ABSTRACT
In the present study, three compounds were isolated from Argyreia acuta, among them, compounds 1 and 2 were new and Compounds 1 and 3 were isomers. They were separated by several types of columns, such as normal phase, RP, size exclusion and preparative HPLC, and their structures were elucidated by several spectroscopic methods, such as 1D- and 2D-NMR and HR-TOF-MS.
Subject(s)
Convolvulaceae/chemistry , Glycosides/chemistry , Resins, Plant/chemistry , Drugs, Chinese Herbal/chemistry , Glycosides/isolation & purification , Isomerism , Mass Spectrometry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial/chemistry , Resins, Plant/isolation & purification , SpectrophotometryABSTRACT
Four pentasaccharide resin glycosides, acutacoside F-I (1-4), were isolated from the aerial parts of Argyreia acuta. These compounds were characterized as a group of macrolactones of operculinic acid A, and their lactonization site of 11S-hydroxyhexadecanoic acid was esterified at the second saccharide moiety (Rhamnose) at C-2. The absolute configuration of the aglycone was S. Their structures were elucidated by established spectroscopic and chemical methods.
Subject(s)
Glycosides/chemistry , Ipomoea/chemistry , Lactones/chemistry , Oligosaccharides/chemistry , Resins, Plant/chemistry , Glycosides/isolation & purification , Lactones/isolation & purification , Molecular Structure , Oligosaccharides/isolation & purification , Palmitic Acids/chemistry , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Rhamnose/chemistryABSTRACT
Three new phenolic compounds, acutacoside C (1), acutacoside D (2) and acutacoside E (3) were isolated from the aerial part of Argyreia acuta. The oligosaccharide chain was composed of two glucoses and three rhamnoses, and the aglycone was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). The core of the three compounds was operculinic acid B, which was rare in resin glycosides. Their structures were established by a combination of spectroscopic and chemical methods. Compounds 1-3 have been evaluated for inhibitory activity against α-glucosidase, which all showed weak inhibitory activities.
Subject(s)
Convolvulaceae/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Glycosides/isolation & purification , Resins, Plant/isolation & purification , Glycosides/chemistry , Glycosides/pharmacology , Plant Components, Aerial/chemistry , Resins, Plant/chemistry , Resins, Plant/pharmacologyABSTRACT
In the present study, two new compounds from Ipomoea cairica were identified and demonstrated to have α-glucosidase inhibitory activity. They were isolated by column chromatography on silica gel and sephadex LH-20 and finally purified by prep-HPLC, with their structures being elucidated by spectroscopic methods, such as 1D- and 2D-NMR and HR-TOF-MS, and chemical methods. Compounds 1 and 2, named cairicoside A and cairicoside B, were evaluated for α-glucosidase inhibitory activity by the MTT method, with the IC50 values being 25.3 ± 1.6 and 28.5 ± 3.3 µmol·L(-1), respectively.
Subject(s)
Glycoside Hydrolase Inhibitors/pharmacology , Ipomoea/chemistry , Plant Extracts/pharmacology , Resins, Plant/pharmacology , Glycoside Hydrolase Inhibitors/isolation & purification , Molecular Structure , Resins, Plant/isolation & purification , Spectrum Analysis , alpha-GlucosidasesABSTRACT
Two new compounds of acutacosides 1 and 2, pentasaccharide resin glycosides were isolated from the aerial parts of Argyreia acuta. The core of the two compounds was operculinic acid A, and they were esterfied at the same position, just one substituent group was linked at C-2 of Rha. The absolute configuration of the aglycone in the two compounds was established by Mosher's method, which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). Their structures were established by a combination of spectroscopic and chemical methods.
Subject(s)
Convolvulaceae/chemistry , Oligosaccharides/chemistry , Resins, Plant/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Oligosaccharides/isolation & purification , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Plants, Medicinal/chemistryABSTRACT
Six pentasaccharide resin glycosides from Ipomoea cairica, including four new acylated pentasaccharide resin glycosides, namely cairicoside I-IV (1-4) and the two known compounds cairicoside A (5) and cairicoside C (6), were isolated from the aerial parts of Ipomoea cairica. Their structures were established by a combination of spectroscopic, including two dimensional (2D) NMR and chemical methods. The core of the six compounds was simonic acid A, and they were esterfied the same sites, just differing in the substituent groups. The lactonization site of the aglycone was bonded to the second saccharide moiety at C-2 in 1-4, and at C-3 in 5-6. Compounds 1 and 5, 4 and 6 were two pairs of isomers. The absolute configuration of the aglycone in 1-6 which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid) was established by Mosher's method. Compounds 1-4 have been evaluated for inhibitory activity against α-glucosidase, which all showed inhibitory activities.