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PHARMAZIE · 2012 ·Vol. 67 ·期 12 ·1002-1006 · IF 1.006

Identification of CYP isoforms involved in the metabolism of thymol and carvacrol in human liver microsomes (HLMs)

Dong Rui-Hua,Fang Zhong-Ze,Zhu Liang-Liang,Ge Guang-Bo,Cao Yun-Feng,Li Xiao-Bao,Hu Cui-Min,Yang Ling,Liu Ze-Yuan

Carvacrol and thymol are phenolic compounds with similar structures isolated from many aromatic plants, and have been demonstrated to exert multiple pharmacological effects. The metabolic and pharmacokinetic behaviour of thymol and carvacrol has received much attention. Carvacrol and thymol have been demonstrated to undergo phase I metabolism such as hydroxylation reaction. However, drug-metabolizing enzymes involved in this process remain unclear. Given that cytochrome P450 s (CYPs) are involved in most phase I metabolism, the aim of the present study was to investigate the role of CYPs in the metabolism of thymol and carvacrol. After incubation with human liver microsomes (HLMs) in the presence of NADPH, a new metabolite and two metabolites were detected for thymol and carvacrol, respectively. A combination of chemical inhibition studies and assays with recombinant CYP isoforms demonstrated that CYP2A6 was the predominant drug-metabolizing enzyme involved in the metabolism of thymol and carvacrol. All these results remind the researchers that special attention should be paid on pharmacokinetic and clinical outcomes when thymol or carvacrol was co-administrated with other compounds mainly undergoing CYP2A6-mediated metabolism.

CAS / MDL: 499-75-2 89-83-8
研究领域: 药理学 · 生物化学
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FOOD CHEMISTRY · 2025 · IF 9.8

Electrospinning PCL-CA packaging membranes with transmittance response to ethanol for monitoring grape freshness

Li Xia,Zhina Chen,Hui Liu,Ying Xue,Hualin Wang

In recent years, there has been an increasing focus on the development of active films for monitoring and maintaining food freshness. However, its further functional diversification remains highly desirable. In this study, the active polycaprolactone (PCL) based membranes loaded with carvacrol (CA) are fabricated via electrospinning technique for grape preservation. Upon touching with ethanol exudate, the resulting membrane is capable of changing from opaque to a reversible transparent packaging (RTP) through interfibrillar fusion during food storage. The RTP exhibits good reusability with light transparency above 80 % after 10 cycles. CA is well-dispersed in the fiber matrix by hydrogen bonding and enriching the membrane with strong antibacterial activity. Furthermore, the release of CA from film matrix is well controlled and predominantly governed by Fickian diffusion. In addition to freshness monitoring, PCL-CA15 can effectively extend the shelf life of grape by about 4 days at 25 °C.

CAS / MDL: 24980-41-4 499-75-2
研究领域: 食品科学 · 材料科学 · 生物学
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Foods · 2023 ·Vol. 12 ·期 13 ·2560 · IF 5.2

Inhibition of Salmonella Enteritidis by Essential Oil Components and the Effect of Storage on the Quality of Chicken

Wu Wang,Tingting Li,Jing Chen,Yingwang Ye

This research investigates the antibacterial potential of plant essential oil components including thymol, carvacrol, citral, cinnamaldehyde, limonene, and β-pinene againstSalmonellaEnteritidis (S.Enteritidis). Through the determination of minimum inhibitory concentration, three kinds of natural antibacterial agents with the best inhibitory effect onS.Enteritidis were determined, namely thymol (128 μg/mL), carvacrol (256 μg/mL), and cinnamaldehyde (128 μg/mL). Physical, chemical, microbial, and sensory characteristics were regularly monitored on days 0, 2, 4, and 6. The findings of this study reveal that both thymol at MIC of 128 μg/mL and carvacrol at MIC of 256 μg/mL not only maintained the sensory quality of chicken, but also decreased the pH, moisture content, and TVB-N value. Additionally, thymol, carvacrol and cinnamaldehyde successfully inhibited the formation ofS.Enteritidis biofilm, thereby minimizing the number ofS.Enteritidis and the total aerobic plate count in chicken. Hence, thymol, carvacrol, and cinnamaldehyde have more effective inhibitory activities againstS.Enteritidis, which can effectively prevent the spoilage of chicken and reduce the loss of its functional components.Keywords:SalmonellaEnteritidis;thymol;carvacrol;cinnamaldehyde

研究领域: 食品安全 · 微生物学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2024 · IF 3.3

Carvacrol enhances antioxidant activity and slows down cell wall metabolism by maintaining the energy level of ‘Guifei’ mango

Xiaogang Wang,Donglan Luo,Xiaohong Kou,Shenjie Ye,Jiangkuo Li,Liangjie Ba,Sen Cao

BACKGROUND Postharvest mango fruit are highly susceptible to rapid ripening, softening and senescence, greatly limiting their distribution. In this study, we evaluated the potential effects of carvacrol (0.06 g L −1 ) on mango (25 ± 1 °C) and the mechanisms by which it regulates antioxidant activity, energy and cell wall metabolism. RESULTS The results showed that carvacrol treatment delayed the ‘Guifei’ mango color transformation (from green to yellow) and the decrease in firmness, titratable acidity, weight loss and soluble solids content, and suppressed the increase in relative conductivity, malondialdehyde content and reactive oxygen species (H 2 O 2 and O 2 ·– ) as well as enhancing antioxidant activity. In addition, carvacrol treatment increased ascorbic acid and reduced glutathione levels, ascorbate peroxidase, glutathione reductase, monodehydroascorbate reductase and dehydroascorbate reductase activities in mango. Meanwhile, energy level (adenosine triphosphate, adenosine diphosphate, adenosine monophosphate and energy charge) content and energy metabolizing enzyme activities (H + -ATPase, Ca 2+ -ATPase, succinate dehydrogenasepears and cytochrome C oxidase) were increased on carvacrol treatment, which resulted in the maintenance of higher energy levels. Finally, the application of carvacrol was effective in maintaining firmness and cell wall components by inhibiting the activities of polygalacturonase, cellulase, pectin methyl esterase and β -galactosidase. CONCLUSION The current study demonstrates that carvacrol effectively delays the ripening and softening of mangoes by modulating energy metabolism and cell wall dynamics through the attenuation of oxidative stress. © 2024 Society of Chemical Industry.

CAS / MDL: 499-75-2
研究领域: 植物生理学 · 食品科学 · 园艺学
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Food Bioscience · 2025 · IF 5.9

Transcriptome analysis revealed the effects of preharvest carvacrol spraying on postharvest antioxidant activity and cell wall metabolism in peppers

Xiaogang Wang,Jianye Chen,Sen Cao,Donglan Luo,Liangjie Ba

Pepper is susceptible to softening and decay during storage and transportation, resulting in loss of fruit quality and severely affecting the commercial value of peppers. To investigate the effects of preharvest carvacrol spraying on postharvest antioxidant capacity and fruit softening in peppers, we applied a 0.015 mg/mL carvacrol solution to the peppers and evaluated its influence on antioxidant activity and cell wall metabolism during storage. The results demonstrated that treatment with 0.015 mg/mL carvacrol significantly ( P  < 0.05) reduced the weight loss rate by 48.51%, increased titratable acid (TA) content by 47.30%, and effectively maintained chlorophyll levels Additionally, there was a significant reduction in firmness by 13.2%. Carvacrol enhanced the antioxidant capacity of peppers during postharvest storage by augmenting the activities of superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), ascorbate peroxidase (APX), and chalcone isomerase (CHI) enzymes, and retarding the accumulation of H 2 O 2 and O 2 •- contents. The application of carvacrol retarded the softening of pepper fruits by delaying the reduction of the pectin, protopectin, soluble pectin, and cellulose content, inhibiting the β -galactosidase ( β -Gal), polygalacturonase (PG), pectin methyl esterase (PME), cellulase (Cx), and glucosidase (GLU) enzyme activities, and reducing the rate of cell wall metabolism during postharvest storage. In the transcriptome WGCNA analysis, a total of 11 distinct modules were identified. Notably, genes associated with antioxidant functions and cell wall metabolism were significantly enriched in the blue-green, blue, green, and brown modules. In conclusion, it can be posited that carvacrol may enhance the antioxidant system of pepper fruits and maintain postharvest storage quality by increasing antioxidant activity and delaying the cell wall metabolism pathways.

CAS / MDL: 499-75-2
研究领域: 植物学 · 食品科学 · 园艺学
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PHYTOPATHOLOGY · 2023 · IF 3.2

In Addition to Damaging the Plasma Membrane, Phenolic Monoterpenoid Carvacrol can Bind to Minor Groove of DNA of Phytopathogenic Fungi to Potentially Control Tea Leaf Spot Caused by Lasiodiplodia theobromae

Mr. Jiayu Yin,Ms. Shuang Wu,Ms. Yongli Yang,Dr. Delu Wang,Prof. Yue Ma,Dr. Yongtian Zhao,Prof. Sujitraj Sheth,Miss Honglin Huang,Dr. Baoan Song,Dr. Zhuo Chen

Carvacrol expresses a wide range of biological activities, but the studies of its mechanisms focused on bacteria, mainly involving the destruction of the plasma membrane. In this study, carvacrol exhibited strong antifungal activities against several phytopathogenic fungi and determined a novel antifungal mechanism against Lasiodiplodia theobromae. RNA sequencing indicated that many genes of L. theobromae hyphae were predominately induced by carvacrol, particularly those involved in replication and transcription. Hyperchromic, hypsochromic, and bathochromic effects in the UV-visible absorption spectrum were observed following titration of calf thymus DNA (ctDNA) and carvacrol, which indicated the formation of a DNA–carvacrol complex. Circular dichroism (CD) spectroscopy indicated the response of DNA to carvacrol was similar to 4’, 6-diamidino-2-phenylindole (DAPI), but different from that of ethidium bromide (EB), implying the ionic bonds between carvacrol and ctDNA. Fluorescence spectrum (FS) analysis indicated that carvacrol quenched the fluorescence of double-stranded DNA more than single-stranded DNA, indicating that carvacrol mainly bound to double-stranded DNA. A displacement assay showed that carvacrol reduced the fluorescence intensity of the DNA–DAPI complex through competing with DAPI, but this did not occur for DNA–EB. FS assay revealed that carvacrol bound to AAA sequence on the minor groove of ds-oligonucleotides. The hydroxyl of carvacrol was verified to bind to ctDNA through a comparative test in which structural analogs of carvacrol, including thymol, 4-ethyl-1,2-dimethyl, etc. were analyzed. The current study indicated carvacrol can destruct plasma membranes and bind to the minor groove of DNA, which inhibited the fungal proliferation by disturbing the stability of dsDNA.

研究领域: 植物病理学 · 分子生物学
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PEST MANAGEMENT SCIENCE · 2019 ·Vol. 76 ·期 2 ·589-596 · IF 3.255

Efficacy of binary combinations between methyl salicylate and carvacrol against thrips Anaphothrips obscurus: laboratory and field trials

Xiao-Peng Lu,Jia-Huan Liu,Hua Weng,Zhi-Qing Ma,Xing Zhang

BACKGROUND Thrips Anaphothrips obscurus are one of the cosmopolitan major pests feeding on cereals and other grasses. In order to develop alternatives of chemical insecticides for thrips control, based on fumigant activity screening and evaluation of 22 essential oil (EO) compounds against the thrips, the binary interactions of methyl salicylate and carvacrol (MS-C) with high fumigant toxicity were studied systematically by bioassay and field trials. RESULTS The bioassay results showed that six in 22 EO compounds had high fumigant toxicity against both the second-instar nymphs and adults of A. obscurus , including methyl salicylate, carvacrol, thymol, trans -cinnamaldehyde, diallyl trisulfide, and L-perillaldehyde. Furthermore, the combination of methyl salicylate mixed with carvacrol at a volume ratio of 5:5 exhibited the most significant synergism against A. obscurus , with a poison ratio value of 1.32 and a co-toxicity coefficient of 151.15. The optimal formulation of microemulsion (ME) was composed of 5% methyl salicylate, 5% carvacrol, 46% adjuvant and 44% deionized water. The result of dynamic light scattering and stability showed that MS-C 10% ME was a transparent, single-phase and homogeneous liquid system. Field trials indicated that the ME displayed a significant control efficacy of about 89.17% on thrips in peppers, and 82.59% in broad bean on the seventh day post application with a dosage of 600.0 g A.I hm –2 , respectively. CONCLUSION The binary combination of MS-C possesses strikingly synergistic action against thrips A. obscurus , and the MS-C 10% ME has the potential to be developed as a botanical pesticide product for thrips control. © 2019 Society of Chemical Industry

研究领域: 植物保护 · 昆虫学
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FLAVOUR AND FRAGRANCE JOURNAL · 2016 ·Vol. 32 ·期 2 ·102-111 · IF 1.693

Host-guest complexes of estragole with β-cyclodextrin: an experimental and theoretical investigation

Zujin Yang,Liyun Huang,Xingdong Yao,Hongbing Ji

Estragole (ES) has multiple biological activities and is widely used in food preservation. However, the applications of ES are limited because of its low water solubility and high volatility nature. In this paper, the β-cyclodextrin (β-CD) inclusion complex of ES was prepared by a co-precipitation method with the aim of enhancing its thermal stability and realize its controlled release. Solubility experiments were performed to evaluate the effect of β-CD on ES aqueous solubility. Release experiments of ES from its inclusion complexes were carried out at different temperatures with a relative humidity (RH) and Avrami's equation was used to analyse the release data. The antimicrobial activity of the free and included ES was also examined. The results indicated that the host–guest interactions played a crucial role in enhancing the properties of ES. The inclusion complex was investigated using physico-chemical techniques such as Fourier transform infrared spectroscopy (FTIR), thermal analysis (TGA and DSC), 1H and 2D nuclear magnetic resonance (NMR). The inclusion processes between β-CD and ES were simulated using the semi-empirical PM3 and ONIOM [B3LYP/6-31g(d):PM3] methods. Copyright © 2016 John Wiley & Sons, Ltd.

CAS / MDL: 140-67-0
研究领域: 食品科学 · 药物化学 · 分子生物学
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Food Bioscience · 2024 · IF 4.8

Isoreticular metal-organic framework-3 post-synthetic modification: Application in a new active film based on sodium alginate and carvacrol for pork preservation

Haoyue Ning,Lixin Lu,Yuemei Zhang

To achieve long-term effective protection of food by continuously controlling the release of active substances in an active film, IRMOF-3 was post-synthetic modified with benzoic acid (BA) to obtain BA-IRMOF-3. This modification enhanced the loading capacity of carvacrol (CA) and slowed down its release rate. Research on IRMOF-3 synthesis has found that increasing the proportion of metal nodes can improve its crystallinity. The post-synthesis modification of IRMOF-3 through amide reaction successfully enhanced the binding energy with CA from −5.1 kcal/mol to −6 kcal/mol, resulting in an improved CA loading rate of 28.62% ± 0.15% and delayed release. Furthermore, the BA-IRMOF-3/CA assembly was added to the sodium alginate matrix to prepare the active film BMC@SA, which improved the mechanical and physical properties of the film. The release and antibacterial/antioxidant properties were investigated. The results demonstrated that the active film BMC@SA exhibited significant sustained-release properties and antibacterial/antioxidant activities, reducing the growth of E. coli and S. aureus by 61.95% and 49.33% respectively. In refrigerated pork experiments, the film BMC@SA slowed down the color, weight, pH changes and inhibited microbial growth of fresh pork effectively, and extended the shelf life of pork from 6 d to 12 d, which demonstrated the potential application of active film BMC@SA in food preservation.

CAS / MDL: 9005-38-3 2592-95-2
研究领域: 食品科学 · 材料科学
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Frontiers in Sustainable Food Systems · 2025 · IF 3.1

Antifungal mechanism of carvacrol and osthole can disrupt cell structure integrity and interfere with energy metabolism in Neopestalotiopsis ellipsospora

Huifang Liu,Jianmei Yao,Rongxiu Yin,Chiyu Ma,Lulu Li,Wen Yang,Zhiwei Lei

Introduction: Tea gray blight disease is a major leaf disease in tea plants, significantly reducing tea quality and yield. Plants are rich in bioactive compounds that are safe, non-toxic, and biodegradable. In this study, we evaluated the antifungal activities and mechanisms of 11 plant extracts against N. ellipsospora.Methods: This study evaluated the antifungal activity of 11 plant extracts against N. ellipsospora of tea gray blight disease and systematically examined the impacts of osthole and carvacrol on the mycelial morphology, mycelial weight, cell microstructure, membrane permeability, various biochemical substrate levels and related gene expression levels of N. ellipsospora.Results: The results showed that carvacrol and osthole exhibited significant antifungal effects among 11 plant extracts with EC50 values of 24.40 and 9.38 mg/L, respectively. Further research demonstrated that carvacrol and osthole significantly inhibited mycelial growth, reduced lesion areas on tea leaves, and markedly affected mycelial morphology and ultrastructure. Observations of mycelial morphology and ultrastructure revealed that carvacrol and osthole caused shrinkage and distortion of the mycelial surface, damage to cell wall and membrane, and disorganization of cellular organelles. Particularly carvacrol and osthole significantly increased chitinase activity, inhibited β-1,3-glucanase activity, and regulated the expression of genes encoding these enzymes.Discussion: The findings indicated that carvacrol and osthole could inhibit the growth of N. ellipsospora by disrupting the integrity of the cell wall and membrane and interfere with energy metabolism. This study would provide a theoretical basis for the development of novel plant-based fungicides.

研究领域: 植物学 · 微生物学 · 生物化学 · 农业科学
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JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH · 2021 · IF 1.571

Synthesis of sulfonate derivatives of carvacrol and thymol as anti-oomycetes agents

Gen-Qiang Chen,Di Sun,Jin-Ming Yang,Song Zhang,Yue-E Tian,Zhi-Ping Che,Sheng-Ming Liu,Jia Jiang,Xiao-Min Lin

Two series of sulfonate derivatives of carvacrol and thymol were synthesized and screened in vitro for their anti-oomycete activity against Phytophthora capsici, respectively. Among all of 32 derivatives, five compounds 3a, 4a, 4k, 3n, and 4n exhibited more potent anti-oomycete activity against P. capsici with EC50 values of 66.66, 62.94, 68.65, 61.24, and 52.91 mg/L, respectively. This suggested that introduction of different substitutions at the hydroxyl position of 1/2 could have remarkable effect on anti-oomycete activity. Overall, when R1 = isopropyl and R2 = methyl, the anti-oomycete activities of the compounds were higher than that of the corresponding compounds of R1 = methyl and R2 = isopropyl.

研究领域: 植物化学 · 农药科学 · 微生物学
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FOOD CONTROL · 2021 · IF 5.548

Efficient formation of carvacrol inclusion complexes during β-cyclodextrin glycosyltransferase-catalyzed cyclodextrin synthesis

Tonghui Liu,Chuqi Feng,Zhaofeng Li,Zhengbiao Gu,Xiaofeng Ban,Yan Hong,Li Cheng,Caiming Li

Carvacrol has strong antibacterial and antiinflammatory effects and has been increasingly employed in the food and pharmaceutical industries. However, carvacrol is volatile, easily oxidized, and difficult to dissolve in water. In this study, carvacrol was encapsulated with mixed cyclodextrins during enzymatic cyclodextrin synthesis and microencapsulated carvacrol was obtained by spray drying. The encapsulation efficiency and encapsulation yield of microencapsulated carvacrol were 92.16% and 72.30%, respectively. The encapsulation yield for the pure β-cyclodextrin/carvacrol inclusion complex (38.96%) was lower than that of microencapsulated carvacrol (50.44%) when the guest/host ratio was 1:4. No significant difference ( P  > 0.05) in the amount of encapsulated carvacrol was found when the guest/host ratio was less than 1:6. Microencapsulated carvacrol appeared in scanning electron micrographs as spherical particles with obvious invaginations. Determination of the inclusion formation constant, NMR analysis, and molecular modeling revealed that cavity size affected the ability of cyclodextrins to include carvacrol. Finally, the rate constants ( k ) of carvacrol release from microencapsulated carvacrol (1.09–8.53 × 10 −4 ) at various temperatures and relative humidities were systematically lower than those of β-cyclodextrin/carvacrol inclusion complexes (5.20–199 × 10 −4 ). This study transcended traditional essential oil-cyclodextrin inclusion formation by developing a mixed-cyclodextrin inclusion compound that achieved better encapsulation and superior release.

CAS / MDL: 499-75-2
研究领域: 食品科学 · 生物化学
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