The fundamental structure of cycasin, (methyl-ONN-azoxy)methyl β-D-glucopyranoside

Abstract

CsHI6N20 7 is monoclinic, space group C2, with a = 15. solved by the direct method using three-dimensional X-ray data and refined by the least-squares method to a final R = 0.100 for 849 observed reflexions. In the crystal, a glucosyl part linked to the neighbouring glucosyl moieties by four different hydrogen bonds forms 0567-7408/81 / 112026-04501.00 a double layer parallel to the (001) plane, and the aglycone parts are stretched in a direction perpendicular to the layers and have van der Waals contacts with other molecules.

Chemistry and Biology of Natural Azoxy Compounds

“…Furthermore, macrozamin ( 47 ) was found to be easily converted to cycasin ( 48 ) via hydrolysis . X-ray crystal structures of 47 and 48 confirmed the Z -configuration of the azoxy moiety in both azoxyglycosides. − Ecologically, macrozamin ( 47 ) and cycasin ( 48 ) have been suggested to act as defense agents for cyads against herbivores. , In addition, both compounds have been reported to be neurotoxic, carcinogenic, teratogenic, and mutagenic. ,, The toxic effect has been reported to be derived from the enzymatic hydrolysis of the azoxyglycosides to methylazoxymethanol (49) . Several other azoxyglycosides such as neocycasins, with a common methylazoxymethanol aglycone, have also been reported as minor components in cycads. − …”