title: Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.
abstract: From the polar extracts of Origanum vulgare L. ssp. hirtum 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, p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, thymoquinol 2-O-beta-glucopyranoside, thymoquinol 5-O-beta-glucopyranoside, thymoquinol 2,5-O-beta-diglucopyranoside, 12-hydroxyjasmonic acid, 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside, lithospermic acid B, rosmarinic acid, 10-epi-lithospermic acid, and epi-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), p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, 12-hydroxyjasmonic acid, and 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside were isolated for the first time from Origanum species.
authors.affiliation: Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece.
authors.forename: Catherine
authors.initials: C
authors.lastname: Koukoulitsa
authors.forename: Anastasia
authors.initials: A
authors.lastname: Karioti
authors.forename: Maria Camilla
authors.initials: MC
authors.lastname: Bergonzi
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Di Bari
authors.forename: Helen
authors.initials: H
authors.lastname: Skaltsa
mesh_terms: D002942:Circular Dichroism; D005419:Flavonoids / Q000032:analysis; D005960:Glucosides / Q000032:analysis; D006115:Greece; D009682:Magnetic Resonance Spectroscopy; D031341:Origanum / Q000737:chemistry*; D010636:Phenols / Q000032:analysis; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D013729:Terpenes / Q000032:analysis
chemical_list: D005419:Flavonoids; D005960:Glucosides; D010636:Phenols; D010936:Plant Extracts; D013729:Terpenes