The crystal structure of a peracetylated glucosyl ester of kaurenic acid, (4α)-kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside, C34H48O11, is reported. The synchrotron X-ray diffraction experiment showed that the glucosyl moiety adopts an α-perpendicular orientation with respect to the plane of the kaurenic acid. This conformation would allow the sugar hydroxyl groups, one unprotected, to interact with solvent or with biological membranes, enhancing its in vitro activity against murine melanoma in mice.
Tópico:
Natural product bioactivities and synthesis
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FuenteActa Crystallographica Section E Structure Reports Online