Calysolins I–IV, Resin Glycosides from Calystegia soldanella

Abstract

Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella , along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.

Five New Nortriterpenoid Glycosides from the Bulbs of <i>Scilla scilloides</i>

“…All instruments and materials used were the same as cited in a previous report 16) unless otherwise specified. Plant Material The bulbs of S. scilloides were cultivated in Kumamoto prefecture, Japan, and were harvested in August 2005, and identified by one of authors (T. Nohara).…”

Calysolins X–XIII, Resin Glycosides from <i>Calystegia soldanella</i>, and Their Antiviral Activity toward Herpes Simplex Virus

“…In addition, the HR-positive-ion FAB-MS of the peracetate (4a) of 4 revealed a fragment ion peak at m/z 371.1337, which was assigned to the fragment ion of the 6-O-tigloyl-2,3,4-O-triacetyl-glucopyranosyl unit. 4) Consequently, 4 was determined to be a 11S-jalapinolic acid 11-O- Fig. 1.…”

“…4,5) As a part of an ongoing study of the resin glycosides from this plant, the current study deals with the isolation and structural elucidation of four new resin glycosides named calysolins X (1)-XIII (4). Additionally, the antiviral activity of 1-4 toward HSV-1 is described herein.…”

Calysolins V–IX, Resin Glycosides from <i>Calystegia soldanella</i> and Their Antiviral Activity toward Herpes

“…4) As part of an ongoing study of the resin glycosides from this plant, the present report deals with the isolation and structural elucidation of five new resin glycosides named calysolins V-IX. Additionally, the antiviral activity of calysolins I-IX and soldanelline B toward herpes simplex virus type 1 (HSV-1) 5) is described.…”

“…The obtained extract was suspended in H 2 O and then extracted successively with ethyl acetate and n-butanol. The ethyl acetate-soluble fraction was subjected to silica gel column chromatography and HPLC on octadecyl silica (ODS) and naphthylethyl group bonded silica to yield five resin glycosides (1)(2)(3)(4)(5). H-NMR spectrum with that of an authentic sample.…”