A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of <i>Ipomoea muricata</i>

Abstract

Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3Shydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.

Chemistry and biological activity of resin glycosides from Convolvulaceae species

“…Albinosides VIII ( 16 ) and IX ( 17 ) were derived from albinosinic acids F ( 23 ) and G ( 24 ), respectively, and their lactonization sites were both placed at C‐3 of the second monosaccharide unit, while the two Tga units esterified the saccharide core in the C‐2 on the rhamnose unit and C‐4 on the fucose unit 52 . Ono et al also isolated a glycosidic acid, muricatic acid D, and a new resin glycoside, muricatin X ( 18 ), from the seeds of Ipomoea muricata 53 . Although muricatic acid D has the identical structure with albinosinic acid G ( 24 ), the author claimed that the NMR data of these two glycosidic acids were not consistent.…”

“…Although muricatic acid D has the identical structure with albinosinic acid G ( 24 ), the author claimed that the NMR data of these two glycosidic acids were not consistent. Muricatin X ( 18 ) possessed the same macrolactone structure with albinoside IX ( 17 ), with an Mba residue located at the C‐2 of the rhamnose unit 53 …”

“…Albinosides VI-XI (14-17, 19, and 20) were isolated from the seeds of Ipomoea alba, and were presented as tetrasaccharide macrolactones. [52][53][54] By basic hydrolysis, six new glycosidic acids, albinosinic acids D-I (21-26), were afforded, respectively. 52,54 Albinosinic acid D [21, 11S-…”

“…52 Ono et al also isolated a glycosidic acid, muricatic acid D, and a new resin glycoside, muricatin X (18), from the seeds of Ipomoea muricata. 53 Although muricatic acid D has the identical structure with albinosinic acid G (24), the author claimed that the NMR data of these two glycosidic acids were not consistent. Muricatin X (18) possessed the same macrolactone structure with albinoside IX (17), with an Mba residue located at the C-2 of the rhamnose unit.…”

“…Muricatin X (18) possessed the same macrolactone structure with albinoside IX (17), with an Mba residue located at the C-2 of the rhamnose unit. 53 Albinosinic acids H (25) and I (26) also shared the same oligosaccharide core (one D-quinose, two L-rhamnoses, and one D-fucose units) and different aglycone units [11S-hydroxytetradecanoic acid in albinosinic acid H (25), 11S-hydroxyhexadecanoic acid in albinosinic acid I (26)]. 54 Both of albinosides X (19) and XI (20) contained the lactonization sites at C-3 of the second monosaccharide unit and the two Tga units esterified at the saccharide core in the position C-2 on the second rhamnose unit and C-4 on the fucose unit, respectively.…”