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Pereda-Miranda, R. et al.

Pereda-Miranda, Escalante-Sánchez, Escobedo-Martínez,

Characterization of lipophilic pentasaccharides from beach morning glory (Ipomoea pes-caprae).

The hexane-soluble extract from the aerial parts of the herbal drug Ipomoea pes-caprae (beach morning-glory), through preparative-scale recycling HPLC, yielded six lipophilic glycosides, namely, five new pentasaccharides of jalapinolic acid, pescaproside A (1) and pescapreins I-IV (2-5), as well as the known stoloniferin III (6). Saponification of the crude resin glycoside mixture yielded simonic acid B (7) as the glycosidic acid component, whereas the esterifying residues of the natural oligosaccharides comprised five fatty acids: 2-methylpropanoic, (2S)-methylbutyric, n-hexanoic, n-decanoic, and n-dodecanoic acids. Pescaproside A (1), an acylated glycosidic acid methyl ester, is related structurally to the product obtained from the macrolactone hydrolysis of pescapreins I-IV (2-5). All the isolated compounds (1-6), characterized through high-field NMR spectroscopy, were found to be weakly cytotoxic to a small panel of cancer cell lines.[1]

References

Characterization of lipophilic pentasaccharides from beach morning glory (Ipomoea pes-caprae). Pereda-Miranda, R., Escalante-Sánchez, E., Escobedo-Martínez, C. J. Nat. Prod. (2005) [Pubmed]

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