Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens

Lu, Jing-Guang; Wang, Yingwei; Yang, Ming-Rong; Wang, Cai-Yun; Meng, Jie-Ru; Liu, Jiazheng; Yang, Zifeng; Wu, Kongsong; Bai, Liping; Zhu, Guo‐Yuan; Jiang, Zhihong

doi:10.1007/s12272-022-01401-6

Cited by 8 publications

(3 citation statements)

References 37 publications

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“…The coordinates of the protein active site were set according to the location of the original ligand in the GST. To increase the accuracy of the calculation and to generate more docking conformations, the Pose Cluster Radius parameter was set to 0.5, and the default values were used for all other parameters . Finally, the conformation with the highest docking score was selected for the binding mode analysis.…”

Section: Methodsmentioning

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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Section: Methodsmentioning

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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“…Racemic decumicorine A 13 and a diepimer, from rhizomes of Corydalis decumbens , are the first examples of phenylpropanoid-conjugated protoberberine alkaloids. 12 The structures of the alkaloids were confirmed by X-ray analyses and biomimetic synthesis involving a Diels–Alder cycloaddition. The hydrothermal vent-associated fungus Penicillium citrinum TW132-59 produces a range of citrinin-derived metabolites including citrinidines A 14 – E that have an unusual tetracyclic core.…”

mentioning

confidence: 90%

Hot off the press

Hill

Sutherland

2022

Nat. Prod. Rep.

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“…Phenylpropanoids, including magnolol, coumarin, and arctigenin, are characterised by the possession of a C6-C3 backbone and have been widely reported for their antiviral activity. 137,138 Therefore, studying the SAR of these compounds is necessary to provide a basis for the development of aquatic-specific antiviral drugs. Previous research has shown that the hydroxyl group of magnolol is their main active group and cannot be oxidised or substituted.…”

Section: Structure Activity Relationship Of Active Ingredients Isolat...mentioning

confidence: 99%

The antiviral activity of currently used medicinal plants in aquaculture and structure–activity relationship of their active ingredients

Zhang

Shan

et al. 2023

Reviews in Aquaculture

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Aquaculture is an important source of high‐quality protein and plays a crucial role in ensuring global food security. However, viral diseases have caused significant damage to aquaculture production, making it necessary to develop effective measures to treat them. Although drugs are commonly used to treat viral diseases, recent studies have shown that crude extracts of medicinal plants and their active ingredients have potential applications in the treatment of aquatic viral diseases. Furthermore, natural small molecule compounds from herbs could be used as lead compounds to develop more potent anti‐aquatic virus derivatives. As such, there is an urgent need to develop and apply drugs for the treatment of viral disease outbreaks in aquaculture. In this review, we summarize previous studies on the efficacy of different agents used as antiviral drugs in aquaculture, with a focus on their protective effects. Additionally, we highlight the potential of active natural compounds isolated from medicinal plants, which could serve as lead compounds for developing aquatic‐specific drugs. However, the relationship between the structure of a compound and its antiviral activity in aquaculture has not been clearly elucidated, posing a challenge for further drug optimisation. Therefore, this study also analyses the structure–activity relationship of several reported lead compounds and their derivatives in aquaculture, providing a reference for subsequent drug development efforts.

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Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens

Cited by 8 publications

References 37 publications

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

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

Hot off the press

The antiviral activity of currently used medicinal plants in aquaculture and structure–activity relationship of their active ingredients

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