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Sesquiterpene Lactones from Artemisia Genus: Biological Activities and Methods of Analysis
Open accessAbstract
Sesquiterpene lactones are a large group of natural compounds, found primarily in plants of Asteraceae family, with over 5000 structures reported to date. Within this family, genus Artemisia is very well represented, having approximately 500 species characterized by the presence of eudesmanolides and guaianolides, especially highly oxygenated ones, and rarely of germacranolides. Sesquiterpene lactones exhibit a wide range of biological activities, such as antitumor, anti-inflammatory, analgesic, antiulcer, antibacterial, antifungal, antiviral, antiparasitic, and insect deterrent. Many of the biological activities are attributed to the α-methylene-γ-lactone group in their molecule which reacts through a Michael-addition with free sulfhydryl or amino groups in proteins and alkylates them. Due to the fact that most sesquiterpene lactones are thermolabile, less volatile compounds, they present no specific chromophores in the molecule and are sensitive to acidic and basic mediums, and their identification and quantification represent a difficult task for the analyst. Another problematic aspect is represented by the complexity of vegetal samples, which may contain compounds that can interfere with the analysis. Therefore, this paper proposes an overview of the methods used for the identification and quantification of sesquiterpene lactones found in Artemisia genus, as well as the optimal conditions for their extraction and separation.
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“This latter class, of which artemisinin is a member, are typically bioactive and therefore potential targets for development as pharmaceuticals (22).”
From Artemisia annua mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [22]
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Sesquiterpene Lactones with COX ‐2 Inhibition Activity from Artemisia lavandulaefolia
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Kim, K. O., Lee, D. Y., Hiep, N. T., Song, J. H., Lee, H., Lee, D., & Kang, K. S. (2019) · Molecules · doi:10.3390/molecules24010195 · Cited by 18
“argyi, exhibit various biological and pharmaceutical activities, including anti-oxidant, anti-inflammatory and anti-apoptosis activities [15,22,23,28].”
BackgroundBăieș, M.-H., Gherman, C. M., Boros, Z., Olah, D. I., Vlase, A.-M., Cozma-Petruț, A. P., Györke, A., Miere, D., Vlase, L., Crișan, G., et al. (2022) · Pathogens · doi:10.3390/pathogens11091065 · Cited by 20
Ruggieri, F., Hance, P., Gioia, B., Biela, A., Roussel, P., Hilbert, J., & Willand, N. (2023) · Pharmaceuticals · doi:10.3390/ph16050771 · Cited by 17
“The wide range of biological activities exhibited by STLs is mainly attributed to the α-methylene-γ-lactone group present in their structure [4].”
BackgroundPhytochemical diversity and pharmacological effects of sesquiterpenes from Artemisia spp.
Rezaei, A., Emami, S. A., & Akaberi, M. (2024) · Phytochemistry Reviews · doi:10.1007/s11101-024-09962-8 · Cited by 16
Selim, D. A., Shawky, E. M., Ghareeb, D. A., Abdulmalek, S. A., & El-Khair, R. M. A. (2022) · Food Bioscience · doi:10.1016/j.fbio.2022.102306 · Cited by 14
“…dide-hydro, 4-ketone respectively, where the most prominent peaks corresponded to the protonated ions [M + H] + , loss of carboxylic acid from ester 58, followed by loss of water molecule from each corresponding lactone (Ivanescu, Miron, & Corciova, 2015) (Barbero & Prandi, 2018).”
BackgroundNatural sources and pharmacological properties of santalenes and santalols
Hachlafi, N. E., Benkhaira, N., Mssillou, I., Touhtouh, J., Aanniz, T., Chamkhi, I., Omari, N. E., Khalid, A., Abdalla, A. N., Aboulagras, S., et al. (2024) · Industrial Crops and Products · doi:10.1016/j.indcrop.2024.118567 · Cited by 15
Intakhan, N., Saeung, A., Oliveira, S. M. R., Pereira, M. D. L., & Chanmol, W. (2024) · Antibiotics · doi:10.3390/antibiotics13090806 · Cited by 14
“Artemisinin and its derivatives are sesquiterpene trioxanes [23] that have demonstrated efficacy against human parasitic infections such as malaria [24].”
BackgroundLatin American Natural Product Database (LANaPDB): An Update
Gómez‐García, A., Jiménez, D. A. A., Zamora, W. J., Barazorda-Ccahuana, H. L., Chávez‐Fumagalli, M. Á., Valli, M., Andricopulo, A. D., Bolzani, V. D. S., Olmedo, D. A., Solís, P. N., et al. (2024) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.4c01560 · Cited by 20
Abdel-dayem, S. I. A., Khalil, M. N. A., Abdelrahman, E. H., El-Gohary, H. M. A., & Kamel, A. S. E. D. (2020) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2020.113407 · Cited by 14
Arglabin could target inflammasome-induced ARDS and cytokine storm associated with COVID-19
Manayi, A., Nabavi, S. M., Khayatkashani, M., Habtemariam, S., & Kashani, H. R. K. (2021) · Molecular Biology Reports · doi:10.1007/s11033-021-06827-7 · Cited by 14
Tuasha, N., Escobar, Z., Seifu, D., Gadisa, E., Petros, B., Sterner, O., & Oredsson, S. (2022) · Toxicology Reports · doi:10.1016/j.toxrep.2022.02.011 · Cited by 16
“Studies involving structure-activity relationships indicate that rapid Michael type of addition takes place when cytotoxic SLs react with thiols, such as free sulfhydryl groups in mainly the amino acid cystine in proteins [17,21].”
BackgroundWang, Y., Ma, Y., Huang, X., Li, T.-Z., He, X.-F., Zhang, X., & Chen, J. (2022) · Fitoterapia · doi:10.1016/j.fitote.2022.105399 · Cited by 13
Băieș, M.-H., Cotuţiu, V.-D., Spînu, M., Mathe, A., Cozma-Petruț, A. P., Bolboaca, S. D., Engberg, R. M., Collin, A., & Cozma, V. (2024) · BMC Veterinary Research · doi:10.1186/s12917-024-03983-3 · Cited by 16
“Sesquiterpene lactones, such as artemisinin, dihydroartemisinin, ridentin, hanphyllin, dehydroleucodine, and santonin, constitute the most important molecules responsible for the antiparasitic activity of plants from the Artemisia genus [26–28].”
BackgroundGanash, A. A., & Alghamdi, R. A. (2021) · Journal of the Chinese Chemical Society · doi:10.1002/jccs.202100348 · Cited by 13
Halophyte Artemisia caerulescens L.: Metabolites from In Vitro Shoots and Wild Plants
Pieracci, Y., Vento, M., Pistelli, L., Lombardi, T., & Pistelli, L. (2022) · Plants · doi:10.3390/plants11081081 · Cited by 12
Hu, X., Xu, S., & Maimone, T. J. (2017) · Angewandte Chemie · doi:10.1002/ange.201611078 · Cited by 12
Li, Q., Liu, X., Zhang, X., Du, Y., Chen, G., Xiang, P., Ling, W., & Wang, D. (2021) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.202100905 · Cited by 11
Two new eudesmane sesquiterpene glucosides from the aerial parts of Artemisia vulgaris
Hạnh, T. T. H., Vinh, L. B., Cường, N. X., & Quang, T. H. (2022) · Natural Product Research · doi:10.1080/14786419.2022.2025591 · Cited by 11
“The (1)H and (13)C NMR data of 1 exhibited the characteristic resonance for an eudesmane-type sesquiterpene glycoside, one of main components reported from Artemisia species (Ivanescu et al. 2015).”
BackgroundHe, X., Ma, Y., Li, T.-Z., & Chen, J. (2023) · Phytochemistry · doi:10.1016/j.phytochem.2023.113930 · Cited by 11
Hajj, J. E., Karam, L., Jaber, A., Cheble, E., Akoury, E., Kobeissy, P. H., Ibrahim, J.-N., & Yassin, A. (2024) · Molecules · doi:10.3390/molecules29225431 · Cited by 12
Li, Y., Du, X., & Mao, J. (2025) · International Journal of Oncology · doi:10.3892/ijo.2025.5766 · Cited by 11
“…annua , Artemisia atrovirens , Capillary artemisia , Artemisia mongolica and Artemisia nilagirica ) have been used as traditional medicines to treat a variety of diseases (145), such as malaria, dysmenorrhea, amenorrhea, hepatitis, inflam‑ mation, bruising, jaundice, bleeding and cancer (27,146).”
InfluentialGuaianolides from Artemisia codonocephala suppress interleukine-1β secretion in macrophages
Wang, Q., Zhang, T., Ke, C., Tang, C., Yao, S., Lin, L., & Ye, Y. (2021) · Phytochemistry · doi:10.1016/j.phytochem.2021.112955 · Cited by 11
Trifan, A., Czerwińska, M. E., Mardari, C., Zengin, G., Sinan, K. I., Korona‐Głowniak, I., Skalicka‐Woźniak, K., & Luca, S. V. (2022) · Plants · doi:10.3390/plants11212874 · Cited by 11
“Moreover, sesquiterpene lactones are acknowledged to act as anti-inflammatory and immunomodulatory effectors and their underlying mechanism relates to the inhibition of the NF-κB pathway [66].”
BackgroundSecondary metabolites from Ajania salicifolia and their chemotaxonomic significance
Shi, Z.-N., Wu, H., Pang, X., Chen, J., & Zhu, Y. (2016) · Biochemical Systematics and Ecology · doi:10.1016/j.bse.2016.11.012 · Cited by 11
“In the tribe Anthemideae, sesquiterpenoids were isolated from species in the genera Achillea (Saeidnia et al., 2011), Anthemis (Staneva et al., 2008), Artemisia (Ivanescu et al., 2015), Chrysanthemum (Kumar et al., 2005), and Tanacetum (Ivanescu et al., 2015).”
BackgroundRP-HPLC Method for the Determination and Quantification of Artesunate
Saeed, M. A., Ansari, M. T., Ahmad, B., & Zaman, M. (2020) · Journal of Chromatographic Science · doi:10.1093/chromsci/bmaa037 · Cited by 11
Bioactive principles, antibacterial and anticancer properties of Artemisia arborescens L.
Sultana, S., Makeen, H. A., Alhazmi, H. A., Mohan, S., Bratty, M. A., Najmi, A., Homeida, H. E., Khuwaja, G., Ullah, S. N. M. N., Zafar, A., et al. (2023) · Notulae Botanicae Horti Agrobotanici Cluj-Napoca · doi:10.15835/nbha51113008 · Cited by 11
Vu, Q. V., Sayama, S., Ando, M., & Kataoka, T. (2024) · Molecules · doi:10.3390/molecules29081866 · Cited by 13
“…including eudesmanolides (e.g., alantolactone) and germacranolides (e.g., parthenolide and costunolide) [19,20]. into several The biological activities of sesquiterpene lactones are mainly attributed to an α -methylene- γ -lactone moiety, which mainly reacts with the thiol groups of proteins [21].”
BackgroundCombating multidrug-resistant (MDR) Staphylococcus aureus infection using terpene and its derivative
Salikin, N. H., Keong, L. C., Azemin, W.-A., Philip, N., Yusuf, N., Daud, S. A., & Rashid, S. A. (2024) · World Journal of Microbiology and Biotechnology · doi:10.1007/s11274-024-04190-w · Cited by 10
“Sesquiterpenes have demonstrated antimicrobial, anti-inflammatory, antitumor, analgesic, antifungal, antiparasitic, antiviral, and insect deterrent properties, rendering them an appealing reservoir of natural therapeutic metabolites (Ivanescu et al. 2015).”
Intakhan, N., Siriyasatien, P., & Chanmol, W. (2021) · Acta Tropica · doi:10.1016/j.actatropica.2021.106260 · Cited by 10
Abdalla, M. A., Famuyide, I. M., Wooding, M., McGaw, L. J., & Mühling, K. H. (2022) · Pharmaceutics · doi:10.3390/pharmaceutics14112267 · Cited by 10
“Sesquiterpene lactones are well known for their anti-inflammatory, antimicrobial, anticancer, antiviral, immunomodulatory and anti-ulcer properties [15].”
BackgroundSainz, P., Cruz-Estrada, Á., Diaz, C. E., & González‐Coloma, A. (2017) · Phytochemistry Reviews · doi:10.1007/s11101-017-9516-2 · Cited by 10
“In Artemisia species, the most common ones are guaianolides, eudesmanolides and germacranolides (Ivanescu et al. 2015) (Fig.”
BackgroundAntifungal Activity of the Sesquiterpene Lactones from Psephellus bellus
Nawrot, J., Adamski, Z., Kamińska-Kolat, B., Kubisiak-Rzepczyk, H., Kroma, A., Nowak, G., & Gornowicz‐Porowska, J. (2021) · Plants · doi:10.3390/plants10061180 · Cited by 10
“Moreover, reported data indicated [18] that the MIC is of little value without the corresponding ability to interpret its clinical meaning.”
BackgroundChen, J., Zhang, Y., Guo, X., Qiao, Y., & Yu, P. (2024) · Separation and Purification Technology · doi:10.1016/j.seppur.2024.126523 · Cited by 9
Indira, M., Suluvoy, J. K., Thathapudi, J. J., & Srirama, K. (2024) · Beni-Suef University Journal of Basic and Applied Sciences · doi:10.1186/s43088-024-00556-z · Cited by 9
“Its potent anticancer affects are primarily due to the endoperoxide bond, which is activated by ferrous (Fe 2 + ) ions leading to cytotoxic activity [119].”
Mechanistic elucidations of sesquiterpenes ameliorating viral infections: A review
Katiyar, D., Bansal, P., Kumar, A., Prakash, S., & Rao, N. G. R. (2022) · Journal of Food Biochemistry · doi:10.1111/jfbc.14452 · Cited by 9
Huo, G., Li, X., Abubaker, M. A., Liang, T., Zhang, J., & Chen, X. (2022) · Molecules · doi:10.3390/molecules27217300 · Cited by 9
“longipedunculata [9], sesquiterpene lactones exhibit a wide range of biological activities, such as antitumor, anti-inflammatory, analgesic, antiulcer, antibacterial, antifungal, antiviral, antiparasitic, and insect deterrent [10].”
BackgroundFeng, Y., Xia, J., Xu, X., Zhao, T., Tan, Z., Wang, Q., Wang, J., Meng, J., Sanderson, C. M., Lu, Z.-L., et al. (2021) · Anti-Cancer Drugs · doi:10.1097/cad.0000000000001073 · Cited by 9
Powder-George, Y. L., Ludwiczuk, A., Skalicka‐Woźniak, K., & Georgiev, M. I. (2023) · Elsevier eBooks · doi:10.1016/b978-0-443-18657-8.00006-2 · Cited by 9
Sesquiterpenes from Artemisia princeps regulate inflammatory responses in RAW 264.7 macrophages
Kim, N. Y., Kim, S., Lee, H. J., & Ryu, J. (2022) · Natural Product Research · doi:10.1080/14786419.2022.2089881 · Cited by 8
“…were reported from Artemisia genus including A. kulbadica, A. glabella, A. macrocephala and A. tridentata, and they were reported to have anti-oxidant, anti-cancer, anti-nociceptive, immunomodulatory activities (Ezzatzadeh et al. 2012; Turi et al. 2014; Ivanescu et al. 2015; Shoaib et al. 2017).”
Backgroundla Pava, L. D. A.-D., González‐Cortazar, M., Zamilpa, A., Cuéllar-Ordaz, J. A., de la Crúz-Crúz, H. A., Higuera-Piedrahita, R. I., & López‐Arellano, R. (2024) · PLoS ONE · doi:10.1371/journal.pone.0305155 · Cited by 8
Metadata
- Authors
- Ivanescu, B., Miron, A., & Corciova, A.
- Affiliations
- Department of Pharmaceutical Botany, Faculty of Pharmacy, University of Medicine and Pharmacy “Grigore T. Popa”, 16 Universitatii Street, 700150 Iasi, Romania
- Grigore T. Popa University of Medicine and Pharmacy (RO)
- Department of Drug Analysis, Faculty of Pharmacy, University of Medicine and Pharmacy “Grigore T. Popa”, 16 Universitatii Street, 700150 Iasi, Romania
- ORCID
- Miron, Anca
- Venue
- Journal of Analytical Methods in Chemistry
- Publisher
- Wiley
- Published
- 2015
- Volume
- 2015
- Pages
- 1-21
- ISSN
- 2090-8865 (ISSN-L)
- 2090-8873
- PMC
- PMC4606394
- OpenAlex
- W1950362769
- Cited by
- 201
- References
- 156
- Citations by year
- 2026: 18 · 2025: 20 · 2024: 34 · 2023: 19 · 2022: 34 · 2021: 21 · 2020: 19 · 2019: 11 · 2018: 10 · 2017: 11 · 2016: 4
- FWCI
- 0.81
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Journal of Analytical Methods in Chemistry (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- European Social Fund (POSDRU/159/1.5/S/136893)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant chemical constituents analysis
- Keywords
- sesquiterpene lactones, Artemisia, eudesmanolides, guaianolides, germacranolides, α-methylene-γ-lactones, biological activity, natural product identification, quantification, extraction and separation, thermolabile compounds, Michael addition
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