Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana

Abstract

From the MeOH extract of Sideritis trojana, a new iridoid glycoside, 10- O-( E)-feruloylmelittoside ( 1) was obtained in addition to four known iridoid glycosides [melittoside ( 2), 10- O-( E)- p-coumaroylmelittoside ( 3), stachysosides E ( 4) and G ( 5)]. Moreover, five phenylethanoid glycosides [verbascoside ( 6), isoacteoside ( 7), lamalboside ( 8), leonoside A ( 9), isolavandulifolioside ( 10), three flavone glycosides (isoscutellarein 7- O-[6‴- O-acetyl- β-allopyranosyl-(1 → 2)]-β-glucopyranoside ( 11), 4′- O-methyisoscutellarein 7- O-[6‴- O-acetyl- β-allopyranosyl-(1 → 2)]-β-glucopyranoside ( 12), 3′-hydroxy-4′- O-methyisoscutellarein 7- O-[6‴- O-acetyl- β-allopyranosyl-(1 → 2)]-β-glucopyranoside ( 13) and a benzylalcohol derivative (di- O-methylcrenatin) were obtained and identified. The structures were elucidated on the basis of NMR and HRMS data. All compounds were tested for their antioxidant activity by in vitro TEAC assay and some of them exhibited moderate activity (0.97–1.44 mM) when compared with the reference compound (quercetin 1.86 mM). Glycosides 6– 13, the most active compounds in the TEAC assay, were also tested by flow cytometry to evaluate their ability to affect the levels of reactive oxygen species (ROS) in human prostate cancer cells (PC3).