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Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida

Fan, Peihong
Hay, Anne-Emmanuelle
Marston, Andrew
Published in Pharmaceutical Biology. 2008, vol. 46, no. 9, p. 596 - 601
Abstract In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier Levier (Apiaceae), Buddleja davidii Franch. (Buddlejaceae), and Ambrosia artemisiifolia L. (Asteraceae) was prescreened by a bioautographic TLC assay. Activity was found in the methanol extract of the leaves of the common ornamental bush B. davidii. Its fractionation by centrifugal partition chromatography led to the isolation of linarin as the most active compound. While extracts of Buddleja nitida Benth. (Buddlejaceae) from Panama were inactive, some constituents were identified on the basis of a comparison with B. davidii by HPLC-MS/MS. Structure-activity relationships of linarin and related flavonoids were investigated. For this purpose, fortunellin and tilianin were prepared by methylation reactions. It appears that the structural elements important for acetylcholinesterase inhibition are not only the 4' -OMe group, but also the 7-substituted sugar and the pattern of substitution on the B-ring.
Keywords Acetylcholinesterase inhibitionBuddleja davidiiBuddleja nitidaInvasive plantsLinarin
Stable URL http://archive-ouverte.unige.ch/unige:11006
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