Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.
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.
Koukoulitsa
Catherine
C
Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece.
Karioti
Anastasia
A
Bergonzi
Maria Camilla
MC
Pescitelli
Gennaro
G
Di Bari
Lorenzo
L
Skaltsa
Helen
H
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
D005419:Flavonoids; D005960:Glucosides; D010636:Phenols; D010936:Plant Extracts; D013729:Terpenes