Glycosidic Acids with Unusual Aglycone Units from Convolvulus arvensis

Abstract

Six new glycosidic acids, arvensic acids E–J (1–6), were obtained from a glycosidic acid fraction afforded by alkaline hydrolysis of the crude resin glycosides from Convolvulus arvensis whole plants. Their structures were established from the spectroscopic data obtained and by chemical evidence. They were defined as heptasaccharides or hexasaccharides, comprising d-fucose, d-glucose, and l-rhamnose units. Compounds 1, 3, and 5 were assigned the 11S-hydroxyheptadecanoic acid as the aglycone, while compounds 2, 4, and 6 were found to possess 11S-hydroxyhexadecanoic acid as the aglycone. Compounds 1, 3, and 5 are the first representatives of resin glycosides with 11S-hydroxyheptadecanoic acid as the aglycone.

Dereplication and Quantification of Major Compounds of Convolvulus arvensis L. Extracts and Assessment of Their Effect on LPS-Activated J774 Macrophages

“…C. arvensis is reported to possess antioxidant [8], antiarthritic [9,10], hepatoprotective [11], and hypoglycemic [12] activities. Phytochemical investigation has shown the presence of tropane alkaloids [13], coumarins [12], resin glycosides [14], flavonoids [15], phenolic acids [8], and phytosterols [16] in C. arvensis.…”

Angucycline and angucyclinone derivatives from the marine‐derived Streptomyces sp.

“…Compounds 5 to 12 were identified as SNA-8073-B (5), 17 X-14881 A (6), X-14881 B (7), X-14881 C (rubiginone B2, 8), X-14881 D (9), 18 actinosporin G (10), 13 atramycins A (11), and B (12), 14 respectively, by comparing of their NMR and MS data with those in the literature. 3).…”

Chemistry and biological activity of resin glycosides from Convolvulaceae species

“…Alkaline hydrolysis of the crude resin glycosides from C. arvensis whole plants afforded a series of glycosidic acid, among which four were new hexasaccharide glycosidic acids, arvensic acids G–J ( 185 – 188 ) 34 . Arvensic acids G ( 185 ) and H ( 186 ) have a same heptasacharride core, β ‐ d ‐glucopyranosyl‐(1 → 4)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→6)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ O ‐[ α ‐ l ‐rhamnopyranosyl‐(1→2)]‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→2)‐ O ‐ β ‐ d ‐fucopyranoside, while the oligosaccharide core of arvensic acids H ( 187 ) and I ( 188 ) is β ‐ d ‐fucopyranosyl‐(1→6)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→4)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ O ‐[ α ‐ l ‐rhamnopyranosyl‐(1→2)]‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→2)‐ O ‐ β ‐ d ‐fucopyranoside.…”

“…Arvensic acids G ( 185 ) and H ( 186 ) have a same heptasacharride core, β ‐ d ‐glucopyranosyl‐(1 → 4)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→6)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ O ‐[ α ‐ l ‐rhamnopyranosyl‐(1→2)]‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→2)‐ O ‐ β ‐ d ‐fucopyranoside, while the oligosaccharide core of arvensic acids H ( 187 ) and I ( 188 ) is β ‐ d ‐fucopyranosyl‐(1→6)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→4)‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→3)‐ O ‐[ α ‐ l ‐rhamnopyranosyl‐(1→2)]‐ O ‐ β ‐ d ‐glucopyranosyl‐(1→2)‐ O ‐ β ‐ d ‐fucopyranoside. The aglycone of arvensic acids G ( 185 ) and I ( 187 ) is a rare 11 S ‐hydroxyheptadecanoic acid, which is 11 S ‐hydroxyhexadecanoic acid for arvensic acids H ( 186 ) and J ( 188 ) 34 …”