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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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“SLs barrelierin, artemalin, barrelin, and desoxyvulgarin from Artemisia barrelieri also exhibited anti-inflammatory activities [69].”
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“The extraction methods of SLs may include common procedures, such as extraction using shaker, sonication process, reflux extraction, or Soxhlet extraction, but also less handy methods, like supercritical fluid extraction (SFE) and microwave-assisted extraction (MAE).”
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“Sesquiterpene lactones exhibit a wide range of biological activities, such as antitumor, anti-inflammatory, analgesic, antiulcer, antibacterial, antifungal, antiviral, antiparasitic, and insect deterrent.”
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Klayman, D. L., Lin, A. J., Acton, N., Scovill, J. P., Hoch, J. M., Milhous, W. K., Theoharides, A. D., & Dobek, A. S. (1984) · Journal of Natural Products · doi:10.1021/np50034a027 · Cited by 251 · cited 1×
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“In an extensive study comprising over 100 sesquiterpene lactones, researchers established that guaianolides are most potent inhibitors of NF-κB and their efficacy is due mostly to the α,β-unsaturated carbonyl group [45].”
Romero, M. R., Efferth, T., Serrano, M. A., Castaño, B., Macı́as, R. I. R., Briz, Ó., & Marı́n, J. J. G. (2005) · Antiviral Research · doi:10.1016/j.antiviral.2005.07.005 · Cited by 233 · cited 1×
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“Artesunate is therapeutically relevant to inflammatory responses of microglial cells [52] and inhibits production of interleukin IL-1β, IL-6, and IL-8 in human rheumatoid arthritis through NF-κB inhibition [53].”
BackgroundFungicidal activity of natural and synthetic sesquiterpene lactone analogs
Wedge, D. E., Galindo, J. C. G., & Macías, F. A. (2000) · Phytochemistry · doi:10.1016/s0031-9422(00)00008-x · Cited by 213 · cited 1×
“Also, nonpolar or weakly polar compounds were more bioactive and sesquiterpene lactones of a guaianolide structure had the greatest antifungal potency [91].”
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Kreuger, M. R. O., Grootjans, S., Biavatti, M. W., Vandenabeele, P., & D'Herde, K. G. M. A. (2012) · Anti-Cancer Drugs · doi:10.1097/cad.0b013e328356cad9 · Cited by 213
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The history of qing hao in the Chinese materia medica
Hsü, E. (2006) · Transactions of the Royal Society of Tropical Medicine and Hygiene · doi:10.1016/j.trstmh.2005.09.020 · Cited by 199 · cited 1×
“They are classified depending on their carboxylic skeleton into the following main groups: germacranolides (10-membered rings), the largest group and biogenetic precursors of the majority of sesquiterpene lactones; eudesmanolides and eremophilanolides (6/6-bicyclic compounds); and guaianolides,…”
BackgroundInfluentialAbderrazak, A., Couchie, D., Mahmood, D. F. D., Elhage, R., Vindis, C., Laffargue, M., Mateo, V., Büchele, B., Ayala, M. R., Gaafary, M. E., et al. (2015) · Circulation · doi:10.1161/circulationaha.114.013730 · Cited by 177
Artesunate in the treatment of metastatic uveal melanoma - first experiences
Berger, T. G., Dieckmann, D., Efferth, T., Schultz, E. S., Funk, J.-O., Baur, A. S., & Schuler, G. (2005) · Oncology Reports · doi:10.3892/or.14.6.1599 · Cited by 176 · cited 1×
“The most common SLs in Artemisia species are guaianolides, eudesmanolides, and germacranolides.”
BackgroundShapira, M. Y., Resnick, I. B., Chou, S., Neumann, A. U., Lurain, N. S., Stamminger, T., Caplan, O., Saleh, N., Efferth, T., Marschall, M., et al. (2008) · Clinical Infectious Diseases · doi:10.1086/587106 · Cited by 157 · cited 1×
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BackgroundStructure-Activity Relationships of Sesquiterpene Lactones
Schmidt, T. J. (2006) · Studies in natural products chemistry · doi:10.1016/s1572-5995(06)80030-x · Cited by 150 · cited 2×
“The αMγL acts as aMichael acceptor and reacts with nucleophiles (sulfhydryl or amino groups) in enzymes, transcription factors, and other proteins, alkylating them irreversibly [8, 14].”
BackgroundThe anti-malaria drug artesunate inhibits replication of cytomegalovirus in vitro and in vivo
Kaptein, S. J. F., Efferth, T., Leis, M., Rechter, S., Auerochs, S., Kalmer, M., Bruggeman, C. A., Vink, C., Stamminger, T., & Marschall, M. (2005) · Antiviral Research · doi:10.1016/j.antiviral.2005.10.003 · Cited by 148 · cited 1×
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MethodSesquiterpene lactones: Adverse health effects and toxicity mechanisms
Amorim, M. H. R., da Costa, R. M. G., Lopes, C., & Bastos, M. M. S. M. (2013) · Critical Reviews in Toxicology · doi:10.3109/10408444.2013.813905 · Cited by 146
The Gastric Cytoprotective Effect of Several Sesquiterpene Lactones
Giordano, Ó. S., Guerreiro, E., Pestchanker, M. J., Guzmán, J. A., Pastor, D., & Guardia, T. (1990) · Journal of Natural Products · doi:10.1021/np50070a004 · Cited by 140 · cited 2×
“Desacetoxymatricarin did not show cytoprotective activity, suggesting that the presence of the alpha-methylene-gamma-lactone moiety is a requirement for the antiulcerogenic activity [71].”
BackgroundMethodEfficacy of artemisinin in experimental visceral leishmaniasis
Sen, R., Ganguly, S., Saha, P., & Chatterjee, M. (2010) · International Journal of Antimicrobial Agents · doi:10.1016/j.ijantimicag.2010.03.008 · Cited by 135 · cited 3×
“In in vivo studies on mouse model, treatment with artemisinin led to a significant reduction in splenic weight, a significant inhibition of parasites and a restoration of cytokines such as interferon-𝛾 and interleukin2 (IL-2) [84].”
BackgroundInfluentialTetraploid Artemisia annua hairy roots produce more artemisinin than diploids
Jesus-Gonzalez, L. D., & Weathers, P. J. (2003) · Plant Cell Reports · doi:10.1007/s00299-003-0587-8 · Cited by 133
Efferth, T., Herrmann, F., Tahrani, A., & Wink, M. (2011) · Phytomedicine · doi:10.1016/j.phymed.2011.06.008 · Cited by 128 · cited 1×
“However, other bioactive compounds in Artemisia annua contribute to the overall activity of extracts: SLs arteannuin B and artemisitene, but also scopoletin and 1,8-cineole [23].”
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Romero, M. R., Serrano, M. A., Vallejo, M., Efferth, T., Alvarez, M., & Marı́n, J. J. G. (2006) · Planta Medica · doi:10.1055/s-2006-947198 · Cited by 122 · cited 1×
“Several in vitro studies showed that artemisinin has antiviral effect on hepatitis B and C viruses [92, 93], a range of human herpes viruses (human cytomegalovirus, herpes simplex virus type 1, and EpsteinBarr virus) [94–96], influenza virus A [97], and a bovine viral diarrhea virus [98] in the low micromolar range.”
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“Detection methods applied in sesquiterpene lactones analysis include GC-MS [141], GCECD, and GC-FID [139].”
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“A clinical trial in 120 patients with advanced non-small cell lung cancer tested the effect of artesunate in combinationwith traditional chemotherapeutic drugs [26].”
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“1465 [151] and artemisinin m/z 305 [153], [M + H] in case of artecaninm/z 279.”
Dihydroartemisinin exhibits antitumor activity toward hepatocellular carcinoma in vitro and in vivo
Zhang, C. Z., Zhang, H., Yun, J., Chen, G. G., & Lai, P. B. S. (2012) · Biochemical Pharmacology · doi:10.1016/j.bcp.2012.02.002 · Cited by 115 · cited 1×
“The 𝛾-lactone ring, usually with an 𝛼-methylene group, is a significant characteristic of SLs.”
BackgroundNew Trends in Extraction, Identification and Quantification of Artemisinin and its Derivatives
Christen, P., & Veuthey, J. (2001) · Current Medicinal Chemistry · doi:10.2174/0929867013371563 · Cited by 114 · cited 2×
“Pressure had no noticeable influence on the recovery of artemisinin, whatever the solvent used, but a higher temperature significantly favoured artemisinin extraction, particularly in water [114].”
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Köhler, M., Haerdi, W., Christen, P., & Veuthey, J. (1997) · Journal of Chromatography A · doi:10.1016/s0021-9673(97)00403-2 · Cited by 93 · cited 7×
“The analysis of artemisinin by GC-FID is made via major degradation products, unlike HPLC-ELSD [138].”
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Fraga, B. M. (2011) · Natural Product Reports · doi:10.1039/c1np00046b · Cited by 84
A colorimetric field method to assess the authenticity of drugs sold as the antimalarial artesunate
Green, M. D., Mount, D. L., Wirtz, R. A., & White, N. J. (2000) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/s0731-7085(00)00360-5 · Cited by 81 · cited 1×
“Just like artemisinin, determination of artesunate is challenging because it has not a distinct chromophore and presents a peroxide bridge which absorbs at lower wavelengths [114, 124].”
BackgroundNew sesquiterpene–monoterpene lactone, artemisolide, isolated from Artemisia argyi
Kim, J. H., Kim, H., Jeon, S. B., Son, K., Kim, E. H., Kang, S. K., Sung, N., & Kwon, B. (2002) · Tetrahedron Letters · doi:10.1016/s0040-4039(02)01315-1 · Cited by 81 · cited 1×
“Another cytotoxic compound produced by Artemisia argyi is artemisolide (Figure 1), sesquiterpene lactone with a cyclopropane ring which exhibits in vitro activity against human acute lymphoblastic leukaemia Molt-4, promyelocytic leukaemia HL60, and SW620 colon cancer cell lines [38].”
BackgroundCase report of a laryngeal squamous cell carcinoma treated with artesunate
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“For some compounds, individual clinical cases were reported: artemether oral treatmentwas used in a patientwith pituitary macroadenoma [28], and artesunate was used in laryngeal squamous cell carcinoma [29] and metastatic uveal melanoma [30] with good results and lack of side effects.”
BackgroundHemin potentiates the anti-hepatitis C virus activity of the antimalarial drug artemisinin
Paeshuyse, J., Coelmont, L., Vliegen, I., hemel, J. V., Vandenkerckhove, J., Peys, E., Sas, B., Clercq, E. D., & Neyts, J. H. (2006) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2006.07.014 · Cited by 76 · cited 1×
“Several in vitro studies showed that artemisinin has antiviral effect on hepatitis B and C viruses [92, 93], a range of human herpes viruses (human cytomegalovirus, herpes simplex virus type 1, and EpsteinBarr virus) [94–96], influenza virus A [97], and a bovine viral diarrhea virus [98] in the low micromolar range.”
BackgroundCase Report of a Pituitary Macroadenoma Treated With Artemether
Singh, N. P., & Panwar, V. K. (2006) · Integrative Cancer Therapies · doi:10.1177/1534735406295311 · Cited by 76 · cited 1×
“For some compounds, individual clinical cases were reported: artemether oral treatmentwas used in a patientwith pituitary macroadenoma [28], and artesunate was used in laryngeal squamous cell carcinoma [29] and metastatic uveal melanoma [30] with good results and lack of side effects.”
BackgroundAnti-inflammatory and immunomodulatory mechanisms of artemisinin on contact hypersensitivity
Tan, L., Chen, H., Wei, N., Mei, X., Zhang, S., Liu, D., Gao, Y., Shu-fang, B., Liu, X., & Zhou, Y.-X. (2011) · International Immunopharmacology · doi:10.1016/j.intimp.2011.11.004 · Cited by 75 · cited 1×
“Moreover, in a mouse model of contact hypersensitivity, topical administration of artemisinin produced anti-inflammatory and immunomodulatory effects [47].”
BackgroundA comparative study of mist and bubble column reactors in the in vitro production of artemisinin
Kim, Y., Wyslouzil, B. E., & Weathers, P. J. (2001) · Plant Cell Reports · doi:10.1007/s002990100342 · Cited by 75 · cited 1×
“An example is that of artemisinin extracted with toluene from the vegetal product in [134] and subjected to a process of alkaline hydrolysis at 50C for 45 minutes.”
MethodPeng, C. A., Ferreira, J., & Wood, A. J. (2006) · Journal of Chromatography A · doi:10.1016/j.chroma.2006.08.043 · Cited by 74 · cited 4×
“HPLC is the most commonly used technique for the quantification of artemisinin and its derivatives in plants, using detection methods like UV detection (HPLC-UV) or diode array detection (HPLC-DAD), mass spectrometry (HPLC-MS), HPLC/tandemmass spectrometry (LC/MS/MS), evaporative light scattering detector (HPLC-ELSD),…”
BackgroundMethodInfluentialNO inhibitory guaianolide-derived terpenoids from Artemisia argyi
Wang, S., Li, J., Sun, J. L., Zeng, K., Cui, J., Jiang, Y., & Tu, P. (2012) · Fitoterapia · doi:10.1016/j.fitote.2012.12.005 · Cited by 71 · cited 1×
“The chloroform extract was repeatedly fractioned and the resulting subfractions were purified by semipreparative HPLC to afford artemisinin A and isoartemisolide [120].”
MethodLiu, C., Zhou, H.-Y., & Zhao, Y. (2006) · Analytica Chimica Acta · doi:10.1016/j.aca.2006.08.038 · Cited by 69 · cited 3×
“On the other hand, its sensitivity is lower than other detection methods, such as ECD and MS [113, 138, 139].”
BackgroundMethodFraga, B. M. (2008) · Natural Product Reports · doi:10.1039/b806216c · Cited by 67
Noori, S., Naderi, G., Hassan, Z. M., Habibi, Z., Bathaie, S. Z., & Hashemi, S. M. (2004) · International Immunopharmacology · doi:10.1016/j.intimp.2004.05.003 · Cited by 65 · cited 1×
“Both artemisinin and dihydroartemisinin suppress delayed hypersensitivity to sheep blood cells in mice, manifesting immunosuppressive action [49, 50].”
BackgroundReview : Role of mast cells in gastrointestinal mucosal defense
Penissi, A. B., Rudolph, M. I., & Piezzi, R. (2003) · Biocell · doi:10.32604/biocell.2003.27.163 · Cited by 62 · cited 1×
“Thus, it is believed that stabilization of mast cells may be a key mechanism in the protection of gastrointestinal tract from injury [73, 74].”
BackgroundTZENG, T., Lin, Y., Jong, T., & Chang, C. (2007) · Separation and Purification Technology · doi:10.1016/j.seppur.2007.01.010 · Cited by 62 · cited 1×
“25% ethanol as cosolvent to the supercritical fluid extraction with CO 2 , the artemisinin extraction yields were substantially improved [115, 116].”
BackgroundGreen, M. D., Mount, D. L., & Wirtz, R. A. (2001) · Tropical Medicine & International Health · doi:10.1046/j.1365-3156.2001.00793.x · Cited by 61 · cited 2×
“This compound was diazo-coupled with the same diazonium Fast Red TR salt, producing a yellow colour in 5 minutes [132].”
BackgroundMethodAnti-Helicobacter pylori Potential of Artemisinin and Its Derivatives
Goswami, S., Bhakuni, R. S., Chinniah, A., Pal, A., Kar, S. K., & Das, P. K. (2012) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00407-12 · Cited by 61
Anti-tumor effects of dihydroartemisinin on human osteosarcoma
Ji, Y., Zhang, Y.-C., Pei, L., Shi, L., Yan, J., & Ma, X.-H. (2011) · Molecular and Cellular Biochemistry · doi:10.1007/s11010-011-0716-6 · Cited by 61 · cited 1×
“The 𝛾-lactone ring, usually with an 𝛼-methylene group, is a significant characteristic of SLs.”
BackgroundLee, I., Ryu, D.-K., Lim, J., Cho, S., Kang, B. Y., & Choi, H. J. (2011) · Neuroscience Letters · doi:10.1016/j.neulet.2011.12.034 · Cited by 60 · cited 1×
“Artesunate is therapeutically relevant to inflammatory responses of microglial cells [52] and inhibits production of interleukin IL-1β, IL-6, and IL-8 in human rheumatoid arthritis through NF-κB inhibition [53].”
BackgroundAnalysis of Artemisinin in Artemisia annua L. by LC-MS with Selected Ion Monitoring
Wang, M., Park, C., Wu, Q., & Simon, J. E. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf051061p · Cited by 59
Sesquiterpene lactones from the endemic Cape Verdean Artemisia gorgonum
Ortet, R., Prado, S., Mouray, E., & Thomas, O. (2008) · Phytochemistry · doi:10.1016/j.phytochem.2008.09.022 · Cited by 59 · cited 1×
“The antimalarial activity may be attributed to the exomethylene group of the lactone function [81].”
BackgroundThomas, C. G., Ward, S. A., & Edwards, G. (1992) · Journal of Chromatography B Biomedical Sciences and Applications · doi:10.1016/0378-4347(92)80355-t · Cited by 58 · cited 1×
“Thus, it is necessary to have an intermediate step in which by treatment with acids or bases they are transformed into more reactive compounds, such as enolate/carboxylates or α,β-unsaturated decalones, and then reaction with certain reagents to form colored compounds or to bleach, depending on concentration [122, 127…”
BackgroundDimeric Guaianolides and Sesquiterpenoids from Artemisia anomala
Wen, J., Shi, H., Xu, Z., Chang, H., Jia, C., Zan, K., Jiang, Y., & Tu, P. (2009) · Journal of Natural Products · doi:10.1021/np900462u · Cited by 58 · cited 1×
“Other anti-inflammatory sesquiterpene lactones mentioned in the literature are dimeric guaianolides from Artemisia anomala [67], and those isolated from Artemisia khorassanica Podl.”
BackgroundNaesens, L. M. J., Bonnafous, P., Agut, H., & Clercq, E. D. (2006) · Journal of Clinical Virology · doi:10.1016/s1386-6532(06)70015-4 · Cited by 57 · cited 1×
“Another NF-𝜅B inhibitor, artemisolide, was isolated from Artemisia asiatica by activity-guided fractionation using the NF-𝜅B mediated reporter gene assay [56, 57].”
MethodShishan, Z., & Mei-Yi, Z. (1986) · Analytical Chemistry · doi:10.1021/ac00293a006 · Cited by 56 · cited 1×
“Thus, it is necessary to have an intermediate step in which by treatment with acids or bases they are transformed into more reactive compounds, such as enolate/carboxylates or α,β-unsaturated decalones, and then reaction with certain reagents to form colored compounds or to bleach, depending on concentration [122, 127…”
BackgroundLee, S. H., Lee, M.-Y., Kang, H., Han, D. C., Son, K., Yang, D. C., Sung, N., Lee, C. W., Kim, H. M., & Kwon, B. (2003) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2003.08.008 · Cited by 56 · cited 1×
“They inhibit tumor growth in mouse xenograft models and in human tumour xenograft [37].”
BackgroundZhu, X., Yang, L., Li, Y. J., Zhang, D., Chen, Y., Kostecká, P., Kmonı́èková, E., & Zídek, Z. (2013) · Pharmacological Reports · doi:10.1016/s1734-1140(13)71016-8 · Cited by 55 · cited 3×
“Arteannuin B also inhibited lipopolysaccharide- (LPS-) induced in vitro production of nitric oxide (NO) and secretion of cytokines (VEGF, IL-1b, IL-6, and TNF-α) [54].”
BackgroundMethodInfluentialHypoglycemic properties of some preparations and compounds from Artemisia ludoviciana Nutt
Anaya‐Eugenio, G. D., Rivero‐Cruz, I., Rivera‐Chávez, J., & Mata, R. (2014) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2014.05.051 · Cited by 53 · cited 1×
“One of the compounds was the known guaianolide ludartin which manifested significant hypoglycemic effect on its own [103].”
BackgroundNoori, S., & Hassan, Z. M. (2012) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2012.01.026 · Cited by 53 · cited 1×
“Tehranolide selectively inhibits proliferation of breast cancer cells through cell cycle arrest and apoptosis [43] and also modifies the immune responses and increases antitumor immunity [44].”
BackgroundLangroudi, L., Hassan, Z. M., Ebtekar, M., Mahdavi, M., Pakravan, N., & Noori, S. (2010) · International Immunopharmacology · doi:10.1016/j.intimp.2010.06.005 · Cited by 53 · cited 1×
“Artemisinin diminishes the number of regulatory T cells in murine breast cancer model [51].”
BackgroundGravett, A. M., Liu, W. M., Krishna, S., Chan, W., Haynes, R. K., Wilson, N., & Dalgleish, A. G. (2010) · Cancer Chemotherapy and Pharmacology · doi:10.1007/s00280-010-1355-4 · Cited by 52 · cited 1×
“The antimalarial drug artemisinin and its derivatives are very potent anticancer compounds, highly selective on cancer cells with almost no side effects on normal cells and a broad spectrum of action: leukaemia, colon, melanoma, osteosarcoma, pancreas, breast, ovarian, prostate, hepatic, renal, central nervous system,…”
BackgroundJia, Q.-Q., Wang, J., Long, J., Zhao, Y. D., Chen, S., Zhai, J., Wei, L.-B., Zhang, Q., Chen, Y., & Long, H. (2013) · Molecules · doi:10.3390/molecules181013061 · Cited by 52 · cited 1×
“Since these methods are difficult, time consuming, and expensive, we have also chosen to present some analysis methods that are cheaper and available to all laboratories, such as spectrophotometric techniques (UV-Vis) and TLC.”
MethodMartínez, M. J. A., Bedoya, L. M., Ticona, L. A., & Bermejo, P. (2012) · Studies in natural products chemistry · doi:10.1016/b978-0-444-59514-0.00002-x · Cited by 51
Antiulcerogenic Activity of Some Sesquiterpene Lactones Isolated from Artemisia annua
Foglio, M. A., Dias, P. C., Antônio, M. A., Possenti, A., Rodrigues, R. A. F., da Silva, É. F., Rehder, V. L. G., & de Carvalho, J. E. (2002) · Planta Medica · doi:10.1055/s-2002-32570 · Cited by 49 · cited 1×
“Previous treatment with indomethacin, a cyclooxygenase inhibitor, blocked the antiulcerogenic activity of compounds on ethanol-induced ulcer, suggesting that the activity is the consequence of an increase in prostaglandin synthesis [76].”
BackgroundEffect of ultrasound on the extraction of artemisinin from Artemisia annua
Briars, R., & Paniwnyk, L. (2012) · Industrial Crops and Products · doi:10.1016/j.indcrop.2012.06.043 · Cited by 48 · cited 1×
“After HPLC analysis it was observed that ultrasonic extraction at lower temperature is better than at a higher temperature, also improving the purity [110].”
BackgroundDetermination of Artemisinin in Artemisia annua L. by Reversed Phase HPLC
Qian, G., Yang, Y., & Ren, Q. (2005) · Journal of Liquid Chromatography & Related Technologies · doi:10.1081/jlc-200048890 · Cited by 46
Vulgarone B, the Antifungal Constituent in the Steam-Distilled Fraction of Artemisia douglasiana
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Bhandari, P., Gupta, A. P., Singh, B., & Kaul, V. K. (2005) · Journal of Separation Science · doi:10.1002/jssc.200500198 · Cited by 45 · cited 1×
“2% trifluoroacetic acid in water/acetonitrile (35 : 65, v/v), derivatization with anisaldehyde reagent in acidic medium, and densitometric determination at 426 nm in absorptionreflectance mode [144].”
MethodBrengio, S. D., Belmonte, S. A., Guerreiro, E., Giordano, Ó. S., Pietrobon, E. O., & Sosa, M. A. (2000) · Journal of Parasitology · doi:10.1645/0022-3395(2000)086[0407:tsldda]2.0.co;2 · Cited by 45 · cited 1×
“After removing impurities by treatment with lead tetraacetate solution, the filtrate was extracted three times with chloroform and the resulting extract was chromatographed with ethyl acetate-hexane (1 : 9) to yield dehydroleucodine [71, 100].”
MethodHairy roots induction and artemisinin analysis in Artemisia dubia and Artemisia indica
Mannan, A., Shaheen, N., Arshad, W., Qureshi, R. A., Zia, M., & Mirza, B. (2008) · AFRICAN JOURNAL OF BIOTECHNOLOGY · doi:10.4314/ajb.v7i18.59272 · Cited by 41
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“Chagas disease or American Trypanosomiasis is caused by the flagellated protozoan parasite Trypanosoma cruzi and is one of the world’s neglected tropical diseases [83].”
BackgroundSusceptibility of Pneumocystis carinii to artemisinin in vitro
Merali, S., & Meshnick, S. (1991) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.35.6.1225 · Cited by 40 · cited 1×
“Artemisinin and its derivatives showed antifungal properties against Pneumocystis carinii in vitro [89, 90].”
BackgroundLone, S. H., Bhat, K. A., Naseer, S., Rather, R. A., Khuroo, M. A., & Tasduq, S. A. (2013) · Journal of Chromatography B · doi:10.1016/j.jchromb.2013.09.027 · Cited by 40 · cited 1×
“Yet, other factors can influence the potency of SLs: number of alkylating groups, lipophilicity, molecular geometry and size, chemical environment, other functional groups neighboring the 𝛼M𝛾L, and the target sulfhydryl [2, 5].”
BackgroundInhibitors of the LPS-induced NF-?B activation from
Jin, H. Z., Lee, J.-H., LEE, D., HONG, Y., KIM, Y., & LEE, J. (2004) · Phytochemistry · doi:10.1016/j.phytochem.2004.06.034 · Cited by 39 · cited 2×
“(iv )i nj ec tio n vo lu m e: 1μ L [1 58 ]”
BackgroundEmami, S. A., Rabe, S. Z. T., Iranshahi, M., Ahi, A., & Mahmoudi, M. (2010) · Immunopharmacology and Immunotoxicology · doi:10.3109/08923971003677808 · Cited by 39 · cited 1×
“Since these methods are difficult, time consuming, and expensive, we have also chosen to present some analysis methods that are cheaper and available to all laboratories, such as spectrophotometric techniques (UV-Vis) and TLC.”
MethodYomogin, an inhibitor of nitric oxide production in LPS-activated macrophages
Ryu, J., Lee, H. J., Jeong, Y. S., Ryu, S. Y., & Han, Y. N. (1998) · Archives of Pharmacal Research · doi:10.1007/bf02974648 · Cited by 39
Antimicrobial activity of Artemisia douglasiana and dehydroleucodine against Helicobacter pylori
Vega, A. E., Wendel, G. H., María, A., & Pelzer, L. E. (2009) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2009.04.051 · Cited by 37 · cited 2×
“As mentioned earlier, artemisinin and dehydroleucodine show strong antimicrobial activity againstHelicobacter pylori, the major cause of chronic gastritis and peptic ulcer [77, 78].”
BackgroundGuardia, T., Juárez, A., Guerreiro, E., Guzmán, J. A., & Pelzer, L. E. (2003) · Journal of Ethnopharmacology · doi:10.1016/s0378-8741(03)00211-3 · Cited by 36 · cited 2×
“The sesquiterpene lactone also inhibited inflammation in the granuloma test, probably by interfering with transcription factors, such as NF-κB and cytokines [59].”
BackgroundWang, Y., Huang, Z., Wang, C., Wang, L., Meng, S., Zhang, Y., Chen, T., & Fan, Y. (2010) · Clinical and Experimental Pharmacology and Physiology · doi:10.1111/j.1440-1681.2010.05454.x · Cited by 35 · cited 1×
“Since these methods are difficult, time consuming, and expensive, we have also chosen to present some analysis methods that are cheaper and available to all laboratories, such as spectrophotometric techniques (UV-Vis) and TLC.”
MethodReddy, A. M., Lee, J., Seo, J. H., Kim, B. H., Chung, E. Y., Ryu, S. Y., Kim, Y. S., Lee, C.-K., Min, K. R., & Kim, Y. (2006) · Archives of Pharmacal Research · doi:10.1007/bf02969271 · Cited by 34 · cited 1×
“Another NF-κB inhibitor, artemisolide, was isolated from Artemisia asiatica by activity-guided fractionation using the NF-κB mediated reporter gene assay [56, 57].”
MethodFerreira, J., Charles, D. J., Wood, K. V., Janick, J., & Simon, J. E. (1994) · Phytochemical Analysis · doi:10.1002/pca.2800050306 · Cited by 34
Noori, S., Taghikhani, M., Hassan, Z. M., Allameh, A., & Mostafaei, A. (2010) · Molecular Immunology · doi:10.1016/j.molimm.2010.01.007 · Cited by 33 · cited 1×
“Since these methods are difficult, time consuming, and expensive, we have also chosen to present some analysis methods that are cheaper and available to all laboratories, such as spectrophotometric techniques (UV-Vis) and TLC.”
MethodDias, P. C., Foglio, M. A., Possenti, A., Nogueira, D. C. F., & de Carvalho, J. E. (2001) · Phytotherapy Research · doi:10.1002/ptr.758 · Cited by 33 · cited 1×
“For the medium polarity fraction, it was demonstrated that the active compounds of Artemisia annua act by increasing the prostaglandin levels in the gastric mucosa [75].”
BackgroundChung, E. Y., Byun, Y. H., Shin, E. J., Chung, H. S., Lee, Y. H., & Shin, S. (2009) · Archives of Pharmacal Research · doi:10.1007/s12272-009-2208-8 · Cited by 32
Repetto, M. G., & Boveris, A. (2010) · Mini-Reviews in Medicinal Chemistry · doi:10.2174/138955710791383992 · Cited by 31 · cited 1×
“Sesquiterpene lactones of the guaianolide and eudesmanolide types are considered to be of interest in treatment of gastric and peptic ulcers because they have an effect in the regulation and prevention of oxidative damage and inflammation-mediated biological damage [70].”
BackgroundAlejos-Gonzalez, F., Qu, G., Zhou, L.-L., Saravitz, C. H., Shurtleff, J. L., & Xie, D.-Y. (2011) · Planta · doi:10.1007/s00425-011-1430-z · Cited by 31 · cited 2×
“In the case of MS analysis, generally using ESI positive ionisation mode, the pseudo-molecular ions are in the form [M + Na], [M + H], [2M + Na], [2M + K], and [M + NH4] [148, 152].”
MethodPreparation and Characterization of Solid Dispersions of Artemether by Freeze-Dried Method
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“Some disadvantages of artemisinin, such as low solubility, short plasma half-life, and poor bioavailability [19], were surpassed by the semisynthetic or fully synthetic derivatives, such as artesunate, artemether, dihydroartemisinin, and artemisone.”
BackgroundArantes, F. F. P., Barbosa, L. C. A., Maltha, C. R. A., Demuner, A. J., Fidêncio, P. H., & Carneiro, J. W. D. M. (2011) · Journal of Chemometrics · doi:10.1002/cem.1385 · Cited by 30
In vitro Antitumoral Activity of Compounds Isolated from Artemisia gorgonum Webb
Martins, A., Mignon, R., Bastos, M., Batista, D., Neng, N. R., Nogueira, J. M. F., Vizetto‐Duarte, C., Custódio, L. M. B., Varela, J. C. S., & Rauter, A. P. (2014) · Phytotherapy Research · doi:10.1002/ptr.5133 · Cited by 29
Natividad, G. M., Broadley, K. J., Kariuki, B. M., Kidd, E. J., Ford, W. R., & Simons, C. (2011) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2011.06.042 · Cited by 29 · cited 2×
“Yomogin was separated through repeated recrystallization with methanol and its structure was confirmed by X-ray crystallography [62].”
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Artemisia annua L.: evidence of sesquiterpene lactones’ fraction antinociceptive activity
Favero, F. D. F., Grando, R., Nonato, F. R., Sousa, I. M. D. O., Queiroz, N. D. C. A., Longato, G. B., Zafred, R. R. T., de Carvalho, J. E., Spindola, H. M., & Foglio, M. A. (2014) · BMC Complementary and Alternative Medicine · doi:10.1186/1472-6882-14-266 · Cited by 28
A spectrophotometric assay for quantification of artemisinin
Bharati, A., & Sabat, S. C. (2010) · Talanta · doi:10.1016/j.talanta.2010.06.015 · Cited by 27 · cited 1×
“The reaction is completed in 15 minutes and the reaction product is stable for 5 hours [123].”
BackgroundHighly Oxygenated Guaianolides fromArtemisia dubia
Huang, Z., Pei, Y., Liu, C.-M., Lin, S. H., Tang, J., Huang, D., Song, T.-F., Lu, L.-H., Gao, Y., & Zhang, W. (2010) · Planta Medica · doi:10.1055/s-0030-1249957 · Cited by 27 · cited 1×
“Eight highly oxygenated guaianolides, named artemdubolides A–H, were isolated from Artemisia dubia and two of them manifested reduced cytotoxicity on human colon carcinoma Colo205 and human melanoma MDA-MB-435 cells in vitro [42].”
BackgroundCho, S.-H., Na, Y.-E., & Ahn, Y. (2003) · Journal of Applied Microbiology · doi:10.1046/j.1365-2672.2003.01998.x · Cited by 27 · cited 1×
“casei) and Escherichia coli [86].”
Quality of Artesunate Tablets Sold in Pharmacies in Kumasi, Ghana
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Ryu, S., Oak, M.-H., & Kim, K.-M. (2000) · Planta Medica · doi:10.1055/s-0029-1243124 · Cited by 27 · cited 1×
“7 cells by suppressing i-NOS enzyme expression [60] and blocks the degranulation ofmast cells by inhibiting the release of beta-hexosaminidase from the cultured RBL-2H3 cells in a dose-dependent manner [61].”
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“The aerial parts of Artemisia amygdalina Decne produce significant amounts of ludartin, a highly cytotoxic guaianolide, also found in Artemisia indica [34].”
BackgroundKim, H. G., Yang, J. H., Han, E. H., Choi, J. H., Khanal, T., Jeong, M. H., Jeong, T. C., & Jeong, H. G. (2013) · Food and Chemical Toxicology · doi:10.1016/j.fct.2013.02.017 · Cited by 23 · cited 1×
“decreased PMA-induced COX-2 expression and PGE 2 production, as well as COX-2 promoter-driven luciferase activity in a dose-dependent manner [48].”
BackgroundDetermination of Artemisinin in Selected Artemisia L. Species of Turkey by Reversed Phase HPLC
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ANALYSIS OF ARTEMISININ ISOLATED FROM Artemisia Annua L. BY TLC AND HPLC
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“It was observed that after derivatization the extinction coefficient increased 30–40 times [136].”
BackgroundReys, J. R. M., Lima, P., Cioletti, A. G., Ribeiro, A. S., DEABREU, F., Goulart, M. O. F., & Kubota, L. T. (2008) · Talanta · doi:10.1016/j.talanta.2008.07.043 · Cited by 21 · cited 1×
“developed a feasible alternative method that uses an amperometric detector based on hemin adsorbed on silica gel modified for quantification of artemisinin [146].”
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Hemisynthesis of a naturally occurring clinically significant antitumor arglabin from ludartin
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“Ludartin is a position isomer of arglabin and can be easily converted into clinically important antitumor arglabin [36].”
BackgroundQuantitative HPTLC Analysis of Artemisinin in Dried Artemisia annua L.: A Practical Approach
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“developed an extract fromArtemisia annua leaves (obtained by sonication in toluene) on silica gel 60 plates with mobile phase cyclohexane : ethyl acetate : acetic acid (20 : 10 : 1), derivatization with anisaldehyde reagent in ethanol : water (10 : 8), heated at 100C, for 12 minutes, and densitometric evaluation of fl…”
MethodArtemisia scoparia – A new source of artemisinin
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Koobkokkruad, T., Chochai, A., Kerdmanee, C., & De‐Eknamkul, W. (2007) · Phytochemical Analysis · doi:10.1002/pca.976 · Cited by 19 · cited 1×
“This is based on the transformation of artemisinin after treatment with ammonia vapors in a compound containing chromophore group, 10-azadesoxyartemisinin, detected by UV based TLC densitometry [143].”
MethodNoori, S., Hassan, Z. M., Taghikhani, M., Rezaei, B., & Habibi, Z. (2009) · International Immunopharmacology · doi:10.1016/j.intimp.2009.11.002 · Cited by 17 · cited 2×
“Dihydroartemisinin also impaired growth of ductal carcinoma in mice and decreased the levels of interleukin IL-4 [50].”
Background[Extraction of artemisinin and synthesis of its derivates artesunate and artemether].
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Three new eudesmane sesquiterpenes from Artemisia vestita
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“So, these combinations can be used in therapy of myeloid leukemias [40].”
BackgroundInduction of Apoptosis by Yomogin in Human Promyelocytic Leukemic HL-60 Cells
Jeong, S.-H., Koo, S.-J., Ha, J., Ryu, S., Park, H.-J., & Lee, K. (2004) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.27.1106 · Cited by 15 · cited 1×
“Moreover, yomogin induces apoptosis in human promyelocytic leukemia HL-60 cells through caspase-8 activation, Bid cleavage, and Bax translocation to mitochondria, followed by release of cytochrome c into the cytoplasm [41].”
BackgroundCytotoxic Components ofArtemisia princeps
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“Yomogin (Figure 1), a eudesmane sesquiterpene lactone isolated from Artemisia princeps, has been shown to inhibit tumor cell proliferation [39].”
BackgroundDehydroleucodine and dehydroparishin-B inhibit proliferation and motility of B16 melanoma cells
Priestap, H. A., Galvis, A., Rivero, N., Costantino, V., López, L. A., & Barbieri, M. A. (2012) · Phytochemistry Letters · doi:10.1016/j.phytol.2012.05.018 · Cited by 14 · cited 1×
“The organic phase was evaporated to dryness and subjected to column chromatography, while monitoring the resulting fractions by TLC to give pure dehydroparishinB [101].”
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Synthesis of Dihydroartemisinin using Ni/TiO 2 catalyst Prepared by Sol Gel Method
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Arvestolides A–C, new rare sesquiterpenes from the aerial parts of Artemisia vestita
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“1465 [151] and artemisinin m/z 305 [153], [M + H] in case of artecaninm/z 279.”
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“The active ethyl acetate-soluble fraction was purified trough repeated column chromatography to yield five compounds, characterized based on EI-MS, UV, IR, and NMR spectral data [104].”
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A search for santonin in artemisia pontica, the other wormwood of old absinthe
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“maritima, through chloroform extraction, formation of a barium salt, precipitation of the lactone by acidification, and crystallization from ethanol : water [105].”
BackgroundEvidence for the spectroscopic determination of artesunate in dosage form.
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Artemisinin from minor to major ingredient in Artemisia annua cultivated in Egypt
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[In vitro study of the anti-pneumocystis carinii effect of arteminsin derivatives].
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Therapeutic Potential of Certain Terpenoids as Anticancer Agents: A Scoping Review
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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
About these checks
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