{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,19]],"date-time":"2026-06-19T15:56:27Z","timestamp":1781884587750,"version":"3.54.5"},"reference-count":46,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2024,6,8]],"date-time":"2024-06-08T00:00:00Z","timestamp":1717804800000},"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>The current study was designed to uncover the chemistry and bioactivity potentials of Bupleurum lancifolium growing wild in Jordan. In this context, the fresh aerial parts obtained from the plant material were subjected to hydrodistillation followed by GC\/MS analysis. The main components of the HDEO were \u03b3-patchoulene (23.79%), \u03b2-dihydro agarofuran (23.50%), \u03b1-guaiene (14.11%), and valencene (13.28%). Moreover, the crude thanolic extract was partitioned to afford two main major fractions, the aqueous methanol (BLM) and butanol (BLB). Phytochemical investigation of both fractions, using conventional chromatographic techniques followed by careful inspection of the spectral data for the isolated compounds (NMR, IR, and UV-Vis), resulted in the characterization of five known compounds, including \u03b1-spinasteryl (M1), ethyl arachidate (M2), ethyl myristate (M3), quercetin-3-O-\u03b2-d-glucopyranosyl-(1-4\u201d)-\u03b1-L-rhamnopyranosyl (B1), and isorhamnetin-3-O-\u03b2-d-glucopyranosyl-(1-4\u201d)-\u03b1-L-rhamnopyranosyl (B2). The TPC, TFC, and antioxidant activity testing of both fractions and HDEO revealed an interesting ABTS scavenging potential of the BLB fraction compared to the employed positive controls, which is in total agreement with its high TP and TF contents. Cytotoxic evaluation tests revealed that BLM had interesting cytotoxic effects on the normal breast cell line MDA-MB-231 (ATCC\u2013HTB-26) and the normal dermal fibroblast (ATCC\u00ae PCS-201-012) and normal African green monkey kidney Vero (ATCC-CCL-81) cell lines. Despite both the BLB and BLM fractions showing interesting AChE inhibition activities (IC50 = 217.9 \u00b1 5.3 \u00b5g\/mL and 139.1 \u00b1 5.6 \u00b5g\/mL, respectively), the HDEO revealed an interestingly high AChE inhibition power (43.8 \u00b1 2.7 \u00b5g\/mL) that far exceeds the one observed for galanthamine (91.4 \u00b1 5.2 \u00b5g\/mL). The HDEO, BLM, and BLB exhbitied no interesting antimicrobial activity against Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, or Pseudomonas aeruginosa.<\/jats:p>","DOI":"10.3390\/molecules29122730","type":"journal-article","created":{"date-parts":[[2024,6,10]],"date-time":"2024-06-10T08:59:06Z","timestamp":1718009946000},"page":"2730","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Uncovering the Chemical Composition and Biological Potentials of Bupleurum lancifolium Hornem. from Jordan"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3362-2247","authenticated-orcid":false,"given":"Nezar","family":"Al-Bataineh","sequence":"first","affiliation":[{"name":"College of Pharmacy, Al Ain University of Science and Technology, Abu Dhabi 112612, United Arab Emirates"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sultan T.","family":"Abu-Orabi","sequence":"additional","affiliation":[{"name":"Department of Medical Analysis, Faculty of Science, Tishk International University, Erbil 44001, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Suhair B.","family":"Shannag","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Yarmouk University, P.O. Box 566, Irbid 21163, Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5665-057X","authenticated-orcid":false,"given":"Hala I.","family":"Al-Jaber","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Al-Balqa Applied University, Al-Salt 19117, Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tareq T.","family":"Bataineh","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Yarmouk University, P.O. Box 566, Irbid 21163, Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7671-0426","authenticated-orcid":false,"given":"Wael A.","family":"Al-Zereini","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences, Faculty of Science, Mutah University, Al-Karak 61710, Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7179-8249","authenticated-orcid":false,"given":"Mahmoud A.","family":"Al-Qudah","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Yarmouk University, P.O. Box 566, Irbid 21163, Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,8]]},"reference":[{"key":"ref_1","first-page":"139","article-title":"The Asian Umbelliferae biodiversity database (ASIUM) with particular reference to South-West Asian taxa","volume":"28","author":"Pimenov","year":"2004","journal-title":"Turk. J. Bot."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1017\/S0960428600002997","article-title":"Umbelliferae of Southern Africa: An introduction and annotated check-list","volume":"48","author":"Burtt","year":"1991","journal-title":"Edinb. J. Bot."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Yaniv, Z., and Bachrach, U. (2005). Handbook of Medicinal Plants, CRC Press.","DOI":"10.1201\/9781482278026"},{"key":"ref_4","unstructured":"Al-Eisawi, D.M.H. (1982). List of Jordan Vascular Plants, Editeur Inconnu."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1248\/yakushi1947.115.2_145","article-title":"Seasonal variation on growth and saikosaponins concentration of Bupleurum falcatum L","volume":"115","author":"Minami","year":"1995","journal-title":"Yakugaku Zasshi"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1016\/S0024-3205(98)00376-2","article-title":"In vivo and in vitro anti-inflammatory activity of saikosaponins","volume":"63","author":"Benito","year":"1998","journal-title":"Life Sci."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/0304-3835(94)90184-8","article-title":"Antitumor effects of saikosaponins, baicalin and baicalein on human hepatoma cell lines","volume":"86","author":"Motoo","year":"1994","journal-title":"Cancer Lett."},{"key":"ref_8","unstructured":"Wu, J.N. (2005). An Illustrated Chinese Materia Medica, Oxford University Press."},{"key":"ref_9","unstructured":"World Health Organization (1999). World Health Organization Monographs on Selected Medicinal Plants, WHO."},{"key":"ref_10","unstructured":"World Health Organization (1998). Medicinal Plants in the Republic of Korea: Information on 150 Commonly Used Medicinal Plants, WHO."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"566","DOI":"10.1016\/j.jep.2016.09.052","article-title":"Toxic polyacetylenes in the genus Bupleurum (Apiaceae)\u2014Distribution, toxicity, molecular mechanism and analysis","volume":"193","author":"Lin","year":"2016","journal-title":"J. Ethnopharmacol."},{"key":"ref_12","first-page":"245","article-title":"Traditional use, pharmacology, toxicology, and quality control of species in genus Bupleurum L.","volume":"5","author":"Yao","year":"2013","journal-title":"Chin. Herb. Med."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1021\/np50115a015","article-title":"Phenylpropanoids from Bupleurum fruticosum","volume":"58","author":"Pistelli","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/S0031-9422(96)00461-X","article-title":"Phenylpropanoids from Bupleurum fruticosum","volume":"44","author":"Massanet","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Pan, S.L. (2006). Bupleurum Species: Scientific Evaluation and Clinical Applications, CRC Press.","DOI":"10.1201\/9781420009071"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1111\/j.2042-7158.2010.01170.x","article-title":"Genus Bupleurum: A review of its phytochemistry, pharmacology and modes of action","volume":"63","author":"Ashour","year":"2011","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2286","DOI":"10.1080\/14786419.2017.1324960","article-title":"Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae)","volume":"31","author":"Achouri","year":"2017","journal-title":"Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1501\/Vetfak_0000002537","article-title":"Chemical composition and antibacterial activity of essential oils from different parts of endemic Bupleurum L. species","volume":"59","author":"Mehtap","year":"2012","journal-title":"Ank. \u00dcniversitesi Vet. Fak\u00fcltesi Derg."},{"key":"ref_19","first-page":"527","article-title":"A comparative study on the fatty acid composition of the oils from five Bupleurum species collected from Turkey","volume":"36","author":"Zengin","year":"2012","journal-title":"Turk. J. Biol."},{"key":"ref_20","first-page":"3758","article-title":"Antioxidant, antimicrobial activities and fatty acid components of leaf and seed of Bupleurum lancifolium Hornem","volume":"5","author":"Shafaghat","year":"2011","journal-title":"J. Med. Plant Res."},{"key":"ref_21","first-page":"12","article-title":"Roles of flavonoids in plants","volume":"100","author":"Samanta","year":"2011","journal-title":"Carbon"},{"key":"ref_22","first-page":"171","article-title":"Flavonol 3-O-glycosides from three Algerian Bupleurum species","volume":"6","author":"Bencheraiet","year":"2012","journal-title":"Rec. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Zhang, H.Y., Gao, Y., and Lai, P.X. (2017). Chemical composition, antioxidant, antimicrobial and cytotoxic activities of essential oil from Premna microphylla Turczaninow. Molecules, 22.","DOI":"10.3390\/molecules22030381"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1107\/S2053229617006817","article-title":"dihydro-\u03b2-agarofuran sesquiterpene from Maytenus boaria","volume":"73","author":"Paz","year":"2017","journal-title":"Acta Crystallogr. Sect. C Struct. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"487","DOI":"10.18016\/ksutarimdoga.vi.1121276","article-title":"Bupleurum lancifolium Hornem.\u2019un Antibakteriyel Etkisinin \u0130ncelenmesi","volume":"26","author":"Akin","year":"2023","journal-title":"KSU J. Agric Nat."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"996","DOI":"10.2174\/138920008786927794","article-title":"Evolutionary advantage and molecular modes of action of multi-component mixtures used in phytomedicine","volume":"9","author":"Wink","year":"2008","journal-title":"Curr. Drug Metab."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Gong, G., Guan, Y.Y., Zhang, Z.L., Rahman, K., Wang, S.J., Zhou, S., Luan, X., and Zhang, H. (2020). Isorhamnetin: A review of pharmacological effects. Biomed. Pharmacother., 128.","DOI":"10.1016\/j.biopha.2020.110301"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1038\/emm.2005.15","article-title":"Antitumor activity of spinasterol isolated from Pueraria roots","volume":"37","author":"Jeon","year":"2005","journal-title":"Exp. Mol. Med."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1016\/j.phymed.2009.09.005","article-title":"Antiproliferative, apoptotic and antimutagenic activity of isolated compounds from Polyalthia cerasoides seeds","volume":"17","author":"Ravikumar","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3892","DOI":"10.1002\/jcb.26515","article-title":"The molecular basis of cytotoxicity of \u03b1-spinasterol from Ganoderma resinaceum: Induction of apoptosis and overexpression of p53 in breast and ovarian cancer cell lines","volume":"119","author":"Sedky","year":"2018","journal-title":"J. Cell. Biochem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1473","DOI":"10.4314\/tjpr.v19i7.20","article-title":"Novel cholinesterase inhibitory effect of \u03b1-spinasterol isolated from the leaves of Acacia auriculiformis A. CUNN Ex. Benth (Fabaceae)","volume":"19","author":"Lawal","year":"2020","journal-title":"Trop. J. Pharm. Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1845","DOI":"10.1080\/14756366.2022.2091554","article-title":"Dyhidro-\u03b2-agarofurans natural and synthetic as acetylcholinesterase and COX inhibitors: Interaction with the peripheral anionic site (AChE-PAS), and anti-inflammatory potentials","volume":"37","author":"Cespedes","year":"2022","journal-title":"J. Enzym. Ihib. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1515\/znc-2008-11-1212","article-title":"Inhibition of acetylcholinesterase activity by dihydro-\u03b2-agarofuran sesquiterpenes isolated from Chilean Celastraceae","volume":"63","author":"Astudillo","year":"2008","journal-title":"Z. Naturforsch. C."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"286","DOI":"10.3923\/rjmp.2016.286.294","article-title":"Cyclooxygenase, 5-lipoxygenase and acetylcholinesterase inhibitory effects of fractions containing, \u03b1-guaiene and oil isolated from the root of Xylocarpus moluccensis","volume":"10","author":"Eldeen","year":"2016","journal-title":"Res. J. Med. Plant"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1016\/j.brainres.2019.02.017","article-title":"Isorhamnetin enhanced cortico-hippocampal learning and memory capability in mice with scopolamine-induced amnesia: Role of antioxidant defense, cholinergic and BDNF signaling","volume":"1712","author":"Ishola","year":"2019","journal-title":"Brain Res."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Olennikov, D.N., Kashchenko, N.I., Chirikova, N.K., Akobirshoeva, A., Zilfikarov, I.N., and Vennos, C. (2017). Isorhamnetin and quercetin derivatives as anti-acetylcholinesterase principles of marigold (Calendula officinalis) flowers and preparations. Int. J. Mol. Sci., 18.","DOI":"10.3390\/ijms18081685"},{"key":"ref_37","first-page":"6256","article-title":"Antioxidant activity and chemical composition of essential oils of selected Cleome species growing in Saudi Arabia","volume":"14","author":"Alotaibi","year":"2019","journal-title":"JJC"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"6256","DOI":"10.1016\/j.arabjc.2020.05.043","article-title":"Antioxidant activity of crude extracts and essential oils from flower buds and leaves of Cistus creticus and Cistus salviifolius","volume":"13","author":"Saleh","year":"2020","journal-title":"Arab. J. Chem."},{"key":"ref_39","unstructured":"Adams, R.P. (2012). Identification of Essential Oils by Ion Trap Mass Spectroscopy, Academic Press."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Al-Dalahmeh, Y., Almahmoud, S.A.J., Al-Bataineh, N., Alghzawi, T.A., Alhamzani, A.G., Al-Mutairi, A.A., and Al-Qudah, M.A. (2023). Scrophularia peyronii Post. from Jordan: Chemical composition of essential oil and phytochemical profiling of crude extracts and their in vitro antioxidant activity. Life, 13.","DOI":"10.3390\/life13061404"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/j.fitote.2017.03.011","article-title":"A novel method for synthesis of \u03b1-spinasterol and its antibacterial activities in combination with ceftiofur","volume":"119","author":"Yang","year":"2017","journal-title":"Fitoterapia"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2020\/8797284","article-title":"Anti-inflammatory and analgesic effect of arachic acid ethyl ester isolated from propolis","volume":"2020","author":"Sokeng","year":"2020","journal-title":"Biomed Res. Int."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"952","DOI":"10.1016\/j.tetasy.2010.05.024","article-title":"Separation of secondary alcohols via enzymatic kinetic resolution using fatty esters as reusable acylating agents","volume":"21","author":"Monteiro","year":"2010","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_44","first-page":"43","article-title":"Antifouling alkaloids from Crinum augustum (Amaryllidaceae)","volume":"1","author":"Refaat","year":"2009","journal-title":"Pharmacogn. Res."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1515\/znc-2022-0056","article-title":"Antibacterial, antioxidant, and cytotoxic activities of Syzygium aromaticum (L.) Merr. & Perry essential oil with identification of its chemical constituents","volume":"78","author":"TumAllah","year":"2023","journal-title":"Z. Naturforsch. C"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"755","DOI":"10.56499\/jppres21.1077_9.6.755","article-title":"Antibacterial, antioxidant and neuroprotective activities of crude extract from the endophytic fungus Fusarium sp. isolate OQ-Fus-2-F from Euphorbia sp. plant","volume":"9","year":"2021","journal-title":"JPPRes"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/12\/2730\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:55:41Z","timestamp":1760108141000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/12\/2730"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,8]]},"references-count":46,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2024,6]]}},"alternative-id":["molecules29122730"],"URL":"https:\/\/doi.org\/10.3390\/molecules29122730","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,8]]}}}