Gibberellic and kaurenoic hybrid strigolactone mimics for seed germination of parasitic weeds

Pereira, Rondinelle Gomes; Cala, Antonio; Fernández‐Aparicio, Mónica; Molinillo, José M. G.; Boaventura, Maria Amélia D.; Macías, Francisco A.

doi:10.1002/ps.4650

Cited by 13 publications

(20 citation statements)

References 37 publications

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“…Strigolactones are one of the principal broomrape/witchweed stimulators in suicidal germination methods, including their analogs and mimics (Fig. ).…”

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

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Recent advances in allelopathy for weed control: from knowledge to applications

Macías

Mejías

Molinillo

2019

Pest Management Science

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210

131

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Allelopathy is the biological phenomenon of chemical interactions between living organisms in the ecosystem, and must be taken into account in addressing pest and weed problems in future sustainable agriculture. Allelopathy is a multidisciplinary science, but in some cases, aspects of its chemistry are overlooked, despite the need for a deep knowledge of the chemical structural characteristics of allelochemicals to facilitate the design of new herbicides. This review is focused on the most important advances in allelopathy, paying particular attention to the design and development of phenolic compounds, terpenoids and alkaloids as herbicides. The isolation of allelochemicals is mainly addressed, but other aspects such as the analysis and activities of derivatives or analogs are also covered. Furthermore, the use of allelopathy in the fight against parasitic plants is included. The past 12 years have been a prolific period for publications on allelopathy. This critical review discusses future research areas in this field and the state of the art is analyzed from the chemist's perspective. © 2019 Society of Chemical Industry

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“…Strigolactones are one of the principal broomrape/witchweed stimulators in suicidal germination methods, including their analogs and mimics (Fig. ).…”

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

“…This compound inhibited germination of more than half of the seed population of O. crenata. 211 Strigolactones are one of the principal broomrape/witchweed stimulators in suicidal germination methods, 212 including their analogs 213 and mimics 214,215 (Fig. 11).…”

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

Recent advances in allelopathy for weed control: from knowledge to applications

Macías

Mejías

Molinillo

2019

Pest Management Science

Self Cite

210

131

View full text Add to dashboard Cite

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“…It is worth noting that more axillary growth1 (MAX1) has additive effects on N-PL activity in Arabidopsis, which indicates that N-PL might be subjected to further oxidation by MAX1, leading to a more active product. Various other scaffolds, such as acyclic carbon chain [347], GA 3 (compound 6, 179) [348], phthalimides (180) [349], and triazole (181) [350], have been recruited and coupled with a butenolide ring for the development of SL mimics (Figure 9(A)). Chemical genetic screening using yeast and Arabidopsis led to the identification of SL-related cotylimides (CTLs, 182; Figure 9(A)) that can induce suicidal germination [351,352].…”

Section: Strigolactonesmentioning

confidence: 99%

Chemical regulators of plant hormones and their applications in basic research and agriculture*

Jiang

Asami

2018

Bioscience, Biotechnology, and Biochemistry

119

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Plant hormones are small molecules that play versatile roles in regulating plant growth, development, and responses to the environment. Classic methodologies, including genetics, analytic chemistry, biochemistry, and molecular biology, have contributed to the progress in plant hormone studies. In addition, chemical regulators of plant hormone functions have been important in such studies. Today, synthetic chemicals, including plant growth regulators, are used to study and manipulate biological systems, collectively referred to as chemical biology. Here, we summarize the available chemical regulators and their contributions to plant hormone studies. We also pose questions that remain to be addressed in plant hormone studies and that might be solved with the help of chemical regulators.

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“…17 Since these compounds possess a lactone moiety (C-ring in strigolactones), the addition of an extra butenolide ring connected by an enol ether bond to 1 and 5 allows strigolactone analogues to be obtained. 18 The main objective of the work reported here is the preparation of new strigolactone analogues by the addition of the butenolide ring to the hydroxylated derivatives of 2, 3, 8 (Figure 2a), and 5 (Figure 2c). This is the first time that strigolactone analogues based on eudesmanolides have been reported.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Active Strigolactone Analogues Based on Eudesmane- and Guaiane-Type Sesquiterpene Lactones

Zorrilla

Cala

Rial

et al. 2020

J. Agric. Food Chem.

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Strigolactones are natural products that are exuded by plants and stimulate parasitic weed germination. Their use in herbicides is limited since they are produced in small quantities, but the synthesis of bioactive analogues provides an alternative source. In this work, eleven analogues have been synthesized. Among them, nine compounds belong to a novel family named eudesmanestrigolactones. The procedure is short (3–6 steps), the starting materials are isolated on a multigram scale, and global yields are up to 8%, which significantly enhance isolated yields. In bioassay, the compounds germinated high percentages of Phelipanche ramosa, Orobanche cumana, and Orobanche crenata seeds, even at nanogram doses (100 nM). Bioactivity was stereochemistry-dependent, and it was discussed in terms of the presence and geometry of the enol ether, orientation of the butenolide, and unsaturation of ring A. The reported compounds provide a set of readily obtained allelochemicals with potential applications as preventive herbicides.

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Gibberellic and kaurenoic hybrid strigolactone mimics for seed germination of parasitic weeds

Cited by 13 publications

References 37 publications

Recent advances in allelopathy for weed control: from knowledge to applications

Recent advances in allelopathy for weed control: from knowledge to applications

Chemical regulators of plant hormones and their applications in basic research and agriculture*

Synthesis of Active Strigolactone Analogues Based on Eudesmane- and Guaiane-Type Sesquiterpene Lactones

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