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Triterpene glycosides from Astragalus icmadophilus. 2010

Ibrahim Horo, and Erdal Bedir, and Angela Perrone, and Fevzi Ozgökçe, and Sonia Piacente, and Ozgen Alankuş-Calişkan
Ege University, Faculty of Science, Department of Chemistry, Bornova, Izmir, Turkey.

Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxy cycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3,4-diacetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.

UI MeSH Term Description Entries
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014315 Triterpenes A class of terpenes (the general formula C30H48) formed by the condensation of six isoprene units, equivalent to three terpene units. Triterpene,Triterpenoid,Triterpenoids
D014421 Turkey Country in Southeastern Europe and Southwestern Asia bordering the Black Sea, between Bulgaria and Georgia, and bordering the Aegean Sea and the Mediterranean Sea, between Greece and Syria. The capital is Ankara. Turkiye
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D019906 Nuclear Magnetic Resonance, Biomolecular NMR spectroscopy on small- to medium-size biological macromolecules. This is often used for structural investigation of proteins and nucleic acids, and often involves more than one isotope. Biomolecular Nuclear Magnetic Resonance,Heteronuclear Nuclear Magnetic Resonance,NMR Spectroscopy, Protein,NMR, Biomolecular,NMR, Heteronuclear,NMR, Multinuclear,Nuclear Magnetic Resonance, Heteronuclear,Protein NMR Spectroscopy,Biomolecular NMR,Heteronuclear NMR,Multinuclear NMR,NMR Spectroscopies, Protein,Protein NMR Spectroscopies,Spectroscopies, Protein NMR,Spectroscopy, Protein NMR
D027883 Astragalus Plant A plant genus in the family FABACEAE, subfamily Papilionaceae, order Fabales, subclass Rosidae. Many of the species are associated with poisoning of grazing animals. Some of the species are used medicinally. Milk Vetch,Locoweed, Wooly,Astragalus Plants,Locoweeds, Wooly,Milk Vetchs,Plant, Astragalus,Plants, Astragalus,Vetch, Milk,Vetchs, Milk,Wooly Locoweed,Wooly Locoweeds

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