Eleven new glycosidic acid methyl esters from the crude resin glycoside fraction of Ipomoea alba seeds

• Published in: Journal of natural medicines 2024-09, Vol.78 (4), p.1057-1070
• Main Authors: Misuda, Nodoka, Nishikawa, Hirotaka, Yasuda, Shin, Miyashita, Hiroyuki, Yoshimitsu, Hitoshi, Tsuchihashi, Ryota, Okawa, Masafumi, Kinjo, Junei, Ono, Masateru
• Format: Article
• Language: English
• Subjects: Antiviral activity; Antiviral agents; Biomedical and Life Sciences; Biomedicine; Complementary & Alternative Medicine; Convolvulaceae; Cytotoxicity; Esters - chemistry; Esters - pharmacology; Glucose; Glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Humans; Ipomoea - chemistry; Ipomoea alba; L-Rhamnose; Magnetic Resonance Spectroscopy; Mass spectroscopy; Medicinal Chemistry; Medicinal plants; Molecular Structure; Monosaccharides; Multidrug resistance; Organic acids; Pharmacology/Toxicology; Pharmacy; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Sciences; Promyeloid leukemia; Resins; Resins, Plant - chemistry; Seeds; Seeds - chemistry; Spectrometry, Mass, Electrospray Ionization
• ISSN: 1340-3443; 1861-0293; 1861-0293
• DOI: 10.1007/s11418-024-01838-7

Resin glycosides are characteristic of plants of the Convolvulaceae family and are well-known purgative ingredients in crude drugs, such as Rhizoma Jalapae, Orizaba Jalapa Tuber, and Pharbitidis Semen, which are used in traditional medicine and derived from plants belonging to this family. Isolated resin glycosides have demonstrated diverse biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. These compounds consist of hydroxyl fatty acid oligoglycosides (glycosidic acids), with portions of the saccharide moieties acylated with some organic acids to form the core structure. This study investigated the glycosidic acid components of a crude resin glycoside fraction obtained from a methanolic extract of Ipomoea alba L. seeds (Convolvulaceae). Eleven new glycosidic acid methyl esters and one known methyl ester were isolated from a glycosidic acid fraction treated with trimethylsilyldiazomethane in hexane. Their structures were determined using acidic hydrolysis and electrospray ionization-time of fight mass spectrometry and NMR spectral analyses. These compounds are penta-, tetra-, or triglycosides, with methyl 11 S -hydroxytetradecanoate or methyl 11 S -hydroxyhexadecanoate as the aglycone. Although d -quinovose and l -rhamnose are common monosaccharide components, the remaining monosaccharides are d -glucose, d -xylose, or d -fucose. The crude resin glycoside fraction showed non-negligible cytotoxicity against HL-60 human promyelocytic leukemia cells. Graphical abstract