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.
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http://dx.doi.org/10.1016/j.carres.2009.08.021 | DOI Listing |
Molecules
May 2023
Department of Pharmaceutical Biology, Faculty of Pharmacy, University of Surabaya, Surabaya 60293, Indonesia.
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 PDFJ Insect Physiol
November 2015
Department of Chemical Ecology, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany.
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 PDFJ Ethnopharmacol
December 2012
Laboratory of Applied Biotechnologies, Institute of Microbiology, Bulgarian Academy of Sciences, Plovdiv, Bulgaria.
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).
Insect Biochem Mol Biol
June 2012
Biozentrum Grindel, Martin-Luther-King-Platz 3, 20146 Hamburg, Germany.
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 PDFCarbohydr 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.
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