Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters

Hu, Qiong; Lin, Guo‐Qiang; Duan, Wengui; Huang, Min; Lei, Fuhou

doi:10.3390/molecules22101678

Cited by 23 publications

(28 citation statements)

References 26 publications

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“…scoparius flowering branches and flowers, as linalool, terpinen-4-ol or α -terpineol have well known phytotoxic activity, e.g., [ 34 , 61 ]. Also, verbenone, a semiochemical with reputed pest deterrent properties because of its ecological role as anti-aggregation pheromone (see [ 62 ] as a review), has very recently been explored for its phytotoxicity [ 63 ]. Verbenone is synthetically obtained from the abundantly available pinenes in pine oleoresins, and then commercially used in tree protection [ 64 ].…”

Section: Discussionmentioning

confidence: 99%

“…As far as we know, only two recent studies dealt with the phytotoxicity of verbenone added to the culture solution [ 63 , 72 ]. These studies showed that verbenone applied at 100 to 150 μg mL -1 exerted extremely weak inhibition of the seedling growth of Echinochloa crus-galli and Brassica campestris [ 63 ], or just a delay on L . sativa germination [ 72 ].…”

Section: Discussionmentioning

confidence: 99%

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On the bioherbicide potential of Ulex europaeus and Cytisus scoparius: Profiles of volatile organic compounds and their phytotoxic effects

et al. 2018

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The phytotoxic potential of the legume shrubs Ulex europaeus L. (gorse) and Cytisus scoparius (L.) Link. (Scotch broom) is studied in this work for the first time. On the basis of their richness in active principles, the previous evidence of biological activity, and the abundance of biomass in their native range and invaded areas, a question arose: can U. europaeus and C. scoparius be considered as potential sources of natural herbicides for sustainable agriculture? By means of volatile bioassays, the flowering fresh plant material of both shrub species was shown to produce and emit volatile organic compounds (VOCs) able to inhibit the germination and/or early growth of two agricultural weeds: Amaranthus retroflexus and Digitaria sanguinalis. Novel complete VOCs profiles from the volatile extracts of the shrub species were obtained by GC and GC/MS. A total of 20 compounds were identified from U. europaeus flowering biomass, theaspirane and eugenol, among others, being described in gorse for the first instance. The chemical profile of C. scoparius yielded 28 compounds and was rich in oxygenated monoterpenes such as terpinen-4-ol, verbenol, α-terpineol, and verbenone, which were also identified in this species for the first time. Using dose-response bioassays with pure compounds, these VOCs were argued to be involved in the phytotoxicity observed for the plant materials, even at very low concentrations. The phytotoxic effects were predominantly irreversible, particularly for D. sanguinalis, since the seeds exposed to the VOCs produced damaged seedlings, were unable to recover germination capacity after removing the phytotoxin or, when recovered, produced unviable seedlings. Our results extend the interest of the abundant U. europaeus and C. scoparius for the obtention of natural products with bioherbicide potential, or to be used as allelopathic biomass in the development of new sustainable agricultural practices.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

On the bioherbicide potential of Ulex europaeus and Cytisus scoparius: Profiles of volatile organic compounds and their phytotoxic effects

et al. 2018

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“…Verbenone presents good repellent properties, as well as anti-inflammatory [277] and bronchodilator [278] activity. Verbenone derivatives present important biological characteristics such as antifungal [279], antiviral [280], antioxidant activities and (in cortical neurons) anti-ischemic properties [281]. Given these promising effects, Melo et al [282] evaluated the anticonvulsant activity of verbenone at doses of 150, 200, and 250 mg/kg (i.p.).…”

Section: (-)-Verbenonementioning

confidence: 99%

Anticonvulsant Essential Oils and Their Relationship with Oxidative Stress in Epilepsy

et al. 2019

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Epilepsy is a most disabling neurological disorder affecting all age groups. Among the various mechanisms that may result in epilepsy, neuronal hyperexcitability and oxidative injury produced by an excessive formation of free radicals may play a role in the development of this pathology. Therefore, new treatment approaches are needed to address resistant conditions that do not respond fully to current antiepileptic drugs. This paper reviews studies on the anticonvulsant activities of essential oils and their chemical constituents. Data from studies published from January 2011 to December 2018 was selected from the PubMed database for examination. The bioactivity of 19 essential oils and 16 constituents is described. Apiaceae and Lamiaceae were the most promising botanical families due to the largest number of reports about plant species from these families that produce anticonvulsant essential oils. Among the evaluated compounds, β-caryophyllene, borneol, eugenol and nerolidol were the constituents that presented antioxidant properties related to anticonvulsant action. These data show the potential of these natural products as health promoting agents and use against various types of seizure disorders. Their properties on oxidative stress may contribute to the control of this neurological condition. However, further studies on the toxicological profile and mechanism of action of essential oils are needed.

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“…In continuation of our long-term focus on natural product-based bioactive compounds [ 28 , 29 , 30 , 31 , 32 ], a series of novel nopol-derived 1,3,4-thiadiazole-thiourea compounds were synthesized by integrating bioactive 1,3,4-thiadiazole and thiourea moieties into the molecular skeleton of nopol. Structural characterization, antifungal evaluation, and structure–activity relationships of the title compounds were determined as well.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

Chen¹,

Duan²,

Lin³

et al. 2021

Molecules

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A series of novel nopol derivatives bearing the 1,3,4-thiadiazole-thiourea moiety were designed and synthesized by multi-step reactions in search of potent natural product-based antifungal agents. Their structures were confirmed by FT-IR, NMR, ESI-MS, and elemental analysis. Antifungal activity of the target compounds was preliminarily evaluated by in vitro methods against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. All the target compounds exhibited better antifungal activity against P. piricola, C. arachidicola, and A. solani. Compound 6j (R = m, p-Cl Ph) showed the best broad-spectrum antifungal activity against all the tested fungi. Compounds 6c (R = m-Me Ph), 6q (R = i-Pr), and 6i (R = p-Cl Ph) had inhibition rates of 86.1%, 86.1%, and 80.2%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Moreover, compounds 6h (R = m-Cl Ph) and 6n (R = o-CF3 Ph) held inhibition rates of 80.6% and 79.0% against C. arachidicola and G. zeae, respectively, much better than that of the commercial fungicide chlorothalonil. In order to design more effective antifungal compounds against A. solani, analysis of the three-dimensional quantitative structure–activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.992, q2 = 0.753) has been established. Furthermore, some intriguing structure–activity relationships were found and are discussed by theoretical calculation.

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Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters

Cited by 23 publications

References 26 publications

On the bioherbicide potential of Ulex europaeus and Cytisus scoparius: Profiles of volatile organic compounds and their phytotoxic effects

On the bioherbicide potential of Ulex europaeus and Cytisus scoparius: Profiles of volatile organic compounds and their phytotoxic effects

Anticonvulsant Essential Oils and Their Relationship with Oxidative Stress in Epilepsy

Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

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