Iridoid glycosides from the leaves of Sambucus ebulus.
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.
Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Josef-Moeller-Haus, Innrain 52c, 6020 Innsbruck, Austria.
Valerio
V
Pieri
Stefan
S
Schwaiger
Ernst P
EP
Ellmerer
Hermann
H
Stuppner
D001317:Austria; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D027923:Sambucus / Q000737:chemistry*
D006027:Glycosides; D039823:Iridoids