Traveling across Life Sciences with Acetophenone—A Simple Ketone That Has Special Multipurpose Missions

Zubkov, Fedor I.; Kouznetsov, Vladímir V.

doi:10.3390/molecules28010370

Cited by 18 publications

(11 citation statements)

References 120 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The benzoids were most common in the stamens, and their content in other parts was also relatively high. Acetophenone is a precursor of fragrances that is reminiscent of almond, cherry, jasmine, and strawberry . 1-PE is widely used as a fragrance in the cosmetic industry because of its mild floral odor.…”

Section: Resultsmentioning

confidence: 99%

Distribution of and Temporal Variation in Volatiles in Tea (Camellia sinensis) Flowers during the Opening Stages

Cui,

Zhou,

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Distribution of and Temporal Variation in Volatiles in Tea (Camellia sinensis) Flowers during the Opening Stages

Cui,

Zhou,

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

“…Particularly, six of them were shared among treated oranges, but were not present or detected in control oranges, namely D‐ limonene, acetophenone, linalool, nonanal, decanal, and eugenol. Specifically, acetophenone obtained from Lobularia maritima L. flowers was described as an attractant for D. longicaudata females for the floral nectar (Rohrig et al., 2008) and was also described as a semiochemical for other insects, such as the mosquito Aedes aegypti L. and the parasitoid Cotesia vestalis Haliday (review in Zubkov & Kouznetsov, 2023). Nonanal and decanal were reported by several authors as HIPVs that are attractive to parasitoids and predators (DeLury et al., 1999; Birkett et al., 2003; Yu et al., 2008; Dweck et al., 2010; Badra et al., 2021; Du et al., 2022), but there are no records for D. longicaudata .…”

Section: Discussionmentioning

confidence: 99%

Direct and indirect host‐related volatile compounds attract a fruit fly parasitoid, Diachasmimorpha longicaudata

Devescovi,

Fernández,

Bachmann

et al. 2024

Entomologia Exp Applicata

View full text Add to dashboard Cite

Fruit fly pests (Diptera: Tephritidae) are a serious problem for fruit production and for local and international trade. Biological control is increasingly included as a pest control tool within integrated pest management (IPM) programmes, seeking to reduce pesticides and improve fruit quality. Ceratitis capitata Wiedemann, the Mediterranean fruit fly (medfly), is probably the most damaging fruit fly pest, with a global distribution and more than 200 host species. The solitary larval endoparasitoid Diachasmimorpha longicaudata Ashmead (Hymenoptera: Braconidae) is a biocontrol agent widely used against Tephritidae fruit fly pests. Previous studies showed that female wasps locate host larvae using visual, mechanical, and chemical cues. Here, we investigated the chemical basis of female parasitoid attraction to cues that guide D. longicaudata to the host, and thus unveil volatile organic compounds that might be used in IPM programmes. Female orientation to chemical cues was tested in a Y‐tube olfactometer, where attraction to C. capitata‐infested oranges, oranges with residues of larval activity, oranges infected with a green mould, and overripe oranges was confirmed. Volatiles from all these types of fruit were collected and used in gas chromatography‐electroantennographic detection (GC‐EAD) and GC‐mass spectrometry (MS) analyses. These studies allowed us to identify six candidate compounds that were present in all treated oranges but not in the control fruit (ripe and uninfested oranges): D‐limonene, acetophenone, linalool, nonanal, decanal, and eugenol. Electroantennography (EAG) showed that acetophenone, nonanal, and decanal triggered dose‐dependent responses, suggesting a relevant role in the process of host finding. Although responses to D‐limonene, linalool, and eugenol were independent of the dose, they could be involved in host location in areas with high probability of host presence. The fact that these six compounds are shared by the four behaviourally attractive sources opens new possibilities for the development of novel tools to improve biocontrol programmes.

show abstract

“…Methoxy is an essential functional group found in phytochemicals such as curcumin, guaiacol, and methoxyflavone. − Likewise, the acetophenone group plays a crucial role in the action of numerous medications, including pyrovalerone, amfepramone, and bupropion. − For the preparation of medications such as zolpidem, oxiconazole, and cinacalcet, basic acetophenone derivatives are used as raw materials . It is therefore anticipated that the combination of 4-methoxybenzylamine, 3-aminoacetophenone, and 6-nitropiperonal (carrying the MDP group) will exhibit significant biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Rajan,

Karthikeyan,

Desikan

2024

ACS Omega

View full text Add to dashboard Cite

Novel methylenedioxyphenyl-based amides, especially N-(4-methoxybenzyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (MDC) and N-(3-acetylphenyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (ADC), potential cardiovascular preventive agents, are successfully synthesized, and their chemical structures are verified by 1 H and 13 C NMR, Fourier transform infrared (FT-IR), high-resolution mass spectrometry (HRMS), and single-crystal Xray diffraction (SC-XRD) analyses. Data obtained from SC-XRD reveal that MDC and ADC are both monoclinic molecules with Z = 2 and 4, respectively. From density functional theory (DFT) calculations, 3.54 and 3.96 eV are the energy gaps of the optimized MDC and ADC structures, respectively. MDC and ADC exhibit an electrophilicity index value of more than 1.5 eV, suggesting that they can act as an electrophile, facilitating bond formation with biomolecules. Hirshfeld surface analysis demonstrates that more than 25% of atomic interactions in both MDC and ADC are from H•••H interactions. Based on pharmacokinetic predictions, MDC and ADC exhibit drug-like properties, and molecular docking simulations revealed favorable interactions with active site pockets. Both MDC and ADC achieved higher docking scores of −7.74 and −7.79 kcal/mol, respectively, with myeloperoxidase (MPO) protein. From docking results, MPO was found to be most favorable followed by dipeptidyl peptidase-4 (DPP-4) and α-glucosidase (α-GD). Antioxidant, anti-inflammatory, and in vitro enzymatic studies of MDC and ADC indicate that MDC is more selective toward MPO and more potent than ADC. The application of MDC to inhibit myeloperoxidase could be ascertained to reduce the cardiovascular risk factor. This can be supported from the results of computational docking (based on hydrogen bonding and docking score), in vitro antioxidant and anti-inflammatory properties, and MPO enzymatic inhibition (based on the percentage of inhibition and IC 50 values).

show abstract

Traveling across Life Sciences with Acetophenone—A Simple Ketone That Has Special Multipurpose Missions

Cited by 18 publications

References 120 publications

Distribution of and Temporal Variation in Volatiles in Tea (Camellia sinensis) Flowers during the Opening Stages

Distribution of and Temporal Variation in Volatiles in Tea (Camellia sinensis) Flowers during the Opening Stages

Direct and indirect host‐related volatile compounds attract a fruit fly parasitoid, Diachasmimorpha longicaudata

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Contact Info

Product

Resources

About