Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition

Riemer, Martin; Uzunova, Veselina; Riemer, Nastja; Clarkson, Guy J.; Pereira, Nicole; Napier, Richard; Shipman, Michael

doi:10.1039/c8cc03349h

Cited by 7 publications

(3 citation statements)

References 26 publications

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“…This problem can be partially solved by searching and synthesizing simplified analogs of NPs [ 204 ]. For example, reduced active analogs of the fungal phytotoxins phyllostictin A [ 207 ], ophiobolin A [ 208 ], macrocidin A [ 209 ] were obtained.…”

Section: Natural Phytotoxins As Prototypes Of Synthetic Herbicidesmentioning

confidence: 99%

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Berestetskiy

2023

Plants

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Weeds are a permanent component of anthropogenic ecosystems. They require strict control to avoid the accumulation of their long-lasting seeds in the soil. With high crop infestation, many elements of crop production technologies (fertilization, productive varieties, growth stimulators, etc.) turn out to be practically meaningless due to high yield losses. Intensive use of chemical herbicides (CHs) has led to undesirable consequences: contamination of soil and wastewater, accumulation of their residues in the crop, and the emergence of CH-resistant populations of weeds. In this regard, the development of environmentally friendly CHs with new mechanisms of action is relevant. The natural phytotoxins of plant or microbial origin may be explored directly in herbicidal formulations (biorational CHs) or indirectly as scaffolds for nature-derived CHs. This review considers (1) the main current trends in the development of CHs that may be important for the enhancement of biorational herbicides; (2) the advances in the development and practical application of natural compounds for weed control; (3) the use of phytotoxins as prototypes of synthetic herbicides. Some modern approaches, such as computational methods of virtual screening and design of herbicidal molecules, development of modern formulations, and determination of molecular targets, are stressed as crucial to make the exploration of natural compounds more effective.

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Section: Natural Phytotoxins As Prototypes Of Synthetic Herbicidesmentioning

confidence: 99%

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Berestetskiy

2023

Plants

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“…Частично это проблему можно решить путем поиска и синтеза упрощенных аналогов ПС (Sparks, Duke, 2021). Например, получены упрощенные активные аналоги грибных фитотоксинов филлостиктина А (Riemer et al, 2018), офиоболина А (Tao et al, 2020), макроцидинов А и Z (Treiber et al, 2021).…”

Section: природные фитотоксины как прототипы синтетических гербицидовunclassified

Prospects for the development of new herbicides based on natural compounds

Berestetskiy

2023

1727-1320

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Growing most major crops currently involves the use of chemical herbicides to control weeds. However, their regular use can lead to such undesirable consequences as contamination of soil and groundwater, accumulation of their residues in the crop, and the emergence of resistant populations of weeds. Therefore, developing of eco-friendly herbicides with new mechanisms of action is necessary. Natural phytotoxins of plant or microbial origin can serve as prototypes for active ingredients of chemical herbicides. This review considers: 1) the main modern trends in the development of chemical herbicides; 2) practical achievements in the use of natural compounds for weed control; 3) the use of phytotoxins as the basic components of synthetic herbicides. Analysis of the existing literature allowed us to identify some important approaches for the development of nature-derived herbicides: 1) the combination of virtual screening of libraries of natural compounds with high-throughput screening of selected substances in vitro and in vivo; 2) computer modelling and optimization of molecules using physico-chemical predictors and molecular docking; 3) development of new adjuvants and formulations, in particular on nanoscale, to reduce the application rates of active substances and the risks of their accumulation in the environment. The use of these approaches is likely to lead to the discovery of new promising herbicidal molecules for use in both organic and conventional agriculture.

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“…This problem can be partially solved by searching and synthesizing simplified analogues of NPs [204]. For example, reduced active analogues of the fungal phytotoxins phyllostictin A [207], ophiobolin A [208], macrocidins A and Z [209] were obtained.…”

Section: Natural Phytotoxins As Prototypes Of Synthetic Herbicidesmentioning

confidence: 99%

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Berestetskiy¹

2022

Preprint

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Weeds are a permanent component of anthropogenic ecosystems, which requires strict control to avoid the accumulation of their long–lasting seeds in the soil. With high crop infestation, many elements of crop production technologies (fertilization, productive varieties, growth stimulators, etc.) turn out to be practically meaningless due to high yield losses. Intensive use of chemical herbicides (CH) has led to undesirable consequences: contamination of soil and wastewater, accumulation of their residues in the crop, the emergence of CH-resistant populations of weeds. In this regard, the development of environmentally friendly CH with new mechanisms of action is relevant. Natural phytotoxins of plant or microbial origin may be directly explored in herbicidal formulations (biorational CH) or indirectly as scaffolds for nature-derived CH. This review considers: 1) the main current trends in the development of CH that may be important for enhancement of biorational herbicides; 2) advances in the development and practical application of natural compounds for weed control; 3) the use of phytotoxins as prototypes of synthetic herbicides. Some modern approaches such as computational methods of virtual screening and design herbicidal molecules, development of modern formulations, determination of molecular targets are stressed as important to make exploration of natural compounds more effective.

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Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition

Abstract: The first total synthesis of phyllostictine A is reported and evidence presented that the heterocyclic subunit is the key to the μM herbicidal activity.

Cited by 7 publications

References 26 publications

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

Prospects for the development of new herbicides based on natural compounds

Modern Approaches for the Development of New Herbicides Based on Natural Compounds

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