X-ray crystal structure of iridoid glucoside aucubin and its aglycone.

Carbohydr Res

Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi'an, Shaanxi 710069, PR China.

Published: November 2009

X-ray diffraction analyses of iridoid glycoside aucubin (1) and its aglycone aucubigenin (2) are reported. It was found that crystals of 1 are orthorhombic, with P2(1)2(1)2(1) space group, both cyclopentane ring and pyran ring adopt envelope conformations, and the Glc moiety is in the (4)C(1) conformation. Crystals of 2 are monoclinic, with space group P2(1), the cyclopentane and pyran rings also adopt the envelope conformation. The absolute configurations of 1 and 2 were also determined. Intensive O-H . . . O hydrogen bonds in both crystal lattices were observed.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.carres.2009.08.021DOI Listing

Publication Analysis

Top Keywords

aucubin aglycone
8
space group
8
adopt envelope
8
x-ray crystal
4
crystal structure
4
structure iridoid
4
iridoid glucoside
4
glucoside aucubin
4
aglycone x-ray
4
x-ray diffraction
4

Similar Publications

Aucubin is an iridoid glycoside widely spread in the families , , , , , , , and . This review is intended to provide data on the physicochemical characteristics, isolation methods, and biological activities of aucubin and its producing plants. Aucubin is unstable and can be deglycosylated into its aglycone, aucubigenin.

View Article and Find Full Text PDF

Iridoid glycosides are plant defence compounds with potentially detrimental effects on non-adapted herbivores. Some plant species possess β-glucosidases that hydrolyse iridoid glycosides and thereby release protein-denaturing aglycones. To test the hypothesis that iridoid glycosides and plant β-glucosidases form a dual defence system, we used Plantago lanceolata and a polyphagous caterpillar species.

View Article and Find Full Text PDF

Ethnopharmacological Relevance: Verbascum xanthophoeniceum is a representative of mullein species with a strong tradition of use in folk medicine as a remedy in inflammatory and infectious contexts. This plant accumulates phenylethanoid and iridoid metabolites with a partially characterized bioactivity.

Materials And Methods: Here, we compared anti-inflammatory effects of Verbascum xanthophoeniceum crude extract, its fractions, isolated iridoid glycosides, including aucubin, ajugol, harpagide, harpagoside, nigroside III and nigroside VI, and phenylethanoid glycosides verbascoside and forsythoside B in primary cultures of normal human keratinocytes (NHK).

View Article and Find Full Text PDF

Herbivores with polyphagous feeding habits must cope with a diet that varies in quality. One of the most important sources of this variation in host plant suitability is plant secondary chemistry. We examined how feeding on plants containing one such group of compounds, the iridoid glycosides, might affect the growth and enzymatic activity in a polyphagous caterpillar that feeds on over 80 plant species in 50 different families.

View Article and Find Full Text PDF

X-ray crystal structure of iridoid glucoside aucubin and its aglycone.

Carbohydr Res

November 2009

Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi'an, Shaanxi 710069, PR China.

X-ray diffraction analyses of iridoid glycoside aucubin (1) and its aglycone aucubigenin (2) are reported. It was found that crystals of 1 are orthorhombic, with P2(1)2(1)2(1) space group, both cyclopentane ring and pyran ring adopt envelope conformations, and the Glc moiety is in the (4)C(1) conformation. Crystals of 2 are monoclinic, with space group P2(1), the cyclopentane and pyran rings also adopt the envelope conformation.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!