Scholarlink

<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. <i>Ipomoea lacunosa</i> L. (Convolvulaceae) is an herbaceous vine native to the United States. Four new acylated glycosidic acid methyl esters (<b>1</b>–<b>4</b>) and one new glycosidic acid (<b>5</b>) were isolated from the methanol extract of the plant seed. The structures of <b>1</b>–<b>5</b> were elucidated using spectroscopic data in conjunction with our previous studies on the components of the crude resin glycoside fraction from <i>I. lacunosa</i> seeds. Compounds <b>1</b> and <b>2</b> were identified as heptaglycosides, <b>3</b> as an octaglycoside, and <b>4</b> as a nonaglycoside, all sharing methyl 3<i>S</i>,11<i>S</i>-dihydroxytetradecanoate as a common aglycone. The saccharide moieties were partially acylated by glycosidic acid, 7<i>S</i>-hydroxydecanoic acid 7-<i>O</i>-<i>β</i>-<span>d</span>-quinovopyranoside, and organic acids, including (<i>E</i>)-2-methylbut-2-enoic, 2<i>S</i>-methylbutyric, and 2<i>R</i>-methyl-3<i>R</i>-hydroxybutyric acids. Compound <b>5</b> 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.</p> Graphical abstract <p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Four new acylated glycosidic acid methyl esters and a new glycosidic acid from Ipomoea lacunosa seeds

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年2月13日

查看全文
  • Masateru Ono,
  • Renjyu Murakami,
  • Shin Yasuda,
  • Hiroyuki Miyashita,
  • Hitoshi Yoshimitsu,
  • Ryota Tsuchihashi,
  • Masafumi Okawa,
  • Junei Kinjo

摘要

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. Ipomoea lacunosa L. (Convolvulaceae) is an herbaceous vine native to the United States. Four new acylated glycosidic acid methyl esters (1–4) and one new glycosidic acid (5) were isolated from the methanol extract of the plant seed. The structures of 1–5 were elucidated using spectroscopic data in conjunction with our previous studies on the components of the crude resin glycoside fraction from I. lacunosa seeds. Compounds 1 and 2 were identified as heptaglycosides, 3 as an octaglycoside, and 4 as a nonaglycoside, all sharing methyl 3S,11S-dihydroxytetradecanoate as a common aglycone. The saccharide moieties were partially acylated by glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-d-quinovopyranoside, and organic acids, including (E)-2-methylbut-2-enoic, 2S-methylbutyric, and 2R-methyl-3R-hydroxybutyric acids. Compound 5 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.

Graphical abstract