Batatinosides II-VI, acylated lipooligosaccharides from the resin glycosides of sweet potato.
Sweet potato ( Ipomoea batatas) belongs to the Convolvulaceae (morning glory family) and is native to Mexico and Central America. Its edible tuberous roots have been much appreciated since pre-Hispanic times in Mesoamerica and now play an important role as a basic diet staple and a medicinal plant worldwide. The hexane-soluble extract from roots, through preparative-scale recycling HPLC, yielded five new lipophilic oligosaccharides of jalapinolic acid, batatinosides II-VI ( 1- 5), as well as the known pescapreins I ( 6) and VII ( 7) and murucoidin I ( 8), which are part of the purgative resin glycoside mixture. NMR spectroscopy and FAB mass spectrometry were used to characterize their structures. Compounds 1 and 2 are tetraglycosidic lactones of operculinic acid C. The pentasaccharide structures for compounds 3 and 4 were confirmed to be macrolactones of simonic acid B, and that characterized for 5 was derived from operculinic acid A. The lactonization site of the aglycone was placed at C-3 of the second saccharide unit in all compounds except 4, where it was placed at C-2. All compounds contain an esterifying residue that is composed of a long-chain fatty acid, n-decanoic acid (capric) or n-dodecanoic acid (lauric). In compound 3, an additional short-chain fatty acid, (2 S)-methylbutyric acid, was also identified.
Escalante-Sánchez
Edgar
E
Departamento de Farmacia, Facultad de Química and Jardín Botánico, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico City 04510 DF, Mexico.
Rosas-Ramírez
Daniel
D
Linares
Edelmira
E
Bye
Robert
R
Pereda-Miranda
Rogelio
R
D000107:Acetylation; D006027:Glycosides / Q000737:chemistry; D027723:Ipomoea batatas / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry*
D006027:Glycosides; D008070:Lipopolysaccharides; D010936:Plant Extracts; D012116:Resins, Plant; C023023:lipid-linked oligosaccharides