Vapour phase mediated suppression of carvone and citronellol volatiles against Fusarium oxysporum f.sp. lycospercisi

Praveen, T.; Krishnamoorthy, A.S.; Nakkeeran, S.; Sivakumar, U.; Amirtham, D.; Haripriya, S.

doi:10.21276/ap.2021.10.1.33

Cited by 1 publication

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“…[2][3][4] Carvone, a monocyclic monoterpenoid ketone, naturally exists in the plant essential oils of caraway (Carum carvi L.), dill (Anethum graveolens L.) and spearmint (Mentha spicata L.), and has been reported to show anti-manic, [5] anti-inflammatory, [6,7] nematicidal, [8] anti-cancer, [9,10] and antifungal activities. [11,12] According to the publications, [13,14] the carbonyl group and exocyclic allyl group of L-carvone were all chemically active sites for synthesizing L-carvone-based derivatives with antifungal activities. However, it was still insufficient for the exploration of the molecular skeleton of L-carvone as a bioactive building block.…”

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confidence: 99%

Synthesis, Antifungal Activity, and Molecular Simulation Study of L–Carvone‐Derived 1,3,4‐Oxadiazole‐Thioether Compounds

Wen

Fan

Lin

et al. 2023

Chemistry & Biodiversity

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To discover potent antifungal molecules with new and distinctive structures, 20 novel L-carvone-derived 1,3,4-oxadiazolethioether compounds 5 a-5 t were synthesized through multistep reaction of L-carvone, and their structures were confirmed by FT-IR, 1 H-NMR, 13 C-NMR, and HR-MS. The antifungal activities of compounds 5 a-5 t were preliminarily tested by in vitro method, and the results indicated that all of the title compounds displayed certain antifungal activities against the eight tested plant fungi, especially for P. piricola. Among them, compound 5 i (R = p-F) with the most significant antifungal activity deserved further study for discovering and developing novel natural product-based antifungal agents. Moreover, two molecular simulation technologies were employed for the investigation of their structure-activity relationships (SARs). Firstly, a reasonable and effective 3D-QSAR model was established by the comparative molecular field (CoMFA) method, and the relationship of the substituents linked with the benzene rings and the inhibitory activities of the title compounds against P. piricola was elucidated. Then, the binding mode of compound 5 i (R = p-F) and its potential biological target (CYP51) was simulated by molecular docking, and it was found that compound 5 i could readily bind with CYP51 in the active site, and the ligand-receptor interactions involved three hydrogen bonds and several hydrophobic effects.

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