title: A new resin glycoside from Calystegia soldanella and its antiviral activity towards herpes.
abstract: A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-β-d-glucopyranosyl-(1 → 3)-O-(2-O-2S-methylbutyryl,4-O-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 → 2)-[O-β-d-glucopyranosyl-(1 → 6)-O-(34-di-O-2S-methylbutyryl)-β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 2)-β-d-quinovopyranoside, intramolecular 1,2″'″'-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC50value 2.3 μM.
authors.affiliation: a School of Agriculture, Tokai University , Kumamoto , Japan.
authors.forename: Masateru
authors.initials: M
authors.lastname: Ono
authors.affiliation: a School of Agriculture, Tokai University , Kumamoto , Japan.
authors.forename: Yukiyo
authors.initials: Y
authors.lastname: Kanemaru
authors.affiliation: a School of Agriculture, Tokai University , Kumamoto , Japan.
authors.forename: Shin
authors.initials: S
authors.lastname: Yasuda
authors.affiliation: b Faculty of Pharmaceutical Sciences , Fukuoka University , Fukuoka , Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Okawa
authors.affiliation: b Faculty of Pharmaceutical Sciences , Fukuoka University , Fukuoka , Japan.
authors.forename: Junei
authors.initials: J
authors.lastname: Kinjo
authors.affiliation: c Faculty of Pharmaceutical Sciences , Sojo University , Kumamoto , Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Miyashita
authors.affiliation: c Faculty of Pharmaceutical Sciences , Sojo University , Kumamoto , Japan.
authors.forename: Kazumi
authors.initials: K
authors.lastname: Yokomizo
authors.affiliation: c Faculty of Pharmaceutical Sciences , Sojo University , Kumamoto , Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Yoshimitsu
authors.affiliation: c Faculty of Pharmaceutical Sciences , Sojo University , Kumamoto , Japan.
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D031253:Calystegia / Q000737:chemistry*; D002522:Chlorocebus aethiops; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry*; D014709:Vero Cells
chemical_list: D000998:Antiviral Agents; D006027:Glycosides; D012116:Resins, Plant
keywords: 3-hydroxy-2-methylenebutyric acid; Calystegia soldanella; Convolvulaceae; Resin glycoside; antiviral activity; calysolin