The other compounds analyzed and displayed varied modes of inhibition between noncompetitive and uncompetitive with moderate inhibition constants included chaylbemide A (1), chalybeate B (2) and chalybemide C (3), fagaramide (4), ailanthoidol (9), and sesame (11). The important residues of the proteins α-glucosidase and α-amylase were found to have exceptional binding affinities and significant interactions through molecular docking studies. The binding affinities were observed in the range of −9.4 to −13.8 and −8.0 to −12.6 relative to the acarbose affinities at −17.6 and −20.5 kcal/mol on α-amylase and α-glucosidase residue, respectively. H-bonding, π-H, and ionic interactions were noted on variable amino acid residues on both enzymes. The study thus provides the basic information validating the application of extracts of Z. chalybeum in the management of postprandial hyperglycemia. Additionally, the molecular binding mechanism discovered in this study could be useful for optimizing and designing new molecular analogs as pharmacological agents against diabetes.

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α-Amylase and α-glucosidase inhibitors from Zanthoxylum chalybeum Engl. root bark

Cited by 13 publications

References 18 publications

Antidiabetic Medicinal Plants Used in Democratic Republic of Congo: A Critical Review of Ethnopharmacology and Bioactivity Data

Antidiabetic Medicinal Plants Used in Democratic Republic of Congo: A Critical Review of Ethnopharmacology and Bioactivity Data

Major triterpenes, cycloeucalenone and 31‐norcyclolaudenone as inhibitors against both α‐glucosidase and α‐amylase in banana peel

Inhibition Kinetics and Theoretical Studies on Zanthoxylum chalybeum Engl. Dual Inhibitors of α-Glucosidase and α-Amylase

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