{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,24]],"date-time":"2026-04-24T15:30:37Z","timestamp":1777044637395,"version":"3.51.4"},"reference-count":26,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2019,11,5]],"date-time":"2019-11-05T00:00:00Z","timestamp":1572912000000},"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 genus Lasianthus (Rubiaceae) consists of approximately 180 species, of which the greatest species diversity is found in tropical Asia. Some of the Lasianthus species have been used in folk medicine to treat tinnitus, arthritis, fever, and bleeding. Lasianthus verticillatus (Lour.) Merr. (Syn. Lasianthus trichophlebus auct. non Hemsl.) is a shrub, branchlets terete about 1.5\u20133 m in height. This paper studies the chemical composition of the leaves of L. verticillatus for the first time, which resulted in the isolation of five undescribed iridoid glucosides, lasianosides A\u2013E (1\u20135), together with three known compounds (6\u20138). The undescribed structures of isolated compounds (1\u20135) were characterized by physical and spectroscopic data analyses, including one-dimensional (1D) and two-dimensional (2D) NMR, IR, UV, and high-resolution electrospray ionization mass spectra (HR-ESI-MS). Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The free radical scavenging properties of isolated compounds was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and their cytotoxicity was assessed toward human lung cancer cell line A549 by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the isolated compounds, 3 and 4 displayed potent radical scavenging activities with IC50 values of 30.2 \u00b1 1.8 and 32.0 \u00b1 1.2 \u00b5M, which were comparable to that of Trolox (29.2 \u00b1 0.39 \u00b5M), respectively, while 5 possessed moderate activity with an IC50 value of 46.4 \u00b1 2.3 \u00b5M. None of the isolated compounds exerted cytotoxicity against human cell line A549. As a result, lasianosides C, D, and E have the potential to be non-toxic safe antioxidant agents.<\/jats:p>","DOI":"10.3390\/molecules24213995","type":"journal-article","created":{"date-parts":[[2019,11,5]],"date-time":"2019-11-05T06:47:57Z","timestamp":1572936477000},"page":"3995","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Lasianosides A\u2013E: New Iridoid Glucosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. and Their Antioxidant Activity"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5313-7153","authenticated-orcid":false,"given":"Gadah Abdulaziz","family":"Al-Hamoud","sequence":"first","affiliation":[{"name":"Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan"},{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11495, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Raha","family":"Saud Orfali","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11495, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shagufta","family":"Perveen","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11495, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kenta","family":"Mizuno","sequence":"additional","affiliation":[{"name":"Faculty of Integrated Arts and Sciences, The University of Tokushima, 1-1 Minamijosanjima-Cho, Tokushima 770-8502, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshio","family":"Takeda","sequence":"additional","affiliation":[{"name":"Faculty of Integrated Arts and Sciences, The University of Tokushima, 1-1 Minamijosanjima-Cho, Tokushima 770-8502, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tatsuo","family":"Nehira","sequence":"additional","affiliation":[{"name":"Graduate School of Integrated Arts and Sciences, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuma","family":"Masuda","sequence":"additional","affiliation":[{"name":"Graduate School of Integrated Arts and Sciences, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sachiko","family":"Sugimoto","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshi","family":"Yamano","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hideaki","family":"Otsuka","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan"},{"name":"Faculty of Pharmacy, Yasuda Women\u2019s University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima 731-0153, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katsuyoshi","family":"Matsunami","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,11,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"89","DOI":"10.59566\/IJBS.2008.4089","article-title":"Free Radicals, Antioxidants in Disease and Health","volume":"4","author":"He","year":"2008","journal-title":"Int. J. Biomed. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/j.bbcan.2015.08.002","article-title":"Lung cancer: Biology and treatment options","volume":"1856","author":"Hassan","year":"2015","journal-title":"Biochim. Biophys. Acta BBA Rev. Cancer"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1021\/acs.jnatprod.5b01055","article-title":"Natural Products as Sources of New Drugs from 1981 to 2014","volume":"79","author":"Newman","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_4","first-page":"132","article-title":"Tropical Woody Rubiaceae","volume":"Volume 1","author":"Robbrecht","year":"1988","journal-title":"Opera Botanica Belgica"},{"key":"ref_5","first-page":"447","article-title":"Two new subspecies of Lasianthus inodorus (Rubiaceae) from Kinabalu, Borneo, and their biogeographical implication","volume":"46","author":"Zhu","year":"2001","journal-title":"Bumea"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Wiart, C. (2006). Medicinal Plants of the Asia-Pacific\u2014Drugs for the Future, World Scientific Pub Co. Pte Lt.","DOI":"10.1142\/9789812707260"},{"key":"ref_7","first-page":"117","article-title":"Antibacterial property testing of two species of tropical plant lasianthus (rubiaceae)","volume":"48","author":"Napiroon","year":"2017","journal-title":"Southeast Asian J. Trop. Med. Public Health"},{"key":"ref_8","first-page":"426","article-title":"A new sesquiterpene lactone from the roots of Lasianthus acuminatissimus","volume":"41","author":"Li","year":"2006","journal-title":"Acta Pharm. Sin."},{"key":"ref_9","first-page":"75","article-title":"Non\u2013indigenous Rubiaceae grown in Thailand","volume":"31","author":"Puff","year":"2003","journal-title":"Thai. For. Bull. (Bot.)"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1007\/s10600-017-2002-7","article-title":"Chemical Constituents and Antioxidant Activity of Lasianthus hartii","volume":"53","author":"Yang","year":"2017","journal-title":"Chem. Nat. Compd."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1395","DOI":"10.1248\/cpb.50.1395","article-title":"An Iridoid Glucoside Dimer and a Non-glucosidic Iridoid from the Leaves of Lasianthus wallichii","volume":"50","author":"Takeda","year":"2002","journal-title":"Chem. Pharm. Bull."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1248\/cpb.54.297","article-title":"Three New and Antitumor Anthraquinone Glycosides from Lasianthus acuminatissimus Merr.","volume":"37","author":"Li","year":"2006","journal-title":"Chem. Pharm. Bull."},{"key":"ref_13","first-page":"502","article-title":"A new anthraquinone from the root of Lasianthus acuminatissimus","volume":"42","author":"Li","year":"2007","journal-title":"Acta Pharm. Sin."},{"key":"ref_14","first-page":"133","article-title":"Chemical constituents from root of Lasianthus acuminatissimus I","volume":"31","author":"Li","year":"2006","journal-title":"China J. Chin. Mater. Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"911","DOI":"10.1021\/np030374g","article-title":"A New 3, 4-seco-Lupane Derivative from Lasianthus gardneri","volume":"67","author":"Dallavalle","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3767\/000651912X652012","article-title":"A taxonomic revision of the Malasian species of Lasianthus (Rubiaceae)","volume":"57","author":"Zhu","year":"2012","journal-title":"Blumea"},{"key":"ref_17","first-page":"41","article-title":"Comparative phytochemical evaluation and biological control properties from Lasianthus verticillatus (Lour.) Merr. (Rubiaceae) extracts","volume":"14","author":"Napiroon","year":"2019","journal-title":"Res. J. Biotechnol."},{"key":"ref_18","first-page":"525","article-title":"Iridoid, flavonoids and monoterpene glycosides from Galium verum subsp. Verum","volume":"30","author":"Demirezer","year":"2006","journal-title":"Turk. J. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"10644","DOI":"10.20964\/2016.12.73","article-title":"Determination of Antioxidant Activity of Caffeic Acid and p-Coumaric Acid by Using Electrochemical and Spectrophotometric Assays","volume":"11","author":"Masek","year":"2016","journal-title":"Int. J. Electrochem. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5062","DOI":"10.1021\/jf9805799","article-title":"Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotine","volume":"46","author":"Moon","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/j.phytochem.2014.10.008","article-title":"Structure elucidation of secondary metabolites isolated from the leaves of Lxora undulate and their inhibitory activity toward advanced glycation end-products formation","volume":"108","author":"Sugimoto","year":"2014","journal-title":"Phytochemistry"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1248\/cpb.56.1297","article-title":"Medicinal flowers. XXII. Structures of chakasaponins V and VI, chakanoside I, and chakaflavonoside a from flower buds of Chinese tea plant (Camellia sinensis)","volume":"56","author":"Yoshikawa","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1403","DOI":"10.1248\/cpb.54.1403","article-title":"Radical-scavenging activities of new megastimane glucosides from Macaranga tanarius (L.) MULL-ARG","volume":"54","author":"Matsunami","year":"2006","journal-title":"Chem. Pharm. Bull."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/j.phytol.2014.08.009","article-title":"One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande","volume":"10","author":"Samy","year":"2014","journal-title":"Phytochem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Korkina, L., Kostyuk, V., Potapovich, A., Mayer, W., Talib, N., and De Luca, C. (2018). Secondary Plant Metabolites for Sun Protective Cosmetics: From Pre-Selection to Product Formulation. Cosmetics, 5.","DOI":"10.3390\/cosmetics5020032"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1830","DOI":"10.1021\/jo7024543","article-title":"The Unusual Reaction of Semiquinone Radicals with Molecular Oxygen","volume":"73","author":"Valgimigli","year":"2008","journal-title":"J. Org. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/21\/3995\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:31:56Z","timestamp":1760189516000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/21\/3995"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,5]]},"references-count":26,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2019,11]]}},"alternative-id":["molecules24213995"],"URL":"https:\/\/doi.org\/10.3390\/molecules24213995","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,11,5]]}}}