A dimeric pyrrocidine from Neonectria ramulariae is an inhibitor of prolyl oligopeptidase

Four novel alkaloids, bispyrrocidine (5), the epoxy derivative of pyrrocidine B (6), 19-O-methyl-pyrrrocidine B (7) and 19-O-ethyl-pyrrrocidine B (8) were isolated from the endophytic fungus Neonectria ramulariae Wollenw KS-246. Compound 5 showed inhibitory activity against prolyl oligopeptidase in...

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Published in:Phytochemistry letters 2012-03, Vol.5 (1), p.91-95
Main Authors: Shiono, Yoshihito, Kosukegawa, Azusa, Koseki, Takuya, Murayama, Tetsuya, Kwon, Eunsang, Uesugi, Shota, Kimura, Ken-ichi
Format: Article
Language:English
Subjects:
alkaloids
Bispyrrocidine
cytotoxicity
Endophyte
endophytes
epoxides
fungi
inhibitory concentration 50
Neonectria
Neonectria ramulariae
nuclear magnetic resonance spectroscopy
Prolyl oligopeptidase inhibitor
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Summary:Four novel alkaloids, bispyrrocidine (5), the epoxy derivative of pyrrocidine B (6), 19-O-methyl-pyrrrocidine B (7) and 19-O-ethyl-pyrrrocidine B (8) were isolated from the endophytic fungus Neonectria ramulariae Wollenw KS-246. Compound 5 showed inhibitory activity against prolyl oligopeptidase in a non-competitive manner. [Display omitted] ► Four novel pyrrocidine alkaloids were isolated from Neonectria ramulariae. ► The epoxy derivative of pyrrocidine B, exhibited cytotoxicity against HL60 cells. ► Bispyrrocidine showed inhibitory activity against prolyl oligopeptidase. Four novel alkaloids, bispyrrocidine (5), the epoxy derivative of pyrrocidine B (6), 19-O-methyl-pyrrrocidine B (7) and 19-O-ethyl-pyrrrocidine B (8) were isolated from the endophytic fungus Neonectria ramulariae Wollenw KS-246. Their structures were elucidated using 1D- and 2D-NMR spectroscopy. Compound 6 exhibited cytotoxicity against HL60 cells (IC50 4.6μM), whereas 5 showed specific inhibitory activity against prolyl oligopeptidase (IC50 2.6μM) in a non-competitive manner.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2011.10.008