Complexation of sesquiterpene lactones with cyclodextrins: synthesis and effects on their activities on parasitic weeds

Cala, Antonio; Molinillo, José M. G.; Fernández‐Aparicio, Mónica; Ayuso, Jesús; Álvarez, José Ángel Pérez; Rubiales, Diego; Macías, Francisco A.

doi:10.1039/c7ob01394a

Cited by 24 publications

(44 citation statements)

References 41 publications

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“…From these compounds, dehydrocostus lactone was found moderately active in inducing seed germination (EC 50 cca 1 × 10 −5 M ) of P. ramosa . However, it was more effective on P. aegyptiaca and excellently active on O. cumana seeds . From synthetic compounds, phthalimide strigolactone mimics have been reported to be efficient in inducing seed germination of broomrapes .…”

Section: Discussionmentioning

confidence: 99%

Triazolide strigolactone mimics as potent selective germinators of parasitic plant Phelipanche ramosa

Dvořáková

Hýlová

Soudek

et al. 2019

Pest Management Science

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BACKGROUND: Strigolactones are a unique class of plant metabolites which serve as a rhizosphere signal for parasitic plants and evocate their seed germination. The expansion of these parasitic weeds in the food crop fields urgently calls for their increased control and depletion. Simple strigolactone analogues able to stimulate seed germination of these parasitic plants may represent an efficient control measure through the induction of suicidal germination. RESULTS: Triazolide-type strigolactone mimics were easily synthesized in three steps from commercially available materials. These derivatives induced effectively seed germination of Phelipanche ramosa with EC 50 as low as 5.2 × 10 −10 M. These mimics did not induce seed germination of Striga hermonthica even at high concentration (≥1 × 10 −5 M). CONCLUSIONS: Simple and stable strigolactone mimics with selective activity against Phelipanche ramosa were synthesized.

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Section: Discussionmentioning

confidence: 99%

Triazolide strigolactone mimics as potent selective germinators of parasitic plant Phelipanche ramosa

Dvořáková

Hýlová

Soudek

et al. 2019

Pest Management Science

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“…The compounds 1 – 9 were tested for their bioactivity in an etiolated wheat coleoptile bioassay. The conditions for this bioassay were reported previously [ 31 , 32 ] and replicated in this study, using the same herbicide (Logran ® ) as positive control and the buffer solution as negative control. Wheat ( Triticum aestivum ) was the ‘catervo’ variety.…”

Section: Methodsmentioning

confidence: 98%

(+)-epi-Epoformin, a Phytotoxic Fungal Cyclohexenepoxide: Structure Activity Relationships

et al. 2018

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(+)-epi-Epoformin (1), is a fungal cyclohexene epoxide isolated together with diplopimarane and sphaeropsidins A and C, a nor-ent-pimarane and two pimaranes, from the culture filtrates of Diplodia quercivora, a fungal pathogen for cork oak in Sardinia, Italy. Compound 1 possesses a plethora of biological activities, including antifungal, zootoxic and phytotoxic activity. The last activity and the peculiar structural feature of 1 suggested to carry out a structure activity relationship study, preparing eight key hemisynthetic derivatives and the phytotoxicity was assayed. The complete spectroscopic characterization and the activity in the etiolated wheat coleoptile bioassay of all the compounds is reported. Most of the compounds inhibited growth and some of them had comparable or higher activity than the natural product and the reference herbicide Logran. As regards the structure-activity relationship, the carbonyl proved to be essential for their activity of 1, as well as the conjugated double bond, while the epoxide could be altered with no significant loss.

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“…Strigolactams and phthalimide derivatives are examples of mimics that strongly stimulate O. cumana , O. minor , P. ramosa and P. aegyptiaca germination . Other families of compounds, such as benzoxazinoids, sesquiterpene lactones, alkaloids, flavonoids or steroids, stimulate parasitic plant germination.…”

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

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210

163

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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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Complexation of sesquiterpene lactones with cyclodextrins: synthesis and effects on their activities on parasitic weeds

Cited by 24 publications

References 41 publications

Triazolide strigolactone mimics as potent selective germinators of parasitic plant Phelipanche ramosa

Triazolide strigolactone mimics as potent selective germinators of parasitic plant Phelipanche ramosa

(+)-epi-Epoformin, a Phytotoxic Fungal Cyclohexenepoxide: Structure Activity Relationships

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

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