Semisynthesis, biological activities, and mechanism studies of Mannich base analogues of magnolol/honokiol as potential α-glucosidase inhibitors

Chu, Junyan; Yang, Ruige; Cheng, Wanqing; Cui, Liping; Pan, Hanchen; Liu, Jifeng; Guo, Yong

doi:10.1016/j.bmc.2022.117070

Cited by 9 publications

(4 citation statements)

References 29 publications

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“…To improve its α-glucosidase inhibitory activity, Chu et al prepared four series of new HK Mannich analogues by a one-pot reaction. [96] Through enzyme kinetic and molecular docking studies, the α-glucosidase inhibitory activities of all HK analogues in vitro was evaluated, and inhibition mechanism of some potent analogues was investigated. In further, based on its inhibition of α-glucosidase and its association with metabolic disorders, including obesity and diabetes, HK is considered a suitable candidate for the treatment of obesity.…”

Section: Novel Pharmacological Mechanisms Of Hkmentioning

confidence: 99%

“…In some earlier studies, HK was found to have the ability to inhibit α‐glucosidase and reduce blood glucose levels in diabetic mice, but the effect was not very prominent. To improve its α‐glucosidase inhibitory activity, Chu et al prepared four series of new HK Mannich analogues by a one‐pot reaction [96] . Through enzyme kinetic and molecular docking studies, the α‐glucosidase inhibitory activities of all HK analogues in vitro was evaluated, and inhibition mechanism of some potent analogues was investigated.…”

Section: Novel Pharmacological Mechanisms Of Hkmentioning

confidence: 99%

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Delivery Strategies, Structural Modification, and Pharmacological Mechanisms of Honokiol: A Comprehensive Review

Pan,

Li,

Xiong

et al. 2024

Chemistry & Biodiversity

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Honokiol (HK) is a traditional Chinese herbal bioactive compound that originates mainly from the Magnoliaspecies, traditionally used to treat anxiety and stroke, as well as alleviation of flu symptoms. This natural product and its derivatives displayed diverse biological activities, including anticancer, antioxidant, anti‐inflammatory, neuroprotective, and antimicrobial activities. However, its poor bioavailability and pharmacological activity require primary consideration in the development of HK‐based drugs. Recent innovative HK formulations based on the nanotechnology approach allowed for improvement in both bioavailability and therapeutic efficacy. Chemical derivation and drug combination are also effective strategies to ameliorate the drawbacks of HK. In recent years, studies on HK derivatives and compositions have made great progress in the treatment of cancer, inflammation, antibacterial, cardiovascular, and cerebrovascular diseases, demonstrating better activity than HK. The objective of this review is an examination of the recent developments in the field of pharmacological activity of HK and its drug‐related issues, and approaches to improve its physicochemical and biological properties, including solubility, stability, and bioavailability. Recent patents and the ongoing clinical trials in HK are also summarized.

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Section: Novel Pharmacological Mechanisms Of Hkmentioning

confidence: 99%

Section: Novel Pharmacological Mechanisms Of Hkmentioning

confidence: 99%

Delivery Strategies, Structural Modification, and Pharmacological Mechanisms of Honokiol: A Comprehensive Review

Pan,

Li,

Xiong

et al. 2024

Chemistry & Biodiversity

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“…Briefly, the stereochemical structure of compound 3n was first drawn by ChemDraw 19.0 software, and then the above file was imported into Discovery Studio to complement the hydrogen atoms and minimize spatial structure energy using the CHARMM force field. 32 The 3D structure of GST (PDB ID: 3VUR) was downloaded from the RCSB Protein Data Bank (www.rcsb.org), and the structure was preprocessed through Discovery Studio. 33 In this study, the semiflexible molecular docking algorithm CDOCKER was used for molecular docking studies.…”

Section: Synthesis Of 13-bromo-(+)-nootkatone (2)mentioning

confidence: 99%

Discovery of Novel (+)-Nootkatone-Based Amine Derivatives as Potential Insecticide Candidates

Guo,

Han,

Zhong

et al. 2024

J. Agric. Food Chem.

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To discover novel natural product-based insecticides, a series of (+)-nootkatone-based amine derivatives 3a−t were prepared and evaluated for their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal assays showed that most of the title (+)-nootkatone derivatives exhibited stronger insecticidal activities against three insect pests than the precursor (+)-nootkatone after the introduction of amine groups on the parent (+)-nootkatone. Compounds 3a, 3d, 3h, 3m, 3n, 3p, and 3r displayed more promising growth inhibitory (GI) effect against M. separata than the commercially available botanical insecticide toosendanin. Compound 3o exhibited the most potent aphicidal activity with an LD 50 value of 0.011 μg/larvae, which was 2.09-fold higher than the positive control rotenone. Additionally, compounds 3g and 3n showed more promising larvicidal activity against P. xylostella with LC 50 values of 260 and 230 mg/L, respectively, superior to that of rotenone (460 mg/L). Moreover, derivatives 3g and 3n exhibited better control efficacy toward P. xylostella than rotenone under greenhouse conditions. Preliminary mechanistic studies revealed that derivative 3n could inhibit the activity of glutathione Stransferase (GST) in P. xylostella and thus exerted larvicidal activity, and molecular docking further demonstrated that 3n could interact well with some amino acid residues of GST. Finally, the toxicity assay suggested that derivatives 3g and 3n were relatively less toxic to nontarget organisms. These findings will provide insights into the development of (+)-nootkatone derivatives as green pesticides.

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“…For this reason, recent works have been dedicated to the synthesis of new analogues inspired by magnolol and honokiol with the purpose of enhancing their biological activities [ 16 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Reaction with ROO• and HOO• Radicals of Honokiol-Related Neolignan Antioxidants

et al. 2023

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Honokiol is a natural bisphenol neolignan present in the bark of Magnolia officinalis, whose extracts have been employed in oriental medicine to treat several disorders, showing a variety of biological properties, including antitumor activity, potentially related to radical scavenging. Six bisphenol neolignans with structural motifs related to the natural bioactive honokiol were synthesized. Their chain-breaking antioxidant activity was evaluated in the presence of peroxyl (ROO•) and hydroperoxyl (HOO•) radicals by both experimental and computational methods. Depending on the number and position of the hydroxyl and alkyl groups present on the molecules, these derivatives are more or less effective than the reference natural compound. The rate constant of the reaction with ROO• radicals for compound 7 is two orders of magnitude greater than that of honokiol. Moreover, for compounds displaying quinonic oxidized forms, we demonstrate that the addition of 1,4 cyclohexadiene, able to generate HOO• radicals, restores their antioxidant activity, because of the reducing capability of the HOO• radicals. The antioxidant activity of the oxidized compounds in combination with 1,4-cyclohexadiene is, in some cases, greater than that found for the starting compounds towards the peroxyl radicals. This synergy can be applied to maximize the performances of these new bisphenol neolignans.

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Semisynthesis, biological activities, and mechanism studies of Mannich base analogues of magnolol/honokiol as potential α-glucosidase inhibitors

Cited by 9 publications

References 29 publications

Delivery Strategies, Structural Modification, and Pharmacological Mechanisms of Honokiol: A Comprehensive Review

Delivery Strategies, Structural Modification, and Pharmacological Mechanisms of Honokiol: A Comprehensive Review

Discovery of Novel (+)-Nootkatone-Based Amine Derivatives as Potential Insecticide Candidates

Reaction with ROO• and HOO• Radicals of Honokiol-Related Neolignan Antioxidants

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