title: Hepta-, hexa-, penta-, tetra-, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines.
abstract: 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.
authors.affiliation: Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: Ismael
authors.initials: I
authors.lastname: León-Rivera
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, Estados Unidos Mexicanos.
authors.forename: Federico
authors.initials: F
authors.lastname: Del Río-Portilla
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, Estados Unidos Mexicanos.
authors.forename: Raúl G
authors.initials: RG
authors.lastname: Enríquez
authors.affiliation: Laboratorio de Amino Ácidos Excitadores, Instituto Nacional de Neurología y Neurocirugía, Ciudad de México, Estados Unidos Mexicanos.
authors.forename: Edgar
authors.initials: E
authors.lastname: Rangel-López
authors.affiliation: Laboratorio de Patología, Instituto Nacional de Neurología y Neurocirugía, Ciudad de México, Estados Unidos Mexicanos.
authors.forename: Juana
authors.initials: J
authors.lastname: Villeda
authors.affiliation: Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: María Yolanda
authors.initials: MY
authors.lastname: Rios
authors.affiliation: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Navarrete-Vázquez
authors.affiliation: Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: Israel
authors.initials: I
authors.lastname: Hurtado-Días
authors.affiliation: Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: Ulises
authors.initials: U
authors.lastname: Guzmán-Valdivieso
authors.affiliation: Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, Estados Unidos Mexicanos.
authors.forename: Verónica
authors.initials: V
authors.lastname: Núñez-Urquiza
authors.affiliation: Departamento de Farmacia, Universidad de Guanajuato, Guanajuato, Guanajuato, Estados Unidos Mexicanos.
authors.forename: Carolina
authors.initials: C
authors.lastname: Escobedo-Martínez
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D005910:Glioma; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D027741:Ipomoea / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D006027:Glycosides; D009844:Oligosaccharides; D010936:Plant Extracts
keywords: Ipomoea murucoides; Ipomoea purga; Ipomoea stans; cytotoxicity; glioma; resin glycoside