Enterolosaponins A and B, novel triterpene bisdesmosides from Enterolobium contortisiliquum, and evaluation for their macrophage-oriented cytotoxic activity.
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.
Mimaki
Yoshihiro
Y
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan. mimakiy@ps.toyaku.ac.jp
Harada
Hiroshi
H
Sakuma
Chiseko
C
Haraguchi
Mitsue
M
Yui
Satoru
S
Kudo
Tomoya
T
Yamazaki
Masatoshi
M
Sashida
Yutaka
Y
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*
D009844:Oligosaccharides; D012503:Saponins; D014315:Triterpenes; C478749:enterolosaponin A; C478750:enterolosaponin B; D005944:Glucosamine