A new abietane-type diterpenoid from roots of <i>Burkea africana</i> Hook (Fabaceae) with <i>α-</i>amylase inhibitory potential

Feunaing, Romeo Toko; Tamfu, Alfred Ngenge; Ntchapda, Fidèle; Gade, Isaac Silvère; Mbane, Martin Noah; Tagatsing, Maurice Fotsing; Talla, Emmanuel; Henoumont, Céline; Laurent, Sophie; Dinică, Rodica Mihaela

doi:10.1080/14786419.2021.1976176

Cited by 10 publications

(3 citation statements)

References 15 publications

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“…Arjungenin and terminolic acid are constituents of Terminalia arjuna which have demonstrated antidiabetic and cardioprotective effects [ 52 ]. Various natural inhibitors of the AChE, BChE, α-glucosidase, and α-amylase enzymes are useful in managing ailments, especially diabetes and Alzheimer’s disease, and the search for more of such compounds is an important domain in medicinal chemistry [ 53 ].…”

Section: Discussionmentioning

confidence: 99%

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

Feunaing,

Tamfu,

Gbaweng

et al. 2024

Molecules

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Alzheimer’s disease (AD) and diabetes are non-communicable diseases with global impacts. Inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are suitable therapies for AD, while α-amylase and α-glucosidase inhibitors are employed as antidiabetic agents. Compounds were isolated from the medicinal plant Terminalia macroptera and evaluated for their AChE, BChE, α-amylase, and α-glucosidase inhibitions. From 1H and 13C NMR data, the compounds were identified as 3,3′-di-O-methyl ellagic acid (1), 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-xylopyranoside (2), 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-glucopyranoside (3), 3,3′-di-O-methyl ellagic acid-4-O-β-D-glucopyranoside (4), myricetin-3-O-rhamnoside (5), shikimic acid (6), arjungenin (7), terminolic acid (8), 24-deoxysericoside (9), arjunglucoside I (10), and chebuloside II (11). The derivatives of ellagic acid (1–4) showed moderate to good inhibition of cholinesterases, with the most potent being 3,3′-di-O-methyl ellagic acid, with IC50 values of 46.77 ± 0.90 µg/mL and 50.48 ± 1.10 µg/mL against AChE and BChE, respectively. The compounds exhibited potential inhibition of α-amylase and α-glucosidase, especially the phenolic compounds (1–5). Myricetin-3-O-rhamnoside had the highest α-amylase inhibition with an IC50 value of 65.17 ± 0.43 µg/mL compared to acarbose with an IC50 value of 32.25 ± 0.36 µg/mL. Two compounds, 3,3′-di-O-methyl ellagic acid (IC50 = 74.18 ± 0.29 µg/mL) and myricetin-3-O-rhamnoside (IC50 = 69.02 ± 0.65 µg/mL), were more active than the standard acarbose (IC50 = 87.70 ± 0.68 µg/mL) in the α-glucosidase assay. For α-glucosidase and α-amylase, the molecular docking results for 1–11 reveal that these compounds may fit well into the binding sites of the target enzymes, establishing stable complexes with negative binding energies in the range of −4.03 to −10.20 kcalmol−1. Though not all the compounds showed binding affinities with cholinesterases, some had negative binding energies, indicating that the inhibition was thermodynamically favorable.

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Section: Discussionmentioning

confidence: 99%

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

Feunaing,

Tamfu,

Gbaweng

et al. 2024

Molecules

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“…[71] Medicinal plant extracts as well as natural compounds are a considerable source of α-amylase and α-glucosidase therapies with low toxicity. [72,73] By inhibiting these two carbohydrates hydrolysing enzymes (α-amylase and α-glucosidase), reduction of blood glucose levels can be achieved and this is a suitable strategy in the treatment of type 2 diabetes mellitus, hence consuming foods that contain inhibitors of carbohydrate hydrolysing enzymes is recommended diabetic patients. [74] G. kola was more active than C. acuminata and none of them was more active than the standard acarbose though their activities were close of this standard.…”

Section: Discussionmentioning

confidence: 99%

HPLC-DAD Phenolic Composition, Antioxidant, Anticholinesterase, Antidiabetic and Anti-quorum Sensing Properties of Bitter Kola (Garcinia kola) and Kolanut (Cola acuminata)

Boudiba¹,

Küçükaydın²,

Tamfu³

et al. 2023

Pharmacogn. Res.

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Background: Eating Cola acuminata and Garcinia cola nuts in African societies symbolizes in socio-cultural hospitality. They stimulate the nervous system, reduce fatigue and sleep. Objectives: To determine the phenolic composition and bioactivities of G. kola and C. acuminata. Materials and Methods: Hydro-ethanol extracts of the nuts were prepared and their phenolic profiles determined using HPLC-DAD. Antioxidant, anticholinesterase, antidiabetic, antimicrobial, antibiofilm and anti-quorum sensing properties were determined. Results: The most abundant phenolic compound was caffeic acid (105.4±0.75 mg/g) in C. acuminata and myricetin (277.2±0.90 mg/g) in G. kola. The extracts showed good antioxidant activity in five complementary assays and G. kola was more active than both α-tocopherol and BHA standards in the DPPH • , CUPRAC and ABTS •+ assays while C. acuminata was more active than only the α-tocopherol standard in the same assays. Activities were close to those of standards in the β-Carotene-linoleic acid and metal chelation assays. Both extracts had good inhibition of Butyrylcholinesterase (BChE) and Acetylcholinesterase (AChE) with IC 50 values 63.27±0.98 µg/mL and 94.15±1.05 µg/mL for C. acuminata and G. kola respectively compared to 5.50±0.25 µg/mL for galantamine in the AChE assay. In the BChE assay, the inhibitory activity was higher for G. kola (IC 50 = 38.66±0.80 µg/ mL) that the standard galantamine (IC 50 = 42.20±0.48 µg/mL) while that for C. acuminata (IC 50 = 87.31±0.77 µg/mL) was moderate. The extracts inhibited α-amylase and α-glucosidase with G. kola (IC 50 =18.43±0.74 µg/mL) being more active than standard acarbose (IC 50 =20.52±0.84 µg/mL in the α-glucosidase assay. The nuts could inhibit expression of virulence factors in Chomobacterium violaceum CV12472 by disrupting violacein production and flagellated Pseudomonas aeruginosa PA01 by disrupting swarming motility. Conclusion: The results indicate good nutraceutical potential of both nuts.

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“…Certain drugs, including miglitol, voglibose, acarbose and pycnogenol, are usually used to manage hyperglycemia, though some undesirable side effects, such as diarrhea, abdominal pain, flatulence, bloating and discomfort, have been observed [ 21 ]. This issue motivates the ongoing research into natural antidiabetic compounds, such as phenolics, terpenoids, flavonoids, alkaloids and coumarins from medicinal plants [ 22 , 23 , 24 ]. The inhibition of carbohydrate digestive enzymes (α-amylase and α-glucosidase) is a good means of reducing blood glucose levels to normal, and various phytochemicals and several synthetic compounds were previously applied to this effect, especially those that are able to restrict or prevent glycoside and starch hydrolysis [ 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Anticholinesterase and Antidiabetic Effects of Furanolabdanes and Other Constituents from Graptophyllum pictum (Linn.) Griffith

Metiefeng,

Tamfu,

Fotsing Tagatsing

et al. 2023

Molecules

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Graptophyllum pictum is a tropical plant noticeable for its variegated leaves and exploited for various medicinal purposes. In this study, seven compounds, including three furanolabdane diterpenoids, i.e., Hypopurin E, Hypopurin A and Hypopurin B, as well as with Lupeol, β-sitosterol 3-O-β-d-glucopyranoside, stigmasterol 3-O-β-d-glucopyranoside and a mixture of β-sitosterol and stigmasterol, were isolated from G. pictum, and their structures were deduced from ESI-TOF-MS, HR-ESI-TOF-MS, 1D and 2D NMR experiments. The compounds were evaluated for their anticholinesterase activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BchE), as well as their antidiabetic potential through inhibition of α-glucosidase and α-amylase. For AChE inhibition, no sample had IC50 within tested concentrations, though the most potent was Hypopurin A, which had a percentage inhibition of 40.18 ± 0.75%, compared to 85.91 ± 0.58% for galantamine, at 100 µg/mL. BChE was more susceptible to the leaves extract (IC50 = 58.21 ± 0.65 µg/mL), stem extract (IC50 = 67.05 ± 0.82 µg/mL), Hypopurin A (IC50 = 58.00 ± 0.90 µg/mL), Hypopurin B (IC50 = 67.05 ± 0.92 µg/mL) and Hypopurin E (IC50 = 86.90 ± 0.76 µg/mL). In the antidiabetic assay, the furanolabdane diterpenoids, lupeol and the extracts had moderate to good activities. Against α-glucosidase, lupeol, Hypopurin E, Hypopurin A and Hypopurin B had appreciable activities but the leaves (IC50 = 48.90 ± 0.17 µg/mL) and stem (IC50 = 45.61 ± 0.56 µg/mL) extracts were more active than the pure compounds. In the α-amylase assay, stem extract (IC50 = 64.47 ± 0.78 µg/mL), Hypopurin A (IC50 = 60.68 ± 0.55 µg/mL) and Hypopurin B (IC50 = 69.51 ± 1.30 µg/mL) had moderate activities compared to the standard acarbose (IC50 = 32.25 ± 0.36 µg/mL). Molecular docking was performed to determine the binding modes and free binding energies of Hypopurin E, Hypopurin A and Hypopurin B in relation to the enzymes and decipher the structure–activity relationship. The results indicated that G. pictum and its compounds could, in general, be used in the development of therapies for Alzheimer’s disease and diabetes.

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A new abietane-type diterpenoid from roots of Burkea africana Hook (Fabaceae) with α-amylase inhibitory potential

Cited by 10 publications

References 15 publications

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

HPLC-DAD Phenolic Composition, Antioxidant, Anticholinesterase, Antidiabetic and Anti-quorum Sensing Properties of Bitter Kola (Garcinia kola) and Kolanut (Cola acuminata)

In Vitro and In Silico Evaluation of Anticholinesterase and Antidiabetic Effects of Furanolabdanes and Other Constituents from Graptophyllum pictum (Linn.) Griffith

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