{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,9]],"date-time":"2026-07-09T02:54:30Z","timestamp":1783565670357,"version":"3.55.0"},"reference-count":55,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2021,5,30]],"date-time":"2021-05-30T00:00:00Z","timestamp":1622332800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004396","name":"Thailand Research Fund","doi-asserted-by":"publisher","award":["RDG5220056 and RDG5220059"],"award-info":[{"award-number":["RDG5220056 and RDG5220059"]}],"id":[{"id":"10.13039\/501100004396","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Bioassay-guided separation of young leaves extracts of Syzygium antisepticum (Blume) Merr. &amp; L.M. Perry led to the isolation of four triterpenoids (betulinic acid, ursolic acid, jacoumaric acid, corosolic acid) and one sterol glucoside (daucosterol) from the ethyl acetate extract, and three polyphenols (gallic acid, myricitrin, and quercitrin) from the methanol (MeOH) extract. The MeOH extract of S. antisepticum and some isolated compounds, ursolic acid and gallic acid potentially exhibited acetylcholinesterase activity evaluated by Ellman\u2019s method. The MeOH extract and its isolated compounds, gallic acid, myricitrin, and quercitrin, also strongly elicited DPPH radical scavenging activity. In HEK-293 cells, the MeOH extract possessed cellular antioxidant effects by attenuating hydrogen peroxide (H2O2)-induced ROS production and increasing catalase, glutathione peroxidase-1 (GPx-1), and glutathione reductase (GRe). Furthermore, myricitrin and quercitrin also suppressed ROS production induced by H2O2 and induced GPx-1 and catalase production in HEK-293 cells. These results indicated that the young leaves of S. antisepticum are the potential sources of antioxidant and anticholinesterase agents. Consequently, S. antisepticum leaves are one of indigenous vegetables which advantage to promote the health and prevent diseases related to oxidative stress.<\/jats:p>","DOI":"10.3390\/molecules26113295","type":"journal-article","created":{"date-parts":[[2021,5,31]],"date-time":"2021-05-31T01:51:37Z","timestamp":1622425897000},"page":"3295","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Antioxidant and Anticholinesterase Activities of Extracts and Phytochemicals of Syzygium antisepticum Leaves"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3223-1551","authenticated-orcid":false,"given":"Supachoke","family":"Mangmool","sequence":"first","affiliation":[{"name":"Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Issaree","family":"Kunpukpong","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Worawan","family":"Kitphati","sequence":"additional","affiliation":[{"name":"Department of Physiology, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8630-4408","authenticated-orcid":false,"given":"Natthinee","family":"Anantachoke","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand"},{"name":"Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,30]]},"reference":[{"key":"ref_1","unstructured":"United Nations Population Fund (UNFPA) and HelpAge (2012). Setting the Scene. International Ageing in the Twenty-First Century: A Celebration and a Challenge, Pureprint Group."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"757","DOI":"10.2147\/CIA.S158513","article-title":"Oxidative stress, aging, and diseases","volume":"13","author":"Liguori","year":"2018","journal-title":"Clin. Interv. Aging"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"8416763","DOI":"10.1155\/2017\/8416763","article-title":"Oxidative stress: Harms and benefits for human health","volume":"2017","author":"Pizzino","year":"2017","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"118","DOI":"10.4103\/0973-7847.70902","article-title":"Free Radicals, Antioxidants and functional foods: Impact on human health","volume":"4","author":"Lobo","year":"2010","journal-title":"Phamacog. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1192","DOI":"10.3389\/fphar.2018.01192","article-title":"Naturally occurring acetylcholinesterase inhibitors and their potential use for Alzheimer\u2019s disease therapy","volume":"9","author":"Gomes","year":"2018","journal-title":"Front. Pharmacol."},{"key":"ref_6","first-page":"226","article-title":"Pathophysiology and management of Alzheimer\u2019s disease: An overview","volume":"7","author":"Thakur","year":"2018","journal-title":"J. Anal. Pharm. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1080\/10942912.2020.1753769","article-title":"Exploring the multifaceted neuroprotective actions of gallic acid: A review","volume":"23","author":"Shabani","year":"2020","journal-title":"Int. J. Food Prop."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"746","DOI":"10.2174\/156720512801322564","article-title":"N-methyl D-aspartate (NMDA) receptor antagonists and memantine treatment for Alzheimer\u2019s disease, vascular dementia and Parkinson\u2019s disease","volume":"9","author":"Olivares","year":"2012","journal-title":"Curr. Alzheimer Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.ctim.2019.03.016","article-title":"Neuropharmacological and cognitive effects of Bacopa monnieri (L.) Wettst\u2013A review on its mechanistic aspects","volume":"44","author":"Sukumaran","year":"2019","journal-title":"Complement. Ther. Med."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Matthews, D.G., Caruso, M., Murchison, C.F., Zhu, J.Y., Wright, K.M., Harris, C.J., Gray, N.E., Quinn, J.F., and Soumyanath, A. (2019). Centella asiatica improves memory and promotes antioxidative signaling in 5XFAD mice. Antioxidants, 8.","DOI":"10.3390\/antiox8120630"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1002\/ptr.5030","article-title":"Therapeutic potential of turmeric in Alzheimer\u2019s disease: Curcumin or curcuminoids?","volume":"28","author":"Ahmed","year":"2014","journal-title":"Phytother. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1007\/s11130-010-0200-6","article-title":"Consumption of Syzygium gratum promotes the antioxidant defense system in mice","volume":"65","author":"Senggunprai","year":"2010","journal-title":"Plant Foods Hum. Nutr."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"661","DOI":"10.1248\/bpb.30.661","article-title":"Antioxidant and vascular protective activities of Cratoxylum formosum, Syzygium gratum and Limnophila aromatica","volume":"30","author":"Kukongviriyapan","year":"2007","journal-title":"Biol. Pharm. Bull."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Stewart, P., Boonsiri, P., Puthong, S., and Rojpibulstit, P. (2013). Antioxidant activity and ultrastructural changes in gastric cancer cell lines induced by Northeastern Thai edible folk plant extracts. BMC Complement. Altern. Med., 13.","DOI":"10.1186\/1472-6882-13-60"},{"key":"ref_15","first-page":"108","article-title":"Antioxidant activity and cytotoxicity of six selected, regional, Thai vegetables","volume":"4","author":"Woraratphoka","year":"2012","journal-title":"Am Euras. J. Toxicol. Sci."},{"key":"ref_16","first-page":"2393","article-title":"Antioxidant and antibacterial potentials of some Thai native plant extracts","volume":"21","author":"Thummajitasakul","year":"2014","journal-title":"Int. Food Res. J."},{"key":"ref_17","first-page":"15","article-title":"Effects of Syzygium gratum on antioxidant system in \u03b2-thalassemia\/Hb E patients","volume":"7","author":"Bureemas","year":"2007","journal-title":"KKU Res. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1256","DOI":"10.1515\/chem-2020-0175","article-title":"Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review","volume":"18","author":"Aung","year":"2020","journal-title":"Open Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1016\/j.jff.2017.12.055","article-title":"Phenolic compounds from Syzygium jambos (Myrtaceae) exhibit distinct antioxidant and hepatoprotective activities in vivo","volume":"41","author":"Sobeh","year":"2018","journal-title":"J. Funct. Foods"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Sobeh, M., Petruk, G., Osman, S., El-Raey, M.A., Imbimbo, P., Monti, D.M., and Wink, M. (2019). Isolation of myricitrin and 3,5-di-o-methyl from Syzygium samarangense and evaluation of their involvement in protecting keratinocytes against oxidative stress via activation of the Nrf-2 Pathway. Molecules, 24.","DOI":"10.3390\/molecules24091839"},{"key":"ref_21","first-page":"47","article-title":"Protective effect of myricetin derivatives from Syzygium malaccense against hydrogen peroxide-induced stress in ARPE-19 cells","volume":"25","author":"Arumugam","year":"2019","journal-title":"Mol. Vis."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1080\/10286020.2018.1440391","article-title":"Leucoxenols A and B, two new phenolics from Bornean medicinal plant Syzygium leucoxylon","volume":"21","author":"Shamsudin","year":"2018","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1002\/(SICI)1097-458X(199804)36:4<267::AID-OMR256>3.0.CO;2-6","article-title":"Computer-assisted structure elucidation: Application of CISOC-SES to the resonance assignment and structure generation of betulinic acid","volume":"36","author":"Peng","year":"1998","journal-title":"Magn. Reson. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1248\/cpb.28.1006","article-title":"13C nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid","volume":"28","author":"Sholichin","year":"1980","journal-title":"Chem. Pharm. Bull."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1021\/np50056a006","article-title":"Oleanderol, a new pentacyclic triterpene from the leaves of Nerium oleander","volume":"51","author":"Siddiqui","year":"1988","journal-title":"J. Nat. Prod."},{"key":"ref_26","first-page":"48","article-title":"Ursane-type triterpenoids from the aerial parts of Potentilla discolor","volume":"49","author":"Jang","year":"2006","journal-title":"Agric. Chem. Biotechnol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1002\/jccs.200500184","article-title":"Triterpene acids from the leaves of Planchonella duclitan","volume":"52","author":"Lee","year":"2005","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1002\/mrc.855","article-title":"Complete 1H and 13C NMR assignments of stigma-5-en-3-O-\u03b2-glucosides and its acetyl derivative","volume":"39","author":"Faizi","year":"2001","journal-title":"Magn. Reson. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3923\/rjphyto.2009.1.12","article-title":"Pharmaco-chemical studies on the aqueous methanolic extract of Diospyros lotus Leaves","volume":"3","author":"Said","year":"2009","journal-title":"Res. J. Phytochem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1007\/s12039-013-0440-8","article-title":"Antileishmanial polyphenols from Corymbia maculate","volume":"125","author":"Sidana","year":"2013","journal-title":"J. Chem. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1007\/s11746-999-0060-0","article-title":"Antioxidant activity of flavonol aglycones and their glycosides in methyl linoleate","volume":"76","author":"Hopia","year":"1999","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1016\/S1016-8478(23)17016-6","article-title":"Inhibitory effect of ursolic acid purified from Origanum majorana L. on the acetylcholinesterase","volume":"11","author":"Chung","year":"2001","journal-title":"Mol. Cells"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.bioorg.2018.12.013","article-title":"Ursolic and oleanolic acid derivatives with cholinesterase inhibiting potential","volume":"85","author":"Loesche","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1007\/s10068-011-0044-3","article-title":"Neuronal cell protection and acetylcholinesterase inhibitory effect of the phenolics in chestnut inner skin","volume":"20","author":"Kim","year":"2011","journal-title":"Food Sci. Biotechnol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1590\/0004-282x20160065","article-title":"Ursolic acid attenuates beta-amyloid-induced memory impairment in mice","volume":"74","author":"Liang","year":"2016","journal-title":"Arq. Neuropsiquiatr."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"18512048","DOI":"10.1155\/2019\/8512048","article-title":"Antioxidant and anti-inflammatory mechanisms of neuroprotection by ursolic acid: Addressing brain injury, cerebral ischemia, cognition deficit, anxiety, and depression","volume":"2019","author":"Habtemariam","year":"2019","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1078","DOI":"10.1016\/j.bcp.2007.07.007","article-title":"Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose","volume":"74","author":"Lu","year":"2007","journal-title":"Biochem. Pharmacol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1714","DOI":"10.1002\/ptr.4638","article-title":"Inhibitory effects of key compounds isolated from Corni fructuson BACE1 activity","volume":"26","author":"Youn","year":"2012","journal-title":"Phytother. Res."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1007\/s13596-019-00393-x","article-title":"Gallic acid protects against neurochemical alterations in transgenic Drosophila model of Alzheimer\u2019s disease","volume":"20","author":"Ogunsuyi","year":"2020","journal-title":"Adv. Tradit. Med."},{"key":"ref_40","first-page":"97","article-title":"Effect of gallic acid on dementia type of Alzheimer disease in rats: Electrophysiological and histological studies","volume":"7","author":"Hajipour","year":"2016","journal-title":"Basic Clin. Neurosci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.nbd.2018.11.009","article-title":"Gallic acid disruption of A\u03b21\u201342 aggregation rescues cognitive decline of APP\/PS1 double transgenic mouse","volume":"124","author":"Yu","year":"2019","journal-title":"Neurobiol. Dis."},{"key":"ref_42","first-page":"479","article-title":"Polyphenolic compounds and antioxidant activities of the leaves of Glochidion hypoleucum","volume":"10","author":"Anantachoke","year":"2015","journal-title":"Nat. Prod. Commun."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Li, X., Jiang, Q., Wang, T., Liu, J., and Chen, D. (2016). Comparison of the antioxidant effects of quercitrin and isoquercitrin: Understanding the role of the 6\u2033-OH group. Molecules, 21.","DOI":"10.3390\/molecules21091246"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1271\/bbb.120562","article-title":"Separation of the antioxidant compound quercitrin from Lindera obtusiloba Blume and its antimelanogenic effect on B16F10 melanoma cells","volume":"77","author":"Hong","year":"2013","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/j.jff.2011.12.001","article-title":"Quercitrin protects against oxidative stress-induced injury in lung fibroblast cells via up-regulation of Bcl-xL","volume":"4","author":"Ham","year":"2012","journal-title":"J. Funct. Foods."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Anantachoke, N., Lomarat, P., Praserttirachai, W., Khammanit, R., and Mangmool, S. (2016). Thai fruits exhibit antioxidant activity and induction of antioxidant enzymes in HEK-293 cells. Evid. Based. Complement. Alternat. Med., 2016.","DOI":"10.1155\/2016\/6083136"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"e13574","DOI":"10.1111\/jfbc.13574","article-title":"Characteristics and upregulation of antioxidant enzymes of kitchen mint and oolong tea kombucha beverages","volume":"45","author":"Tanticharakunsiri","year":"2021","journal-title":"J. Food Biochem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"e12511","DOI":"10.1111\/jfbc.12511","article-title":"Mangosteen peel extract exhibits cellular antioxidant activity by induction of catalase and heme oxygenase-1 mRNA expression","volume":"42","author":"Jaisupa","year":"2018","journal-title":"J. Food. Biochem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1146\/annurev.bi.64.070195.000525","article-title":"Superoxide radical and superoxide dismutase","volume":"64","author":"Fridovich","year":"1995","journal-title":"Annu. Rev. Biochem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"103844","DOI":"10.1016\/j.jff.2020.103844","article-title":"Amelioration of hyperglycemia-induced oxidative damage in ARPE-19 cells by myricetin derivatives isolated from Syzygium malaccense","volume":"67","author":"Arumugam","year":"2020","journal-title":"J. Funct. Foods"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1016\/j.jphotobiol.2012.05.020","article-title":"Quercitrin protects against ultraviolet B-induced cell death in vitro and in an in vivo zebrafish model","volume":"114","author":"Yang","year":"2012","journal-title":"J. Photochem. Photobiol. B"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1839","DOI":"10.1016\/j.bcp.2005.03.017","article-title":"Quercetin, but not rutin and quercitrin, prevention of H2O2-induced apoptosis via anti-oxidant activity and heme oxygenase 1 gene expression in macrophages","volume":"69","author":"Chow","year":"2005","journal-title":"Biochem. Pharmacol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/S0021-9673(01)00624-0","article-title":"Screening for acetylcholinesterase inhibitors from Amaryllidaceae using s\u00edlica gel thin-layer chromatography in combination with bioactivity staining","volume":"915","author":"Rhee","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_55","first-page":"1107","article-title":"Inhibition of oxidative stress through the induction of antioxidant enzymes of pigmented rice bran in HEK-293 cells","volume":"12","author":"Khammanit","year":"2017","journal-title":"Nat. Prod. Commun."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/11\/3295\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:09:06Z","timestamp":1760162946000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/11\/3295"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,30]]},"references-count":55,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2021,6]]}},"alternative-id":["molecules26113295"],"URL":"https:\/\/doi.org\/10.3390\/molecules26113295","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,30]]}}}