title: Enterolosaponins A and B, novel triterpene bisdesmosides from Enterolobium contortisiliquum, and evaluation for their macrophage-oriented cytotoxic activity.
abstract: Two novel triterpene bisdesmosides, designated as enterolosaponin A (1) and B (2), were isolated from Enterolobium contortisiliquum. The chemical structures of 1 and 2 were determined by analysis of their extensive spectroscopic data, as well as hydrolysis followed by chromatographic study. Enterolosaponins have a 2-amino-2-deoxy-D-glucosyl unit (D-glucosamine) as one of the monosaccharides constituting their oligosaccharide moieties, which have been rarely found in natural product research. Enterolosaponin A (1) exhibited a highly selective cytotoxicity against BAC1.2F5 mouse macrophages, and it should be notable that the macrophage death caused by 1 was shown to be neither necrotic nor due to induction of apoptosis from morphology of the died cells, whose cytosol occurred in vacuolation.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan. mimakiy@ps.toyaku.ac.jp
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Mimaki
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Harada
authors.forename: Chiseko
authors.initials: C
authors.lastname: Sakuma
authors.forename: Mitsue
authors.initials: M
authors.lastname: Haraguchi
authors.forename: Satoru
authors.initials: S
authors.lastname: Yui
authors.forename: Tomoya
authors.initials: T
authors.lastname: Kudo
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Yamazaki
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Sashida
mesh_terms: D000818:Animals; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D045744:Cell Line, Tumor; D007887:Fabaceae / Q000737:chemistry*; D005347:Fibroblasts / Q000187:drug effects; D005944:Glucosamine; D008223:Lymphoma / Q000473:pathology; D008264:Macrophages / Q000187:drug effects*; D051379:Mice; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D009844:Oligosaccharides; D012503:Saponins; D014315:Triterpenes; C478749:enterolosaponin A; C478750:enterolosaponin B; D005944:Glucosamine