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In recent years, essential oils constituents have attracted interest as alternative approach in the traditional medicine for their therapeutics properties. In this field, carvacrol, since it showed strong antimicrobial activity against a wide range of Gram-positive and -negative bacteria, has emerged as active molecule for therapeutic purpose. This review focuses on the antimicrobial properties of carvacrol and highlights the advantageous impact of the medicinal chemistry and technological-based approaches employed to improve its therapeutic profile. Graphical Abstract

Lung cancer remains a major public health concern among all cancer diseases due to the toxicity and side-effects of the available commercially synthesized drugs. Natural product-derived synthesized anticancer drugs are now of promising interest to fight against cancer death. Carvacrol is a major component of most essential oil-bearing plants with potential pharmacological activity, especially against various cancer cell lines. Among the other organometallic compounds, copper complexes have been reported to be effective anticancer agents against various cancer cell lines, especially lung and leukemia cancers, due to the nontoxic nature of copper in normal cells since it is an endogenic metal. In this study, we synthesized three carvacrol derivatives, i.e., carvacrol aldehyde, Schiff base, and copper–Schiff base complex, through an established synthesis protocol and characterized the synthesized product using various spectroscopic techniques. The synthesized derivatives were evaluated for in vitro cytotoxic activity against different cancer cell lines, including human lung cancer (A549) and human fibroblast (BALB-3T3). Our findings showed that the copper–Schiff base complex derived from carvacrol inhibited the proliferation and migration of the A549 cell lines in a dose-dependent manner. This activity might be due to the inhibition of cell proliferation and migration at the G2/M cell-cycle phase, as well as apoptosis, possibly through the activation of the mitochondrial apoptotic pathway. To our knowledge, this is the first report on the activity of the copper–Schiff base complex of carvacrol against A549 cell lines. Our result highlights that a new synthesized copper complex from carvacrol could be a novel potential drug in the treatment of lung cancer.

Cellulose fiber-based textiles are ubiquitous in daily life for their processability, biodegradability, and outstanding flexibility. Integrating cellulose textiles with functional coating materials can unlock their potential functionalities to engage diverse applications. Metal-organic frameworks (MOFs) are ideal candidate materials for such integration, thanks to their unique merits, such as large specific surface area, tunable pore size, and species diversity. However, achieving scalable fabrication of MOFs-textiles with high mechanical durability remains challenging. Here, we report a facile and scalable strategy for direct MOF growth on cotton fibers grafted via the diazonium chemistry. The as-prepared ZIF-67-Cotton textile (ZIF-67-CT) exhibits excellent ultraviolet (UV) resistance and organic contamination degradation via the peroxymonosulfate activation. The ZIF-67-CT is also used to encapsulate essential oils such as carvacrol to enable antibacterial activity against E. coli and S. aureus . Additionally, by directly tethering a hydrophobic molecular layer onto the MOF-coated surface, superhydrophobic ZIF-67-CT is achieved with excellent self-cleaning, antifouling, and oil-water separation performances. More importantly, the reported strategy is generic and applicable to other MOFs and cellulose fiber-based materials, and various large-scale multi-functional MOFs-textiles can be successfully manufactured, resulting in vast applications in wastewater purification, fragrance industry, and outdoor gears. Integrating cellulose textiles with functional coating materials can unlock their potential functionalities to engage diverse applications. Here, authors report a generic strategy to achieve highly stable, large-scale, and multifunctional MOFs-textiles via diazonium chemistry.

Sperm cryopreservation technology underpins genetic advancement in animal breeding and ongoing research aims to minimize cryoinjuries. This study aimed to develop carvacrol-loaded phytosomes (CLNPs) to enhance the physicochemical properties of carvacrol in aqueous cryopreservation extenders. Semen samples from five buffalo bulls were collected, extended and cryopreserved with varying CLNPs concentrations (0, 2.5, 5, 10, and 20 µg/mL). The freshly prepared CLNPs exhibited an average particle size of 286.7 ± 11.27 nm, a polydispersity index of 0.189 ± 0.05, and a zeta potential of − 11.4 ± 0.26 mV. Supplementing the freezing media with CLNPs significantly enhanced sperm progressive motility, viability, and plasma membrane integrity after both equilibration (5 °C for 4 h) and thawing. Furthermore, sperm kinematic parameters were significantly higher in all CLNPs-treated groups ( P  < 0.05). Compared to the CLNPs-free extender, CLNPs supplementation significantly reduced the percentage of dead sperm with intact acrosomes and increased the percentage of live sperm with intact acrosomes ( P  < 0.001). Post-thaw oxidative stress markers, including H 2 O 2 and MDA, were significantly lower in all CLNPs groups ( P  < 0.001). Notably, the addition of 10 or 20 µg/mL of CLNPs increased TAC and significantly decreased nitric oxide levels compared to the control. Mitochondrial membrane potential and viable sperm counts were significantly higher in the CLNPs-treated groups ( P  < 0.001). CLNPs also significantly decreased the total bacterial count, spore-forming bacteria, and coliform bacteria in the post-thawed semen microbiota ( P  < 0.001). Higher CLNPs concentrations (10 or 20 µg/mL) appeared to provide superior protection, as evidenced by a greater proportion of sperm cells displaying normal nuclear, plasma membrane, mitochondrial, and acrosomal morphology. The pregnancy rate in the 20 µg/mL CLNPs group (86%, n = 43/50) was higher than in the control group (72%, n = 36/50). Molecular docking analysis revealed binding energies of − 6.22, − 4.93, − 4.44, and − 5.36 kcal/mol for Cox7c, Hsp70, PrxIII, and ATP1B1, respectively. This study introduces a novel nanotechnology-based approach using CLNPs to enhance buffalo semen cryopreservation, potentially significantly advancing assisted reproductive technologies in buffalo.

Thyme oil (TO) is derived from the flowers of various plants belonging to the genus Thymus. It has been used as a therapeutic agent since ancient times. Thymus comprises numerous molecular species exhibiting diverse therapeutic properties that are dependent on their biologically active concentrations in the extracted oil. It is therefore not surprising that oils extracted from different thyme plants present different therapeutic properties. Furthermore, the phenophase of the same plant species has been shown to yield different anti-inflammatory properties. Given the proven efficacy of TO and the diversity of its constituents, a better understanding of the interactions of the various components is warranted. The aim of this review is to gather the latest research findings regarding TO and its components with respect to their immunomodulatory properties. An optimization of the various components has the potential to yield more effective thyme formulations with increased potency.

Background Here, we investigated the underlying transcriptional-level evidence behind phytochemical differences between two metabolically extreme genotypes of Thymus daenensis. The genotypes ‘Zagheh-11’ (thymol/carvacrol type, poor in essential oil [EO] [2.9%] but rich in triterpenic acids) and ‘Malayer-21’ (thymol type and rich in EO [3.8%]) were selected from an ongoing breeding program and then clonally propagated for further experimental use. Materials and methods GC-MS, GC-FID, and HPLC-PDA were utilized to monitor the fluctuation of secondary metabolites at four phenological stages (vegetative, bud burst, early, and full-flowering stages). The highest phytochemical divergence was observed at early flowering stage. Both genotypes were subjected to mRNA sequencing (approximately 100 million paired reads) at the aforementioned stage. The expression patterns of four key genes involved in the biosynthesis of terpenoids were also validated using qRT-PCR. Results Carvacrol content in ‘Zagheh-11’ (26.13%) was approximately 23 times higher than ‘Malayer-21’ (1.12%). Reciprocally, about 10% higher thymol was found in ‘Malayer-21’ (62.15%). Moreover, the concentrations of three major triterpenic acids in ‘Zagheh-11’ were approximately as twice as those found in ‘Malayer-21’. Transcriptome analysis revealed a total of 1840 unigenes that were differentially expressed, including terpene synthases, cytochrome P450, and terpenoid backbone genes. Several differentially expressed transcription factors (such as MYB , bZIP , HB - HD - ZIP , and WRKY families) were also identified. These results suggest that an active cytosolic mevalonate (MVA) pathway may be linked to higher levels of sesquiterpenes, triterpenic acids, and carvacrol in ‘Zagheh-11’. The chloroplastic pathway of methyl erythritol phosphate (MEP) may have also contributed to a higher accumulation of thymol in Malayer-21. Indeed, ‘Zagheh-11’ showed higher expression of certain genes ( HMGR , CYP71D180 , β-amyrin 28-monooxygenase , and sesquiterpene synthases ) in the MVA pathway, while some genes in the MEP pathway (including DXR, ispG , and γ- terpinene synthase ) were distinctly expressed in Malayer-21. Future efforts in metabolic engineering of MVA/MEP pathways may benefit from these findings to produce increased levels of desired secondary metabolites at commercial scale.

The main purpose of this article is to present the latest research related to selected biological properties of carvacrol, such as antimicrobial, anti-inflammatory, and antioxidant activity. As a monoterpenoid phenol, carvacrol is a component of many essential oils and is usually found in plants together with its isomer, thymol. Carvacrol, either alone or in combination with other compounds, has a strong antimicrobial effect on many different strains of bacteria and fungi that are dangerous to humans or can cause significant losses in the economy. Carvacrol also exerts strong anti-inflammatory properties by preventing the peroxidation of polyunsaturated fatty acids by inducing SOD, GPx, GR, and CAT, as well as reducing the level of pro-inflammatory cytokines in the body. It also affects the body’s immune response generated by LPS. Carvacrol is considered a safe compound despite the limited amount of data on its metabolism in humans. This review also discusses the biotransformations of carvacrol, because the knowledge of the possible degradation pathways of this compound may help to minimize the risk of environmental contamination with phenolic compounds.

The development of Type I photosensitizers (PSs) is of great importance due to the inherent hypoxic intolerance of photodynamic therapy (PDT) in the hypoxic microenvironment. Compared to Type II PSs, Type I PSs are less reported due to the absence of a general molecular design strategy. Herein, we report that the combination of typical Type II PS and natural substrate carvacrol (CA) can significantly facilitate the Type I pathway to efficiently generate superoxide radical (O 2 –• ). Detailed mechanism study suggests that CA is activated into thymoquinone (TQ) by local singlet oxygen generated from the PS upon light irradiation. With TQ as an efficient electron transfer mediator, it promotes the conversion of O 2 to O 2 –• by PS via electron transfer-based Type I pathway. Notably, three classical Type II PSs are employed to demonstrate the universality of the proposed approach. The Type I PDT against S. aureus has been demonstrated under hypoxic conditions in vitro. Furthermore, this coupled photodynamic agent exhibits significant bactericidal activity with an antibacterial rate of 99.6% for the bacterial-infection female mice in the in vivo experiments. Here, we show a simple, effective, and universal method to endow traditional Type II PSs with hypoxic tolerance. Developing Type I photosensitizers (PSs) is vital for tackling hypoxic intolerance of photodynamic therapy in the hypoxic microenvironment, but elusive due to the lack of a general molecular design strategy. Here the authors report a universal and simple method to covert traditional Type II PSs to Type I PSs.

Thymol and carvacrol are phenolic monoterpenes found in thyme, oregano, and several other species of the Lamiaceae. Long valued for their smell and taste, these substances also have antibacterial and anti-spasmolytic properties. They are also suggested to be precursors of thymohydroquinone and thymoquinone, monoterpenes with anti-inflammatory, antioxidant, and antitumor activities. Thymol and carvacrol biosynthesis has been proposed to proceed by the cyclization of geranyl diphosphate to γ-terpinene, followed by a series of oxidations via p-cymene. Here, we show that γ-terpinene is oxidized by cytochrome P450 monooxygenases (P450s) of the CYP71D subfamily to produce unstable cyclohexadienol intermediates, which are then dehydrogenated by a short-chain dehydrogenase/reductase (SDR) to the corresponding ketones. The subsequent formation of the aromatic compounds occurs via keto–enol tautomerisms. Combining these enzymes with γ-terpinene in in vitro assays or in vivo in Nicotiana benthamiana yielded thymol and carvacrol as products. In the absence of the SDRs, only p-cymene was formed by rearrangement of the cyclohexadienol intermediates. The nature of these unstable intermediates was inferred from reactions with the γ-terpinene isomer limonene and by analogy to reactions catalyzed by related enzymes. We also identified and characterized two P450s of the CYP76S and CYP736A subfamilies that catalyze the hydroxylation of thymol and carvacrol to thymohydroquinone when heterologously expressed in yeast and N. benthamiana. Our findings alter previous views of thymol and carvacrol formation, identify the enzymes involved in the biosynthesis of these phenolic monoterpenes and thymohydroquinone in the Lamiaceae, and provide targets for metabolic engineering of high-value terpenes in plants.