Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha.
The methanol extract of fruiting bodies of the ascomycete Xylaria polymorpha afforded three isopimarane diterpene glycosides, namely, 16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (1), 15-hydroxy-16-alpha-D-mannopyranosyloxyisopimar-7-en-19-oic acid (2), and 16-alpha-D-glucopyranosyloxyisopimar-7-en-19-oic acid (3). Their structures were determined by spectroscopic methods and by single-crystal X-ray analysis. They showed cytotoxicity against human cancer cell lines and exhibited IC50 values ranging from 71 to 607 microM. Further studies on the cytotoxicity of these compounds against HL60 cells demonstrated that they induced apoptosis along with typical DNA fragmentation. It was observed that 2 was less active than 1 and 3.
Shiono
Yoshihito
Y
Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan. yshiono@tds1.tr.yamagata-u.ac.jp
Motoki
Sadayoshi
S
Koseki
Takuya
T
Murayama
Tetsuya
T
Tojima
Masato
M
Kimura
Ken-ichi
K
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D048690:Fruiting Bodies, Fungal / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013098:Xylariales / Q000737:chemistry*
D000970:Antineoplastic Agents; D004224:Diterpenes; D006027:Glycosides