title: Cytotoxic resin glycosides from Ipomoea aquatica and their effects on intracellular Ca2+ concentrations.
abstract: Eleven new resin glycosides, aquaterins I-XI (1-11), were isolated from the whole plants of Ipomoea aquatica. The structures of 1-11 were elucidated by a combination of spectroscopic and chemical methods. They were found to be partially acylated tetra- or pentasaccharides derived from simonic acid B and operculinic acids A and C. The site of the aglycone macrolactonization was placed at C-2 or C-3 of the second saccharide moiety, while the two acylating residues could be located at C-2 (or C-3) of the second rhamnose unit and at C-4 (or C-3) on the third rhamnose moiety. All compounds were evaluated for cytotoxicity against a small panel of human cancer cell lines. Compound 4 exhibited the most potent activity against HepG2 cells with an IC50 value of 2.4 μM. Cell cycle analysis revealed 4 to inhibit the proliferation of HepG2 cells via G0/G1 arrest and apoptosis induction. In addition, compounds 1-4, 7, 9, and 10 were found to elevate Ca(2+) in HepG2 cells, which might be involved in the regulation of the cytotoxic activities observed.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
authors.forename: Bo-Yi
authors.initials: BY
authors.lastname: Fan
authors.forename: Yu-Cheng
authors.initials: YC
authors.lastname: Gu
authors.forename: Ye
authors.initials: Y
authors.lastname: He
authors.forename: Zhong-Rui
authors.initials: ZR
authors.lastname: Li
authors.forename: Jian-Guang
authors.initials: JG
authors.lastname: Luo
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D056945:Hep G2 Cells; D006801:Humans; D027741:Ipomoea / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D006027:Glycosides; D009844:Oligosaccharides; D012116:Resins, Plant; C482480:operculinic acid