Comparative Study of Chemical Composition and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Plant Material
2.3. Isolation of the Essential Oil
2.4. Identification and Quantification of the Chemical Constituents of the Essential Oil by GC–MS
2.5. Cholinesterase Inhibitory Assay
3. Results and Discussion
3.1. Phytochemical Profile
3.2. Cholinesterase Inhibition Potential of Artemisia Essential Oils from Croatia
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Wright, C.W. Artemisia, 1st ed.; CRC Press: London, UK, 2001. [Google Scholar]
- Bora, K.S.; Sharma, A. The Genus Artemisia, a comprehensive review. Pharm. Biol. 2011, 49, 101–109. [Google Scholar] [CrossRef] [PubMed]
- Ekiert, H.; Klimek-Szczykutowicz, M.; Rzepiela, A.; Klin, P.; Szopa, A. Artemisia Species with High Biological Values as a Potential Source of Medicinal and Cosmetic Raw Materials. Molecules 2022, 27, 6427. [Google Scholar] [CrossRef] [PubMed]
- Kaul, V.K.; Nigam, S.S.; Banerjee, A.K. Insecticidal activity of some essential oils. Indian J. Pharm. 1978, 40, 22–26. [Google Scholar]
- Taleghani, A.; Emami, S.A.; Tayarani-Najaran, Z. Artemisia: A promising plant for the treatment of cancer. Bioorganic Med. Chem. 2020, 28, 115180. [Google Scholar] [CrossRef] [PubMed]
- Bolouri, P.; Salami, R.; Kouhi, S.; Kordi, S.; Lajayer, B.A.; Hadian, J.; Astatkie, T. Applications of Essential Oils and Plant Extracts in Different Industries. Molecules 2022, 27, 8999. [Google Scholar] [CrossRef]
- Giacobini, E. Do cholinesterase inhibitors have disease-modifying effects in Alzheimer’s disease? CNS Drugs 2001, 15, 85–91. [Google Scholar] [CrossRef]
- Briggs, R.; Kennelly, S.P.; O’Neill, D. Drug treatments in Alzheimer’s disease. Clin. Med. 2016, 16, 247–253. [Google Scholar] [CrossRef] [PubMed]
- Bektasevic, M.; Jurin, M.; Roje, M.; Politeo, O. Phytochemical Profile, Antioxidant Activity and Cholinesterase Inhibition Potential of Essential Oil and Extracts of Teucrium montanum from Bosnia and Herzegovina. Separations 2023, 10, 421. [Google Scholar] [CrossRef]
- Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy, 4.1st ed.; Allured Publishing Corporation: Carol Stream, IL, USA, 2017. [Google Scholar]
- Dool, H.V.D.; Kratz, P.D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. A 1963, 11, 463–471. [Google Scholar] [CrossRef]
- Ellman, G.L.; Courtney, K.D.; Andres, V., Jr.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88–95. [Google Scholar] [CrossRef]
- Juteau, F.; Jerkovic, I.; Masotti, V.; Milos, M.; Mastelic, J.; Besseire, J.M.; Viano, J. Composition and Antimicrobial Activity of the Essential Oil of Artemisia absinthium from Croatia and France. Planta Med. 2003, 69, 158–161. [Google Scholar] [CrossRef] [PubMed]
- Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T. Composition of the essential oil of Artemisia absinthium L. of different geographical origin. Proc. Estonian Acad. Sci. Chem. 2006, 55, 155–165. [Google Scholar] [CrossRef]
- Blagojevic, P.; Radulovic, N.; Palic, R.; Stojanovic, G. Chemical Composition of the Essential Oils of Serbian Wild-Growing Artemisia absinthium and Artemisia vulgaris. J. Agric. Food Chem. 2006, 54, 4780–4789. [Google Scholar] [CrossRef] [PubMed]
- Mucciarelli, M.; Caramiello, R.; Maffei, M. Essential Oils from Some Artemisia Species Growing Spontaneously in North-West Italy. Flavour. Frag. J. 1995, 10, 25–32. [Google Scholar] [CrossRef]
- Saunoriūtė, S.; Ragažinskienė, O.; Ivanauskas, L.; Marksa, M. Essential oil composition of Artemisia abrotanum L. during different vegetation stages in Lithuania. Chemija 2020, 31, 52–56. [Google Scholar]
- Obistioiu, D.; Cristina, R.T.; Schmerold, I.; Chizzola, R.; Stolze, K.; Nichita, I.; Chiurciu, V. Chemical characterization by GC-MS and in vitro activity against Candida albicans of volatile fractions prepared from Artemisia dracunculus, Artemisia abrotanum, Artemisia absinthium and Artemisia vulgaris. Chem. Cent. J. 2014, 8, 6. [Google Scholar] [CrossRef] [PubMed]
- Vidic, D.; Copra-Janicijevic, A.; Milos, M.; Maksimovic, M. Effects of different methods of isolation on volatile composition of Artemisia annua L. Int. J. Anal. Chem. 2018, 2018, 9604183. [Google Scholar] [CrossRef] [PubMed]
- Cavar, S.; Maksimovic, M.; Vidic, D.; Paric, A. Chemical composition and antioxidant and antimicrobial activity of essential oil of Artemisia annua L. from Bosnia. Ind. Crops Prod. 2012, 37, 479–485. [Google Scholar] [CrossRef]
- Vidic, D.; Cavar Zeljkovic, S.; Dizdar, M.; Maksimovic, M. Essential oil composition and antioxidant activity of four Asteraceae species from Bosnia. J. Essent. Oil Res. 2016, 28, 445–457. [Google Scholar] [CrossRef]
- Acimovic, M.; Stankovic Jeremic, J.; Todosijevic, M.; Kiprovski, B.; Vidovic, S.; Vladic, J.; Pezo, L. Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia. Chem. Biodivers. 2022, 19, 202100954. [Google Scholar] [CrossRef]
- Ickovski, J.D.; Stepic, K.D.; Stojanovic, G.S. Composition of essential oils and headspace constituents of Artemisia annua L. and A. scoparia Waldst. et Kit. J. Serb. Chem. Soc. 2020, 85, 1565–1575. [Google Scholar] [CrossRef]
- Radulovic, N.S.; Randjelovic, P.J.; Stojanovic, N.M.; Blagojevic, P.D.; Stojanovic-Radic, Z.Z.; Ilic, I.R.; Djordjevic, V.B. Toxic essential oils. Part II: Chemical, toxicological, pharmacological and microbiological profiles of Artemisia annua L. volatiles. Food Chem. Toxicol. 2013, 58, 37–49. [Google Scholar] [CrossRef] [PubMed]
- Janackovic, P.; Rajcevic, N.; Gavrilovic, M.; Novakovic, J.; Giwelib, A.; Stesevic, D.; Marin, P.D. Essential oil composition of five Artemisia (Compositae) species in regards to chemophenetics. Biochem. Syst. Ecol. 2019, 87, 103960. [Google Scholar] [CrossRef]
- Bedini, S.; Flamini, G.; Cosci, F.; Ascrizzi, R.; Echeverria, M.C.; Guidi, L.; Landi, M.; Lucchi, A.; Conti, B. Artemisia spp. essential oils against the disease-carrying blowfly Calliphora vomitoria. Parasites Vectors 2017, 10, 80–90. [Google Scholar] [CrossRef]
- Bili, A.R.; Flamini, G.; Morgenni, F.; Isacchi, B.; Vincieri, F.F. GC MS Analysis of the Volatile Constituents of Essential Oil and Aromatic Waters of Artemisia annua L. at Different Developmental Stages. Nat. Prod. Commun. 2008, 3, 2075–2078. [Google Scholar] [CrossRef]
- Héthelyi, E.B.; Cseko, I.B.; Grósz, M.; Márk, G.; Palinkás, J.J. Chemical Composition of the Artemisia annua Essential Oils from Hungary. J. Essent. Oil Res. 1995, 7, 45–48. [Google Scholar] [CrossRef]
- Ornano, L.; Venditti, A.; Ballero, M.; Sanna, C.; Quassinti, L.; Bramucci, M.; Lupidi, G.; Papa, F.; Vittori, S.; Maggi, F.; et al. Chemopreventive and antioxidant activity of the chamazulene-rich essential oil obtained from Artemisia arborescens L. growing on the Isle of La Maddalena, Sardinia, Italy. Chem. Biodivers. 2013, 10, 1464–1474. [Google Scholar] [CrossRef]
- Said, M.E.-A.; Militello, M.; Saia, S.; Settanni, L.; Aleo, A.; Mammina, C.; Bombarda, I.; Vanloot, P.; Roussel, C.; Dupuy, N. Artemisia arborescens Essential Oil Composition, Enantiomeric Distribution, and Antimicrobial Activity from Different Wild Populations from the Mediterranean Area. Chem. Biodivers. 2016, 13, 1095–1102. [Google Scholar] [CrossRef]
- Lo Presti, M.; Crupi, M.L.; Zellner, B.D.A.; Dugo, G.; Mondello, L.; Dugo, P.; Ragusa, S. Characterization of Artemisia arborescens L. (Asteraceae) leaf-derived essential oil from Southern Italy. J. Essent. Oil Res. 2007, 19, 218–224. [Google Scholar] [CrossRef]
- Militello, M.; Carrubba, A.; Blázquez, M.A. Artemisia arborescens L.: Essential oil composition and effects of plant growth stage in some genotypes from Sicily. J. Essent. Oil Res. 2012, 24, 229–235. [Google Scholar] [CrossRef]
- Militello, M.; Settanni, L.; Aleo, A.; Mammina, C.; Moschetti, G.; Giammanco, G.M.; Amparo Blàzquez, M.; Carrubba, A. Chemical composition and antibacterial potential of Artemisia arborescens L. essential oil. Curr. Microbiol. 2011, 62, 1274–1281. [Google Scholar] [CrossRef] [PubMed]
- Chericoni, S.; Flamini, G.; Campeol, E.; Cioni, P.L.; Morelli, I. GC-MS analysis of the essential oil from the aerial parts of Artemisia verlotiorum: Variability during the year. Biochem. Syst. Ecol. 2004, 32, 423–429. [Google Scholar] [CrossRef]
- Williams, J.D.; Campbell, M.A.; Jaskolka, M.C.; Xie, T. Artemisia vulgaris L. Chemotypes. Am. J. Plant Sci. 2013, 4, 1265–1269. [Google Scholar] [CrossRef]
- Jerkovic, I.; Mastelic, J.; Milos, M.; Juteau, F.; Masotti, V.; Viano, J. Chemical variability of Artemisia vulgaris L. essential oils originated from the Mediterranean area of France and Croatia. Flavour. Fragr. J. 2003, 18, 436–440. [Google Scholar] [CrossRef]
- Burcul, F.; Blazevic, I.; Radan, M.; Politeo, O. Terpenes, Phenylpropanoids, Sulfur and Other Essential Oil Constituents as Inhibitors of Cholinesterases. Curr. Med. Chem. 2020, 27, 4297–4343. [Google Scholar] [CrossRef] [PubMed]
- Khan, F.A.; Khan, N.M.; Ahmad, S.; Nasruddin, A.R.; Ullah, I.; Almehmadi, M.; Allahyani, M.; Alsaiari, A.A.; Aljuaid, A. Phytochemical Profiling, Antioxidant, Antimicrobial and Cholinesterase Inhibitory Effects of Essential Oils Isolated from the Leaves of Artemisia scoparia and Artemisia absinthium. Pharmaceuticals 2022, 12, 1221. [Google Scholar] [CrossRef] [PubMed]
- Orhan, I.E.; Belhattab, R.; Şenol, F.S.; Gülpinar, A.R.; Hosbas, S.; Kartal, M. Profiling of cholinesterase inhibitory and antioxidant activities of Artemisia absinthium, A. herba-alba, A. fragrans, Marrubium vulgare, M. astranicum, Origanum vulgare subsp. glandulossum and essential oil analysis of two Artemisia species. Ind. Crop. Prod. 2010, 32, 566–571. [Google Scholar] [CrossRef]
- Wang, B.; Yang, F.; Sun, Q.; Yang, Z.; Zhu, L. Chemical Composition and Antiacetylcholinesterase Activity of Flower Essential Oils of Artemisia annua at Different Flowering Stage. Iran. J. Pharm. Res. 2011, 10, 265–271. [Google Scholar]
Species | Species Code | Locality/Year | Coordinates |
---|---|---|---|
Geogr. Latitude (N) | |||
Geogr. Longitude (E) | |||
Artemisia absinthium L. | AABS | Sinj, Croatia/2020 | 43°43′27.29″ |
16°40′28.29″ | |||
Artemisia abrotanum L. | AABR | Vrgorac, Croatia/2021 | 43°12′36.63″ |
17°24′4.83″ | |||
Artemisia annua L. | AANN | Split, Croatia/2020 | 43°31′34.24″ |
16°28′2.95″ | |||
Artemisia arborescens (Vaill.) L. | AARB | Split, Croatia/2020 | 43°30′30.5″ |
16°25′17.76″ | |||
Artemisia verlotiorum Lamotte | AVER | Zagreb, Croatia/2020 | 45°48′59.08″ |
15°55′55.59″ | |||
Artemisia vulgaris L. | AVUL | Sinj, Croatia/2020 | 43°43′27.29″ |
16°40′28.29″ |
AABS | AABR | AANN | AARB | AVER | AVUL | ||
---|---|---|---|---|---|---|---|
% EO (w/w) | 0.5 | 1.6 | 0.6 | 1.1 | 0.3 | 0.2 | |
Compound | RI | ||||||
ß-thujene | 928 | 1.9 | - | 0.9 | - | - | - |
α-pinene | 937 | 0.4 | 1.7 | 1.2 | 1.6 | 0.5 | 1.2 |
camphene | 952 | - | 7.0 | 2.9 | 2.4 | - | 0.5 |
ß-pinene | 976 | - | - | 1.3 | - | 1.4 | 2.3 |
Sabinene | 979 | - | 5.2 | 0.9 | - | 0.2 | 1.8 |
ß-myrcene | 993 | - | - | - | 2.1 | - | - |
α-phellandrene | 1006 | - | - | - | - | - | 0.7 |
α-terpinene | 1018 | - | - | 0.4 | 0.8 | - | 0.2 |
p-cymene | 1027 | 0.8 | 1.9 | 0.4 | 0.5 | 1.2 | 2.9 |
Limonene | 1031 | - | - | - | - | 0.2 | 0.4 |
γ-terpinene | 1061 | - | - | 0.6 | 1.4 | 0.3 | 0.4 |
Monoterpene | 3.1 | 15.8 | 8.6 | 8.8 | 3.8 | 10.4 | |
yomogi alcohol | 1000 | - | - | 1.2 | - | - | - |
1,8-cineole | 1034 | 1.0 | 3.0 | 16.2 | - | 10.9 | 3.2 |
artemisia ketone | 1065 | - | - | 22.3 | - | - | - |
cis-sabinene hydrate | 1069 | - | - | 0.3 | 1.5 | 0.3 | 0.3 |
artemisia alcohol | 1086 | - | - | 3.2 | - | - | - |
linalool | 1100 | 0.8 | - | 1.5 | - | - | - |
trans-sabinene hydrate | 1102 | - | - | - | - | 0.3 | - |
trans-3-caren-2-ol | 1103 | - | - | - | - | 0.5 | - |
cis-thujone | 1107 | 3.1 | - | - | - | 46.3 | 5.6 |
trans-thujone | 1118 | 0.9 | - | - | - | 9.0 | 40.3 |
cis-p-menth-2-en-1-ol | 1122 | - | 0.9 | 0.3 | - | 0.4 | - |
chrysanthenone | 1127 | - | 4.7 | 0.3 | - | - | - |
cis-epoxy-ocimene | 1136 | 28.8 | - | - | - | - | 15.5 |
ß-pinone | 1139 | - | 0.8 | - | - | - | |
trans-p-menth-2-en-1-ol | 1141 | - | 0.8 | 0.6 | - | 0.5 | - |
trans-sabinol | 1142 | 0.8 | - | 0.6 | - | - | 0.2 |
trans-epoxyocimene | 1143 | 1.1 | - | - | - | - | - |
camphor | 1146 | - | 9.5 | 22.0 | 39.5 | 0.7 | 2.7 |
ß-pinene oxide | 1160 | - | - | 1.2 | - | 0.5 | - |
pinocarvone | 1165 | - | 0.9 | 0.6 | - | 0.4 | - |
borneol | 1167 | - | 48.0 | 0.3 | 0.5 | 0.3 | 0.7 |
lavandulol | 1169 | - | - | 0.4 | |||
terpinen-4-ol | 1178 | 0.8 | - | 1.2 | 3.2 | 0.7 | 0.5 |
trans-p-mentha-1(7),8-dien-2-ol | 1188 | 0.5 | - | - | - | - | - |
α-terpineol | 1191 | - | - | 0.5 | 0.4 | - | - |
myrtenol | 1196 | - | - | - | - | 0.3 | 0.4 |
myrtenal | 1202 | - | 0.7 | 0.8 | - | - | - |
trans-piperitol | 1210 | - | 1.0 | - | - | - | - |
trans-carveol | 1220 | - | - | - | - | 2.3 | - |
neral | 1229 | - | - | - | - | 0.3 | - |
carvotanacetone | 1245 | - | - | - | - | 0.7 | - |
cis-chrysanthenyl acetate | 1264 | 1.8 | - | - | - | - | - |
perilla aldehyde | 1275 | - | - | - | - | 0.5 | - |
isobornyl acetate | 1287 | - | 3.6 | - | - | - | - |
thymol | 1293 | - | 0.5 | - | - | - | - |
perilla alcohol | 1297 | - | - | 0.2 | - | 0.3 | - |
cis-sabinyl acetate | 1299 | 38.5 | - | - | - | - | - |
Monoterpenoid | 78.1 | 74.4 | 74.0 | 45.5 | 75.2 | 69.4 | |
α-copaene | 1377 | - | - | 1.1 | - | - | 0.3 |
ß-bourbonene | 1385 | - | - | - | - | - | 0.2 |
ß-caryophyllene | 1419 | 1.3 | - | 1.3 | 0.5 | 5.8 | 1.3 |
α-humulene | 1454 | - | - | - | - | 0.9 | 0.1 |
γ-muurolene | 1477 | - | - | 0.5 | - | - | 0.3 |
γ-himachalene | 1480 | 0.4 | - | - | - | - | - |
α-amorphene | 1484 | 0.5 | - | - | - | - | - |
germacrene D | 1485 | - | - | 0.4 | 1.1 | 1.1 | - |
ß-selinene | 1486 | 1.5 | - | 2.3 | - | 0.3 | 1.2 |
α-selinene | 1496 | - | - | - | - | 0.3 | - |
δ-cadinene | 1524 | - | - | - | - | 0.4 | - |
Sesquiterpene | 3.7 | 0.0 | 5.6 | 1.6 | 8.8 | 4.4 | |
spathulenol | 1577 | - | - | 0.2 | - | 1.5 | - |
caryophyllene oxide | 1582 | 1.3 | - | 5.3 | - | 6.0 | 2.5 |
davanone | 1589 | - | - | - | - | - | 3.2 |
humulene epoxide | 1608 | - | - | 0.3 | - | 0.4 | 1.1 |
α-copaen-4-ol | 1611 | - | - | 0.3 | - | - | 0.3 |
10-epi-γ-eudesmol | 1623 | - | - | 0.7 | - | - | - |
longifolenaldehyde | 1629 | - | - | 0.6 | 1.8 | - | 0.8 |
torreyol | 1655 | - | - | - | - | 0.5 | 3.7 |
cubenol | 1656 | - | - | 0.2 | - | - | - |
ß-bisabolol | 1671 | - | - | 0.3 | - | - | - |
eudesma-4,15(7)-dien-1ß-ol | 1685 | - | - | 0.3 | 0.4 | 0.2 | |
chamazulene | 1728 | 0.8 | - | - | 33.9 | - | 0.2 |
Sesquiterpenoid | 2.1 | 0.0 | 8.2 | 35.7 | 8.8 | 12.3 | |
hexanal | 800 | - | - | - | - | - | 0.3 |
trans-hex-2-en-1-ol | 853 | - | - | - | - | 0.9 | 0.8 |
oct-1-en-3-ol | 980 | - | - | - | - | 0.8 | |
2-pentylfuran | 989 | - | 0.9 | - | - | - | - |
phenylacetaldehyde | 1046 | - | 0.8 | - | - | - | 0.5 |
benzyl isovalerate | 1388 | - | - | 1.6 | - | - | - |
eugenol | 1359 | - | - | 0.3 | - | 0.3 | |
2-ethyl-4-methyl-1,3-pentadienyl benzene *# | 1515 | 2.9 | - | - | 0.8 | - | 0.2 |
2-ethyl-4-methyl-1,3-pentadienyl benzene *# | 1616 | 4.5 | - | - | 1.9 | - | 0.6 |
hexadecanoic acid | 1960 | - | - | - | - | - | 0.3 |
Other Compounds | 7.4 | 1.7 | 1.9 | 2.7 | 2.0 | 2.7 | |
TOTAL | 94.4 | 91.9 | 98.3 | 94.3 | 98.6 | 99.2 |
Inhibition % | AABS * | AABR * | AANN * | AARB * | AVER * | AVUL * | Huperzine A & | Galantamine # |
---|---|---|---|---|---|---|---|---|
AChE | 29.7 | 49.6 | 55.2 | 41.1 | 34.3 | 54.4 | 90.7 | 78.60 |
BChE | 33.8 | 47.0 | 35.8 | 33.5 | 31.4 | 23.0 | 58.8 | 40.9 |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Politeo, O.; Cajic, I.; Simic, A.; Ruscic, M.; Bektasevic, M. Comparative Study of Chemical Composition and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia. Separations 2023, 10, 546. https://doi.org/10.3390/separations10100546
Politeo O, Cajic I, Simic A, Ruscic M, Bektasevic M. Comparative Study of Chemical Composition and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia. Separations. 2023; 10(10):546. https://doi.org/10.3390/separations10100546
Chicago/Turabian StylePoliteo, Olivera, Ivana Cajic, Anja Simic, Mirko Ruscic, and Mejra Bektasevic. 2023. "Comparative Study of Chemical Composition and Cholinesterase Inhibition Potential of Essential Oils Isolated from Artemisia Plants from Croatia" Separations 10, no. 10: 546. https://doi.org/10.3390/separations10100546