Dracotanosides A−D, Spermidine Glycosides from Dracocephalum tanguticum: Structure and Amide Rotational Barrier

Abstract

Four new spermidine glycosides, dracotanosides A-D (1-4), have been isolated from Dracocephalum tanguticum. These molecules represent the first spermidine glycosides from this plant genus. The structures, including absolute configurations, were determined by spectroscopic and chemical methods. The amide bond rotational barrier of aglycone 1a was calculated by density functional theory (DFT) computation.

Cyclic Spermidine Alkaloids and Flavone Glycosides from Meehania fargesii

“…27,28) Polyamine alkaloids have a rich diversity of skeletons and biological activities. 21,34,35) The 13-membered ring moieties of 1 and 2 were a periphylline-type skeleton, and different from that of cyclic spermidine alkaloidal glycosides from M. urticifolia, which have a celacinnine-type skeleton. Periphylline and celacinnine had been isolated from Celastraceae plants.…”

New glycosides from Dracocephalum tanguticum maxim

“…Previous studies on this plant revealed the presence of triterpenoids (Zhang et al, 1994;Li, 2006;Li and Jia, 2006;Zheng et al, 2007), steroids (Zhang et al, 1994;Li and Jia, 2006), flavonoids (Zhang et al, 1994;Li, 2006;Liu et al, 2009), alkaloids (Wang et al, 2009), lignans (Li, 2006), and coumarins (Zhang et al, 1994). In this paper, we report the isolation and structural elucidation of four new glycosides (1-4) from D. tanguticum, together with three known compounds: benzyl-β-D-glucopyranoside (5), 2-methoxy-4-(2-propen-1-yl)penyl-β-D-glucopyranoside (6), and pectolarigenin (7) (Fig.…”

Chemical Constituents of Plants from the Genus Dracocephalum

“…Four spermidine alkaloid glycosides, dracotanosides A -D (218 -221, resp. ), were isolated from whole plant of D. tanguticum [43]. bovine brain-derived phospholipids against HO .…”