Spectral, structural, and pharmacological studies of perillaldehyde and myrtenal based benzohydrazides

Garberová, Monika; Potočňák, Ivan; Tvrdoňová, Monika; Bago-Pilátová, Martina; Bekešová, Slávka; Kudlicková, Z; Samoľová, Erika; Kešeľáková, Alexandra; Elečko, Ján; Vilková, Mária

doi:10.1016/j.molstruc.2022.134112

Cited by 4 publications

(4 citation statements)

References 51 publications

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“…High-resolution fragmentation spectra were obtained with the use of the Orbitrap Fusion™ Lumos™ Tribrid™ Mass Spectrometer (Thermo Fisher Scientific, Waltham, MA, USA), following the procedure mentioned in our previous publication [ 40 ]. Data processing: To confirm the structure of the studied molecules ( 11a – k and 12a – c , 13a – c , 14a – c , 18c , and 19c ), the precursor ions underwent exhaustive fragmentation using various fragmentation techniques (CID, HCD) at multiple collision energies.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity

Kudličková,

Michalková,

Salayová

et al. 2023

Molecules

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The synthesis, anticancer, and antioxidant activities of a series of indole-derived hybrid chalcones are reported here. First, using the well-known Claisen–Schmidt condensation method, a set of 29 chalcones has been designed, synthesized, and consequently characterized. Subsequently, screening for the antiproliferative activity of the synthesized hybrid chalcones was performed on five cancer cell lines (HCT116, HeLa, Jurkat, MDA-MB-231, and MCF7) and two non-cancer cell lines (MCF-10A and Bj-5ta). Chalcone 18c, bearing 1-methoxyindole and catechol structural features, exhibited selective activity against cancer cell lines with IC50 values of 8.0 ± 1.4 µM (Jurkat) and 18.2 ± 2.9 µM (HCT116) and showed no toxicity to non-cancer cells. Furthermore, antioxidant activity was evaluated using three different methods. The in vitro studies of radical scavenging activity utilizing DPPH radicals as well as the FRAP method demonstrated the strong activity of catechol derivatives 18a–c. According to the ABTS radical scavenging assay, the 3-methoxy-4-hydroxy-substituted chalcones 19a–c were slightly more favorable. In general, a series of 3,4-dihydroxychalcone derivatives showed properties as a lead compound for both antioxidant and antiproliferative activity.

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Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity

Kudličková,

Michalková,

Salayová

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

“…High-resolution fragmentation spectra were obtained with the use of Orbitrap Fusion™ Lumos™ Tribrid™ Mass Spectrometer (Thermo Fisher Scientific, Waltham, MA, USA), according to the procedure mentioned in our previous publication [43]. Data processing: To verify the structure of the studied molecules ( 11a-k and 12a-c, 13a-c, 14a-c, 18c, and 19c) the precursor ions were exhaustively fragmented using different fragmentation techniques (CID, HCD) at multiple collision energies.…”

Section: General Methods and Materialsmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Anticancer and Antioxidant Activity

Kudličková,

Michalková,

Salayová

et al. 2023

Preprint

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The synthesis, anticancer and antioxidant activity of a series of indole-derived hybrid chalcones are reported here. First, using well known Claisen-Schmidt condensation method a set of 29 chalcones has been designed, synthesized, and consequently characterized. Subsequently, screening for the antiproliferative activity of the synthesized hybrid chalcones was performed on the on five cancer (HCT116, HeLa, Jurkat, MDA-MB-231 and MCF7) and two non-cancer (MCF-10A and Bj-5ta) cell lines. Chalcone 18c bearing 1-methoxyindole and catechol structural features, exhibited selective activity against cancer cell lines with IC50 values of 8.0 ± 1.4 µM (Jurkat) and 18.2 ± 2.9 µM (HCT116) and showed no toxicity to non-cancer cells. Furthermore, antioxidant activity was evaluated using tree different methods. The in vitro studies of radical scavenging activity utilizing DPPH radicals, as well as FRAP method, demonstrated the strong activity of catechol derivatives 18a-c. According to the ABTS radical scavenging assay, the 3-methoxy-4-hydroxy substituted chalcones 19a–c were slightly more favorable. In general, a series of 3,4-dihydroxychalcone derivatives showed properties as a lead compound for both antioxidant and anticancer activity.

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“…Zieli ńska-Błajet and Feder-Kubis (2020) provided an overview of diverse therapeutic effects on selected aliphatic, monocyclic, and bicyclic monoterpenes such as geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures [89]. A recent study with fourteen newly synthesized perillaldehyde and myrtenal-based benzohydrazides revealed the antiproliferative potential for two of them [145]. Increasingly more literature data are available regarding new modifications of these natural compounds, including their biological effects and medical applications.…”

Section: Antitumor Potentialmentioning

confidence: 99%

Therapeutic Potential of Myrtenal and Its Derivatives—A Review

Dragomanova,

Andonova,

Volcho

et al. 2023

Life

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The investigation of monoterpenes as natural products has gained significant attention in the search for new pharmacological agents due to their ability to exhibit a wide range in biological activities, including antifungal, antibacterial, antioxidant, anticancer, antispasmodic, hypotensive, and vasodilating properties. In vitro and in vivo studies reveal their antidepressant, anxiolytic, and memory-enhancing effects in experimental dementia and Parkinson’s disease. Chemical modification of natural substances by conjugation with various synthetic components is a modern method of obtaining new biologically active compounds. The discovery of new potential drugs among monoterpene derivatives is a progressive avenue within experimental pharmacology, offering a promising approach for the therapy of diverse pathological conditions. Biologically active substances such as monoterpenes, for example, borneol, camphor, geraniol, pinene, and thymol, are used to synthesize compounds with analgesic, anti-inflammatory, anticonvulsive, antidepressant, anti-Alzheimer’s, antiparkinsonian, antiviral and antibacterial (antituberculosis) properties. Myrtenal is a perspective monoterpenoid with therapeutic potential in various fields of medicine. Its chemical modifications often lead to new or more pronounced biological effects. As an example, the conjugation of myrtenal with the established pharmacophore adamantane enables the augmentation of several of its pivotal properties. Myrtenal–adamantane derivatives exhibited a variety of beneficial characteristics, such as antimicrobial, antifungal, antiviral, anticancer, anxiolytic, and neuroprotective properties, which are worth examining in more detail and at length.

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Spectral, structural, and pharmacological studies of perillaldehyde and myrtenal based benzohydrazides

Cited by 4 publications

References 51 publications

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Antiproliferative and Antioxidant Activity

Design, Synthesis, and Evaluation of Novel Indole Hybrid Chalcones and Their Anticancer and Antioxidant Activity

Therapeutic Potential of Myrtenal and Its Derivatives—A Review

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