Bis[14β-hydroxy-3β-O-(L-thevetosyl)-5β-card-20(22)-enolide] methanol solvate monohydrate and 3β-O-(L-2′-o-acetylthevetosyl)-14β-hydroxy-5β-card-20(22)-enolide

The title compounds, 2C(30)H(46)O(8).CH3OH.H2O, (I), and C32H48O9, (II), respectively, are cardenolide glycosides which were isolated from the seeds of Cerbera odollam. There are two crystallographically independent cardenolide molecules in (I), together with one methanol and one water solvate molecule. In both (I) and (II), the steroid nuclei are in cis/trans/cis configurations, with the cyclopentane rings showing conformational flexibility, viz. an envelope conformation in (I) and a twisted conformation in (II). In both compounds, the lactone ring is nearly orthogonal to the cyclopentane ring. The packing of (I) is composed of molecular layers stabilized by five O-H...O hydrogen bonds. In the packing of (II), the molecules are packed into columns by one O-H...O hydrogen bond, and are further interconnected into a three-dimensional network by one O-H...O and three C-H...O interactions.