A review on biosynthesis, regulation, and applications of terpenes and terpenoids
الموضوعات :
Anjali Singh
1
(Faculty of Biosciences, Shri Ramswaroop Memorial University, Lucknow-Deva Road, Barabanki, Uttar Pradesh-225003, India)
Dhananjay Singh
2
(Department of Biosciences, Integral University, Kursi Road, Lucknow, Uttar Pradesh-226026, India)
Sapna Sharma
3
(Faculty of Biosciences, Shri Ramswaroop Memorial University, Lucknow-Deva Road, Barabanki, Uttar Pradesh-225003, India)
Nishu Mittal
4
(Faculty of Biosciences, Shri Ramswaroop Memorial University, Lucknow-Deva Road, Barabanki, Uttar Pradesh-225003, India)
الکلمات المفتاحية: Essential oil, Antimicrobial, anticancer, terpenoids, Anti-inflammatory, biosynthesis, Shikimic acid pathway,
ملخص المقالة :
Essential oils (EOs) are concentrated liquids extracted from various parts of plants and can be classified based on their phytochemical compounds. Terpenes and terpenoids have a wide range of biological activities, including anticancer, anti-inflammatory, antimicrobial, antioxidant, and antiallergic properties. Terpenes are plant-based compounds commonly used in the pharmaceutical, food, biofuel, and chemical industries by humans. In synthetic biology, genomic resources and emerging tools facilitate the production of high-quality terpenoids in plants and microbes. Terpenoids, however, are difficult to produce in large quantities due to their complex chemical structures and the limited amounts found in plants. The regulation of terpenoid biosynthesis has gradually emerged as a research priority. This review presents an overview of the biological activities, synthesis pathways, and key enzymes involved in the biosynthetic pathways and regulation of terpenes or terpenoids. This review will also include references for further research on molecular regulation, biological advancements, and increasing the content of terpenes or terpenoids in plants.
A.M. Abdel-Rahman, I., E. Raslan, A., Dawy, A., Wail, A., Ahmed, F., Hany, K., M. Al-Monair, M., Ahmed, O., I. Rushdi, M., A.E. Allam, A., 2022. Cymbopogon schoenanthus (L.) Spreng: A comprehensive review on phytochemical and pharmacological biodiversity. Trends Phytochem. Res. 6(4), 259-281.
Abdollahi, M., Karimpour, H., Monsef-Esfehani, H.R., 2003. Antinociceptive effects of Teucrium polium L total extract and essential oil in mouse writhing test. Pharmacol. Res. 48, 31-35.
Abdullah, S., Nadeem, M., 2016. Screening of local medicinal plant extracts against multi drugs resistance bacteria. Int. J. Bioassays. 5, 4985-4989.
Abraham, E.J., Kellogg, J.J., 2021. Chemometric-guided approaches for profiling and authenticating botanical materials. Front. Nutr. 8, 780-228.
Aguirre, A., Borneo, R., León, A.E., 2013. Antimicrobial, mechanical and barrier properties of triticale protein films incorporated with oregano essential oil. Food Biosci. 1, 2-9.
Ali, M., Miao, L., Soudy, F.A., Darwish, D.B.E., Alrdahe, S.S., Alshehri, D., Benedito, V.A., Tadege, M., Wang, X., Zhao, J., 2022. Overexpression of terpenoid biosynthesis genes modifies root growth and nodulation in soybean (Glycine max). Cells. 11, 2622.
Al-Saleh, I.A., Billedo, G., El-Doush, I.I., 2006. Levels of selenium, dl-α-tocopherol, dl-γ-tocopherol, all-trans-retinol, thymoquinone and thymol in different brands of Nigella sativa seeds. J. Food Compost. Anal. 19, 167-175.
Alsherbiny, M. A., Abd-Elsalam, W. H., El Badawy, S. A., Taher, E., Fares, M., Torres, A., 2018. Ameliorative and protective effects of ginger and its main constituents against natural, chemical and radiation-induced toxicities: A comprehensive review. Food Chem. Toxicol. 123, 72-97.
Alvarez-Martínez, F.J., Barraj on-Catalan, E., H erranz-Lopez, M., Micol, V., 2021. Antibacterial plant compounds, extracts, and essential oils: An updated review on their effects and putative mechanisms of action. Phytomedicine 90, 153-626.
Ament K., Schie V.C., Bouwmeester H.J., 2006. Induction of a leaf specific geranyl geranyl pyrophosphate synthase and emission of (E, E)-4, 8, 12-trimethyltrideca-1, 3, 7, 11-tetraene in tomato are dependent on both jasmonic acid and salicylic acid signaling pathways. Planta. 224, 1197-1208.
Ashaari N.S., Rahim M.H., Sabri S., 2020. Functional characterization of a new terpene synthase from Plectranthusam boinicus. PLoS One. 15, 235-416.
Ashour, M., Wink, M., Gershenzon, J., 2010. Biochemistry of terpenoids: monoterpenes, sesquiterpenes and diterpenes. Annu. Rev. Biochem. 40, 258-303.
Aslam M.Z., Lin X., Li X., Yang N., Chen L., 2020. Molecular cloning and functional characterization of CpMYC2 and CpBHLH13 transcription tactors from Wintersweet (Chimonanthus praecox L.). Plants. 9, 785.
Banf, M., Zhao, K., Rhee, S.Y., 2019. METACLUSTER- an R package for context-specific expression analysis of metabolic gene clusters. J. Bioinform. 35, 3178-3180.
Bansod, S., Chilvery, S., Saifi, M. A., Das, T. J., Tag, H., Godugu, C., 2021. Borneol protects against cerulein-induced oxidative stress and inflammation in acute pancreatitis mice model. Environ. Toxicol. 36, 530-539.
Battistini M.R, Shoji C, Handa S., 2016. Mechanistic binding insights for 1-deoxy-D-Xylulose-5-Phosphate synthase, the enzyme catalyzing the first reaction of isoprenoid biosynthesis in the malaria-causing protists, Plasmodium falciparum and Plasmodium vivax. Protein Expr. Purif. 120, 16-27.
Bazylko, A., Strzelecka, H., 2000. Quantitative determination of phenol derivatives from Oleum thyme. Chromatographia. 52, 112-114.
Bellik, F.Z., Benkaci-Ali, F., Alsafra, Z., Eppe, G., Tata, S., Sabaou, N., Zidane, R., 2019. Chemical composition, kinetic study and antimicrobial activity of essential oils from Cymbopogon schoenanthus L. Spreng extracted by conventional and microwave-assisted techniques using cryogenic grinding, Inds. Crops Prod. 139, 111505.
Bento-Silva, A., Duarte, N., Mecha, E., Belo, M., Vaz Patto, M.C. and Bronze, M.D.R., 2020. Hydroxycinnamic acids and their derivatives in broa, a traditional ethnic maize bread. Foods. 9, 1471.
Bergman, M.E., Davis, B., Phillips, M.A., 2019. Medically useful plant terpenoids: Biosynthesis, occurrence, and mechanism of action. Molecules. 24, 3961.
Berthelot K., Estevez Y., Deffieux A., Peruch F., 2012. Isopentenyl diphosphate isomerase: a checkpoint to isoprenoid biosynthesis. Biochem. 94, 1621-1634.
Bhavaniramya, S., Vishnupriya, S., Al-Aboody, M. S., Vijayakumar, R., Baskaran, D., 2019. Role of essential oils in food safety: Antimicrobial and antioxidant applications. Grain Oil Sci. Technol. 2, 49-55.
Blazickova, M., Blasko, J., Kubinec, R., Kozics, K., 2022. Newly synthesized thymol derivative and its effect on colorectal cancer cells. Molecules. 27, 26-22.
Bonda, A. F., Regis, L., Giovannelli, L., Segale, L., 2020. Alginate/maltodextrin and alginate/shellac gum core-shell capsules for the encapsulation of peppermint essential oil. Int. J. Biol. Macromol. 162, 1293-1302.
Boskovic, M., Glisic, M., Djordjevic, J., Starcevic, M., Glamoclija, N., Djordjevic, V., Baltic, M. Z., 2019. Antioxidative activity of thyme (Thymus vulgaris) and oregano (Origanum vulgare) essential oils and their effect on oxidative stability of minced pork packaged under vacuum and modified atmosphere. J. Food Sci. 84, 2467-2474.
Boutanaev, A.M., Moses, T., Zi, J., Nelson, D.R., Mugford, S.T., Peters, R.J., Osbourn, A., 2015. Investigation of terpene diversification across multiple sequenced plant genomes. Proc. Nat. Acad. Sci. USA. 11, 81-88.
Boye, A., Addo, J.K., Acheampong, D.O., Thomford, A.K., Asante, E., Amoaning, R.E., Kuma, D. N., 2020. The hydroxyl moiety on carbon one (C1) in the monoterpene nucleus of thymol is indispensable for anti-bacterial effect of thymol. Heliyon. 6, 34-92.
Burke C, Croteau R., 2002. Geranyl diphosphate synthase from Abies grandis: cDNA isolation, functional expression,and characterization. Arch. Biochem. Biophy. 405, 130-136.
Carpena, M., Nunez-Estevez, B., Soria-Lopez, A., Garcia-Oliveira, P., Prieto, M.A. 2021. Essential oils and their application on active packaging systems: A review. Resources. 10, 7.
Cebi, N., Arici, M., Sagdic, O., 2021. The famous Turkish rose essential oil: Characterization and authenticity monitoring by FTIR, Raman and GC-MS techniques combined with chemometrics. Food Chem. 354, 129-495.
Chen, F., Tholl, D., Bohlmann, J., Picher sky, E., 2011. The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J. 66, 212-229.
Chen, Jie, Dong-Li Li., Ling-Na Xie, Yu-ran Ma, Pan-Pan Wu, Chen Li., 2020. Synergistic anti-inflammatory effects of silibinin and thymol combination on LPS-induced RAW264.7 cells by inhibition of NF-κB and MAPK activation. Phytomedicine 78, 153-309.
Chen, Y., Mensah, A., Wang, Q., Li, D., Qiu, Y., Wei, Q., 2022. Hierarchical porous nano fibers containing thymol/beta-cyclodextrin: Physico-chemical characterization and potential biomedical applications. Mater. Sci Eng.115.
Cheng, Y.W., Kong, X.W., Wang, N., Wang, T.T., Chen, J., Shi, Z.Q., 2020. Thymol confers tolerance to salt stress by activating anti-oxidative defense and modulating Na+ homeostasis in rice root. Ecotoxicol. Environ. Saf. 188, 109-894.
Chung I. M., Rekha K., Rajakumar G., Thiruvengadam M., 2016. Production of glucosinolates, phenolic compounds and associated gene expression profiles of hairy root cultures in turnip (Brassica rapa ssp. rapa) 3 Biotech. 6, 175.
Contant, C., Rouabhia, M., Loubaki, L., Chandad, F., Semlali, A. 2021 Anethole induces anti-oral cancer activity by triggering apoptosis, autophagy and oxidative stress and by modulation of multiple signaling pathways, Sci. Rep. 11,13-87.
Costa, M.D.S., Rocha, J.E., Campina, F.F., Silva, A.R.P., Da Cruz, R.P., Pereira, R.L.S., Coutinho, H.D.M., 2019. Comparative analysis of the antibacterial and drug-modulatory effect of d-limonene alone and complexed with β-cyclodextrin. Eur. J. Pharm. Sci. 128, 158-161.
Crocoll, C., Asbach, J., Novak, J., Gershenzon, J., Degenhardt, J., 2010. Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis. Plant Mol. Biol. 73, 587-603.
D’Onofrio C., Matarese F., Cuzzola A., 2018. Effect of methyl jasmonate on the aroma of sangiovese grapes and wines. Food Chem. 242, 352-361.
De Castro, R.D., de Souza, T.M.P.A., Bezerra, L. M. D., Ferreira, G. L. S., de Brito Costa, E. M. M., Cavalcanti, A.L., 2015. Antifungal activity and mode of action of thymol and its synergism with nystatin against Candida species involved with infections in the oral cavity: An in vitro study. BMC Complement. Med. Ther. 15, 1-7.
De Sousa, D.P., Damasceno, R.O.S., Amorati, R.; Elshabrawy, H.A., de Castro, R.D., 2023. Essential Oils: Chemistry and Pharmacological Activities. Biomolecules 13, 1144.
Degenhardt J., Kollner T.G., Gershenzon J., 2009. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 70, 1621-1637.
Demissie, Z.A., Sarker, L.S., Mahmoud, S.S., 2011. Cloning and functional characterization of β-phellandrene synthase from Lavandula angustifolia. Planta 233, 685-696.
Devi, K.P., Nisha, S.A., Sakthivel, R., Pandian, S. K., 2010. Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi by disrupting the cellular membrane. J. Ethnopharmacol. 130, 107.
Dhalwal, K., Shinde, V.M., Mahadik, K.R., Namdeo, A.G., 2007. Rapid densitometry method for simultaneous analysis of umbelliferone, psoralen, and eugenol in herbal raw materials using HPTLC. J. Sep. Sci. 30, 2053-2058.
Dietsch M., Behle A., Westhoff P., Axmann I.M., 2021. Metabolic engineering of Synechocystis sp. PCC 6803 for the photoproduction of the sesquiterpene valencene. Metab Eng Commun. 13, e00178.
Dolatkhahi, M., Dolatkhahi, A., Nejad, J.B., 2014. Ethnobotanical study of medicinal plants used in Arjan-Parishan protected area in Fars Province of Iran. Avicenna J. Phytomed. 4(6), 402.
Doost, A. S., Nasrabadi, M. N., Kassozi, V., Nakisozi, H., Van der Meeren, P., 2020. Recent advances in food colloidal delivery systems for essential oils and their main components. Trends in Food Sci. Technol. 99, 474-486.
Duan Q., Kleiber A., Jansen K., 2019. Effects of elevated growth temperature and enhanced atmospheric vapourpressure deficit on needle and root terpenoid contents of two douglas fir provenances. Enviro. Exp. Bot. 166, 103-819.
Dubey, D., Rath, S., Sahu, M. C., Nayak, N., Debata, N.K., Padhy, R.N., 2013. Status of multidrug resistance in tubercle bacillus and phytochemicals for the control. Eur. J. Public Health 21, 115-119.
Eid, A.M., Hawash, M., 2021. Biological evaluation of Safrole oil and Safrole oil Nanoemulgel as antioxidant, antidiabetic, antibacterial, antifungal and anticancer. BMC Complement. Med. Thera. 21, 159.
Falara, V., Akhtar, T.A., Nguyen, T.T.H., Spyropoulou, E.A., Bleeker, P.M., Schauvinhold, I., Matsuba, Y., Bonini, M.E., Schilmiller, A.L. Last, R.L., 2011. The tomato terpene synthase gene family. Plant Physiol. 157, 770-789.
Filipe, A., Cardoso, J.C.R., Miguel, G., Anjos, L., Trindade, H., Figueiredo, A.C., Barroso, J., Power, D.M., Marques, N.T., 2017. Molecular cloning and functional characterization of a monoterpene synthase isolated from the aromatic wild shrub Thymus albicans. J. Plant Physiol. 218, 35-44.
Franz, C., Novak, J., 2009. Sources of essential oils. Handbook of essential oils: Science, Technology, and Applications. CRC press. 39-81.
Gavahian, M., Farhoosh, R., Farahnaky, A., Javidnia, K., Shahidi, F., 2015. Comparison of extraction parameters and extracted essential oils from Mentha piperita L. using hydrodistillation and steam distillation. Int. Food Res. J. 22, 283-288.
Gomes F.I.A., Teixeira P., Azeredo J., Oliveira R., 2009. Effect of farnesol on planktonic and biofilm cells of Staphylococcus epidermidis. Curr. Microbiol. 59, 118-122.
Gozari, M., Alborz, M., El-Seedi, H.R., Jassbi, A.R., 2021. Chemistry, biosynthesis and biological activity of terpenoids and meroterpenoids in bacteria and fungi isolated from different marine habitats. Eur. J. Med. Chem. 210, 112957.
Grassmann J., 2005. Terpenoids as plant antioxidants. Vitam. Horm. 72, 505-535.
Grau, E., Mecking, S., 2013. Polyterpenes by ring opening Metathesis polymerization of caryophyllene and humulene. Green Chem. 15, 1112-1115.
Guimaraes, A.C., Meireles, L.M., Lemos, M.F., Guimaraes, M.C.C., Endringer, D.C., Fronza, M., Scherer, R., 2019. Antibacterial activity of terpenes and terpenoids present in essential oils. Molecules 24, 2471.
Gunes-Bayir, A., Kiziltan, H.S., Kocyigit, A., Güler, E.M., Karatas, E., Toprak, A., 2017. Effects of natural phenolic compound carvacrol on the human gastric adenocarcinoma (AGS) cells in vitro. AntiCancer Drugs 28, 522-530.
Han J.L., Liu B.Y., Ye H.C., 2006. Effects of overexpression of the endogenous farnesyl diphosphate synthase on the artemisinin content in artemisia annua L. J. Integr. Plant Biol. 48, 482-487.
Hartikainen K., Riikonen J., Nerg A.M., 2012. Impact of elevated temperature and ozone on the emission of volatile organic compounds and gas exchange of silver birch (Betula pendula roth). Environ. Exper. Bot. 84, 33-43.
Hassan, H.F.H., Mansour, A.M., Salama, S.A., El-Sayed, E.S.M., 2021. The chemopreventive effect of thymol against dimethylhydrazine and/or high fat diet-induced colon cancer in rats: Relevance to NF-κB. Life Sci. 274, 119-335.
Havasi, M.H., Ressler, A.J., Parks, E.L., Cocolas, A.H., Weaver, A., Seeram, N.P., Henry, G.E., 2020. Antioxidant and tyrosinase docking studies of heterocyclic sulfide derivatives containing a thymol moiety. Inorganica Chim. Acta. 505, 119-495.
He, M., Yang, C., Geng, R., Zhao, X., Hong, L., Piao, X., Li, D., 2015. Monitoring of phthalates in foodstuffs using gas purge microsyringe extraction coupled with GC-MS. Anal. Chim. Acta. 879, 3-68.
Henriquez M.A., Soliman A, Li G., 2016. Molecular cloning, functional characterization and expression of potato (Solanum tuberosum) 1-deoxy-D-xylulose 5-phosphatesynthase 1 (StDXS1) in response to Phytophthora infestans. Plant Sci. 243, 71-83.
Hong G.J., Xue X.Y., Mao Y.B., Wang L.J., Chen X.Y., 2012. Arabidopsis MYC2 interacts with DELLA proteins in regulating sesquiterpene synthase gene expression. Plant Cell 24, 2635-48.
Huang D., Dai W., 2015. Molecular characterization of the basic helix-loop-helix (bHLH) genes that are differentially expressed and induced by iron deficiency in Populus. Plant Cell Rep. 34(7), 1211-24.
Huang, A.C., Kautsar, S.A., Hong, Y.J., Medema, M.H., Bond, A.D., Tantillo, D.J., Osbourn, A., 2017. Unearthing a sesterterpene biosynthetic repertoire in the Brassicaceae through genome mining reveals convergent evolution. Proc. Nat. Acad. Sci. 114, 6005-6014.
Huang, J., Yang, L., Zou, Y., Luo, S., Wang, X., Liang, Y., Wei, Q., 2021. Antibacterial activity and mechanism of three isomeric terpineols of Cinnamomum longepaniculatum leaf oil. Folia Microbiol. 66, 59-67.
Hyldgaard, M., Mygind, T., Meyer, R. L., 2012. Essential oils in food preservation: Mode of action, synergies, and interactions with food matrix components. Front. Microbiol. 3, 12.
Iijima, Y., Davidovich-Rikanati, R., Fridman, E., Gang, D.R., Bar, E., Lewinsohn, E., Pichersky, E., 2004. The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol. 136, 3724-3736.
Ismail H., Dilshad E., Waheed M. T., Mirza B., 2017. Transformation of lettuce with rol ABC genes: extracts show enhanced antioxidant, analgesic, anti-inflammatory, antidepressant, and anticoagulant activities in rats. Appl. Biochem. Biotechnol. 181(3), 1179-1198.
Isman, M. B., Machial, C. M., 2006. Pesticides based on plant essential oils: from traditional practice to commercialization, Int. J. Phytomedicine 3, 29-44.
Jayakumar, T., Liu, C.H., Wu, G.Y., Lee, T.Y., Manubolu, M., Hsieh, C.Y., Sheu, J.R., 2018. Hinokitiol Inhibits Migration of A549 Lung Cancer Cells via Suppression of MMPs and Induction of Antioxidant Enzymes and Apoptosis. Int. J. Mol. Sci. 19, 939.
Jeppesen P.B., Dyrskog S.E., Agger A., 2006. Can stevioside in combination with a soy-based dietary supplement be a new useful treatment of type 2 diabetes? an in vivo study in the diabetic Goto-Kakizaki rat. Rev Diabet Stud. 3(4), 189-199.
Jin, X., Zhang, M., Lu, J., Duan, X., Chen, J., Liu, Y., Lou, H., 2021. Hinokitiol chelates intracellular iron to retard fungal growth by disturbing mitochondrial respiration. J. Adv. Res. 34, 65-77.
Kampranis, S.C., Ioannidis, D., Purvis, A., Mahrez, W., Ninga, E., Katerelos, N.A., Anssour,S., Dunwell, J.M., Degenhardt, J., Makris, A.M., Goodenough, P.W., Johnson, C.B., 2007. Rational conversion of substrate and product specificity in a Salvia monoterpenesynthase: structural insights into the evolution of terpene synthase function. Plant Cell 19, 1994-2005.
Kang, S.H., Kim, Y.S., Kim, E.K., Hwang, J.W., Jeong, J.H., Dong, X., Lee, J.W., Moon, S.H., Jeoon, B.T., and Park, P.J., 2016. Anticancer effect of thymol on AGS human gastric carcinoma cells. J. Microbiol. Biotechnol. 26, 28-37.
Kleine S., Muller C., 2014. Drought stress and leaf herbivore affect root terpenoid concentrations and growth of tanacetum vulgare. J. Chem. Ecol. 40, 1115-1125.
Kong, J., Xie, Y., Yu, H., Guo, Y., Cheng, Y., Qian, H., Yao, W., 2020. Synergistic antifungal mechanism of thymol and salicylic acid on Fusarium solani. LWT 140, 110-787.
Kougan, G.B., Tabopda, T., Kuete, V. and Verpoorte, R., 2013. Simple phenols, phenolic acids, and related esters from the medicinal plants of Africa. J. Med. Plant Res. 225-249.
Kowalcze, M., Jakubowska, M., 2019. Voltammetric determination of carvacrol on boron doped diamond electrode. Anal. Chim. Acta. 1045, 98-107.
Krause, S.T., Kollner, T.G., Asbach, J., Degenhardt, J., 2013. Stereochemical mechanism of two sabinene hydrate synthases forming antipodal monoterpenes in thyme (Thymus vulgaris). Arch. Biochem. Biophys. 529, 112-121.
Lalle, M., Hanevik, K., 2018. Treatment-refractory giardiasis: challenges and solutions. Infect. Drug Resistance 11, 1921.
Landmann, C., Fink, B., Festner, M., Dregus, M., Engel, K.H., Schwab, W., 2007. Cloning and functional characterization of three terpene synthases from lavander (Lavandula angustifolia) Arch. Biochem. Biophys, 465, 417-429.
Lane, A., Boecklemann, A., Woronuk, G.N., Sarker, L., Mahmoud, S.S., 2010. A genomics resource for investigating regulation of essential oil production in Lavandula angustifolia. Planta. 231, 835-845.
Lanzotti, V., 2013 Diterpenes for therapeutic use, in: Ramawat, K.G., Merillon, J.M. (Eds.), Natural products: phytochemistry, botany and metabolism of alkaloids, phenolics and terpenes. Springer-Verlag, Berlin Heidelberg, pp. 317191.
Lee G.W., Lee S., Chung M.S., 2015. Rice terpene synthase20 (OsTPS20) plays an important role in producing terpene volatiles in response to abiotic stresses. Protoplasm 252, 997-1007.
Lee, S.J., Umano, K., Shibamoto, T., Lee, K.G., 2005. Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties. Food Chem. 91, 131-137.
Li M.Y., Feng K., Hou X.L., 2020. The genome sequence of celery (Apium graveolens L.), an important leaf vegetable crop rich in apigenin in the apiaceae family. Hortic Res. 7-9.
Li, J., Liu, H., Wang, C., Yang, J., Han, G., 2018. Stable isotope labeling‐assisted GC/MS/MS method for determination of methyl eugenol in food samples. J. Sci. Food Agric. 98, 3485-3491.
Li, X., Yang, X., Deng, H., Guo, Y., Xue, J., 2020. Gelatin films incorporated with thymol nanoemulsions: Physical properties and antimicrobial activities. Int. J. Biol. Macromol. 150, 161-168.
Liu, Q., Wang, Z., Mukhamadiev, A., Feng, J., Gao, Y., Zhuansun, X. Jafari, S. M., 2022. Formulation optimization and characterization of carvacrol-loaded nanoemulsions: In vitro antibacterial activity/mechanism and safety evaluation. Ind. Crops and Prod. 181, 114-816.
Liu, T., Kang, J., Liu, L., 2021. Thymol as a critical component of Thymus vulgaris L. essential oil combats Pseudomonas aeruginosa by intercalating DNA and inactivating biofilm, LWT 136, 110-354.
López-García S., Castañeda-Sanchez J.I., Jiménez-Arellanes A., 2015. Macrophage activation by ursolic and oleanolic acids during mycobacterial infection. Molecules 20, 14348-14364.
Ludwiczuk, A., Skalika-Woziak, K., Georgiev, M., 2017. Terpenoids pharmacogsy, in: Badal, S., Delgoda, R., (Eds.), Academic Press, Cambridge, MA, USA, pp. 233-266.
Lukas, B., Schmiderer, C., Mitteregger, U., Novak, J., 2010. Geraniol synthases from perilla and their taxonomical significance. Phytochemistry 68, 446-453.
Mafud A.C., Silva M.P.N., Monteiro D.C., 2016. Structural parameters, molecular properties, and biological evaluation of some terpenes targeting Schistosoma mansoni parasite. Chem Biol Interact. 244, 129-139.
Malhotra, K., Subramaniyan, M., Rawat, K., Kalamuddin, M., Qureshi, M. I., Malhotra, P. Kumar, S., 2016. Compartmentalized metabolic engineering for artemisinin biosynthesis and effective malaria treatment by oral delivery of plant cells. Mol. Plant 9, 1464-1477.
Mander, L., Liu, H.W., 2010. Comprehensive natural products II: chemistry and biology, 1st Ed. Elsevier, The Boulevard Langford Lane, Oxford, UK.
Maoka T., 2020. Carotenoids as natural functional pigments. J. Nat. Med. 74(1), 1-16.
Marianna V.S., Aline L.X., Tamires C.L., Damiao P.S., 2014. Antitumor activity of monoterpenes found in essential oils. Sci. World J. 953451, 1-35.
Martins, B. X., Arruda, R.F., Costa, G.A., Jerdy, H., De Souza, S.B., Santos, J.M., De Freitas, W. R., Façanha, A.R., 2019. Myrtenal-induced V-ATPase inhibition - A toxicity mechanism behind tumor cell death and suppressed migration and invasion in melanoma. Biochimica et Biophysica Acta - General Subjects 1863, 1-12.
Mediratta, P. K., Sharma, K. K., Singh, S., 2002. Evaluation of immunomodulatory potential of Ocimum sanctum seed oil and its possible mechanism of action. J. Ethnopharmacol. 80, 15-20.
Mertens J., Pollier J., Vanden B.R., López Vidriero I., Franco-Zorrilla J.M., Goossens A., 2016. The bHLH transcription factors TSAR1 and TSAR2 regulate triterpene saponin biosynthesis in Medicago truncatula. Plant Physiol. 170(1), 194-210.
Mika, J., Barek, J., Zima, J., Dejmkova, H., 2015. New flow-through coulometric detector with renewable working electrode material for flow injection analysis and HPLC. Electrochim. Acta. 154, 397-403.
Mohammadhosseini, M., 2017a. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crops Prod. 105, 164-192.
Mohammadhosseini, M., 2017b. Essential oils extracted using microwave-assisted hydrodistillation from aerial parts of eleven Artemisia species: Chemical compositions and diversities in different geographical regions of Iran. Rec. Nat. Prod. 11(2), 114-129.
Mohammadhosseini, M., Akbarzadeh, A., Flamini, G., 2017. Profiling of compositions of essential oils and volatiles of Salvia limbata using traditional and advanced techniques and evaluation for biological activities of their extracts. Chem. Biodivers. 14(5), e1600361.
Mohammadhosseini, M., Frezza, C., Venditti, A., Akbarzadeh, A., 2019. Ethnobotany and phytochemistry of the genus Eremostachys Bunge. Curr. Org. Chem. 23, 1828-1842.
Mohammadhosseini, M., Venditti, A., Mahdavi, B., Kianasab, M.R., Shirazi, R., 2022. Profiling of the essential oil compositions from the flowers and leaves of Tanacetum fisherae Aitch. & Hemsl., an endemic plant in Kerman province, Iran. Nat. Prod. Res. 30(20), 5347-5352.
Muchlinski A., Ibdah M., Ellison S., 2020. Diversity and function of terpene synthases in the production of carrot aroma and flavor compounds. Sci. Rep. 10, 99-89.
Nafisi, S., Hajiakhoondi, A., Yektadoost, A., 2004. Thymol and carvacrol binding to DNA: Model for drug-DNA interaction. Biopolymers 74, 345-351.
Nan, J., Wang, J., Piao, X., Yang, C., Wu, X., Quinto, M., Li, D., 2015. Novel and rapid method for determination of organophosphorus pesticide residues in edible fungus using direct gas purge microsyringe extraction coupled on-line with gas chromatography-mass spectrometry. Talanta 142, 64-71.
Niu, F.X., He, X., Wu, Y.Q., Liu, J.Z., 2018. Enhancing production of pinene in Escherichia coli by using a combination of tolerance, evolution, and modular co-culture engineering. Front. Microbiol. 9:1623.
Nowroozi F.F, Baidoo E.E., Ermakov S., Redding-Johanson A.M., Batth T.S., Petzold C..J., Keasling J.D., 2014. Metabolic pathway optimization using ribosome binding site variants and combinatorial gene assembly. Appl Microbiol Biotechnol. 98(4), 1567-1581.
Ogunlakin, A.D., Sonibare, M.A., 2022. Phytochemistry and biological activities of Tetracera species. Trends Phytochem. Res. 6(4), 339-352.
Okada, K., Saito, T., Nakagawa, T., Kawamukai, M., Kamiya, Y., 2000. Five geranyl geranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis. Plant Physiol. 122, 1045-1056.
Oldfield E., Lin F.Y., 2012. Terpene biosynthesis: modularity rules. Angew. Chem. 51, 1124-1137.
Pandey, A.K., Kumar, P., Singh, P., Tripathi, N.N., Bajpai, V.K., 2017. Essential oils: Sources of antimicrobials and food preservatives. Front. Microbiol. 7, 2161.
Pandey, A.K., Sonker, N., Singh, P., 2016. Efficacy of some essential oils against Aspergillus flavus with special reference to lippia alba oil an inhibitor of fungal proliferation and aflatoxin B1 production in green gram seeds during storage. J. Food Sci. 81, 928-934.
Peebles C.A., Sander G.W., Hughes E.H., 2011. The expression of 1-deoxy-D-xylulose synthase and geraniol-10-hydroxylase or anthranilate synthase increases terpenoid indole alkaloid accumulation in Catharanthus roseus hairy roots. Metab. Eng. 13, 234-240.
Perveen, S. Al-Taweel, A., 2018. Introductory chapter: Terpenes and terpenoids. Terpenes and terpenoids. 1, 1-12.
Pudełek, M., Catapano, J., Kochanowski, P., Mrowiec, K., Janik-Olchawa, N., Ryszawy, D., 2019. Therapeutic potential of monoterpene α-thujone, the main compound of Thuja occidentalis L. essential oil, against malignant glioblastoma multiforme cells in vitro. Fitoterapia 134, 172-181.
Pudziuvelyte, L., Jakstas, V., Ivanauskas, L., Laukeviciene, A., Ibe, C.F.D., Kursvietiene, L., Bernatoniene, J., 2018. Different extraction methods for phenolic and volatile compounds recovery from Elsholtzia ciliata fresh and dried herbal materials. Ind Crops Prod. 120, 286-294.
Qoorchi Moheb Seraj, F., Heravi-Faz, N., Soltani, A., Ahmadi, S. S., Talebpour, A., Afshari, A. R., Bahrami, A., 2022. Thymol has anticancer effects in U-87 human malignant glioblastoma cells. Mol. Biol. Rep. 49, 9623-9632.
Rajkumar, V., Gunasekaran, C., Paul, C.A., Dharmaraj, J., 2020. Development of encapsulated peppermint essential oil in chitosan nanoparticles: Characterization and biological efficacy against stored-grain pest control. Pestic. Biochemistry Phys. 170, 104679.
Ranjbar, A., Ramezanian, A., Shekarforoush, S., Niakousari, M.,Eshghi, S., 2022. Antifungal activity of thymol against the main fungi causing pomegranate fruit rot by suppressing the activity of cell wall degrading enzymes. LWT 161, 113-303.
Raymond, C.A., Davies, N.W., Larkman, T., 2017. GC-MS method validation and levels of methyl eugenol in a diverse range of tea tree (Melaleuca alternifolia) oils. Anal. Bioanal. Chem. 409.
Riedlmeier M., Ghirardo A., Wenig M., 2017. Monoterpenes support systemic acquired resistance within and between plants. Plant Cell 29, 1440-1459.
Rigby, C.M., Roy, S., Deep, G., Guillermo-Lagae, R., Jain, A.K., Dhar, D., Orlicky, D.J., Agarwal, C., Agarwal, R., 2017. Role of p53 in silibinin-mediated inhibition of ultravioletB radiation-induced DNA damage, inflammation and skin carcinogenesis. Bgw 38, 40-50.
Robledo S., Osorio E., Muñoz D., 2005. In vitro and in vivo cytotoxicities and antileishmanial activities of thymol and hemisynthetic derivatives. Antimicrob Agents Chemother. 49(4), 1652-1655.
Rodenak-Kladniew, B., Castro, A., Starkel, P., De Saeger, C., Garcia De Bravo, M., Crespo, R., 2018. Linalool induces cell cycle arrest and apoptosis in HepG2 cells through oxidative stress generation and modulation of Ras/MAPK and Akt/mTOR pathways. Life Sci. 199, 48-59.
Rodriguez-Concepcion M., Boronat A., 2015. Breaking new ground in the regulation of the early steps of plant isoprenoid biosynthesis. Curr. Opi. Plant Biol. 25, 17-22.
Said-Al Ahl, H.A., Hikal, W.M. and Mahmoud, A.A., 2017. Essential oils: Biosynthesis, chemistry and biological functions. J. Chem. Pharm. Res. 9,190-200.
Schmiderer, C., Grausgruber-Gröger, S., Grassi, P., Steinborn, R., Novak, J., 2010. Influence of gibberellin and daminozide on the expression of terpene synthases and on monoterpenes in common sage (Salvia officinalis). J. Plant Physiol. 167, 779-786.
Schultenkämper K., Brito L.F., Wendisch V.F., 2020. Impact of CRISPR interference on strain development in biotechnology. Biotechnol Appl Biochem. 67(1), 7-21.
Shakeri, A., D’Urso, G., Taghizadeh, S.F., Piacente, S., Norouzi, S., Soheili, V., Salarbashi, D., 2019. LC-ESI/LTQOrbitrap/MS/MS and GC-MS profiling of Stachys parviflora L. and evaluation of its biological activities. J. Pharma. Biomed. Anal. 168, 209-216.
Sheikh, B.Y., Sarker, M.M.R., Kamarudin, M.N.A., Mohan, G., 2017. Antiproliferative and apoptosis inducing effects of citral via p53 and ROS-induced mitochondrial-mediated apoptosis in human colorectal HCT116 and HT29 cell lines. Biomed. Pharmacothe. 96, 834-846.
Shen G., Pang Y., Wu W., 2006. Cloning and characterization of a root-specific expressing gene encoding3-hydroxy-3-methylglutaryl coenzyme a reductase from ginkgo biloba. Mol. Bio. Rep. 33, 117-127.
Shrestha P.M., Dhillion S.S., 2003. Medicinal plant diversity and use in the highlands of Dolakha district, Nepal. J. Ethnopharmacol. 86(1), 81-96.
Shrivastava G., Ownley B.H., Auge R.M., 2015. Colonization by arbuscular mycorrhizal and endophytic fungi enhanced terpene production in tomato plants and their defense against an herbivorous insect. Symbiosis. 65, 65-74.
Shukal S., Chen X., Zhang C., 2019. Systematic engineering for high-yield production of viridiflorol and amorphadiene in auxotrophic Escherichia coli. Metab Eng 55, 170-178.
Silva, G.L., Luft, C., Lunardelli, A., Amaral, R.H., Melo, D.A., Donadio, M.V., De Oliveira, J.R., 2015. Antioxidant, analgesic and anti-inflammatory effects of lavender essential oil. An Acad Bras Cienc. 87, 1397-1408.
Silva, J.K.R.D., Figueiredo, P.L.B., Byler, K.G., Setzer, W.N., 2020. Essential Oils as antiviral Agents, potential of essential oils to treat SARS-CoV-2 infection: An in- silico investigation. Int. J. Mol. Sci. 21, 34-26.
Singh, D., Mittal, N., Siddqui, M.H., 2023. A review on pharmacological potentials of phenolic diterpenes carnosic acid and carnosol obtained from Rosmarinus officinalis L. and modern extraction methods implicated in their recovery. Trends Phytochem. Res. 7(3) 156-169
Stankovic, D.M., 2015. Sensitive voltammetric determination of thymol in essential oil of Carum copticum seeds using boron-doped diamond electrode. Anal. Biochem. 486, 1-4.
Stephane, F.F.Y., Jules, B.K.J., 2020. Terpenoids as important bioactive constituents of essential oils, in: Oliveira, M.S.D., Costa, W.A.D., Silva S.G. (Eds.), Essential Oils-Bioactive Compounds, New Perspectives and Applications. Intech Open Limited, Princes Gate Court, London, UK, pp. 1-15.
Stevanovic, Z.D., Sieniawska, E., Glowniak, K., Obradovic, N., Pajic-Lijakovic, I., 2020. Natural Macromolecules as Carriers for Essential Oils: From Extraction to Biomedical Application. Front Bioeng. Biotechnol. 8, 563.
Sun, C., Cao, J., Wang, Y., Chen, J., Huang, L., Zhang, H., Sun, C., 2021. Ultrasound-mediated molecular self-assemble of thymol with 2-hydroxypropyl-β-cyclodextrin for fruit preservation. Food Chem. 363, 130-327.
Sung, H., Ferlay, J., Siegel, R. L., Laversanne, M., Soerjomataram, I., Jemal, A., Bray, F., 2021. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J. Clin. 71, 209-249.
Taghavi, D., Majidi, M., Mollaei, S., Panahi, B., 2020. Effect of methyl jasmonate on expression of some genes related to shikonin biosynthetic pathway in Lithosperm um officinale. J. Plant Mole Breed. 8,1-9.
Takaichi, S., 2013. Tetraterpenes: carotenoids. in: Ramawat, K., Mérillon, J.M., (Eds.), Natural Products. Springer, Berlin, Heidelberg, pp. 3251-3283.
Tetali, S. D., 2019. Terpenes and isoprenoids: A wealth of compounds for global use. Planta, 249, 1-8.
Thagriki, D.S., 2022. Quercetin and its derivatives are potent inhibitors of the dengue virus. Trends Phytochem. Res. 6(1), 70-85.
Tian T, Kang J.W., Kang A., Lee T.S., 2019. Redirecting metabolic flux via combinatorial multiplex CRISPRi-mediated repression for isopentenol production in Escherichia coli. ACS Synth. Biol. 8(2), 391-402.
Turner, G.W., Croteau, R., 2004. Organization of monoterpene biosynthesis in Mentha Immuno cytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase. Plant physiol. 136, 4215-4227.
Valliammai, A., Selvaraj, A., Muthuramalingam, P., Priya, A., Ramesh, M., Pandian, S. K., 2021. Staphyloxanthin inhibitory potential of thymol impairs antioxidant fitness, enhances neutrophil mediated killing and alters membrane fluidity of methicillin resistant Staphylococcus aureus. Biomed. Pharmacother. 141, 111-933.
Van Poecke R.M., Posthumus M.A., Dicke M., 2001. Herbivore-induced volatile production by Arabidopsis thaliana leads to attraction of the parasitoid cotesiarubecula: chemical, behavioral, and gene-expression analysis. J. Chem. Ecol. 27, 1911-1928.
Vogt, T., 2010. Phenylpropanoid biosynthesis. Mol. Plant 3, 2-20.
Wan Q., Ma X., Zhang Z.J., 2017. Ginsenoside reduces cognitive impairment during chronic cerebral hypoperfusion through brain-derived neurotrophic factor regulated by epigenetic modulation. Mol Neurobiol. 54(4), 2889-2900.
Wang R., Zhao S., Wang Z., Koffas M. A., 2020. Recent advances in modular co-culture engineering for synthesis of natural products. Curr. Opin. Biotechnol. 62, 65-71.
Wang, H., Peng, Z., Sun, H., 2021. Antifunga`l activities and mechanisms of trans‐cinnamaldehyde and thymol against food‐spoilage yeast Zygosaccharomyces rouxii. J. Food Sci. 87, 1197-1210.
Wang, J., 2006. Analytical electrochemistry Third edition (Hoboken, New Jersey: A John Wiley & sons, Inc.
Wang, Q., Lei, J., Ma, J., Yuan, G., Sun, H., 2018. Effect of chitosan-carvacrol coating on the quality of Pacific white shrimp during iced storage as affected by caprylic acid. Int. J. Biol. Macromol. 106, 123-129.
Wang, W., Wang, H., Zhao, Z., Huang, X., Xiong, H., Mei, Z., 2021. Thymol activates TRPM8-mediated Ca2+ influx for its antipruritic effects and alleviates inflammatory response in Imiquimod-induced mice. Toxicol. Appl. Pharmacol. 407, 115-247.
Wei, T., Gao, Y., Deng, K., 2019. Enhancement of tanshinone production in Salvia miltiorrhiza hairy root cultures by metabolic engineering. Plant Methods 15, 53.
World Health Organization, 2013. WHO traditional medicine strategy: 2014-2023. World Health Organization.
Xie J-T., Shao Z-H., Vanden Hoek T.L., 2006. Antioxidant effects of ginsenoside re in cardiomyocytes. Eur J Pharmacol. 532(3), 201-207.
Xu, Q., Li, M., Yang, M., Yang, J., Xie, J., Lu, X., Chen, W., 2018. α-pinene regulates miR-221 and induces G (2)/M phase cell cycle arrest in human hepatocellular carcinoma cells. Biosci. Rep. 38.
Yadav V.G., De Mey M., Lim C.G., Ajikumar P.K, Stephanopoulos G., 2012. The future of metabolic engineering and synthetic biology: towards a systematic practice. Metab. Eng. 14(3), 233-241.
Yadava, N., Yadava, R., Goyalb, A., 2014. Chemistry of terpenoids. Int. J. Pharm. Sci. Review 27, 272-278.
Yang, L., Liao, M., 2021. Influence of myrcene on inflammation, matrix accumulation in the kidney tissues of streptozotocin-induced diabetic rat. Saudi J. Biol. Sci. 28, 5555-5560.
Yoon, S.J., Sukweenadhi, J., Khorolragchaa A., 2016. Overexpression of panax ginseng sesquiterpene synthase gene confers tolerance against Pseudomonas syringaepv tomato in Arabidopsis thaliana. Physiol. Mol. Bio. Plants. 22, 485-495.
Yousefi, M., Khorshidian, N., Hosseini, H., 2020. Potential application of essential oils for mitigation of Listeria monocytogenes in meat and poultry products. Front. Nutri. 7, 577228.
Yu, Y.M., Chao, T.Y., Chang, W.C., Chang, M.J., Lee, M.F., 2016. Thymol reduces oxidativestress, aortic intimal thickening, and inflammation-related gene expression inhyperlipidemic rabbits. J. Food Drug Anal. 24, 556-563.
Yun, S.M., Lee, M.H., Lee, K.J., Ku, H.O., Son, S.W., Joo, Y.S., 2010. Quantitative analysis of eugenol in clove extract by a validated HPLC method. J. AOAC Int. 93, 1810.
Zahi, M. R., El Hattab, M., Liang, H., Yuan, Q., 2017. Enhancing the antimicrobial activity of d- limonene nanoemulsion with the inclusion of ε-polylysine. Food Chem. 221, 18-23.
Zhang, M., Liu, H., Wang, Q., 2020. The3-hydroxy-3-methylglutaryl-coenzyme a reductase 5gene from Malus domestica enhances oxidative stress tolerance in Arabidopsis thaliana. Plant Physiol. Biochem. 146, 269-277.
Zhang, T., Sun, M., Guo, Y., 2018. Overexpression of LiDXS and LiDXR from lily (lilium siberia) enhances the terpenoid content in tobacco flowers. Front. Plant Sci. 909.
Zhao, D. D., Jiang, L.-L., Li, H.Y., Yan, P.F., Zhang, Y.L., 2016. Chemical components and pharmacological activities of terpene natural products from the genus Paeonia. Molecules 21, 1362.
Zhao, X., He, M., Shang, H., Yu, H., Wang, H., Li, H., Li, D., 2018. Biomonitoring polycyclic aromatic hydrocarbons by Salix matsudana leaves: a comparison with the relevant air content and evaluation of environmental parameter effects. Atmos. Environ. 181, 47-53.
Zhou, F.,Pichersky, E., 2020. More is better: the diversity of terpene metabolism in plants. Curr. Opi. Plant Bio. 55, 1-10.
Zhu, Q., Zeng, D., Yu, S., Cui, C., Li, J., Li, H., Liu, Y. G., 2018. From golden rice to a STARice: bioengineering astaxanthin biosynthesis in rice endosperm. Molecular Plant 11, 1440-1448.
