New neuroprotective dibenzylbutane lignans isolated from Machilus thunbergii

Two new dibenzylbutane lignans, namely rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″R)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate (1) and rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″S)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate (2), were isolated from the...

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Bibliographic Details
Published in:Natural product research 2010-04, Vol.24 (6), p.562-568
Main Authors: Je Ma, Choong, Sung, Sang Hyun, Choong Kim, Young
Format: Article
Language:English
Subjects:
Animals
Biological Assay
Cells, Cultured
Drug Evaluation, Preclinical
Female
Lauraceae - chemistry
lignans
Lignans - chemistry
Lignans - isolation & purification
Machilus thunbergii
neuroprotective
Neuroprotective Agents - isolation & purification
Plant Bark - chemistry
Rats
Rats, Sprague-Dawley
rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″R)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate
rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″S)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate
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Summary:Two new dibenzylbutane lignans, namely rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″R)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate (1) and rel-methyl (2S)-2-hydroxy-2-2′-((2″R,3″S)-4″-guaiacyl-2″,3″dimethylbutyl)-5′-oxo-2′,5′-dihydro-2-furanylethnoate (2), were isolated from the bark of Machilus thunbergii. Their structures were elucidated by spectral analysis. These two lignans exerted significant neuroprotective activities against glutamate-induced neurotoxicity in primary cultures of rat cortical cells. Compounds 1 and 2 represent a new type of lignan skeleton that has not been reported so far from nature.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786410902823279