Cargando…

Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity

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 es...

Descripción completa

Detalles Bibliográficos
Autores principales: Pan, Jie-Tao, Yu, Bang-Wei, Yin, Yong-Qin, Li, Jie-Hong, Wang, Li, Guo, Li-Bing, Shen, Zhi-Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272348/
https://www.ncbi.nlm.nih.gov/pubmed/25875039
http://dx.doi.org/10.3390/molecules20046601
_version_ 1783377136081436672
author Pan, Jie-Tao
Yu, Bang-Wei
Yin, Yong-Qin
Li, Jie-Hong
Wang, Li
Guo, Li-Bing
Shen, Zhi-Bin
author_facet Pan, Jie-Tao
Yu, Bang-Wei
Yin, Yong-Qin
Li, Jie-Hong
Wang, Li
Guo, Li-Bing
Shen, Zhi-Bin
author_sort Pan, Jie-Tao
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6272348
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62723482018-12-03 Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity Pan, Jie-Tao Yu, Bang-Wei Yin, Yong-Qin Li, Jie-Hong Wang, Li Guo, Li-Bing Shen, Zhi-Bin Molecules Article 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. MDPI 2015-04-14 /pmc/articles/PMC6272348/ /pubmed/25875039 http://dx.doi.org/10.3390/molecules20046601 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pan, Jie-Tao
Yu, Bang-Wei
Yin, Yong-Qin
Li, Jie-Hong
Wang, Li
Guo, Li-Bing
Shen, Zhi-Bin
Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title_full Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title_fullStr Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title_full_unstemmed Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title_short Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
title_sort four new pentasaccharide resin glycosides from ipomoea cairica with strong α-glucosidase inhibitory activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272348/
https://www.ncbi.nlm.nih.gov/pubmed/25875039
http://dx.doi.org/10.3390/molecules20046601
work_keys_str_mv AT panjietao fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT yubangwei fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT yinyongqin fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT lijiehong fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT wangli fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT guolibing fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity
AT shenzhibin fournewpentasaccharideresinglycosidesfromipomoeacairicawithstrongaglucosidaseinhibitoryactivity