title: New cardenolides from the seeds of Adonis aestivalis.
abstract: Chemical investigation of the seeds of Adonis aestivalis has led to the isolation of a new cardenolide (3β,5α,14β,17β-tetrahydroxycard-20,22-enolide) (1), two new glycosides (2, 3) of 1, and a new strophanthidin hexaglycoside (4), together with a known compound, strophanthidin 3-O-β-D-glucopyranoside (5). The structures of 1-4 were determined by 1D- and 2D-NMR spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds (1-5) were examined for their cytotoxic activity against neoplastic HSC-2, HSC-3, HSC-4, and HL-60 cells, as well as HGF, HPLF, and HPC normal cell lines. Compounds 2, 4, and 5 were found to display selective cytotoxicity toward malignant tumor cell lines. Although the morphological observations of HL-60 and HSC-2 cell deaths by 2, 4, and 5 revealed changes characteristic of apoptosis, neither DNA degradation nor activation of caspase-3 was observed. Our findings demonstrated that 2, 4, and 5 may trigger caspase-3-independent apoptotic cell death in HL-60 and HSC-2 cells.
authors.affiliation: Department of Medicinal Pharmacognosy, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kubo
authors.forename: Minpei
authors.initials: M
authors.lastname: Kuroda
authors.forename: Yukiko
authors.initials: Y
authors.lastname: Matsuo
authors.forename: Daichi
authors.initials: D
authors.lastname: Masatani
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Mimaki
mesh_terms: D031843:Adonis / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002298:Cardenolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D045744:Cell Line, Tumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D012639:Seeds / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D002298:Cardenolides; D006027:Glycosides