PMID: 11336260May 5, 2001Paper

Transformation of naturally-occurring 1,9-trans-9,5-cis sweroside to all trans sweroside during acetylation of sweroside aglycone

Phytochemistry
M M HornA D Mathekga

Abstract

From the rootstock of Scabiosa columbria L. loganin and sweroside were isolated. Sweroside showed moderate antibacterial activity. Pure sweroside was converted to the sweroside aglycone 1-acetoxy derivative (DABCO/Ac2O) after hydrolysis of the glucose unit. X-ray crystallography of the monoacetate showed unambiguously that it had been transformed to a new seco-iridoid having the novel trans diaxial configuration for the protons on C-1, C-9 and C-5. The mechanism for the rearrangement is discussed.

References

Jun 1, 1996·Journal of Ethnopharmacology·A K JägerJ van Staden
Mar 1, 1981·Planta medica·W G van der Sluis, R P Labadie
Nov 1, 1980·Journal of Natural Products·L J El-Naggar, J L Beal

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Citations

Feb 23, 2008·Chemistry & Biodiversity·Clio ChristopoulouIoanna Chinou
Apr 7, 2015·International Journal of Biological Macromolecules·Malek Besbes HlilaBoulbaba Selmi
Jan 26, 2008·Organic & Biomolecular Chemistry·Anne T StevensKelly Chibale
Nov 28, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fang-Pin ChangYueh-Hsiung Kuo
Sep 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fang-Pin ChangYueh-Hsiung Kuo

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