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Iridoid glycosides from the leaves of Sambucus ebulus.
J Nat Prod. 2009 Oct; 72(10):1798-803.JN

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.

Authors+Show Affiliations

Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Josef-Moeller-Haus, Innrain 52c, 6020 Innsbruck, Austria.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19795902

Citation

Pieri, Valerio, et al. "Iridoid Glycosides From the Leaves of Sambucus Ebulus." Journal of Natural Products, vol. 72, no. 10, 2009, pp. 1798-803.
Pieri V, Schwaiger S, Ellmerer EP, et al. Iridoid glycosides from the leaves of Sambucus ebulus. J Nat Prod. 2009;72(10):1798-803.
Pieri, V., Schwaiger, S., Ellmerer, E. P., & Stuppner, H. (2009). Iridoid glycosides from the leaves of Sambucus ebulus. Journal of Natural Products, 72(10), 1798-803. https://doi.org/10.1021/np900373u
Pieri V, et al. Iridoid Glycosides From the Leaves of Sambucus Ebulus. J Nat Prod. 2009;72(10):1798-803. PubMed PMID: 19795902.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iridoid glycosides from the leaves of Sambucus ebulus. AU - Pieri,Valerio, AU - Schwaiger,Stefan, AU - Ellmerer,Ernst P, AU - Stuppner,Hermann, PY - 2009/10/3/entrez PY - 2009/10/3/pubmed PY - 2009/12/16/medline SP - 1798 EP - 803 JF - Journal of natural products JO - J Nat Prod VL - 72 IS - 10 N2 - 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. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/19795902/Iridoid_glycosides_from_the_leaves_of_Sambucus_ebulus_ L2 - https://doi.org/10.1021/np900373u DB - PRIME DP - Unbound Medicine ER -