PHYTOCHEMICAL AND CHEMOTAXONOMICAL INVESTIGATIONS OF LAMIACEAE FROM NORTH MACEDONIA

Petar  D. Marin; Nemanja  Rajčević; Ana  Alimpić Aradski

doi:10.20903/masa/nmbsci.2023.44.20

PHYTOCHEMICAL AND CHEMOTAXONOMICAL INVESTIGATIONS OF LAMIACEAE FROM NORTH MACEDONIA

Authors

Petar D. Marin Institute of Botany and Botanical Garden "Jevremovac", Faculty of Biology, University of Belgrade, Serbia Author
Nemanja Rajčević Institute of Botany and Botanical Garden "Jevremovac", Faculty of Biology, University of Belgrade, Serbia Author
Ana Alimpić Aradski Institute of Botany and Botanical Garden "Jevremovac", Faculty of Biology, University of Belgrade, Serbia Author

DOI:

https://doi.org/10.20903/masa/nmbsci.2023.44.20

Keywords:

Lamiaceae; North Macedonia; phytochemistry; chemotaxonomy, biological activity

Abstract

The flora of North Macedonia and the entire Balkan Peninsula is very rich, hosting numerous species of Lamiaceae. To date, many Lamiaceae species have been studied from various perspectives, including phytochemistry, chemotaxonomy, biological activity, molecular phylogeny, pharmacology, ethnobotany, and more. This review summarizes the results of studies on the phytochemistry, chemotaxonomy, and biological activity of Lamiaceae, with a particular focus on those species that grow wild in North Macedonia. The findings suggest that this region is a rich source of plants that could be of interest for further research, both from fundamental and applied perspectives. Academician Vlado Matevski made significant contributions to the study of plants from North Macedonia and the broader Balkan Peninsula. His passion as a botanist and collaborative work with regional scientists led to the publication of numerous papers in national and international journals.

References

E. Kostadinova, K. Alipieva, M. Stefova, T. Stafi-lov, D. Antonova, L. Evstatieva, V. Matevski, S. Kulevanova, G. Stefkov, V. Bankova, Chemical composition of the essential oils of three Mi-cromeria species growing in Macedonia and Bul-garia, Maced. J. Chem. Chem. Eng., 26 (2007), pp. 3–7.

D. Kremer, V. Dunkić, M. Ruščić, V. Matevski, D. Ballian, F. Bogunić, E. Eleftheriadou, D. Stešević, I. Kosalec, N. Bezić, Micromorphological traits and essential oil contents of Micromeria kerneri Murb. and M. juliana (L.) Benth. (Lamiaceae), Phytochemistry, 98 (2014), pp. 128–136.

V. Kostik, B. Bauer, Chemical composition of essential oils of wild-growing Mentha piperita L and Mentha spicata L from the Mariovo region, Republic of Macedonia, Second Mediterr. Symp. Med. Aromat. Plants Book Abstr., (2015), p.185.

A. Hajdari, B. Mustafa, L. Hyseni, A. Bajrami, G. Mustafa, C. L. Quave, D. Nebija, Phytochemical study of eight medicinal plants of the Lamiaceae family traditionally used as tea in the Sharri Mountains region of the Balkans, Sci. World J., 2020 (2020), pp.1–9.

B. Lukas, C. Schmiderer, J. Novak, Essential oil diversity of European Origanum vulgare L. (La-miaceae), Phytochemistry, 119 (2015), pp. 32–40.

B. Qazimi, G. Stefkov, M. Karapandzova, I. Cvetkovikj, S. Kulevanova, Volatile aroma сompounds in infusions of stems and rosette leaves of Sideritis raeseri Boiss. & Heldr. from R. Maсedonia, Albania and Greeсe, Maced. Pharm. Bull., 60 (2014), pp. 27–33.

S. Kulevanova, T. Stafilov, M. Ristić, D. Brkić, Isolation and identification of flavonoid from Thymus longidens var. lanicaulis and T. lon-gidens var. dassareticus (Lamiaceae), Acta Pharm., 47 (1997), pp. 281–286.

O. Tusevski, M. Trpevski, I. Lozanovska, A. Talevska, D. Ugurovska, S. Gadzovska-Simic, Antioxidant activity of phenolic compounds in methanolic extracts of some Macedonian medic-inal plants collected on Jablanica Mountain, Bull. Biol. Stud. Res. Soc., 4 (2010), pp. 103–111.

I. Mitreski, J. P. Stanoeva, M. Stefova, G. Stef-kov, S. Kulevanova, Polyphenols in Representa-tive Teucrium Species in the Flora of R. Macedo-nia: LC/DAD/ESI-MSn Profile and Content, Nat. Prod. Commun., 9 (2014), 1934578X1400900.

B. Janeska, M. Stefova, K. Alipieva, Assay of flavonoid aglycones from species of the genus Sideritis (Lamiaceae) from Macedonia with HPLC UV DAD, Acta Pharm., 57 (2007), pp. 371–377.

J. Petreska, G. Stefkov, S. Kulevanova, K. Alipieva, V. Bankova, M. Stefova, Phenolic Compounds of Mountain Tea from the Balkans: LC/DAD/ESI/MSn Profile and Content, Nat. Prod. Commun., 6 (2011), 1934578X1100600107.

A. Ibraliu, A. Trendafilova, B. Andjelković, B. Qazimi, D. Godjevac, E. Bebeci, G. Stefkov, G. Zdunic, I. Aneva, I. Pasho, Comparative Study of Balkan Sideritis Species from Albania, Bulgaria and Macedonia, Eur. J. Med. Plants, 5 (2015), pp. 328–340.

B. Qazimi, M. Karapandzova, G. Stefkov, S. Kulevanova, Chemical composition of ultrasonic-assisted n-hexane extracts of Sideritis scardica Griseb. and Sideritis raeseri Boiss. & Heldr. (La-miaceae) from Macedonia and Albania, Maced Pharm Bull, 56 (2010), pp. 45–56.

D. Kitić, B. Zlatković, R. Palić, T. Jovanović, M. Ristić, Fatty acids of some plants of the genus Calamintha, Chem. Nat. Compd., 45 (2009), pp. 231–233.

V. Slavkovska, R. Jančić, S. Milosavljević, D. Djoković, Variability of the essential oil composi-tion of the species Satureja montana L. (Lami-aceae), J. Essent. Oil Res., 9 (1997), pp. 629–634.

V. Slavkovska, R. Jančić, S. Bojović, S. Mi-losavljević, D. Djoković, Variability of essential oils of Satureja montana L. and Satureja kitaibelii Wierzb. ex Heuff. from the central part of the Balkan peninsula, Phytochemistry, 57 (2001), pp. 71–76.

T. Dodoš, J. Novaković, L. Vujisić, P. D. Marin, N. Rajčević, Geographic variability of winter savory essential oil, Ind. Crops Prod., 210 (2024), 118167.

N. Radulović, J. Lazarević, N. Ristić, R. Palić, Chemotaxonomic significance of the volatiles in the genus Stachys (Lamiaceae): Essential oil composition of four Balkan Stachys species, Bio-chem. Syst. Ecol., 35 (2007), pp. 196–208.

D. Kremer, V. Matevski, V. Dunkić, N. Bezić, E. Stabentheiner, Essential oil contents and micro-morphological traits of Stachys iva Griseb. and S. horvaticii Micevski (Lamiaceae), Rec. Nat. Prod., 10 (2016), pp. 228–239.

V. Dunkić, D. Kremer, R. J. Grubešić, J. V. Rodríguez, D. Ballian, F. Bogunić, D. Stešević, I. Kosalec, N. Bezić, E. Stabentheiner, Micromor-phological and phytochemical traits of four Clinopodium L. species (Lamiaceae), South Afr. J. Bot., 111 (2017), pp. 232–241.

D. Kremer, V. Dunkić, I. Radosavljević, F. Bogunić, D. Ivanova, D. Ballian, D. Stešević, V. Matevski, V. Ranđelović, E. Eleftheriadou, Phy-tochemicals and their correlation with molecular data in Micromeria and Clinopodium (Lamiace-ae) taxa, Plants, 11 (2022), 3407.

N. S. Radulović, P. D. Blagojević, Plant Volatiles Providing Additional Evidences to the Occurence of a Wild-Growing Population of Calamintha vardarensis (Greuter et Burdet) Šilić Outside of Its Natural Habitat, Chem. Biodivers., 7 (2010), pp. 2856–2868.

E.-M. Tomou, P. Fraskou, K. Dimakopoulou, E. Dariotis, N. Krigas, H. Skaltsa, Chemometric Analysis Evidencing the Variability in the Com-position of Essential Oils in 10 Salvia Species from Different Taxonomic Sections or Phyloge-netic Clades, Molecules, 29 (2024), 1547.

P. D. Marin, Hemotaksonomska i mikromorfolo-ška studija roda Micromeria Benth. i srodnih rodova iz tribusa Satureineae (Lamiaceae), Doktorska disertacija, Biološki fakultet, Univer-zitet u Beogradu, (1989), pp. 1–11.

F. A. Tomas-Barberan, M. I. Gil, P. D. Marin, F. Tomas-Lorente, Flavonoids from some Yugosla-vian Micromeria species: Chemotaxonomical as-pects, Biochem. Syst. Ecol., 19 (1991), pp.697–698.

P. D. Marin, A chemotaxonomic study of vacuo-lar flavonoids from some Balkan Micromeria Benth. species (Lamiaceae), Arch. Biol. Sci., 48 (1996), pp. 49–55.

P. D. Marin, R. J. Grayer, P. Janacković, External flavonoids from Satureja cuneifolia and S. ada-movicii, Second International Balkan Botanical Congress, Sarajevo, 2003, Book of Abstracts p. 296.

P. D. Marin, R. J. Grayer, G. C. Kite, V. Matevski, External leaf flavonoids of Thymus species from Macedonia, Biochem. Syst. Ecol., 31 (2003), pp. 1291–1307.

A. Karioti, J. Kukić-Marković, A. R. Bilia, M. Ni-ketić, S. Petrović, Chemical profiling of six Sta-chys taxa from Balkan Peninsula, Biochem. Syst. Ecol., 104 (2022), 104482.

J. P. Stanoeva, M. Stefova, G. Stefkov, S. Kule-vanova, K. Alipieva, V. Bankova, I. Aneva, L. N. Evstatieva, Chemotaxonomic contribution to the Sideritis species dilemma on the Balkans, Bio-chem. Syst. Ecol., 61 (2015), pp. 477–487.

T. Dodoš, N. Rajčević, V. Tešević, V. Matevski, P. Janaćković, P. D. Marin, Composition of Leaf n-Alkanes in Three Satureja montana L. Subspecies from the Balkan Peninsula: Ecological and Tax-onomic Aspects, Chem. Biodivers., 12 (2015), pp. 157–169.

F. Les, G. Cásedas, V. López, Bioactivity of me-dicinal plants and extracts, Biology, 10 (2021), p. 634.

M. Nikolova, I. Aneva, European Species of Ge-nus Salvia: Distribution, Chemodiversity and Bio-logical Activity, in: V. Georgiev, A. Pavlov (Eds.), Salvia Biotechnology, Springer International Pub-lishing, Cham, 2017, pp. 1–30.

V. Matevski, Salvia L., in: Flora na RS Makedon-ija, G. Jovanovski (ed), tom II, sv. 2, Make-donska akademija na naukite i umetnostite, Skopje, 2021, pp. 397–416.

A. Alimpić, M. Oaldje, V. Matevski, P. Marin, S. Duletić-Laušević, Antioxidant activity and total phenolic and flavonoid contents of Salvia am-plexicaulis Lam. Extracts, Arch. Biol. Sci., 66 (2014), pp. 307–316.

A. Z. Alimpić, N. Kotur, B. Stanković, P. D. Marin, V. Matevski, N. Al Sheef, S. Duletić-Laušević, The in vitro antioxidative and cytotoxic effects of se-lected Salvia species water extracts, J. Appl. Bot. Food Qual., 88 (2015), pp. 115–119.

A. Alimpić, A. Knežević, M. Milutinović, T. Stević, K. Šavikin, M. Stajić, S. Marković, P.D. Marin, V. Matevski, S. Duletić-Laušević, Biological activi-ties and chemical composition of Salvia amplexi-caulis Lam. extracts, Ind. Crop. Prod., 105 (2017), pp. 1–9.

A. Alimpić, D. Pljevljakušić, K. Šavikin, A. Knežević, M. Ćurčić, D. Veličković, T. Stević, G. Petrović, V. Matevski, J. Vukojević, Composition and biological effects of Salvia ringens (Lami-aceae) essential oil and extracts, Ind. Crops Prod., 76 (2015), pp. 702–709.

A. Alimpić, K. Šavikin, D. Pljevljakušić, V. Mat-evski, P. D. Marin, I. Petrović, S. Duletić-Laušević, Polyphenolic Content and Biological Activities of Post-Distillation Waste of Three Sage Species from the Republic of Macedonia, Agroznanje, 18 (2017), pp. 27–36.

A. Alimpić, A. Knežević, K. Šavikin, M. Ćurčić, D. Veličković, T. Stević, V. Matevski, M. Stajić, S. Marković, P. D. Marin, S. Duletić-Laušević, Com-position and biological activities of different ex-tracts of Salvia jurisicii, a rare and endemic Macedonian species, Plant Biosyst. – Int. J. Deal. Asp. Plant Biol., 151 (2017), pp. 1002–1011.

O. Tusevski, A. Kostovska, A. Iloska, L. Trajkovska, S. G. Simic, Phenolic production and antioxidant properties of some Macedonian me-dicinal plants, Centr. Eur. J. Biol., 9 (2014), pp. 888–900.

S. Ćavar Zeljković, M. Maksimović, Chemical composition and bioactivity of essential oil from Thymus species in Balkan Peninsula, Phytochem. Rev., 14 (2015), pp. 335–352.

S. Kulevanova, A. Kaftandzieva, A. Dimitrovska, G. Stefkov, N. Panovski, Potential antimicrobial activity of the essential oil of some Macedonian Thymus tosevii Vel. (Lamiaceae) varieties, Acta Pharm., 52 (2002), pp. 305–311.

V. Kostik, B. Gjorgjeska, S. Petkovska, Mentha L. essential oils composition and in vitro antifungal activity, IOSR J. Pharm., 5 (2015), pp. 1–7.

J. Petreska, M. Stefova, F. Ferreres, D. A. Moreno, F. A. Tomás-Barberán, G. Stefkov, S. Kulevano-va, A. Gil-Izquierdo, Potential bioactive phenolics of Macedonian Sideritis species used for medici-nal "Mountain Tea", Food Chem., 125 (2011), pp. 13–20.

M. Todorova, A. Trendafilova, Sideritis scardica Griseb., an endemic species of Balkan peninsula: Traditional uses, cultivation, chemical composi-tion, biological activity, J. Ethnopharmacol., 152 (2014), pp. 256–265.

K. Tasheva, A. Georgieva, P. Denev, L. Dimitrova, M. Dimitrova, S. Misheva, P. Petkova-Kirova, M. Lazarova, M. Petrova, Antioxidant and Anti-tumor Potential of Micropropagated Balkan En-demic Sideritis scardica Griseb, Plants, 12 (2023), 3924.

S. Branković, D. Kitić, M. Radenković, S. Vel-jković, T. Janković, K. Savikin, G. Zdunić, Spas-molytic Activity of the Ethanol Extract of Sider-itis raeseri ssp. raeseri Boiss. & Heldr. on the Iso-lated Rat Ileum Contractions, J. Med. Food, 14 (2011), pp. 495–498.

T. Kadifkova Panovska, S. Kulevanova, M. Stefova, In vitro antioxidant activity of some Teucrium species (Lamiaceae), Acta Pharm., 55 (2005), pp. 207–214.

E. Harlev, E. Nevo, N. Mirsky, R. Ofir, Antidiabet-ic Attributes of Desert and Steppic Plants: A Re-view, Planta Med., 79 (2013), pp. 425–436.

G. Stefkov, S. Kulevanova, B. Miova, S. Dinevska-Kjovkarovska, P. Mølgaard, A. K. Jä-ger, K. Josefsen, Effects of Teucrium polium ssp. capitatum flavonoids on the lipid and carbohy-drate metabolism in rats, Pharm. Biol., 49 (2011), pp. 885–892.