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The chemical structures of the compounds were determined as \u03b2-sitosterol (<jats:bold>1<\/jats:bold>), apigenin (<jats:bold>2<\/jats:bold>), nonacosanoic acid (<jats:bold>3<\/jats:bold>), astragalin (<jats:bold>4<\/jats:bold>), \u03b2-sitosterol-3-<jats:italic>O<\/jats:italic>-\u03b2-D-glucopyranoside (<jats:bold>5<\/jats:bold>), helichrysin A (<jats:bold>6<\/jats:bold>), helichrysin B (<jats:bold>7<\/jats:bold>), and isosalipurposide (<jats:bold>8<\/jats:bold>) by spectroscopic and chromatographic\/spectrometric methods, including 1D and 2D nuclear magnetic resonance and liquid chromatography-tandem mass spectrometry. Nonacosanoic acid (<jats:bold>3<\/jats:bold>) was isolated for the first time from<jats:italic>H. plicatum<\/jats:italic>DC. subsp.<jats:italic>plicatum<\/jats:italic>. The MeOH extract and isolated compounds were evaluated for their in vitro human carbonic anhydrase I (hCAI) and II (hCAII), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and \u03b1-glycosidase inhibitory activities. The IC<jats:sub>50<\/jats:sub>values of<jats:italic>H. plicatum<\/jats:italic>DC. subsp.<jats:italic>plicatum<\/jats:italic>MeOH extract for hCAI, hCAII, AChE, BChE, and \u03b1-glycosidase were found to be 77.87, 52.90, 115.50, 117.46, and 81.53 mg\/mL, respectively. The compounds showed IC<jats:sub>50<\/jats:sub>values of 1.43\u20134.47, 1.40\u20134.32, 1.69\u20132.90, 1.09\u20133.89, and 1.61\u20133.80 \u03bcM against hCAI, hCAII, AChE, BChE, and \u03b1-glycosidase, respectively. In summary,<jats:italic>H. plicatum<\/jats:italic>DC. subsp.<jats:italic>plicatum<\/jats:italic>secondary metabolites demonstrated strong inhibitory effects especially against hCAI and hCAII, whereas the MeOH extract showed a weak inhibitory effect on all enzymes.<\/jats:p>","DOI":"10.1515\/znc-2020-0026","type":"journal-article","created":{"date-parts":[[2020,5,29]],"date-time":"2020-05-29T10:43:08Z","timestamp":1590748988000},"page":"153-159","source":"Crossref","is-referenced-by-count":14,"title":["Secondary metabolites of<i>Helichrysum plicatum<\/i>DC. subsp.<i>plicatum<\/i>flowers as strong carbonic anhydrase, cholinesterase and \u03b1-glycosidase inhibitors"],"prefix":"10.1515","volume":"75","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7653-6480","authenticated-orcid":false,"given":"Tuba","family":"Aydin","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy , Agri Ibrahim Cecen University , 04100 Agri , Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"374","published-online":{"date-parts":[[2020,5,8]]},"reference":[{"key":"2021062203234033197_j_znc-2020-0026_ref_001_w2aab3b7c31b1b6b1ab2b1b1Aa","doi-asserted-by":"crossref","unstructured":"Bayir Y, Halici Z, Keles MS, Colak S, Cakir A, Kaya Y, et al. 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