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 a...

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Published in:Journal of agricultural and food chemistry 2006-07, Vol.54 (15), p.5388-5392
Main Authors: Koukoulitsa, Catherine, Karioti, Anastasia, Bergonzi, Maria Camilla, Pescitelli, Gennaro, Di Bari, Lorenzo, Skaltsa, Helen
Format: Article
Language:English
Subjects:
Biological and medical sciences
chemical structure
Circular Dichroism
Flavonoids - analysis
Food industries
Fundamental and applied biological sciences. Psychology
glucosides
Glucosides - analysis
Greece
leaves
Magnetic Resonance Spectroscopy
monoterpenoids
Origanum - chemistry
Origanum vulgare
Origanum vulgare subsp. hirtum
phenolic acids
phenolic compounds
Phenols - analysis
plant extracts
Plant Extracts - chemistry
Plant Leaves - chemistry
shoots
stereochemistry
Terpenes - analysis
wild relatives
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Summary: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-β-glucopyranoside, thymoquinol 2-O-β-glucopyranoside, thymoquinol 5-O-β-glucopyranoside, thymoquinol 2,5-O-β-diglucopyranoside, 12-hydroxyjasmonic acid, 12-hydroxyjasmonic acid 12-O-β-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-β-glucopyranoside, 12-hydroxyjasmonic acid, and 12-hydroxyjasmonic acid 12-O-β-glucopyranoside were isolated for the first time from Origanum species. Keywords: Origanum vulgare L. ssp. hirtum; Lamiaceae; Nepetoideae; phenolic acids; monoterpene glucosides; phenolic glucosides; hydroxyjasmonic acid
ISSN:0021-8561
1520-5118
DOI:10.1021/jf061477i