The genus Micromeria Benth.: An overview on ethnobotany, chemotaxonomy and phytochemistry

Subject Areas : Phytochemistry: Isolation, Purification, Characterization

Majid Mohammadhosseini ¹ , Alessandro Venditti ² , Guido Flamini ³ , Satyajit Sarker ⁴ , Mohammadreza Kalaee ⁵

1 - Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood, Iran|Nanotechnology Research Center, Islamic Azad University, South Tehran Branch, Tehran, Iran
2 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Rome, Italy
3 - Dipartimento di Farmacia, Via Bonanno 6, 56126 Pisa, Italy
4 - Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, United Kingdom
5 - Nanotechnology Research Center, Islamic Azad University, South Tehran Branch, Tehran, Iran|Polymer Engineering Group, Faculty of Engineering, Islamic Azad University, South Tehran Branch, Tehran, Iran

Received: 2022-08-25 Accepted : 2022-08-25 Published : 2022-09-01

Keywords:

References:

Abdelwahab, M.F., Hussein, M.H., Kadry, H.H., 2015. Cytotoxicity and antioxidant activity of new biologically active constituents from Micromeria nervosa grown in Egypt. Bull. Fac. Pharm. Cairo Univ. 53, 185-194.
Abu-Reidah, I.M., Arráez-Román, D., Al-Nuri, M., Warad, I., Segura-Carretero, A., 2019. Untargeted metabolite profiling and phytochemical analysis of Micromeria fruticosa L. (Lamiaceae) leaves. Food Chem. 279, 128-143.
Al-Rehaily, A.J., 2006. Composition of the essential oil of Micromeria biflora ssp. arabica K. Walth. Pak. J. Biol. Sci. 9, 2726-2728.
Ali-Shtayeh, M.S., Al-Nuri, M.A., Yaghmour, R.M.R., Faidi, Y.R., 1997. Antimicrobial activity of Micromeria nervosa from the Palestinian area. J. Ethnopharmacol. 58, 143-147.
Ali-Shtayeh, M.S., Jamous, R.M., Al-Shafie, J.H., Elgharabah, W.A., Kherfan, F.A., Qarariah, K.H., Isra'S, K., Soos, I.M., Musleh, A.A., Isa, B.A., 2008. Traditional knowledge of wild edible plants used in Palestine (Northern West Bank): a comparative study. J. Ethnobiology Ethnomedicine 4, 13.
Alipieva, K.I., Taskova, R.M., Evstatieva, L.N., Handjieva, N.V., Popov, S.S., 2003. Benzoxazinoids and iridoid glucosides from four Lamium species. Phytochemistry 64, 1413-1417.
Alizadeh, A., Ranjbaran, J., 2017. Chemical composition and antimicrobial activity of Micromeria hedgei Rech. f. oil from Iran. Nat. Prod. Res. 31, 210-213.
Allam, A.E., 2020. New flavonoid glycoside from Vicia faba L. Trends Phytochem. Res. 4, 213-218.
Alwan, S., El Omari, K., Soufi, H., Zreika, S., Sukarieh, I., Chihib, N.E., Jama, C., Hamze, M., 2016. Evaluation of the antibacterial activity of Micromeria barbata in Lebanon. J. Essent. Oil-Bear. Plants 19, 321-327.
Arslan, M., 2012. Effects of intra-row spacing on herbage yield, essential oil content and composition of Micromeria fruticosa. Farmacia 60, 925-931.
Asadi, H., Nejad Ebrahimi, S., Omrani, M., Esmaeili, H., 2022. Benzofurans nor-sesquiterpenoids from Petasites hybridus rhizomes and absolute configuration by circular dichroism. Trends Phytochem. Res. 6, 145-154.
Bailly, C., 2021. Bioactive biflavonoids from Wikstroemia indica (L.) C.A. Mey. (Thymelaeaceae): a review. Trends Phytochem. Res. 5, 190-198.
Baser, K.H.C., Demirçakmak, B., 1997. Composition of the essential oil of Micromeria cremnophila Boiss. et Heldr. subsp. amana (Rech.fil) P.H.Davis. J. Essent. Oil Res. 9, 725-726.
Baser, K.H.C., Kirimer, N., Özek, T., Tümen, G., Karaer, F., 1996. Essential oil composition of three Labiatae endemic to Turkey (Micromeria fruticosa (L.) Druce subsp. giresunica P.H. Davis, Sideritis lycia Boiss. et Heldr. and S. arguta Boiss. et Heldr. J. Essent. Oil Res. 8, 699-701.
Baytop, T., 1984. Therapy with Medicinal Plants in Turkey (Past and Present) No: 3255. Publications of the Istanbul University, Istanbul.
Benamar, H., Tomassini, L., Venditti, A., Marouf, A., Bennaceur, M., Nicoletti, M., 2016. Pyrrolizidine alkaloids from Solenanthus lanatus DC. with acetylcholinesterase inhibitory activity. Nat. Prod. Res. 30, 2567-2574.
Benamar, H., Tomassini, L., Venditti, A., Marouf, A., Bennaceur, M., Serafini, M., Nicoletti, M., 2017. Acetylcholinesterase inhibitory activity of pyrrolizidine alkaloids from Echium confusum Coincy. Nat. Prod. Res. 31, 1277-1285.
Benomari, F.Z., Djabou, N., Medbouhi, A., Khadir, A., Bendahou, M., Selles, C., Desjobert, J.M., Costa, J., Muselli, A., 2016. Chemical variability and biological activities of essential oils of Micromeria inodora (Desf.) Benth. from Algeria. Chem. Biodivers. 13, 1559-1572.
Bianchi, A., 2015. The Mediterranean aromatic plants and their culinary use. Nat. Prod. Res. 29, 201-206.
Brahmi, F., Guendouze, N., Hauchard, D., Okusa, P., Kamagaju, L., Madani, K., Duez, P., 2017. Phenolic profile and biological activities of Micromeria graeca (L.) Benth. ex Rchb. Int. J. Food Prop. 20, 2070-2083.
Bukvički, D., Cirić, A., Soković, M., Vannini, L., Nissen, L., Novaković, M., Vujisić, L., Asakawa, Y., Marin, P.D., 2016. Micromeria thymifolia essential oil suppresses quorum-sensing signaling in Pseudomonas aeruginosa. Nat. Prod. Commun. 11, 1903-1906.
Çalmaşur, O., Aslan, I., Şahin, F., 2006. Insecticidal and acaricidal effect of three Lamiaceae plant essential oils against Tetranychus urticae Koch and Bemisia tabaci Genn. Ind. Crop Prod. 23, 140-146.
Cheriet, T., Aouabdia, S., Mancini, I., Defant, A., Seghiri, R., Boumaza, O., Mekkiou, R., Sarri, D., León, F., Brouard, I., 2014. Chemical constituents of Linaria reflexa Desf.(Scrophulariaceae). Der. Pharm. Lett. 6, 54-57.
Cos, P., Vlietinck, A.J., Vanden Berghe, D., Maes, L., 2006. Anti-infective potential of natural products: How to develop a stronger in vitro 'proof-of-concept'. J. Ethnopharmacol. 106, 290-302.
Damtoft, S., Franzyk, H., Jensen, S.R., 1992a. Excelsioside, a secoiridoid glucoside from Fraxinus excelsior. Phytochemistry 31, 4197-4201.
Damtoft, S., Jensen, S.R., Nielsen, B.J., 1992b. Biosynthesis of iridoid glucosides in Lamium album. Phytochemistry 31, 135-137.
Diab, Y., Auezova, L., Chebib, H., Chalchat, J.C., 2005. Chemical composition of the essential oil of Micromeria libanotica Boiss., an endemic species of Lebanon. J. Essent. Oil Res. 17, 449-450.
Ding, J., Xuejian, Y., Yu, W., Ding, Z., Chen, Z., Hayashi, N., Komae, H., 1994. Aromatic components of the essential oils of four Chinese medicinal plants (Asarum petelotii, Elsholtzia souliei, Eupatorium adenophorum, Micromeria biflora) in Yunnan. Z. Naturforsch. C Bio. Sci. 49, 703-706.
Dudai, N., Larkov, O., Mayer, A.M., Poljakoff-Mayber, A., Putievsky, E., Lerner, H.R., 2000. Metabolism of Essential Oils During Inhibition of Wheat Seed Germination. CABI Publishing, Wallingford, UK.
Dudai, N., Poljakoff-Mayber, A., Mayer, A.M., Putievsky, E., Lerner, H.R., 1999. Essential oils as allelochemicals and their potential use as bioherbicides. J. Chem. Ecol. 25, 1079-1089.
Dulger, B., 2008. Antibacterial activity of three endemic Micromeria species. Asian J. Chem. 20, 6518-6522.
Duru, M.E., Öztürk, M., Uǧur, A., Ceylan, Ö., 2004. The constituents of essential oil and in vitro antimicrobial activity of Micromeria cilicica from Turkey. J. Ethnopharmacol. 94, 43-48.
Duvoisin, R.C., 1967. Cholinergic-anticholinergic antagonism in parkinsonism. Arch. Neurol. 17, 124-136.
El-Hawary, S.S., Al-Yahya, M.A., Al-Meshal, I.A., Mossa, J.S., Hifnawy, M.S., 1991. Aromatic plants of Saudi Arabia, Part 13. Essential oil of Micromeria sinaica. Int. J. Pharm. 29, 193-196.
El-Seedi, H.R., Khattab, A., Gaara, A.H.M., Mohamed, T.K., Hassan, N.A., El-Kattan, A.E., 2008. Essential oil analysis of Micromeria nubigena H.B.K. and its antimicrobial activity. J. Essent. Oil Res. 20, 452-456.
El Khoury, R., Caceres, I., Puel, O., Bailly, S., Atoui, A., Oswald, I.P., El Khoury, A., Bailly, J.D., 2017. Identification of the anti-aflatoxinogenic activity of Micromeria graeca and elucidation of its molecular mechanism in Aspergillus flavus. Toxins 9.
Fleisher, Z., Fleisher, A., 1991. The essential oil of Micromeria fruticosa (L.) Druce subsp. barbata (Boiss et. ky.), P. H. Davis: Aromatic plants of the Holy Land and the Sinai, part VII. J. Essent. Oil Res. 3, 477-479.
Formisano, C., Mignola, E., Rigano, D., Senatore, F., Bellone, G., Bruno, M., Rosselli, S., 2007. Chemical composition and antimicrobial activity of the essential oil from aerial parts of Micromeria fruticulosa (Bertol.) Grande (Lamiaceae) growing wild in Southern Italy. Flav. Fragr. J. 22, 289-292.
Formisano, C., Oliviero, F., Rigano, D., Saab, A.M., Senatore, F., 2014. Chemical composition of essential oils and in vitro antioxidant properties of extracts and essential oils of Calamintha origanifolia and Micromeria myrtifolia, two Lamiaceae from the Lebanon flora. Ind. Crop Prod. 62, 405-411.
Fraga, B.M., Hernández, M.G., Fernández, C., Santana, J.M., 2009. A chemotaxonomic study of nine Canarian Sideritis species. Phytochemistry 70, 1038-1048.
Frezza, C., Venditti, A., Giuliani, C., Foddai, S., Maggi, F., Fico, G., Bianco, A., Serafini, M., 2019a. Preliminary study on the phytochemical evolution of different Lamiaceae species based on iridoids. Biochem. Syst. Ecol. 82, 44-51.
Frezza, C., Venditti, A., Marcucci, E., Parroni, A., Reverberi, M., Serafini, M., Bianco, A., 2019b. Phytochemical analysis of Linaria purpurea (L.) Mill. and inhibitory activity on the production of aflatoxin B1 (AFB1) in Aspergillus flavus Link. of one of its metabolites, antirrhinoside. Ind. Crop Prod. 139, 111554.
Frezza, C., Venditti, A., Serafini, M., Bianco, A., 2019c. Phytochemistry, Chemotaxonomy, Ethnopharmacology, and Nutraceutics of Lamiaceae, Stud. Nat. Prod. Chem. Elsevier, pp. 125-178.
Ganesan, K., Xu, B., 2017. Ethnobotanical studies on folkloric medicinal plants in Nainamalai, Namakkal District, Tamil Nadu, India. Trends Phytochem. Res. 1, 153-168.
Giacobini, E., 1990. The Cholinergic System in Alzheimer Disease, Prog. Brain Res. Elsevier, pp. 321-332.
Giuliani, C., Maleci Bini, L., 2008. Insight into the structure and chemistry of glandular trichomes of Labiatae, with emphasis on subfamily Lamioideae. Plant Syst. Evol. 276, 199-208.
Glasl, S., Presser, A., Werner, I., Wawrosch, C., Kastner, U., Jurenitsch, J., Haslinger, E., Kubelka, W., 1999. Two proazulenes from Achillea ceretanica Sennen. Phytochemistry 50, 629-631.
Goodman, L.S., 1996. Goodman and Gilman's the Pharmacological Basis of Therapeutics. McGraw-Hill, New York.
Guarrera, P.M., Salerno, G., Caneva, G., 2005. Folk phytotherapeutical plants from Maratea area (Basilicata, Italy). J. Ethnopharmacol. 99, 367-378.
Güllüce, M., Sökmen, M., Şahin, F., Sökmen, A., Adigüzel, A., Özer, H., 2004. Biological activities of the essential oil and methanolic extract of Micromeria fruticosa (L) Druce ssp serpyllifolia (Bieb) PH Davis plants from the Eastern Anatolia region of Turkey. J. Sci. Food Agric. 84, 735-741.
Hammer, K., Laghetti, G., Pistrick, K., 2005. Calamintha nepeta (L.) Savi and Micromeria thymifolia (Scop.) Fritsch cultivated in Italy. Genet. Resour. Crop Evol. 52, 215-220.
Harley, R.M., Atkins, S., Budantsev, A.L., Cantino, P.D., Conn, B.J., Grayer, R., Harley, M.M., De Kok, R.D., Krestovskaja, T.D., Morales, R., 2004. Labiatae, Flowering Plants· Dicotyledons. Springer, pp. 167-275.
Hashemi-Moghaddam, H., Mohammadhosseini, M., Azizi, Z., 2018. Impact of amine- and phenyl-functionalized magnetic nanoparticles impacts on microwave-assisted extraction of essential oils from root of Berberis integerrima Bunge. J. Appl. Res. Med. Aromat. Plants 10, 1-8.
Herken, E.N., Celik, A., Aslan, M., Aydnlk, N., 2012. The constituents of essential oil: Antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from east Anatolia. J. Med. Food 15, 835-839.
Hong, Y.J., Yang, K.S., 2013. Inhibition of melanin production and tyrosinase expression of crocetin derivatives from processed Gardenia jasminoides. Nat. Prod. Sci. 19, 206-214.
https://en.wikipedia.org/wiki/Medicinal_plants.
Hussain, M.S., Mazumder, T., 2021. A comprehensive review of pharmacological and toxicological properties of Cheilocostus speciosus (J.Koenig) C.D.Specht. Trends Phytochem. Res. 5, 1-12.
Inouye, H., Ueda, S., Uesato, S., Kobayashi, K., 1978. Studies on monoterpene glucosides and related natural products. XXXVII. Biosynthesis of the iridoid glucosides in Lamium amplexicaule, Deutzia crenata and Galium spurium var. echinospermon. Chem. Pharm. Bull. (Tokyo). 26, 3384-3394.
Jafari, E., Ghanbarian, G., Bahmanzadegan, A., 2018. Essential oil composition of aerial parts of Micromeria persica Boiss. from Western of Shiraz, Iran. Nat. Prod. Res. 32, 991-996.
Jensen, S.R., 1992. Systematic implications of the distribution of iridoids and other chemical compounds in the Loganiaceae and other families of the Asteridae. Ann. Missouri Bot. Gard. 79, 284-302.
Jensen, S.R., Lyse-Petersen, S.E., Nielsen, B.J., 1979. Novel bis-iridoid glucosides from Dipsacus sylvestris. Phytochemistry 18, 273-277.
Kalaki Kordkolaei, S., Kanani, M.R., Tabefam, M., Namazi Sarvestani, N., Hamburger, M., Moridi Farimani, M., 2019. Terpenoids and phenolics of Micromeria persica. Nat. Prod. Res. 34, 2913-2918.
Kikuchi, M., Onoguchi, R., Yaoita, Y., 2009. Three new monoterpene glucosides from Lamium amplexicaule. Helv. Chim. Acta 92, 2063-2070.
Kim, B.H., Park, K.C., Park, J.H., Lee, C.G., Ye, S.K., Park, J.Y., 2016. Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone. Biochem. Biophys. Res. Commun. 480, 648-654.
Kirimer, N., 1992. The essential oil of Micromeria fruticosa (L.) Druce ssp. brachycalyx P. H. Davis. J. Essent. Oil Res. 4, 521-522.
Kırımer, N., Baser, K.H.C., 1997. Essential oils of Micromeria species, in: Coskun, M. (Ed.), 11th International Symposium on Plant Originated Crude Drugs, Ankara Universitesi Basimeui, Ankara, Turkey, pp. 130-138.
Kirimer, N., Özek, T., Baser, K.H.C., 1991. Composition of the essential oil of Micromeria congesta. J. Essent. Oil Res. 3, 387-393.
Kirimer, N., Özek, T., Baser, K.H.C., Harmandar, M., 1993a. The essential oil of Micromeria fruticosa (L.) Druce subsp. serpyllifolia (Bieb.) P. H. Davis. J. Essent. Oil Res. 5, 199-200.
Kirimer, N., Tümen, G., Özek, T., Baser, K.H.C., 1993b. The essential oil of Micromeria fruticosa (L.) Druce subsp. barbata (Boiss & Kotschy) P. H. Davis of Turkish origin. J. Essent. Oil Res. 5, 79-80.
Konishi, K., Hori, K., Tani, M., Tomioka, H., Kitajima, Y., Akashi, N., Inamoto, A., Kurosawa, K., Yuda, H., Hanashi, T., 2015. Hypothesis of endogenous anticholinergic activity in Alzheimer's disease. Neurodegener. Dis. 15, 149-156.
Kremer, D., Dunkić, V., Ruščić, M., Matevski, V., Ballian, D., Bogunić, F., Eleftheriadou, E., Stešević, D., Kosalec, I., Bezić, N., Stabentheiner, E., 2014a. Micromorphological traits and essential oil contents of Micromeria kerneri Murb. and M. juliana (L.) Benth. (Lamiaceae). Phytochemistry 98, 128-136.
Kremer, D., Dunkić, V., Stešević, D., Kosalec, I., Ballian, D., Bogunić, F., Bezić, N., Stabentheiner, E., 2014b. Micromorphological traits and essential oil of Micromeria longipedunculata Bräuchler (Lamiaceae). Cent. Eur. J. Biol. 9, 559-568.
Kremer, D., Müller, I.D., Stabentheiner, E., Vitali, D., Kopričanec, M., Ruščić, M., Kosalec, I., Bezić, N., Dunkić, V., 2012. Phytochemical and micromorphological traits of endemic Micromeria pseudocroatica (Lamiaceae). Nat. Prod. Commun. 7, 1667-1670.
Krimer, N., Tumen, G., Ozek, T., Baser, K.H.C., 1993. Essential oil of Micromeria fruticosa (L.) Druce subsp. barbata (Boiss & Kotschy) P. H. Davis of Turkish origin. J. Essent. Oil Res. 5, 7980.
Lang, A., Blair, R., 1989. Anticholinergic Drugs and Amantadine in the Treatment of Parkinson’s Disease, Drugs for the Treatment of Parkinson’s Disease. Springer, pp. 307-323.
Mallavarapu, G.R., Ramesh, S., Subrahmanyam, K., 1997. Composition of the essential oil of Micromeria biflora. J. Essent. Oil Res. 9, 23-26.
Marin, P.D., Grayer, R.J., Veitch, N.C., Kite, G.C., Harborne, J.B., 2001. Acacetin glycosides as taxonomic markers in Calamintha and Micromeria. Phytochemistry 58, 943-947.
Marinković, B., Marin, P.D., Knez̧ević-Vukçević, J., Soković, M.D., Brkić, D., 2002. Activity of essential oils of three Micromeria species (Lamiaceae) against micromycetes and bacteria. Phytother. Res. 16, 336-339.
Masoudi, S., Azad, L., Arabshahi, B., Yari, M., Jamzad, M., Akhlaghi, H., Motevalizadeh, A., Rustaiyan, A., 2009. Volatile constituents of Micromeria persica Boiss., Hymenocrater platystegius Rech. f. and Scutellaria pinnatifida A. Hamilt. subsp. pinnatifida, three Labiatae herbs growing wild in Iran. J. Essent. Oil Res. 21, 515-518.
Mastelić, J., Jerković, I., Kuštrak, D., 2005. Aromatic compounds of Micromeria juliana (L.) Bentham Ex Reichenb. from Croatia. J. Essent. Oil Res. 17, 516-518.
Medina, J., Pena, C., de Stein Levi, M., Wolfman, C., Paladini, A., 1989. Benzodiazepine-like molecules, as well as other ligands for the brain benzodiazepine receptors, are relatively common constituents of plants. Biochem. Biophys. Res. Commun. 165, 547-553.
Medina, J.H., Viola, H., Wolfman, C., Marder, M., Wasowski, C., Calvo, D., Paladini, A.C., 1997. Overview—flavonoids: a new family of benzodiazepine receptor ligands. Neurochem. Res. 22, 419-425.
Mohammadhosseini, M., 2016. A Comprehensive Review on New Methods for Processing, Separation and Identification of the Essential Oils. Islamic Azad University of Shahrood Press, Shahrood, Iran.
Mohammadhosseini, M., 2017. The ethnobotanical, phytochemical and pharmacological properties and medicinal applications of essential oils and extracts of different Ziziphora species. Ind. Crop Prod. 105, 164-192.
Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., 2016. Gas chromatographic-mass spectrometric analysis of volatiles obtained by HS-SPME-GC-MS technique from Stachys lavandulifolia and evaluation for biological activity: A review. J. Essent. Oil-Bear. Plants 19, 1300-1327.
Mohammadhosseini, M., Frezza, C., Venditti, A., Mahdavi, B., 2021. An overview of the genus Aloysia Palau (Verbenaceae): Essential oil composition, ethnobotany and biological activities. Nat. Prod. Res.
Mohammadhosseini, M., Sarker, S.D., Akbarzadeh, A., 2017. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol. 199, 257-315.
Mohammadhosseini, M., Venditti, A., Sarker, S.D., Nahar, L., Akbarzadeh, A., 2019. The genus Ferula: Ethnobotany, phytochemistry and bioactivities – A review. Ind. Crop Prod. 129, 350-394.
Moncayo, S., Cornejo, X., Castillo, J., Valdez, V., 2021. Preliminary phytochemical screening for antioxidant activity and content of phenols and flavonoids of 18 species of plants native to western Ecuador. Trends Phytochem. Res. 5, 93-104.
Nahar, L., Sarker, S.D., 2021. ‘Gandho badali’ (Paederia foetida L.): Horrendous smell, but tremendous medicinal value. Trends Phytochem. Res. 5, 166-167.
Nekoei, M., Mohammadhosseini, M., 2017. Chemical composition of essential oils of Salvia leriifolia by three different extraction methods prior to gas chromatographic-mass spectrometric determination: comparison of HD with SFME and HS-SPME. J. Essent. Oil-Bear. Plants 20, 410-425.
Opiyo, S.A., 2019. A review of 13C NMR spectra of drimane sesquiterpenes. Trends Phytochem. Res. 3, 147-180.
Özcan, M., 1999. Antifungal effects of Micromeria myrtifolia Boiss. & Hohen. In Boiss. and Prangos uechtritzii Boiss. Hawsskn decoctions. Acta Aliment. 28, 355-360.
Özek, T., Kirimer, N., Baser, K.H.C., 1992. Composition of the essential oil of Micromeria myrtifolia Boiss. Et Hohen. J. Essent. Oil Res. 4, 79-80.
Öztürk, M., Kolak, U., Duru, M.E., Harmandar, M., 2009. GC-MS analysis of the antioxidant active fractions of Micromeria juliana with anticholinesterase activity. Nat. Prod. Commun. 4, 1271-1276.
Öztürk, M., Kolak, U., Topu, G., Öksüz, S., Choudhary, M.I., 2011. Antioxidant and anticholinesterase active constituents from Micromeria cilicica by radical-scavenging activity-guided fractionation. Food Chem. 126, 31-38.
Palić, I., Ursić-Janković, J., Stojanović, G., 2010. Essential oil composition of three Balkan Micromeria species. J. Essent. Oil Res. 22, 40-44.
Pedersen, J.A., 2000. Distribution and taxonomic implications of some phenolics in the family Lamiaceae determined by ESR spectroscopy. Biochem. Syst. Ecol. 28, 229-253.
Puppo, P., Curto, M., Velo-Antón, G., de Paz, P.L.P., Meimberg, H., 2014. The influence of geological history on diversification in insular species: Genetic and morphological patterns of Micromeria Benth. (Lamiaceae) in Tenerife (Canary archipelago). J. Biogeogr. 41, 1871-1882.
Radulović, N.S., Blagojević, P.D., 2012. Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): Biosynthetical and chemotaxonomical aspects. Chem. Biodivers. 9, 1303-1319.
Radušiene, J., Gudaityte, O., 2005. Distribution of proazulenes in Achillea millefolium s.l. wild populations in relation to phytosociological dependence and morphological characters. Plant Genet. Resour. 3, 136-143.
Rastrelli, L., Caceres, A., Morales, C., De Simone, F., Aquino, R., 1998. Iridoids from Lippia graveolens. Phytochemistry 49, 1829-1832.
Rauf, A., Bawazeer, S., Rashid, U., El-Esawi, M.A., Khan, M.H., Shah, S.U.A., Mubarak, M.S., Rengasamy, K.R., 2021. Antiglycation and enzyme inhibitory potential of salicylalazine isolated from Micromeria biflora (Buch.-Ham.ex D.Don) Benth. S. Afr. J. Bot. 143 344-349.
Redžić, S.S., 2007. The ecological aspect of ethnobotany and ethnopharmacology of population in Bosnia and Herzegovina. Coll. Antropol. 31, 869-890.
Rivera, D., Obón, C., 1992. The Ethnobotany of Old World Labiatae, in: Harley, R.M., Reynolds, T. (Eds.), Advances in Labiatae Science. Royal Botanic Gardens: Kew, London, pp. 437-454.
Ruscic, M., Vukoa, E., Bezic, N., Kremerb, D., Dunkic, V., 2017. Croatian Micromeria fruticulosa-essential oil composition and antiphytoviral activity. Nat. Prod. Commun. 12, 1133-1135.
Salameh, N., Shraim, N., Jaradat, N., 2018. Chemical composition and enzymatic screening of Micromeria fruticosa serpyllifolia volatile oils collected from three different regions of West Bank, Palestine. BioMed Res. Int. 2018, 6536919.
Salehi, B., Venditti, A., Sharifi-Rad, M., Kręgiel, D., Sharifi-Rad, J., Durazzo, A., Lucarini, M., Santini, A., Souto, E.B., Novellino, E., Antolak, H., 2019. The therapeutic potential of apigenin. Int. J. Mol. Sci. 20, 1305.
Saric-Kundalic, B., Dobes, C., Klatte-Asselmeyer, V., Saukel, J., 2011. Ethnobotanical survey of traditionally used plants in human therapy of east, north and north-east Bosnia and Herzegovina. J. Ethnopharmacol. 133, 1051-1076.
Šavikin, K.P., Menković, N.R., Zdunić, G.M., Tasić, S.R., Ristić, M.S., Stević, T.R., Dajić-Stevanović, Z.P., 2010. Chemical composition and antimicrobial activity of the essential oils of Micromeria thymifolia (Scop.) Fritsch., M. dalmatica Benth., and Satureja cuneifolia Ten. and its secretory elements. J. Essent. Oil Res. 22, 91-96.
Schippmann, U., Leaman, D.J., Cunningham, A., 2002. Impact of Cultivation and Gathering of Medicinal Plants on Biodiversity: Global Trends and Issues. Biodiversity the Ecosystem Approach in Agriculture, Forestry and Fisheries. Inter-Departmental Working Group on Biological Diversity for Food and Agriculture, Rome.
Scognamiglio, M., D’Abrosca, B., Esposito, A., Fiorentino, A., 2015. Chemical composition and seasonality of aromatic Mediterranean plant species by NMR-based metabolomics. J. Anal. Methods Chem. 2015.
Sefidkon, F., Kalvandi, R., 2005. Chemical composition of the essential oil of Micromeria persica Boiss. from Iran. Flav. Fragr. J. 20, 539-541.
Shafaghat, A., Ghorban-Dadras, O., Mohammadhosseini, M., Akhavan, M., Shafaghatlonbar, M., Panahi, A., 2017. A comparative study on chemical composition and antimicrobial activity of essential oils from Tanacetum parthenium (L.) Schultz. Bip. and Tanacetum punctatum (Desr.) Grierson. leaves from Iran. J. Essent. Oil-Bear. Plants 20, 1143-1150.
Shan, B., Cai, Y.Z., Brooks, J.D., Corke, H., 2009. Antibacterial and antioxidant effects of five spice and herb extracts as natural preservatives of raw pork. J. Sci. Food Agric. 89, 1879-1885.
Shehab, N.G., Abu-Gharbieh, E., 2012. Constituents and biological activity of the essential oil and the aqueous extract of Micromeria fruticosa (L.) Druce subsp. serpyllifolia. Pak. J. Pharm. Sci. 25, 687-692.
Sher, H., Aldosari, A., Ali, A., de Boer, H.J., 2014. Economic benefits of high value medicinal plants to Pakistani communities: An analysis of current practice and potential. J. Ethnobiology Ethnomedicine 10, 1-16.
Silva, I.F., Oliveira, F.F.d., Oliveira, R.A.d., 2021. Siparuna Aublet genus (Siparunaceae): from folk medicine to chemical composition and biological activity. Trends Phytochem. Res. 5, 168-189.
Slavkovska, V., Couladis, M., Bojovic, S., Tzakou, O., Pavlovic, M., Lakusic, B., Jancic, R., 2005. Essential oil and its systematic significance in species of Micromeria Bentham from Serbia & Montenegro. Plant Syst. Evol. 255, 1-15.
Stojanović, G., Palić, I., 2008. Antimicrobial and antioxidant activity of Micromeria Bentham species. Curr. Pharm. Des. 14, 3196-3202.
Stojanović, G., Palić, I., Ursić-Janković, J., 2006. Composition and antimicrobial activity of the essential oil of Micromeria cristata and Micromeria juliana. Flav. Fragr. J. 21, 77-79.
Stojanovic, G., Palic, I., Ursic-Jankovic, J., Vajs, V., Dokovic, D., 1999. Chemical composition of the essential oil of Micromeria albanica (Griseb. ex K. Maly) Silic. J. Essent. Oil Res. 11, 785-787.
Stojičić, D., Tošić, S., Slavkovska, V., Zlatković, B., Budimir, S., Janošević, D., Uzelac, B., 2016. Glandular trichomes and essential oil characteristics of in vitro propagated Micromeria pulegium (Rochel) Benth. (Lamiaceae). Planta 244, 393-404.
Tabanca, N., Kirimer, N., Demirci, B., Demirci, F., Can Başer, K.H., 2001. Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol. J. Agric. Food Chem. 49, 4300-4303.
Taskin, T., Dogan, M., Yilmaz, B.N., Senkardes, I., 2020. Phytochemical screening and evaluation of antioxidant, enzyme inhibition, anti-proliferative and calcium oxalate anti-crystallization activities of Micromeria fruticosa spp. brachycalyx and Rhus coriaria. Biocatal. Agric. Biotechnol. 27, 101670.
Telci, I., Ceylan, M., 2007. Essential oil composition of Micromeria fruticosa Druce from Turkey. Chem. Nat. Compd. 43, 629-631.
Thagriki, D.S., 2022. Quercetin and its derivatives are potent inhibitors of the dengue virus. Trends Phytochem. Res. 6, 70-85.
Tomas-Barberan, F.A., Gil, M.I., Marin, P.D., Tomas-Lorente, F., 1991. Flavonoids from some Yugoslavian Micromeria species: Chemotaxonomical aspects. Biochem. Syst. Ecol. 19, 697-698.
Tomás-Barberán, F.A., Grayer-Barkmeijer, R.J., Gil, M.I., Harborne, J.B., 1988. Distribution of 6-hydroxy-, 6-methoxy-and 8-hydroxyflavone glycosides in the Labiatae, the Scrophulariaceae and related families. Phytochemistry 27, 2631-2645.
Toroglu, S., 2011. In-vitro antimicrobial activity and synergistic/antagonistic effect of interactions between antibiotics and some spice essential oils. J. Environ. Biol. 32, 23-29.
Tošić, S., Stojičić, D., Slavkovska, V., Mihailov-Krstev, T., Zlatković, B., Budimir, S., Uzelac, B., 2019. Phytochemical composition and biological activities of native and in vitro-propagated Micromeria croatica (Pers.) Schott (Lamiaceae). Planta 249, 1365-1377.
Tucker, A.O., Maciarello, M.J., McCrory, D., 1992. The essential oil of Micromeria brownei (Swartz) Benth. var. pilosiuscula Gray. J. Essent. Oil Res. 4, 301-302.
Tzakou, O., Couladis, M., 2001. The essential oil of Micromeria graeca (L.) Bentham et Reichenb. growing in Greece. Flav. Fragr. J. 16, 107-109.
Ullah, S., Son, S., Yun, H.Y., Kim, D.H., Chun, P., Moon, H.R., 2016. Tyrosinase inhibitors: A patent review (2011-2015). Expert Opin. Ther. Pat. 26, 347-362.
Venditti, A., 2017. Secondary metabolites from Teucrium polium L. collected in Southern Iran. Arab. J. Med. Arom. Plants 3, 108-123.
Venditti, A., 2020. What is and what should never be: artifacts, improbable phytochemicals, contaminants and natural products. Nat. Prod. Res. 34, 1014-1031.
Venditti, A., Altieri, A., Bianco, A., 2014a. Monoterpenoids glycosides content from two Mediterranean populations of Crucianella maritima L. Nat. Prod. Res. 28, 586-588.
Venditti, A., Ballero, M., Serafini, M., Bianco, A., 2015a. Polar compounds from Parentucellia viscosa (L.) Caruel from Sardinia. Nat. Prod. Res. 29, 602-606.
Venditti, A., Bianco, A., 2018. Secondary metabolites o f Hypericum richeri Vill. collected in Central Italy: Chemotaxonomy and ethnomedicinal relevance. Trends Phytochem. Res. 2, 155-162.
Venditti, A., Bianco, A., Frezza, C., Conti, F., Bini, L.M., Giuliani, C., Bramucci, M., Quassinti, L., Damiano, S., Lupidi, G., Beghelli, D., 2015b. Essential oil composition, polar compounds, glandular trichomes and biological activity of Hyssopus officinalis subsp. aristatus (Godr.) Nyman from central Italy. Ind. Crop Prod. 77, 353-363.
Venditti, A., Bianco, A., Frezza, C., Serafini, M., Giacomello, G., Giuliani, C., Bramucci, M., Quassinti, L., Lupidi, G., Lucarini, D., Papa, F., Maggi, F., 2016a. Secondary metabolites, glandular trichomes and biological activity of Sideritis montana L. subsp. montana from Central Italy. Chem. Biodivers. 13, 1380-1390.
Venditti, A., Bianco, A., Maggi, F., Nicoletti, M., 2013a. Polar constituents composition of endemic Sideritis italica (MILL.) GREUTER et BURTER from Central Italy. Nat. Prod. Res. 27, 1408-1412.
Venditti, A., Bianco, A., Nicoletti, M., Quassinti, L., Bramucci, M., Lupidi, G., Vitali, L.A., Papa, F., Vittori, S., Petrelli, D., Maleci Bini, L., Giuliani, C., Maggi, F., 2014b. Characterization of secondary metabolites, biological activity and glandular trichomes of Stachys tymphaea Hausskn. from the Monti Sibillini National Park (Central Apennines, Italy). Chem. Biodivers. 11, 245-261.
Venditti, A., Bianco, A., Nicoletti, M., Quassinti, L., Bramucci, M., Lupidi, G., Vitali, L.A., Petrelli, D., Papa, F., Vittori, S., 2013b. Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to Central Apennines, Italy. Fitoterapia 90, 94-103.
Venditti, A., Bianco, A., Quassinti, L., Bramucci, M., Lupidi, G., Damiano, S., Papa, F., Vittori, S., Maleci Bini, L., Giuliani, C., Lucarini, D., 2015c. Phytochemical analysis, biological activity, and secretory structures of Stachys annua (L.) L. subsp. annua (Lamiaceae) from Central Italy. Chem. Biodivers. 12, 1172-1183.
Venditti, A., Frezza, C., Bianco, A., Serafini, M., Cianfaglione, K., Nagy, D.U., Iannarelli, R., Caprioli, G., Maggi, F., 2017a. Polar constituents, essential oil and antioxidant activity of marsh woundwort (Stachys palustris L.). Chem. Biodivers. 14, e1600401.
Venditti, A., Frezza, C., Celona, D., Sciubba, F., Foddai, S., Delfini, M., Serafini, M., Bianco, A., 2017b. Phytochemical comparison with quantitative analysis between two flower phenotypes of Mentha aquatica L.: Pink-violet and white. AIMS Mol. Sci. 4, 288-300.
Venditti, A., Frezza, C., Foddai, S., Serafini, M., Nicoletti, M., Bianco, A., 2017c. Chemical traits of hemiparasitism in Odontites luteus. Chem. Biodivers. 14, e1600416.
Venditti, A., Frezza, C., Maggi, F., Lupidi, G., Bramucci, M., Quassinti, L., Giuliani, C., Cianfaglione, K., Papa, F., Serafini, M., Bianco, A., 2016b. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb.(Lamiaceae, Ajugoideae): Two new harpagide derivatives and an unusual iridoid glycosides pattern. Fitoterapia 113, 35-43.
Venditti, A., Frezza, C., Riccardelli, M., Foddai, S., Nicoletti, M., Serafini, M., Bianco, A., 2016c. Secondary metabolites from Scrophularia canina L. Nat. Prod. Res. 30, 1665-1669.
Venditti, A., Frezza, C., Riccardelli, M., Foddai, S., Nicoletti, M., Serafini, M., Bianco, A., 2016d. Unusual molecular pattern in Ajugoideae subfamily: The case of Ajuga genevensis L. from Dolomites. Nat. Prod. Res. 30, 1098-1102.
Venditti, A., Frezza, C., Sciubba, F., Foddai, S., Serafini, M., Nicoletti, M., Bianco, A., 2016e. Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and Pedicularis verticillata L. from Dolomites. Nat. Prod. Res. 30, 1698-1705.
Venditti, A., Frezza, C., Serafini, I., Ciccòla, A., Sciubba, F., Serafini, M., Bianco, A., 2018. Iridoids of chemotaxonomy relevance, a new antirrhinoside ester and other constituents from Kickxia spuria subsp. integrifolia (Brot.) R. Fern. Chem. Biodivers. 15, e1700473.
Venditti, A., Frezza, C., Serafini, M., Bianco, A., 2016f. Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Nat. Prod. Res. 30, 327-331.
Venditti, A., Guarcini, L., Ballero, M., Bianco, A., 2015d. Iridoid glucosides from Pentas lanceolata (Forssk.) Deflers growing on the Island of Sardinia. Plant Syst. Evol. 301, 685-690.
Venditti, A., Serrilli, A.M., Bianco, A., 2013c. Iridoids from Bellardia trixago (L.) All. Nat. Prod. Res. 27, 1413-1416.
Venditti, A., Serrilli, A.M., Bianco, A., 2013d. A new flavonoid and other polar compounds from Galeopsis angustifolia Ehrh. ex Hoffm. Nat. Prod. Res. 27, 412-416.
Vladimir-Kneževic, S., Blažekovic, B., Štefan, M.B., Alegro, A., Koszegi, T., Petrik, J., 2011. Antioxidant activities and polyphenolic contents of three selected Micromeria species from Croatia. Molecules 16, 1454-1470.
Vuko, E., Dunkić, V., Bezić, N., Ruščić, M., Kremer, D., 2012. Chemical composition and antiphytoviral activity of essential oil of Micromeria graeca. Nat. Prod. Commun. 7, 1227-1230.
Vuko, E., Rusak, G., Dunkic, V., Kremer, D., Kosalec, I., Rada, B., Bezic, N., 2019. Inhibition of satellite RNA associated cucumber mosaic virus infection by essential oil of Micromeria croatica (Pers.) Schott. Molecules 24, 1342.
Wansi, J.D., Sewald, N., Nahar, L., Martin, C., Sarker, S.D., 2018. Bioactive essential oils from the Cameroonian rain forest: A review - Part I Trends Phytochem. Res. 2, 187-234.
Wansi, J.D., Sewald, N., Nahar, L., Martin, C., Sarker, S.D., 2019. Bioactive essential oils from the Cameroonian rain forest: A review - Part II. Trends Phytochem. Res. 3, 3-52.
White, A., 1976. Medicinal Plants of Ecuador. Imprenta Mariscal, Quito, Ecuador.
Wielgorskaya, T., Takhtadzhian, A.L., 1995. Dictionary of Generic Names of Seed Plants. Columbia University Press.
Wink, M., 2003. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64, 3-19.
Yaniv, Z., Dudai, N., 2014. Medicinal and Aromatic Plants of the Middle-East, Springer.
Yousefi, B., Shahbazi, K., Khamisabady, H., Gheitury, M., 2021. Assessment of variability of essential oil components in different accessions of Damask rose (Rosa damascena Mill.) by multivariate analysis. Trends Phytochem. Res. 5, 199-208.
Zheljazkov, V.D., Micalizzi, G., Semerdjieva, I., Mondello, L., 2019. Chemical composition of the essential oil of the endemic species Micromeria frivaldszkyana (Degen) Velen. Molecules 24, 440.