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Hepta‐, hexa‐, penta‐, tetra‐, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines
Author(s) -
LeónRivera Ismael,
RíoPortilla Federico,
Enríquez Raúl G.,
RangelLópez Edgar,
Villeda Juana,
Rios María Yolanda,
NavarreteVázquez Gabriel,
HurtadoDías Israel,
GuzmánValdivieso Ulises,
NúñezUrquiza Verónica,
EscobedoMartínez Carolina
Publication year - 2017
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4476
Subject(s) - chemistry , trisaccharide , stereochemistry , convolvulaceae , glycoside , tetrasaccharide , hexa , rhamnose , sialic acid , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , glycosidic bond , biochemistry , galactose , enzyme , polysaccharide , paleontology , biology
Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga , Ipomoea stans , and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1–6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B ( 1 ) consists of a hexasaccharide core bonded to an 11‐hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2‐methylbutanoyl, a 3‐hydroxy‐2‐methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A ( 2 ) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3‐hydroxy‐2‐methylbutanoyl unit. Stansin A ( 4 ) is an ester‐type heterodimer, and consists of two stansoic acid A ( 3 ) units, acylated by 2‐methylbutanoic and 3‐hydroxy‐2‐methylbutanoic acids. The site of lactonization was located at C‐3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C‐4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II ( 5 ) is composed of a pentasaccharide core bonded to an 11‐hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I ( 6 ) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2‐methylbutanoyl and 3‐hydroxy‐2‐methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1–6 toward OVCAR and UISO‐SQC‐1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright © 2016 John Wiley & Sons, Ltd.