Polar Constituents from the Aerial Parts of<i> Origanum vulgare</i> L. Ssp. <i>hirtum</i> Growing Wild in Greece

From the polar extracts of <i>Origanum vulgare</i> L. ssp. <i>hirtum</i> 19 compounds have been isolated. The structures and relative stereochemistry have been elucidated by spectroscopic analysis and determined as apigenin, luteolin, chrysoeriol, diosmetin, quercetin, eriodictyol, cosmoside, vicenin-2, caffeic acid, <i>p</i>-menth-3-ene-1,2-diol 1-<i>O</i>-β-glucopyranoside, thymoquinol 2-<i>O</i>-β-glucopyranoside, thymoquinol 5-<i>O</i>-β-glucopyranoside, thymoquinol 2,5-<i>O</i>-β-diglucopyranoside, 12-hydroxyjasmonic acid, 12-hydroxyjasmonic acid 12-<i>O</i>-β-glucopyranoside, lithospermic acid B, rosmarinic acid, 10-<i>epi</i>-lithospermic acid, and <i>epi</i>-lithospermic acid B. The three latter products display unusual stereochemistry of the 3,4-hydroxyphenyllactic acid unit(s), which to the authors' best knowledge has never been reported before in similar compounds. Moreover, lithospermic acid B (and its stereoisomers), <i>p</i>-menth-3-ene-1,2-diol 1-<i>O</i>-β-glucopyranoside, 12-hydroxyjasmonic acid, and 12-hydroxyjasmonic acid 12-<i>O</i>-β-glucopyranoside were isolated for the first time from <i>Origanum </i>species. Keywords: <i>Origanum vulgare </i>L. ssp. <i>hirtum</i>; Lamiaceae; Nepetoideae; phenolic acids; monoterpene glucosides; phenolic glucosides; hydroxyjasmonic acid