Traditionally Used Sideritis cypria Post.: Phytochemistry, Nutritional Content, Bioactive Compounds of Cultivated Populations

Abstract

Sideritis species are recognized as important medicinal plants and their commercial demand is continuously on the rise both in the European and in the global market. Consequently, the cultivation of Sideritis species has been occurred to successfully meet the need for mass production of high-quality plant material. The present study was undertaken in order to investigate the chemical composition of cultivated S. cypria. Infusions of flowers and leaves were prepared separately, according to the European Medicine Agency (EMA) monograph. The infusion of the flowers revealed the presence of four flavones, isoscutellarein-7-O-[6′″-O-acetyl-b-D-allopyranosyl-(1!2)-b-Dglucopyranoside, its 4′-O-methyl-derivative, 4′-O-methyl-hypolaetin-7-O-[6′″-O-acetylb-D-allopyranosyl-(1!2)-b-D-glucopyranoside, and isoscutellarein-7-O-[6′″-O-acetyl-b-D-allopyranosyl-(1!2)]-6″-O-acetyl-b-D-glucopyranoside; four phenylethanoid glucosides, acteoside, leucosceptoside A, lamalboside, and leonoside A; one iridoid, melittoside, and one phenolic acid, chlorogenic acid, while the infusion of the leaves of the same population afforded the same first two flavones; five phenylethanoid glucosides, acteoside, leucosceptoside A, lavandulifolioside, leonoside A, and lamalboside; melittoside and chlorogenic acid. The structural elucidation of the isolated compounds was undertaken by high-field NMR spectroscopy. Moreover, the essential oils of the flowers and leaves were studied by GC-MS, separately. In addition, the mineral, bioactive compounds, protein and carbohydrate contents were evaluated for both plant materials.

Bio‐Guided Investigation of Sideritis cypria Methanol Extract Driven by in Vitro Antioxidant and Cytotoxic Assays

“…Moreover, in continuation of our previous study, [7] the infusion of the leaves yielded one iridoid: ajugoside ( 4 ) [32] and two more flavone derivatives: apigenin‐7‐ O ‐β‐D‐glucopyranoside ( 11 ) [15] and apigenin‐7‐ O ‐[6′′‐ O ‐ trans‐p ‐coumaroyl]‐β‐D‐glucopyranoside ( 14 ), [18] while the infusion of the flowers afforded one iridoid: geniposidic acid ( 2 ) [33] and one poly‐hydroxy derivative: polybotrin ( 27 ) [27] (Supporting Information, Table S1 ).…”

“…The presence of apigenin derivatives in S. cypria is also confirmed by the study of Hanoğlu et al [5] . The phenylethanoid glycosides 17 – 21 were previously isolated from S. cypria [5,7] . Nonetheless, compound 22 is isolated for the first time in genus Sideritis .…”

“…Regarding the isolated flavonoid derivatives, five compounds ( 10 – 14 ) were apigenin derivatives and the two compounds 15 , 16 were isoscutellarein and hypolaetin analogues, respectively. Comparing the flavonoid profile of the methanol extract with the infusions previously described, [7] it could be observed that 8‐hydroxyflavone derivatives were more abundant in the infusions, whereas the methanol extract was consisted mostly by 5,7‐dihydroxyflavone analogues. A detailed summary of the overall isolated compounds from both traditional infusions and methanol extract is given, herein ( Table 1).…”

“…In genus Sideritis , it is reported in various species such as S. italica , [38] S. montana , S. syriaca , S. trojana , S. perfoliata subsp. perfoliata , S. euboea and S. cypria [7,39–42] . On the other hand, geniposidic acid ( 2 ) is reported for the first time in S. cypria and there are no data about its presence in other Sideritis species, whereas compounds 3 and 4 were both identified in Sideritis species [43,44] .…”

“…Previous studies have investigated the wild S. cypria [5,6] . The first study on the traditional infusions of flowers and leaves, separately, of cultivated populations was carried out by our groups [7] . Rich phenolic and flavonoid load was observed in both infusions confirming their high antioxidant effects.…”