{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,11]],"date-time":"2026-08-11T20:54:31Z","timestamp":1786481671593,"version":"build-2736575974"},"reference-count":32,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,3,23]],"date-time":"2023-03-23T00:00:00Z","timestamp":1679529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Phytochemical investigation of the aerial parts of Artemisia heptapotamica Poljak led to the isolation of ten known compounds, including four alkyl p-coumarates: octadecyl trans-p-coumarate (1), icosy trans-p-coumarate (2), docosyl trans-p-coumarate (3), and tetracosyl trans-p-coumarate (4), one sesquiterpene lactone: santonin (5), four flavonoids; axillarin (6), quercetin 3-O-methyl ether (7), luteolin (8), and quercetin (9), and one phenolic acid derivative: p-coumaric acid (10). The structures of the isolated compounds were identified by various spectroscopic analyses. Additionally, the antimicrobial activity of the total extract and different fractions was screened, and they exhibited no inhibition of the growth of Candida albicans, C. neoformans, Aspergillus fumigatus, methicillin-resistant Staphylococcus aureus (MRS), E. coli, Pseudomonas aeruginosa, Klebsiella pneumonia, and Vancomycin-resistant Enterococci (VRE) at the tested concentrations ranging from 8 to 200 \u03bcg\/mL. The identification and tentative characterization of the secondary metabolites were conducted using LC-QToF analysis. This method helps in the putative characterization of sesquiterpene lactones, flavonoids, coumarate derivatives, and aliphatic compounds. The developed method identified 43 compounds, of which the majority were sesquiterpene lactones, such as eudesmanolides, germacranolides, and guaianolide derivatives, followed by flavonoids. The proposed LC-QToF method helps develop dereplication strategies and understand the major class of chemicals before proceeding with the isolation of compounds.<\/jats:p>","DOI":"10.3390\/molecules28072908","type":"journal-article","created":{"date-parts":[[2023,3,24]],"date-time":"2023-03-24T03:16:46Z","timestamp":1679627806000},"page":"2908","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Isolation and LC-QToF Characterization of Secondary Metabolites from an Endemic Plant Artemisia heptapotamica Poljak"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8753-2883","authenticated-orcid":false,"given":"Umit","family":"Mukatay","sequence":"first","affiliation":[{"name":"Department of Biology and Biotechnology, Al-Farabi Kazakh National University, Almaty 050040, Kazakhstan"},{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2128-5389","authenticated-orcid":false,"given":"Mamdouh Nabil","family":"Samy","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"},{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bharathi","family":"Avula","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8787-4602","authenticated-orcid":false,"given":"Kumar","family":"Katragunta","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8441-1848","authenticated-orcid":false,"given":"Moldir","family":"Kemelbek","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"},{"name":"Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty 050040, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Azhar","family":"Zhubanova","sequence":"additional","affiliation":[{"name":"Department of Biology and Biotechnology, Al-Farabi Kazakh National University, Almaty 050040, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ikhlas A.","family":"Khan","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3807-1299","authenticated-orcid":false,"given":"Samir Anis","family":"Ross","sequence":"additional","affiliation":[{"name":"National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"},{"name":"Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty 050040, Kazakhstan"},{"name":"Department of BioMolecular Science, Division of Phamacognosy, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"101","DOI":"10.3109\/13880209.2010.497815","article-title":"The genus Artemisia: A comprehensive review","volume":"49","author":"Bora","year":"2011","journal-title":"Pharm. Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.jep.2018.03.032","article-title":"Ethnopharmacological properties of Artemisia asiatica: A comprehensive review","volume":"28","author":"Ahuja","year":"2018","journal-title":"J. Ethnopharmacol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2542","DOI":"10.3390\/molecules17032542","article-title":"The Artemisia L. Genus: A Review of Bioactive Essential Oils","volume":"17","author":"Abad","year":"2012","journal-title":"Molecules"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1089\/acm.2008.0327","article-title":"Artemisia species: From traditional medicines to modern antimalarial and back again","volume":"15","author":"Willcox","year":"2009","journal-title":"J. Altern. Complem. Med."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1016\/j.phymed.2018.06.002","article-title":"The activity of Artemisia spp. and their constituents against Trypanosomiasis Janine","volume":"47","author":"Efferth","year":"2018","journal-title":"Phytomedicine"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Nurlybekova, A., Kudaibergen, A., Kazymbetova, A., Amangeldi, M., Baiseitova, A., Ospanov, M., Aisa, H.A., Ye, Y., Ibrahim, M.A., and Jenis, J. (2022). Traditional use, phytochemical profiles and pharmacological properties of Artemisia genus from Central Asia. Molecules, 27.","DOI":"10.3390\/molecules27165128"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1007\/BF00598777","article-title":"Methyl ethers of quercetin from Artemisia heptapotamica","volume":"23","author":"Nikonov","year":"1987","journal-title":"Chem. Nat. Compd."},{"key":"ref_8","first-page":"785","article-title":"Monomeric and dimeric sesquiterpene lactones from Artemisia heptapotamica","volume":"17","author":"Zhamilya","year":"2019","journal-title":"Chin. J. Nat. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1248\/cpb.57.476","article-title":"Synthesis and DNA polymerase alpha and beta inhibitory activity of alkyl p-coumarates and related compounds","volume":"57","author":"Nishimura","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_10","first-page":"865","article-title":"Lipoxygenase and urease inhibition of extracts of Polygonatum verticillatum rhizome: Augmented by its isolated compound, santonin","volume":"36","author":"Khan","year":"2014","journal-title":"J. Chem. Soc. Pak."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1515\/znc-2004-3-415","article-title":"Microbial Transformations of \u03b1-Santonin","volume":"59c","author":"Ata","year":"2004","journal-title":"Z. Naturforsch."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2357","DOI":"10.1016\/S0031-9422(00)81695-7","article-title":"3-Methoxyflavones and coumarins from Artemisia incanescens","volume":"25","author":"Marco","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1018","DOI":"10.1007\/BF02994752","article-title":"Constituents of the stems and fruits of Opuntia ficus-indica var saboten","volume":"26","author":"Lee","year":"2003","journal-title":"Arch. Pharm. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"843","DOI":"10.1016\/j.foodchem.2012.08.057","article-title":"Identification, characterisation, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (Perilla frutescens) cultivars","volume":"136","author":"Lee","year":"2013","journal-title":"Food Chem."},{"key":"ref_15","first-page":"70","article-title":"Modifying effect of quercetin on model biomembranes: Studied by molecular dynamic simulation, DSC and NMR","volume":"4","author":"Sinha","year":"2012","journal-title":"Int. J. Curr. Pharm. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1155\/2012\/546146","article-title":"Spectroscopic (FT-IR, FT-Raman, 1H and 13CNMR) and theoretical studies of p-coumaric acid and alkali metal p-coumarates","volume":"27","author":"Kalinowska","year":"2012","journal-title":"Spectroscopy"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"8825387","DOI":"10.1155\/2020\/8825387","article-title":"Quercetin: Its main pharmacological activity and potential application in clinical medicine","volume":"2020","author":"Yang","year":"2020","journal-title":"Oxid. Med. Cell Longev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"102366","DOI":"10.1016\/j.fbio.2023.102366","article-title":"Luteolin: A flavone with myriads of bioactivities and food applications","volume":"52","author":"Bangar","year":"2023","journal-title":"Food Biosci."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4623","DOI":"10.1016\/S0040-4020(01)92561-X","article-title":"A study of santonins and their derivatives by mass spectrometry","volume":"23","author":"Wasada","year":"1967","journal-title":"Tetrahedron"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.jpba.2012.01.015","article-title":"Phytochemical analysis of herbal tea from Artemisia annua L.","volume":"62","author":"Teresa","year":"2012","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"122735","DOI":"10.1016\/j.jchromb.2021.122735","article-title":"Shotgun chemome characterization of Artemisia rupestris L. using direct infusion-MS\/MSALL","volume":"1176","author":"Piejie","year":"2021","journal-title":"J. Chromatogr. B."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"126070","DOI":"10.1016\/j.foodchem.2019.126070","article-title":"Phytochemical analysis and geographic assessment of flavonoids, coumarins and sesquiterpenes in Artemisia annua L. based on HPLC-DAD quantification and LC-ESI-QTOF-MS\/MS confirmation","volume":"312","author":"Chunqing","year":"2020","journal-title":"Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"114806","DOI":"10.1016\/j.jpba.2022.114806","article-title":"Simultaneous determination and characterization of flavonoids, sesquiterpene lactone, and other phenolics from Centaurea benedicta and dietary supplements using UHPLC-PDA-MS and LC-DAD-QToF","volume":"216","author":"Avula","year":"2022","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_24","unstructured":"(1995). Taylor  Francis Group."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jms.585","article-title":"Mass spectrometry in the structural analysis of flavonoids","volume":"39","author":"Cuyckens","year":"2004","journal-title":"J. Mass Spectrom."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1002\/rcm.5289","article-title":"Characterization and identification of chemical compositions in the extract of Artemisia rupestris L. by liquid chromatography coupled to quadrupole time-of-flight tandem mass spectrometry","volume":"26","author":"Gu","year":"2012","journal-title":"Rapid Commun. Mass Spectrom."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1710","DOI":"10.1055\/s-0030-1249957","article-title":"Highly oxygenated guaianolides from Artemisia dubia","volume":"76","author":"Huang","year":"2010","journal-title":"Planta Med."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"637","DOI":"10.1016\/S0031-9422(00)94711-3","article-title":"Sesquiterpene lactones from Artemisia: Arbusculin-C, rothin-A and rothin-B","volume":"10","author":"Irwin","year":"1971","journal-title":"Phytochemistry"},{"key":"ref_29","first-page":"163","article-title":"Further characterization of foliar flavonoids in Crossostephium chinense and their geographic variation","volume":"9","author":"Uehara","year":"2014","journal-title":"Nat. Prod. Commun."},{"key":"ref_30","first-page":"12","article-title":"Tentative detection of some alkyl coumarates and alkyl ferulates in Lpomoea Carnea subsp. fistulosa by HRESIMS and comparison of these compounds among Convolvulaceae plants","volume":"3","author":"Nidiry","year":"2013","journal-title":"Pharmacogn. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2589","DOI":"10.1021\/jf00047a041","article-title":"Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweet potato [Ipomoea batatas (L.) Lam.]","volume":"42","author":"Snook","year":"1994","journal-title":"J. Agricult. Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Samy, M.N., Mahmoud, B.K., Shady, N.H., Abdelmohsen, U.R., and Ross, S.A. (2022). Bioassay-guided fractionation with antimalarial and antimicrobial activities of Paeonia officinalis. Molecules, 27.","DOI":"10.3390\/molecules27238382"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/7\/2908\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:01:52Z","timestamp":1760122912000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/7\/2908"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,23]]},"references-count":32,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["molecules28072908"],"URL":"https:\/\/doi.org\/10.3390\/molecules28072908","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,23]]}}}