Cyanogenic and non-cyanogenic pyridone glucosides from Acalypha indica (Euphorbiaceae) |
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Authors: | Monika Hungeling Frank R Fronczek |
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Institution: | a Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-Universität, Hittorfstraße 56, D-48149 Münster, Germany b Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA |
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Abstract: | Seven cyanopyridone derivatives and one corresponding seco compound have been isolated from a methanolic extract of the inflorescences and leaves of Acalypha indica L. (Euphorbiaceae). The absolute configuration of the main cyanogenic glucoside acalyphin, (−)-(5R,6S)-5-cyano-5-β-d-glucopyranosyloxy-6-hydroxy-4-methoxy-1-methyl-2(5,6-dihydro)-pyridone, was deduced from an X-ray crystallographic study. In addition, the 6R-epimer of acalyphin, epiacalyphin, and the corresponding pair of N-demethyl derivatives were isolated. The corresponding amide of acalyphin and a 1′,2′-glucosyl-fused epiacalyphin amide were isolated from air-dried material. Structural elucidation was performed by means of 1H and 13C NMR-spectra, chiroptical methods such as CD-spectroscopy and optical rotation. Two further corresponding derivatives, an aromatized compound and an open-chain structure, were isolated from the aqueous phase. |
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Keywords: | Euphorbiaceae Acalyphoideae Acalypha indica Cyanogenic glucosides Acalyphin Epiacalyphin Noracalyphin Epimeric pairs Corresponding amides Absolute configuration ar-Acalyphidone seco-Acalyphin |
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