82345-35-5Relevant articles and documents
Affinoside A and Companion Glycosides from the Stem and Bark of Anodendron affine (Anodendron II)
Abe, Fumiko,Yamauchy, Tatsuo
, p. 1183 - 1193 (2007/10/02)
Cardenolide glycosides, affinosides A, C, D, E, F, G, H and J, were isolated from the stem and bark of Anodendron affine DRUCE, and their structures were elucidated.They have the same sugar moiety as affinoside B, 4,6-dideoxy-3-O-methyl-D-glycero-D-glycero-2-hexosulopyranose, which is doubly linked to the 2α- and 3β-hydroxyl groups of the aglycone with 2'-acetal and 1'-anomeric hydroxyl groups, respectively.The aglycone of A was identified as 2α,3β,11α,14-terahydroxy-12-oxo-14β-carda-4,20(22)-dienolide-7β,8β-epoxide.The others were found to be 2α,3β,14-trihydroxy-11-oxo-, 2α,3β,12α,14-tetrahydroxy-11-oxo-, and 2α,3β,5,12α,14-pentahydroxy-11-oxo-5β,14β-card-20(22)-enolide (C, E, and G, respectively), and 2α,3β,12β,14-tetrahydroxy-11-oxo-14β-carda-4,20(22)-dienolide (F).H, D, and J were Δ16-derivatives of A, C, and F, respectively.C was hydrolyzed to the aglycone by preliminary splitting of the 2-O-2' linkage by NaBH4 reduction, followed by treatment with HCl/acetone.Keywords---Anodendron; Apocynaceae; cardenolide; cardiac glycoside; affinoside; 3'-O-methyl-4',6'-dideoxy-2'-hexosulopyranoside; doubly linked cardenolide glycoside; 11-oxo-cardenolide; 12-oxo-cardenolide; 7,8-epoxy-cardenolide