Iridoid Glycosides from the Leaves of Sambucus ebulus

Abstract

Six new iridoid glycosides (1-6) of the "Valeriana type" were isolated from leaves of Sambucus ebulus. The structures were elucidated by 1D- and 2D-NMR spectroscopy, mass spectrometry, and chemical degradation methods as 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (1), 7-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (2), 10-O-acetylpatrinoside-aglycone-11-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (3), patrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (4), 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside] (5), and patrinoside-aglycone-11-O-2'-deoxy-beta-D-glucopyranoside (6). Compounds 1-4 represent the first examples of acylated iridoid diglycosides bearing the uncommon D-ribohexo-3-ulopyranosyl sugar moiety. Compound 6 is the first iridoid glycoside with a 2-deoxy-D-glucopyranosyl sugar moiety.

Wound healing potential of Sambucus ebulus L. leaves and isolation of an active component, quercetin 3-O-glucoside

“…Recently, six new iridoid glycosides of the Valeriana type were isolated from the leaves of the plant (Pieri et al, 2009). In addition to the secondary metabolites, a new family of acidic type 2 (ebulitins ␣, ␤ and ␥) and basic type 1 (ebulin 1) ribosome-inactivating nontoxic protein derivatives (Girbes et al, 1993;De Benito et al, 1995) and dimeric and mucin binding lectins (Rojo et al, 2003) were isolated from the matured leaves.…”

Metabolic differentiations of dwarf elder by NMR-based metabolomics

“…In addition, Sambucus plants accumulate wide range of secondary metabolites, as flavonoids (Yesilada et al, 2014;Zahmanov et al, 2015), anthocyanins (Duymus et al, 2014), phytosterols (Bubulica et al, 2012), triterpenes (Zahmanov et al, 2015) and iridoid glycosides (Pieri et al, 2009), among others. Sambucus plants, however, also accumulate cyanogenic glycosides, as sambunigrin, prunasin, holocalin (Dellagreca et al, 2000).…”

Identification and pharmacological characterization of the anti-inflammatory principal of the leaves of dwarf elder (Sambucus ebulus L.)

“…Unfortunately, the whole work was published without any experimental results concerning the pharmacological part. This rather unclear situation together with the fact that we recently were able to isolate six new iridoid glycosides from the leaves of Sambucus ebulus L. (Pieri et al, 2009) with unknown pharmacological properties prompted us to perform an activity-guided isolation of an ethanolic extract of the leaves of Sambucus ebulus L. in order to identify the anti-inflammatory principal. Since there are several pathways involved in inflammatory processes, e.g.…”