LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity

Stefanis, I; Hadjipavlou‐Litina, Dimitra; Bilia, Anna-Rita; Karioti, Anastasia

doi:10.1055/a-0927-7041

Cited by 8 publications

(5 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ten µL of compound was dissolved in DMSO (final concentration 100 µM) and incubated with 40 µL mushroom tyrosinase (5370 U/mg–1 mg/2.6 mL buffer) and 200 µL of L-Dopa (1.5 mM) in 0.1 M Na-phosphate buffer (pH = 6.5) for 20 min at 37 °C. Then the enzyme reaction was monitored by measuring the change in absorbance at 490 nm due to the formation of the DOPA-chrome and compared with the standard inhibitor kojic acid [ 60 ].…”

Section: Methodsmentioning

confidence: 99%

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

Self Cite

View full text Add to dashboard Cite

The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer–Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94% and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5%. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a–4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.

show abstract

Section: Methodsmentioning

confidence: 99%

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Several previous studies were conducted on the enzyme inhibitory properties of basil, thyme, and oregano EOs or extracts. The literature indicates that these species had significant potential as natural enzyme inhibitors as well as antioxidants [64][65][66][67][68][69][70][71]. Furthermore, our findings shed light on the valuable activity of post-distillation by-products, which can be used to develop novel enzyme inhibition drugs.…”

Section: Enzyme Inhibitory Activity Of Essential Oils Total Spent And...mentioning

confidence: 64%

Post-Distillation By-Products of Aromatic Plants from Lamiaceae Family as Rich Sources of Antioxidants and Enzyme Inhibitors

et al. 2023

View full text Add to dashboard Cite

There is currently no use for the vast quantities of post-distillation by-products, such as spent plant materials and residual waters, produced by the essential oil (EO) industry of aromatic herbs. In this study, the EOs of three Lamiaceae species (thyme, oregano, and basil) and their total, spent, and residual water extracts were phytochemically characterized and biologically assessed. The collected information was put through a series of analyses, including principal component analysis, heatmap analysis, and Pearson correlation analysis. Concerning the EOs, 58 volatile compounds were present in thyme (e.g., p-cymene, thymol), 44 compounds in oregano (e.g., thymol, carvacrol), and 67 compounds in basil (e.g., eucalyptol, linalool, estragole, (E)-methyl cinnamate). The LC-HRMS/MS analysis of the total, spent, and residual water extracts showed the presence of 31 compounds in thyme (e.g., quercetin-O-hexoside, pebrellin, eriodictyol), 31 compounds in oregano (e.g., rosmarinic acid, apigenin, kaempferol, salvianolic acids I, B, and E), and 25 compounds in basil (e.g., fertaric acid, cichoric acid, caftaric acid, salvianolic acid A). The EOs of the three Lamiaceae species showed the highest metal-reducing properties (up to 1792.32 mg TE/g in the CUPRAC assay), whereas the spent extracts of oregano and basil displayed very high radical-scavenging properties (up to 266.59 mg TE/g in DPPH assay). All extracts exhibited anti-acetylcholinesterase (up to 3.29 mg GALAE/g), anti-tyrosinase (up to 70.00 mg KAE/g), anti-amylase (up to 0.66 mmol ACAE/g), and anti-glucosidase (up to 1.22 mmol ACAE/g) effects. Thus, the present research demonstrated that both the raw extracts (EOs and total extracts) and the post-distillation by-products (spent material and residual water extracts) are rich in bioactive metabolites with antioxidant and enzyme inhibitory properties.

show abstract

“…demonstrated significant anti-tyrosinase activity ( Kim et al, 2021 ). In another study, again phytochemicals isolated from T. vulgaris L. such as 6′,3′,4′-trihydroxy-5,5′-diisopropyl-2,2′-dimethylbiphenyl, thymol, oleanolic acid, ursolic acid, cirsimaritin, and xanthomicrol were capable of inhibiting tyrosinase, which also proves only specific compounds are responsible for the tyrosinase inhibitory activity and this activity is only expected when they are present in the extracts ( Stefanis et al, 2019 ). The same conclusion is also accurate for the anti-urease activity and reported by Boga et al (2021a) ’s study again, no tyrosinase urease activity was demonstrated by the investigated ten Thymus L .…”

Section: Resultsmentioning

confidence: 94%

The Therapeutic Potential of Ethnomedicinally Important Anatolian Thyme Species: A Phytochemical and Biological Assessment

et al. 2022

View full text Add to dashboard Cite

Thyme has been used for various therapeutic purposes in many different cultures, which makes it one of the most riveting medicinal plants throughout history. From its beneficial effects on the respiratory tract or the gastrointestinal system, to its unique skin-related activities, the investigation of the medicinal properties of thyme has always been an alluring topic for researchers aiming to develop conventional medications from this traditional herb. With an incentive to contribute to the extensive thyme research, threeThymusL. species namelyThymus cariensisHub-Mor. & Jalas (endemic),Thymus praceoxsubsp.grossheimii(Ronniger) Jalas, andThymus pubescensBoiss. et Kotschy ex Celak from Turkey were deeply investigated within this study. The analysis of the phytochemical constituents of the extracts was conducted by LC-MS/MS. 12 biologically important secondary metabolites (p-coumaric acid, caffeic acid, salicylic acid, quinic acid, fumaric acid, vanillin, malic acid, rutin, apigenin, naringenin, and nicotiflorin) were detected in all extracts. Their total phenolic and flavonoid contents were calculated (11.15 ± 0.17—61.12 ± 2.59 μg PEs/mg extract, 2.53 ± 0.04—40.28 ± 0.92 μg QEs/mg extract, respectively), and the antioxidant potential of the extracts was evaluated by DPPH and ABTS radical scavenging and CUPRAC activity methods, accordingly, the extracts were shown to possess significant antioxidant activity. Among them,Thymus cariensisHub-Mor. & Jalas was the most active with IC50values of 34.97 ± 1.00 μg/ml and 9.98 ± 0.04 μg/ml regarding the DPPH and ABTS radical scavenging assays, respectively, and an A0.5value of 5.80 ± 0.02 μg/ml according to CUPRAC activity method. Their anticholinesterase, antityrosinase, and antiurease activities were also tested,Thymus cariensisHub-Mor. & Jalas (35.61 ± 1.20%) andThymus pubescensBoiss. et Kotschy ex Celak aerial part extract (33.49 ± 1.39%) exhibited moderate antibutyrylcholinesterase activity at 200 μg/ml concentration. The results of the cell viability assay indicated that the extracts demonstrated moderate-to-low cytotoxicity on A498 human renal cell lines. Furthermore, all studied extracts exerted noteworthy antimicrobial activity, especially againstCandida tropicalis(MIC values: 19.53—78.12 μg/ml). The presented data substantiates the use of thyme extracts as therapeutic agents in both ethnomedicine and conventional therapies.

show abstract

LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity

Cited by 8 publications

References 23 publications

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

Post-Distillation By-Products of Aromatic Plants from Lamiaceae Family as Rich Sources of Antioxidants and Enzyme Inhibitors

The Therapeutic Potential of Ethnomedicinally Important Anatolian Thyme Species: A Phytochemical and Biological Assessment

Contact Info

Product

Resources

About