Unusual Fernane and Gammacerane Glycosides from the Aerial Parts of <i>Spergula fallax</i>

The aerial parts of <i>Spergula fallax</i> afforded four glycosides (<b>1</b>–<b>4</b>) based on two new triterpene aglycones (<b>1a</b> and <b>2a</b>), along with the known hopane glycoside succulentoside A. Compound <b>1</b> was identified as belonging to the fernane class, unusual migrated hopane triterpenoids, mainly isolated from ferns and only rarely from higher plants. Compounds <b>2</b>–<b>4</b> were assigned as gammacerane glycosides, having as aglycone a hydroxylated derivative of tetrahymanol. The structures of the isolated compounds <b>1</b>–<b>4</b> and their aglycones <b>1a</b> and <b>2a</b> obtained by acid hydrolysis were elucidated by spectroscopic data interpretation. The growth inhibitory activity of the isolated compounds and their aglycones was evaluated against the HeLa and DLD-1 cancer cell lines

Triterpene Saponins from the Aerial Parts of Trifolium medium L. var. <i>sarosiense</i>

Seven previously unreported triterpene glycosides (<b>1</b>–<b>7</b>) were isolated from methanol extract of the aerial parts of Trifolium medium var. <i>sarosiense</i> (zigzag clover). Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESI-MS and HRMS analyses. Compounds <b>1</b>–<b>7</b> are oleanane derivatives characterized by the presence of a keto group at C-22 of an aglycone and a primary alcoholic function at C-24 and differing functions at C-30. Among these, compounds <b>1</b>–<b>3</b> and <b>6</b> showed a secondary alcoholic function at C-11, which is methoxylated in compounds <b>4</b> and <b>7</b>. Compound <b>5</b> was shown to possess a known aglycone, wistariasapogenol A; however, it is described here for the first time as a saponin constituent of the <i>Trifolium</i> genus. Some aspects of taxonomic classification of zigzag clover are also discussed