Peptide name : Gamma-terpinene synthase, chloroplastic

Source/Organism : Wild marjoram

Linear/Cyclic : Not found

Chirality : Not found

Peptide length: 594

C-terminal modification: Not found

N-terminal modification : Not found

Non-natural peptide information: None

Assay type : Not specified

Assay time : Not found

Activity : Not found

Cell line : Not found

Cancer type : Not found

Other activity : Anti-fungal activity

Amino acid composition bar chart :

Molecular mass : 69061.9044 Dalton

Aliphatic index : 0.932

Instability index : 38.3561

Hydrophobicity (GRAVY) : -0.283

Isoelectric point : 5.2514

Charge (pH 7) : -19.3119

Aromaticity : 0.121

Molar extinction coefficient (cysteine, cystine): (108180, 108555)

Hydrophobic/hydrophilic ratio : 0.89171974

hydrophobic moment : 0.0386

Missing amino acid : None

Most occurring amino acid : L

Most occurring amino acid frequency : 67

Least occurring amino acid : C

Least occurring amino acid frequency : 6

Secondary structure fraction (Helix, Turn, Sheet): (0.3, 0.2, 0.4)

SMILES Notation: 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1 : Salehi B, et al. Thymol, thyme, and other plant sources: Health and potential uses. Phytother Res. 2018; 32:1688-1706. doi: 10.1002/ptr.6109

2 : Javed H, et al. Carvacrol, a Plant Metabolite Targeting Viral Protease (Mpro) and ACE2 in Host Cells Can Be a Possible Candidate for COVID-19. Front Plant Sci. 2020; 11:601335. doi: 10.3389/fpls.2020.601335

3 : Wang K, et al. Synthesis and antifungal activity of carvacrol and thymol esters with heteroaromatic carboxylic acids. Nat Prod Res. 2019; 33:1924-1930. doi: 10.1080/14786419.2018.1480618

4 : Agliassa C and Maffei ME. Origanum vulgare Terpenoids Induce Oxidative Stress and Reduce the Feeding Activity of Spodoptera littoralis. Int J Mol Sci. 2018; 19:(unknown pages). doi: 10.3390/ijms19092805

5 : Zengin Kurt B, et al. Synthesis, anticholinesterase activity and molecular modeling studies of novel carvacrol-substituted amide derivatives. J Biomol Struct Dyn. 2020; 38:841-859. doi: 10.1080/07391102.2019.1590243

6 : Patricelli D, et al. Plant defences against ants provide a pathway to social parasitism in butterflies. Proc Biol Sci. 2015; 282:(unknown pages). doi: 10.1098/rspb.2015.1111

7 : Crocoll C, et al. Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis. Plant Mol Biol. 2010; 73:587-603. doi: 10.1007/s11103-010-9636-1

8 : Kulkarni SA, et al. Computational evaluation of major components from plant essential oils as potent inhibitors of SARS-CoV-2 spike protein. J Mol Struct. 2020; 1221:128823. doi: 10.1016/j.molstruc.2020.128823

9 : Morshedloo MR, et al. Effect of prolonged water stress on essential oil content, compositions and gene expression patterns of mono- and sesquiterpene synthesis in two oregano (Origanum vulgare L.) subspecies. Plant Physiol Biochem. 2017; 111:119-128. doi: 10.1016/j.plaphy.2016.11.023

10 : Suntres ZE, et al. The bioactivity and toxicological actions of carvacrol. Crit Rev Food Sci Nutr. 2015; 55:304-18. doi: 10.1080/10408398.2011.653458

11 : Kumar A, et al. Identification of phytochemical inhibitors against main protease of COVID-19 using molecular modeling approaches. J Biomol Struct Dyn. 2021; 39:3760-3770. doi: 10.1080/07391102.2020.1772112

12 : Yadalam PK, et al. Antiviral Essential Oil Components Against SARS-CoV-2 in Pre-procedural Mouth Rinses for Dental Settings During COVID-19: A Computational Study. Front Chem. 2021; 9:642026. doi: 10.3389/fchem.2021.642026

Paper title : Thymol, thyme, and other plant sources: Health and potential uses.

Doi : https://doi.org/10.1002/ptr.6109

Abstract : Thymol is a naturally occurring phenol monoterpene derivative of cymene and isomer of carvacrol. Thymol (10-64%) is one of the major constituent of essential oils of thyme (Thymus vulgaris L., Lamiaceae), a medicinal plant with several therapeutic properties. This plant, native to Mediterranean regions, is commonly used as a culinary herb and also with a long history of use for different medicinal purposes. Nowadays, thymol and thyme present a wide range of functional possibilities in pharmacy, food, and cosmetic industry. The interest in the formulation of pharmaceuticals, nutraceuticals, and cosmeceuticals based on thymol is due to several studies that have evaluated the potential therapeutic uses of this compound for the treatment of disorders affecting the respiratory, nervous, and cardiovascular systems. Moreover, this compound also exhibits antimicrobial, antioxidant, anticarcinogenesis, anti-inflammatory, and antispasmodic activities, as well as a potential as a growth enhancer and immunomodulator. In the present review, these bioactivities have been covered because some of them can contribute to explain the ethnopharmacology of thymol and its main source, T. vulgaris. Other important aspects about thymol are discussed: its toxicity and bioavailability, metabolism, and distribution in animals and humans.

Paper title : Carvacrol, a Plant Metabolite Targeting Viral Protease (Mpro) and ACE2 in Host Cells Can Be a Possible Candidate for COVID-19.

Doi : https://doi.org/10.3389/fpls.2020.601335

Abstract : The recent outbreak of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) started in December 2019, resulting in the coronavirus disease-19 (COVID-19) pandemic. Coronaviruses are solely accountable for rising mortality and socioeconomic saddles. Presently, there are few repurposed drugs such as remdesivir or favipiravir approved for the treatment of COVID-19, although vaccines and plasma therapy is also subject to emergency approval. However, some potential natural treatments and cures have also been proposed. Molecules of natural origin showed therapeutic importance such as antiviral, anti-inflammatory, and antioxidant activity, and could be useful drug candidates for treating COVID-19. In recent years, essential oils have shown promising therapeutic effects against many viral diseases. Carvacrol is one of the monoterpene phenol with abundant presence in essential oils of many aromatic plants, including thyme and oregano. It is being used as food flavoring, additive, and preservatives. Carvacrol is also used as a fragrance in cosmetic products. A number of research studies have shown biological actions of carvacrol with its therapeutic potential is of clinical significance. The in vitro and in vivo studies have shown multiple pharmacological properties such as anticancer, anti-fungal, anti-bacterial, anti-oxidant, anti-inflammatory, vasorelaxant, hepatoprotective, and spasmolytic. This review highlights the various biological and pharmacological properties of carvacrol within the scope of COVID-19.

Paper title : Synthesis and antifungal activity of carvacrol and thymol esters with heteroaromatic carboxylic acids.

Doi : https://doi.org/10.1080/14786419.2018.1480618

Abstract : Aiming to obtain the more effective pathogen inhibitive ingredients and explore the influence of introducing different heterocyclic units to carvacrol and thymol esters, twenty ester derivatives with different heterocyclic units were synthesized. And the in vitro antifungal activity of title compounds against five plant pathogenic fungi was evaluated by mycelium growth rate method. The results showed that some carvacrol and thymol esters showed good to excellent antifungal activity, and compound 9d (4-bromo-5-isopropyl-2-methylphenyl picolinate) exhibited a broad antifungal spectrum. Preliminary study indicated that the introduction of furan, thiophene and pyridine unit could enhance the antifungal activity of carvacrol and thymol esters against Botrytis cinerea and a bromine atom on the para position of benzene moiety could enhance their antifungal activity.

Paper title : Origanum vulgare Terpenoids Induce Oxidative Stress and Reduce the Feeding Activity of Spodoptera littoralis.

Doi : https://doi.org/10.3390/ijms19092805

Abstract : Terpenoids are toxic compounds produced by plants as a defense strategy against insect herbivores. We tested the effect of Origanum vulgare terpenoids on the generalist herbivore Spodoptera littoralis and the response of the plant to herbivory. Terpenoids were analyzed by GC-FID and GC-MS and quantitative gene expression (qPCR) was evaluated on selected plant genes involved in both terpene biosynthesis. The insect detoxification response to terpenes was evaluated by monitoring antioxidant enzymes activity and expression of insect genes involved in terpene detoxification. O. vulgare terpenoid biosynthesis and gene expression was modulated by S. littoralis feeding. The herbivore-induced increased level of terpenoids (particularly carvacrol and p-cymene) interacted with the herbivore by decreasing larval survival and growth rate. The assimilation by S. littoralis of more than 50% of ingested terpenes correlated with the possible toxic effects of O. vulgare terpenoids. In choice test experiments, carvacrol and γ-terpinene mediated the larval feeding preferences, wherease the prolonged feeding on O. vulgare terpenoids (particularly on γ-terpinene) exerted relevant antinutritional effects on larvae. S. littoralis was found to react to O. vulgare terpenoids by increasing its antioxidant enzymes activities and gene expression, although this was not sufficient to sustain the toxicity of O. vulgare terpenoids.

Paper title : Synthesis, anticholinesterase activity and molecular modeling studies of novel carvacrol-substituted amide derivatives.

Doi : https://doi.org/10.1080/07391102.2019.1590243

Abstract : In the present study, 23 novel carvacrol derivatives involving the amide moiety as a linker between the alkyl chains and/or the heterocycle nucleus were synthesized and tested in vitro as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. 2-(5-Isopropyl-2-methylphenoxy)-N-(quinolin-8-yl)acetamide (5v) revealed the highest inhibition properties against AChE and BuChE with the IC₅₀ values of 1.93 and 0.05 µM, respectively. The blood-brain barrier (BBB) permeability of the potent inhibitor (5v) was also assessed by the widely used parallel artificial membrane permeability assay (PAMPA-BBB). The results showed that 5v is capable of crossing the BBB. Pharmacokinetic and toxicity profiles of the studied molecule predictions were investigated by MetaCore/MetaDrug comprehensive systems biology analysis suite. Bioactive conformations of the synthesized molecules, their predicted binding energies as well as structural and dynamical profiles of molecules at the binding pockets of AChE and BuChE targets were also investigated using different docking algorithms and molecular dynamics (MD) simulations.Communicated by Ramaswamy H. Sarma.

Paper title : Plant defences against ants provide a pathway to social parasitism in butterflies.

Doi : https://doi.org/10.1098/rspb.2015.1111

Abstract : Understanding the chemical cues and gene expressions that mediate herbivore-host-plant and parasite-host interactions can elucidate the ecological costs and benefits accruing to different partners in tight-knit community modules, and may reveal unexpected complexities. We investigated the exploitation of sequential hosts by the phytophagous-predaceous butterfly Maculinea arion, whose larvae initially feed on Origanum vulgare flowerheads before switching to parasitize Myrmica ant colonies for their main period of growth. Gravid female butterflies were attracted to Origanum plants that emitted high levels of the monoterpenoid volatile carvacrol, a condition that occurred when ants disturbed their roots: we also found that Origanum expressed four genes involved in monoterpene formation when ants were present, accompanied by a significant induction of jasmonates. When exposed to carvacrol, Myrmica workers upregulated five genes whose products bind and detoxify this biocide, and their colonies were more tolerant of it than other common ant genera, consistent with an observed ability to occupy the competitor-free spaces surrounding Origanum. A cost is potential colony destruction by Ma. arion, which in turn may benefit infested Origanum plants by relieving their roots of further damage. Our results suggest a new pathway, whereby social parasites can detect successive resources by employing plant volatiles to simultaneously select their initial plant food and a suitable sequential host.

Paper title : Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis.

Doi : https://doi.org/10.1007/s11103-010-9636-1

Abstract : The aroma, flavor and pharmaceutical value of cultivated oregano (Origanum vulgare L.) is a consequence of its essential oil which consists mostly of monoterpenes and sesquiterpenes. To investigate the biosynthetic pathway to oregano terpenes and its regulation, we identified and characterized seven terpene synthases, key enzymes of terpene biosynthesis, from two cultivars of O. vulgare. Heterologous expression of these enzymes showed that each forms multiple mono- or sesquiterpene products and together they are responsible for the direct production of almost all terpenes found in O. vulgare essential oil. The correlation of essential oil composition with relative and absolute terpene synthase transcript concentrations in different lines of O. vulgare demonstrated that monoterpene synthase activity is predominantly regulated on the level of transcription and that the phenolic monoterpene alcohol thymol is derived from gamma-terpinene, a product of a single monoterpene synthase. The combination of heterologously-expressed terpene synthases for in vitro assays resulted in blends of mono- and sesquiterpene products that strongly resemble those found in vivo, indicating that terpene synthase expression levels directly control the composition of the essential oil. These results will facilitate metabolic engineering and directed breeding of O. vulgare cultivars with higher quantity of essential oil and improved oil composition.

Paper title : Computational evaluation of major components from plant essential oils as potent inhibitors of SARS-CoV-2 spike protein.

Doi : https://doi.org/10.1016/j.molstruc.2020.128823

Abstract : COVID-19, caused by SARS-CoV-2 has recently emerged as a global pandemic. Intense efforts are ongoing to find a vaccine or a drug to control the disease across the globe. Meanwhile, alternative therapies are also being explored to manage the disease. Phytochemicals present in essential oils are promising candidates which have been known to possess wide range of therapeutic activities. In this study, major components of several essential oils which are known for their antimicrobial properties have been docked against the S1 receptor binding domain of the spike (S) glycoprotein, which is the key target for novel antiviral drugs, to ascertain their inhibitory effects based on their binding affinities. It has been found that some monoterpenes, terpenoid phenols and phenyl propanoids such as anethole, cinnamaldehyde, carvacrol, geraniol, cinnamyl acetate, L-4-terpineol, thymol and pulegone from essential oils extracted from plants belonging to families such as Lamiaceae, Lauraceae, Myrtaceae, Apiaceae, Geraniaceae and Fabaceae are effective antiviral agents that have potential to inhibit the viral spikeprotein.

Paper title : Effect of prolonged water stress on essential oil content, compositions and gene expression patterns of mono- and sesquiterpene synthesis in two oregano (Origanum vulgare L.) subspecies.

Doi : https://doi.org/10.1016/j.plaphy.2016.11.023

Abstract : Origanum vulgare L., recognized throughout the world as a popular medicinal and flavoring herb, contains a wide array of medicinally active components, including phenolic glucosides, flavonoids, tannins, sterols and high amounts of terpenoids. Especially the latter are often extracted by hydrodistillation resulting in the so-called essential oil that is rich in monoterpenes (e.g. carvacrol, thymol, linalyl acetate) and/or sesquiterpenes (e.g. (E)-β-caryophyllene, germacrene D, bicyclogermacrene, β-caryophyllene oxide). Water stresses in the arid and semiarid regions of the world severely affect growth and productivity of oregano. To determine the variation in essential oil and gene expression pathway of Iranian oregano under prolonged water stress, two native subspecies of O. vulgare (subsp. virens and subsp. gracile) were studied. The plants, grown in pots, were subjected to three water stress conditions, i.e. no stress, mild stress (60± 5% FMC) and moderate stress (40± 5% FMC). The studied subspecies exhibited significant differences in essential oil content, compositions, and patterns of gene expression under water stress conditions. The essential oil of O. vulgare subsp. gracile was rich in the phenolic monoterpene carvacrol (46.86-52.07%), whereas the sesquiterpene hydrocarbon (Z)-α-bisabolene (39.17-42.64%) was the major constituent in the oil of O. vulgare subsp. virens. Both the mild and moderate water stresses significantly increased the essential oil content of O. vulgare subsp. gracile, but did not significantly change the essential oil content of O. vulgare subsp. virens nor the level of carvacrol and (Z)-α-bisabolene in the investigated subspecies. Interestingly, the amount of (E)-β-caryophyllene in O. vulgare subsp. virens was significantly increased under water stress conditions. Gene expression studies supported the above findings and demonstrated that there are two different pathways affecting the biosynthesis of the terpenoid precursors geranyl pyrophosphate (GPP) and farnesyl pyrophosphate (FPP). In O. vulgare subsp. gracile, HMGR, Ovtps2 and CYP71D180 transcript were up-regulated under mild and moderate water stress conditions. Transcription of FPPS was apparently down-regulated in water-stressed O. vulgare subsp. gracile. Investigation of terpene synthases expression levels in oregano subspecies demonstrated that Ovtps2 and Ovtps6 controlled the concentration of carvacrol and (E)-β-caryophyllene in oregano essential oils, respectively.

Paper title : The bioactivity and toxicological actions of carvacrol.

Doi : https://doi.org/10.1080/10408398.2011.653458

Abstract : Carvacrol is a monoterpenic phenol produced by an abundant number of aromatic plants, including thyme and oregano. Presently, carvacrol is used in low concentrations as a food flavoring ingredient and preservative, as well as a fragrance ingredient in cosmetic formulations. In recent years, considerable research has been undertaken in an effort to establish the biological actions of carvacrol for its potential use in clinical applications. Results from in vitro and in vivo studies show that carvacrol possess a variety of biological and pharmacological properties including antioxidant, antibacterial, antifungal, anticancer, anti-inflammatory, hepatoprotective, spasmolytic, and vasorelaxant. The focus of this review is to evaluate the existing knowledge regarding the biological, pharmacological, and toxicological effects of carvacrol.

Paper title : Identification of phytochemical inhibitors against main protease of COVID-19 using molecular modeling approaches.

Doi : https://doi.org/10.1080/07391102.2020.1772112

Abstract : Severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) is a novel corona virus that causes corona virus disease 2019 (COVID-19). The COVID-19 rapidly spread across the nations with high mortality rate even as very little is known to contain the virus at present. In the current study, we report novel natural metabolites namely, ursolic acid, carvacrol and oleanolic acid as the potential inhibitors against main protease (Mpro) of COVID-19 by using integrated molecular modeling approaches. From a combination of molecular docking and molecular dynamic (MD) simulations, we found three ligands bound to protease during 50 ns of MD simulations. Furthermore, the molecular mechanic/generalized/Born/Poisson-Boltzmann surface area (MM/G/P/BSA) free energy calculations showed that these chemical molecules have stable and favourable energies causing strong binding with binding site of Mpro protein. All these three molecules, namely, ursolic acid, carvacrol and oleanolic acid, have passed the ADME (Absorption, Distribution, Metabolism, and Excretion) property as well as Lipinski's rule of five. The study provides a basic foundation and suggests that the three phytochemicals, viz. ursolic acid, carvacrol and oleanolic acid could serve as potential inhibitors in regulating the Mpro protein's function and controlling viral replication. Communicated by Ramaswamy H. Sarma.

Paper title : Antiviral Essential Oil Components Against SARS-CoV-2 in Pre-procedural Mouth Rinses for Dental Settings During COVID-19: A Computational Study.

Doi : https://doi.org/10.3389/fchem.2021.642026

Abstract : COVID-19 mainly spreads through cough or sneeze droplets produced by an infected person. The viral particles are mostly present in the oral cavity. The risk of contracting COVID-19 is high in the dental profession due to the nature of procedures involved that produce aerosols. Along with other measures to limit the risk of infection, pre-procedural mouth rinses are beneficial in reducing the viral particles in the oral cavity. In this study, the antiviral efficacy of essential oil components has been determined specifically against SARS-CoV-2 by molecular docking and conceptual DFT approach. Based on the binding affinities of the components against the receptor binding domain of the S1 glycoprotein, cuminal, carvacrol, myrtanol, and pinocarveol were found to be highly active. The molecular descriptor values obtained through conceptual DFT also indicated the above-mentioned components to be active based on the correlation between the structure and the activity of the compounds. Therefore, pre-procedural mouth rinses with these components included may be specifically suitable for dental procedures during the COVID-19 period.