{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,29]],"date-time":"2025-11-29T08:04:05Z","timestamp":1764403445254,"version":"3.38.0"},"reference-count":21,"publisher":"Springer Science and Business Media LLC","issue":"2","license":[{"start":{"date-parts":[[2025,2,13]],"date-time":"2025-02-13T00:00:00Z","timestamp":1739404800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,2,13]],"date-time":"2025-02-13T00:00:00Z","timestamp":1739404800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP16K08306","JP20K07117"],"award-info":[{"award-number":["JP16K08306","JP20K07117"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Tokai University, Kumamoto Campus"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["J Nat Med"],"published-print":{"date-parts":[[2025,3]]},"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:p>Resin glycosides, characteristic of plants of the Convolvulaceae family, are well-known purgative constituents found in traditional medicinal crude drugs, such as Rhizoma Jalapae, Rhizoma Jalapae Braziliensis, Orizaba Jalapa Tuber, and Pharbitidis Semen. The isolated compounds exhibited a wide range of biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. <jats:italic>Ipomoea lacunosa<\/jats:italic> L. (Convolvulaceae) is an herbaceous vine native to the United States. Four new acylated glycosidic acid methyl esters (<jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold>) and one new glycosidic acid (<jats:bold>5<\/jats:bold>) were isolated from the methanol extract of the plant seed. The structures of <jats:bold>1<\/jats:bold>\u2013<jats:bold>5<\/jats:bold> were elucidated using spectroscopic data in conjunction with our previous studies on the components of the crude resin glycoside fraction from <jats:italic>I. lacunosa<\/jats:italic> seeds. Compounds <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> were identified as heptaglycosides, <jats:bold>3<\/jats:bold> as an octaglycoside, and <jats:bold>4<\/jats:bold> as a nonaglycoside, all sharing methyl 3<jats:italic>S<\/jats:italic>,11<jats:italic>S<\/jats:italic>-dihydroxytetradecanoate as a common aglycone. The saccharide moieties were partially acylated by glycosidic acid, 7<jats:italic>S<\/jats:italic>-hydroxydecanoic acid 7-<jats:italic>O<\/jats:italic>-<jats:italic>\u03b2<\/jats:italic>-<jats:sc>d<\/jats:sc>-quinovopyranoside, and organic acids, including (<jats:italic>E<\/jats:italic>)-2-methylbut-2-enoic, 2<jats:italic>S<\/jats:italic>-methylbutyric, and 2<jats:italic>R<\/jats:italic>-methyl-3<jats:italic>R<\/jats:italic>-hydroxybutyric acids. Compound <jats:bold>5<\/jats:bold> was identified as a triglycoside with a new aglycone, 4,11-dihydroxyhexadecanoic acid, which is the first glycosidic acid with a hydroxyl group at C-4 of the aglycone moiety.<\/jats:p>\n          <jats:p>\n            <jats:bold>Graphical abstract<\/jats:bold>\n          <\/jats:p>","DOI":"10.1007\/s11418-025-01877-8","type":"journal-article","created":{"date-parts":[[2025,2,13]],"date-time":"2025-02-13T01:57:06Z","timestamp":1739411826000},"page":"422-434","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Four new acylated glycosidic acid methyl esters and a new glycosidic acid from Ipomoea lacunosa seeds"],"prefix":"10.1007","volume":"79","author":[{"given":"Masateru","family":"Ono","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Renjyu","family":"Murakami","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shin","family":"Yasuda","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyuki","family":"Miyashita","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hitoshi","family":"Yoshimitsu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryota","family":"Tsuchihashi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masafumi","family":"Okawa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junei","family":"Kinjo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2025,2,13]]},"reference":[{"key":"1877_CR1","doi-asserted-by":"publisher","first-page":"591","DOI":"10.1007\/s11418-017-1114-5","volume":"71","author":"M Ono","year":"2017","unstructured":"Ono M (2017) Resin glycosides from Convolvulaceae plants. 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