Structural Reassignment of rel-(3′Z,3R,6R,7R,3a′R,6′R)-3,8-Dihydrodiligustilide and the Activity of Diligustilide and 3,8-Dihydro- and 3,8,7′,7a′-Tetrahydrodiligustilides as Progestins

Ávila, José Luis Sánchez; Almeida-Aguirre, Ericka K. P.; Méndez-Cuesta, Carlos A.; Toscano, Rubén A.; Cervantes, Marco Antonio Cerbón; Delgado, Guillermo

doi:10.1021/acs.orglett.9b02762

Cited by 5 publications

(1 citation statement)

References 31 publications

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“…However, the use of SFE to extract large quantities of sanshools is not cost-effective. Meanwhile, the reported procedures for organic synthesis of some of these sanshools are relatively complicated, mainly because of the construction of unsaturated long alkyl carbon chains with specific double-bond configurations in the carbon terminal of the amide bonds [39][40][41][42][43]. These factors have further limited the application of sanshools as herbicide safeners, indicating that their structures need modification (including simplification of the structures).…”

Section: Introductionmentioning

confidence: 99%

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

et al. 2020

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The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a–k, 3a–k, and 4a–k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by 1H-NMR, 13C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection.

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Section: Introductionmentioning

confidence: 99%

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

et al. 2020

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Spiroligustolides A and B: Two pairs of enantiomeric spiro-orthoester-containing phthalide dimers as Cav3.1 calcium channel inhibitors from Ligusticum Chuanxiong Hort

Wang

Zhou

et al. 2022

Bioorganic Chemistry

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Isoindolines and phthalides from the rhizomes of Ligusticum chuanxiong and their relaxant effects on the uterine smooth muscle

et al. 2022

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Structural Reassignment of rel-(3′Z,3R,6R,7R,3a′R,6′R)-3,8-Dihydrodiligustilide and the Activity of Diligustilide and 3,8-Dihydro- and 3,8,7′,7a′-Tetrahydrodiligustilides as Progestins

Abstract: Experimental details, 1 H and 13 C NMR spectra, and Xray crystallography details (PDF)Accession Codes CCDC 1921193−1921194 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

Cited by 5 publications

References 31 publications

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

Spiroligustolides A and B: Two pairs of enantiomeric spiro-orthoester-containing phthalide dimers as Cav3.1 calcium channel inhibitors from Ligusticum Chuanxiong Hort

Isoindolines and phthalides from the rhizomes of Ligusticum chuanxiong and their relaxant effects on the uterine smooth muscle

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