Cytotoxic dihydrobenzofuran neolignans from Mappianthus iodoies

Jiang, Zhihua; Liu, Yan-Ping; Huang, Zehao; Wang, Tingting; Feng, Xing-Yang; Yue, Hao; Guo, Wei; Fu, Yan-Hui

doi:10.1016/j.bioorg.2017.10.003

Cited by 33 publications

(5 citation statements)

References 17 publications

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“…The absolute configuration was confirmed as 7 R ,8 S by the negative Cotton effect at 270 nm in the ECD spectrum ( Fig. 2 B; Jiang et al, 2017 ). So, compound 1 was identified and named (7 R ,8 S )-crataegifin A-4- O - β - D -glucopyranoside.…”

Section: Resultsmentioning

confidence: 80%

Chemical constituents from leaves of Jatropha curcas

Wang

Zhou

Bai

et al. 2023

Chinese Herbal Medicines

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Section: Resultsmentioning

confidence: 80%

Chemical constituents from leaves of Jatropha curcas

Wang

Zhou

Bai

et al. 2023

Chinese Herbal Medicines

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“…In this sense, Jiang and col. [9] have suggested that this behavior is not the same with all cell lines, where tested, and that it depends on the type of lignan for its cytotoxicity. Multiple lignans are being studied, particularly for their effectiveness against breast cancer.…”

Section: Introductionmentioning

confidence: 98%

Cytotoxicity and Antitumor Action of Lignans and Neolignans

Esquivel-Campos¹,

Pérez-Gutiérrez²,

Sánchez-Pérez³

et al. 2022

Secondary Metabolites - Trends and Reviews

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Lignans and neolignans are plant’s secondary metabolites, widely distributed in the plant kingdom, and have been identified in more than 70 plant families. These compounds are mainly localized in lignified tissues, seeds, and roots. Lignans and neolignans present a great variety of biological activities, such as antioxidant, anti-inflammatory, antineurodegenerative, antiviral, antimicrobial, and antitumor. By 2040, it is estimated that the number of new cancer cases per year will rise to 29.5 million; therefore, the development of new anticancer agents and adjuvants is essential. Lignans and neolignans have also indicated a reduction in the risk of cancer at different stages. The objective of this review is to search and analyze the cytotoxic and antitumor activity of lignans and neolignans that can be an important source of new antitumor drugs. We have made a comprehensive summary of 113 lignans and neolignans, obtained from 44 plants and divided between 34 families, which demonstrated cytotoxic activity in several human cancer cell lines evaluated through various in vitro studies and other in vivo models, by inducing mitochondrial apoptosis and cell cycle arrest, inhibiting NF-κβ activity and activation of metalloproteinases (MMPs), among other processes. Overall, 13 compounds, methoxypinoresinol, arctigenin, trachelogenin, 4-O-methylhonokiol, honokiol, bifidenone, (−)-trachelogeninit, deoxypodophyllotoxin, matairesinol, bejolghotin G, H, and I, and hedyotol-B, showed the best anticancer activity.

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“…However, with the increasing resistance of pathogenic fungi to currently used fungicides, it is urgent to develop chiral pesticide antifungal agents with novel chemical structures to improve the antifugal performance. − Based on the previous literature investigation, it was suggested that drugs containing isoxazoline, benzofuran, and sulfonamide fragments maintained good bioactivity. , We attempted to link these three biologically active moieties to form isoxazoline-benzofuran-sulfonamide target compounds through the principle of bioactive group splicing, which has a significant influence on the bioactivity and efficacy (Figure ). To the best of our knowledge, this is the first example of utilizing chiral isoxazoline-benzofuran-sulfonamide as antifungal fungicides reported.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and Molecular Docking Studies of Novel Chiral Isoxazoline-Benzofuran-Sulfonamide Derivatives

Yan,

Bao,

Wang

et al. 2024

J. Agric. Food Chem.

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Succinate dehydrogenase (SDH) is one of the most important molecular targets for the development of novel fungicides. With the emerging problem of resistance in plant fungal pathogens, novel compounds with high fungicidal activity need to be developed, but the study of chiral pesticides for the inhibition of highly destructive plant pathogens has been rarely reported in recent years. Therefore, a series of novel chiral isoxazoline-benzofuran-sulfonamide derivatives were designed to investigate potential novel antifungal molecules. The chiral target compound 3a was cultured as a single crystal and confirmed using X-ray diffraction. All the target compounds were tested for antifungal activity, and compounds 3c, 3i, 3s, and 3r were found to have significant antifungal effects against S. sclerotiorum with EC 50 values of 0.42 mg/L, 0.33 mg/L, 0.37 mg/L, and 0.40 mg/L, respectively, which were superior to the commercial fungicide fluopyram (EC 50 = 0.47 mg/L). The IC 50 value of compound 3i against the SDH of S. sclerotiorum was 0.63 mg/mL, which was further demonstrated by enzyme activity assays. Scanning electron microscopy showed that 3i had a significant inhibitory effect on S. sclerotiorum. In addition, the fluorescence quenching analysis assay indicated that compound 3i had a similar effect with the positive control fluopyram. Molecular docking exhibited that target compounds with chiral configuration had better affinity than racemic configuration, and 3i possessed stronger action than fluopyram, which was in keeping with the in vitro test results. These results would provide a basis and reference for the development of novel chiral fungicides.

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Cytotoxic dihydrobenzofuran neolignans from Mappianthus iodoies

Cited by 33 publications

References 17 publications

Chemical constituents from leaves of Jatropha curcas

Chemical constituents from leaves of Jatropha curcas

Cytotoxicity and Antitumor Action of Lignans and Neolignans

Design, Synthesis, Antifungal Activity, and Molecular Docking Studies of Novel Chiral Isoxazoline-Benzofuran-Sulfonamide Derivatives

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