Synthesis and Anti-Tobacco Mosaic Virus/Fungicidal/Insecticidal/Antitumor Bioactivities of Natural Product Hemigossypol and Its Derivatives

Li, Ling; Zou, Jiyong; Xu, Changjiang; You, Shengyong; Li, Yongqiang; Wang, Qingmin

doi:10.1021/acs.jafc.0c06058

Cited by 19 publications

(19 citation statements)

References 24 publications

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“…TMV was According to Gooding’s method[23], TMV virions maintained in N. tabacum cv. K326 were extracted and purified from the harvested leaves of systemically inoculated seedlings by homogenization in 0.01 M PBS (phosphate-buffered saline) buffer.…”

Section: Methodsmentioning

confidence: 99%

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Feng

Jia

Guan

et al. 2021

Preprint

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Background Acetone ethanol extracts from tobacco leaves have antiviral activity against TMV, but the antiviral effects of their specialized metabolites have not been systematically studied yet, especially the underlying mechanism is still unexplored. Results The tobacco cembranoids α(β)-2,7,11-cembratriene-4,6-diol (α(β)-CBD) were extracted and purified with an effective and green protocol including innovatively added 5% phosphoric acid for elution, one time silica gel chromatographic column separation and impurity removal and further HPLC purification. The results of antiviral activities against tobacco mosaic virus (TMV) with the local lesion counting method showed that α(β)-CBD have in vivo higher protective effects of 73.2% and 71.6%, at 75.0 μM, respectively, than control agent Ningnanmycin (53.1%). Notably, The results of ELISA and and TMV-GFP fluorescent optical imaging assay indicated a obviously reduced viral protein and weaker GFP fluorescence signal and smaller infection area, which confirmed their anti-TMV activities at protein level. Furthermore, the enhanced production of SA and JA and the significantly increased transcription of of JA signaling pathway (COI1 and PDF1.2) and SA signaling pathway genes (PR1, NPR1 and EDS1) in treated plants further conformed that exogenously applied α(β)-CBD can effectively elicit the tobacco plant immunity against TMV. Conclusions The α(β)-CBD mainly stimulates disease resistance of tobacco plants to resist TMV and it can be used as bioagents to control TMV in the future.

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Section: Methodsmentioning

confidence: 99%

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Feng

Jia

Guan

et al. 2021

Preprint

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“…Wang et al . found some β-carboline analogues 7 , hemigossypol 13 , dehydrobufotenine derivatives 14 , pityriacitrin marine alkaloids 15 , pulmonarin alkaloids 16 and hamacanthin derivatives 17 exhibited higher anti-TMV activities than ningnanmycin. Many other natural alkaloids derivatives were also developed as potential TMV inhibitors 18 – 27 .…”

Section: Introductionmentioning

confidence: 98%

Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety

Cui

Cai

et al. 2022

Sci Rep

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Based on the broad-spectrum biological activities of echinopsine and acylhydrazones, a series of echinopsine derivatives containing acylhydrazone moieties have been designed, synthesized and their biological activities were evaluated for the first time. The bioassay results indicated that most of the compounds showed moderate to good antiviral activities against tobacco mosaic virus (TMV), among which echinopsine (I) (inactivation activity, 49.5 ± 4.4%; curative activity, 46.1 ± 1.5%; protection activity, 42.6 ± 2.3%) and its derivatives 1 (inactivation activity, 44.9 ± 4.6%; curative activity, 39.8 ± 2.6%; protection activity, 47.3 ± 4.3%), 3 (inactivation activity, 47.9 ± 0.9%; curative activity, 43.7 ± 3.1%; protection activity, 44.6 ± 3.3%), 7 (inactivation activity, 46.2 ± 1.6%; curative activity, 45.0 ± 3.7%; protection activity, 41.7 ± 0.9%) showed higher anti-TMV activity in vivo at 500 mg/L than commercial ribavirin (inactivation activity, 38.9 ± 1.4%; curative activity, 39.2 ± 1.8%; protection activity, 36.4 ± 3.4%). Some compounds exhibited insecticidal activities against Plutella xylostella, Mythimna separate and Spodoptera frugiperda. Especially, compounds 7 and 27 displayed excellent insecticidal activities against Plutella xylostell (mortality 67 ± 6% and 53 ± 6%) even at 0.1 mg/L. Additionally, most echinopsine derivatives exhibited high fungicidal activities against Physalospora piricola and Sclerotinia sclerotiorum.

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“…8,9 Meanwhile, an increasing number of antiplant virus agents are being discovered and developed from natural products. [10][11][12] Ferulic acid, a kind of natural phenolic acid, was isolated from fruits and vegetables. 13 It has been reported that ferulic acid and its derivatives have various biological activities, including antiviral, 14 antibacterial 15 and herbicidal activities.…”

Section: Introductionmentioning

confidence: 99%

Ferulic acid derivatives with piperazine moiety as potential antiviral agents

Yuan

Wang

Liú

et al. 2022

Pest Management Science

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Background Plant virus diseases are difficult to control and severely threaten the productivity of crops, which leads to huge financial losses. To discover the new antiviral drugs, 34 novel ferulic acid derivatives with piperazine moiety were synthesized, and the antiviral activities were systematically screened as well. Results Bioassay results indicated that most of the target compounds had outstanding antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo. In particular, compound E2 exhibited remarkable curative activities to TMV and CMV with EC50 values of 189.0 and 401.7 μg/mL compared to those for ningnanmycin (387.0, 519.3 μg/mL) and ribavirin (542.1, 721.5 μg/mL). And then the mechanisms of compound E2 were studied by chlorophyll content, differentially expressed proteins and genes tests. Conclusion The excellent antiviral activity of compound E2 was closely associated with the increase in host photosynthesis, which was confirmed by chlorophyll content, differentially expressed proteins and genes assays. Compound E2 can be considered as a lead structure for the discovery of new antiviral agents. © 2022 Society of Chemical Industry.

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Synthesis and Anti-Tobacco Mosaic Virus/Fungicidal/Insecticidal/Antitumor Bioactivities of Natural Product Hemigossypol and Its Derivatives

Cited by 19 publications

References 24 publications

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Extraction, purification and anti-TMV effects of α (β)-2,7,11-cembratriene-4,6-diol from tobacco leaves

Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety

Ferulic acid derivatives with piperazine moiety as potential antiviral agents

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