α-Glucosidase inhibitors from Chinese bayberry (<i>Morella rubra</i>Sieb. et Zucc.) fruit: molecular docking and interaction mechanism of flavonols with different B-ring hydroxylations

Liu, Yilong; Zhan, Liuhuan; Xu, Chang; Jiang, Huamin; Zhu, Changqing; Sun, Lu; Sun, Chongde; Li, Xian

doi:10.1039/d0ra05015f

Cited by 40 publications

(50 citation statements)

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“…Kaempferol (K), quercetin (Q), and myricetin (M) are three major flavonol aglycones that differ in the number of hydroxyl groups on the B‐ring, with M (3′,4′,5′‐trihydroxy) having the highest number (Figure 1). M has been shown to be more beneficial for human health than either Q or K (Lu et al., 2006; Kumamoto et al., 2009; Liu et al., 2020). M has shown significant inhibitory effects on skin cancer (Jung et al., 2008), pancreatic cancer (Phillips et al., 2011), and α‐glucosidase activity (Liu et al., 2020), and is also an effective inhibitor of severe acute respiratory syndrome coronavirus helicase (Keum and Jeong, 2012; Yu et al., 2012).…”

Section: Introductionmentioning

confidence: 99%

“…M has been shown to be more beneficial for human health than either Q or K (Lu et al., 2006; Kumamoto et al., 2009; Liu et al., 2020). M has shown significant inhibitory effects on skin cancer (Jung et al., 2008), pancreatic cancer (Phillips et al., 2011), and α‐glucosidase activity (Liu et al., 2020), and is also an effective inhibitor of severe acute respiratory syndrome coronavirus helicase (Keum and Jeong, 2012; Yu et al., 2012). Recently, a myricetin derivative named montbretin A was identified by screening a library of 50 000 plant natural products as a specific inhibitor of human pancreatic α‐amylase and is therefore an important candidate therapeutic agent for diabetes and obesity treatments (Tarling et al., 2008; Williams et al., 2015).…”

Section: Introductionmentioning

confidence: 99%

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Elucidation of myricetin biosynthesis in Morella rubra of the Myricaceae

et al. 2021

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SUMMARY Flavonols are health‐promoting bioactive compounds important for plant defense and human nutrition. Quercetin (Q) and kaempferol (K) biosynthesis have been studied extensively while little is known about myricetin (M) biosynthesis. The roles of flavonol synthases (FLSs) and flavonoid 3′,5′‐hydroxylase (F3′5′H) in M biosynthesis in Morella rubra, a member of the Myricaceae rich in M‐based flavonols, were investigated. The level of MrFLS transcripts alone did not correlate well with the accumulation of M‐based flavonols. However, combined transcript data for MrFLS1 and MrF3′5′H showed a good correlation with the accumulation of M‐based flavonols in different tissues of M. rubra. Recombinant MrFLS1 and MrFLS2 proteins showed strong activity with dihydroquercetin (DHQ), dihydrokaempferol (DHK), and dihydromyricetin (DHM) as substrates, while recombinant MrF3′5′H protein preferred converting K to M, amongst a range of substrates. Tobacco (Nicotiana tabacum) overexpressing 35S::MrFLSs produced elevated levels of K‐based and Q‐based flavonols without affecting M‐based flavonol levels, while tobacco overexpressing 35S::MrF3′5′H accumulated significantly higher levels of M‐based flavonols. We conclude that M accumulation in M. rubra is affected by gene expression and enzyme specificity of FLS and F3′5′H as well as substrate availability. In the metabolic grid of flavonol biosynthesis, the strong activity of MrF3′5′H with K as substrate additionally promotes metabolic flux towards M in M. rubra.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Elucidation of myricetin biosynthesis in Morella rubra of the Myricaceae

et al. 2021

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“…Furthermore, it has been demonstrated that quercetin and kaempferol in S. lanuginosum and rosmarinic acid present on E. tinifolia are effective inhibitors of this enzyme [55,56]. Considering these compounds as the main polyphenols of extracts activity, the mechanism of α-glucosidase inhibition by wild fruit extracts could be due to the non-competitive or mixed-type interactions that polyphenols such as quercetin, kaempferol [57][58][59], and rosmarinic acid [60] maintain with the enzyme. Further studies must be done to determine the mechanism of action of S. lanuginosum and E. tinifolia extracts.…”

Section: Inhibition Of α-Glucosidasementioning

confidence: 99%

Phenolic Profiles and Biological Activities of Extracts from Edible Wild Fruits Ehretia tinifolia and Sideroxylon lanuginosum

Monroy-García

Carranza-Torres

Carranza-Rosales

et al. 2021

Foods

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Ehretia tinifolia Linnaeus (Boraginacea) and Sideroxylon lanuginosum Michaux (Sapotaceae) are wild fruits consumed in North America and are appreciated for their pleasant flavor and sweet taste. However, details regarding their composition and biological properties in the available literature are scarce. This study reports the phenolic composition, antioxidant, antiproliferative activities, and digestive enzymatic inhibition of amberlite-retained methanolic extracts from both fruits. Results revealed that these wild fruit extracts are rich in antioxidants. S. lanuginosum had lower phenolic but higher flavonoid contents (21.4 ± 1.5 mg GAE/100 g FW and 6.42 ± 0.9 mg CE/100 g FW) than E. tinifolia (64.7 ± 2.6 mg GAE/100 g FW and 5.1 ± 0.4 mg CE/100 g FW). HPLC-DAD-MS/MS analysis showed rosmarinic acid as a major polyphenol in E. tinifolia and quercetin glucoside in S. lanuginosum. Polyphenols content in E. tinifolia was related to a significant free radical scavenging ability: DPPH (EC50 = 0.32 ± 0.03 mg/mL), TEAC (4134 ± 9.7 μM TE/g dry extract), and hemolysis inhibition (IC50 = 58.55 ± 2.4 μg/mL). Both extracts were capable of inhibiting α-glucosidase, partially inhibiting α-amylase, and showed no inhibition against lipase, while showing antiproliferative activity against HeLa, HT-29 and MCF-7 cancer cell lines. Our study revealed that these wild fruit extracts are rich in health-beneficial phytochemicals and hold significant potential for elaborating functional foods.

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“…[1][2][3][4] Control of blood sugar levels is critical in diabetes therapy as it is associated with a marked reduction in the risk of developing complications such as neuropathy, retinopathy, or cardiovascular diseases. [5][6][7] α-Glucosidase plays an important role in carbohydrate digestion and glycoprotein biosynthesis. The inhibition of α-glucosidase involves two small intestinal membrane-bound enzymes: maltase-glucoamylase (MGAM) and sucrase-isomaltase (SI); these are implicated in the breakdown of dietary sugars and starches.…”

Section: Introductionmentioning

confidence: 99%

“…Diabetes mellitus (MD) is a group of metabolic diseases characterized by high blood glucose levels (hyperglycemia), which play a pivotal role in the development of long‐term diabetic complications [1–4] . Control of blood sugar levels is critical in diabetes therapy as it is associated with a marked reduction in the risk of developing complications such as neuropathy, retinopathy, or cardiovascular diseases [5–7] …”

Section: Introductionmentioning

confidence: 99%

Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies

Duong

Nguyen

et al. 2021

Chemistry & Biodiversity

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A new natural Diels-Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4-18). Structural elucidation was conducted using NMR and HR-ESI-MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibited the most potent α-glucosidase inhibition (IC 50 7.80 � 0.1 μM), outperforming the acarbose positive control. This was mixed-mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An in silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α-glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus.

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α-Glucosidase inhibitors from Chinese bayberry (Morella rubraSieb. et Zucc.) fruit: molecular docking and interaction mechanism of flavonols with different B-ring hydroxylations

Abstract: Inhibition of α-glucosidase alleviates postprandial high glycemic levels in diabetic or prediabetic population.

Cited by 40 publications

References 62 publications

Elucidation of myricetin biosynthesis in Morella rubra of the Myricaceae

Elucidation of myricetin biosynthesis in Morella rubra of the Myricaceae

Phenolic Profiles and Biological Activities of Extracts from Edible Wild Fruits Ehretia tinifolia and Sideroxylon lanuginosum

Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies

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