Journal
PHYTOCHEMISTRY
Volume 77, Issue -, Pages 260-267Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2012.01.020
Keywords
Lotaustralin; Hydroxynitrile glucosides; Cyanogenic glucosides; Rhodiocyanosides; Bioactive compounds; Plant defense; 2-Methyl-2-butenenitrile; 3-Methyl-2(5H)-furanone
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Funding
- Danish Research Council for Technology and Production [274-05-0457, 274-08-0532]
- Villum Foundation founded Research Centre Pro-Active Plants
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Lotus japonicus contains the two cyanogenic glucosides, linamarin and lotaustralin, and the non cyanogenic hydroxynitriles, rhodiocyanoside A and D, with rhodiocyanoside A as the major rhodiocyanoside. Rhodiocyanosides are structurally related to cyanogenic glucosides but are not cyanogenic. In vitro administration of intermediates of the lotaustralin pathway to microsomes prepared from selected L.japonicus accessions identified 2-methyl-2-butenenitrile as an intermediate in the rhodiocyanoside biosynthetic pathway. In vitro inhibitory studies with carbon monoxide and tetcyclacis indicate that the conversion of (Z)-2-methylbutanal oxime to 2-methyl-2-butenenitrile is catalyzed by cytochrome P450(s). Carbon monoxide inhibited cyanogenic glucosides as well as rhodiocyanosides synthesis, but inhibition of the latter pathway was much stronger. These results demonstrate that the cyanogenic glucoside and rhodiocyanosides pathways share CYP79D5 to obtain (Z)-2-methylbutanaloxime from L-iso-leucine, whereas the subsequent conversions are catalyzed by different P450s. The aglycon of rhodiocyanoside A forms the cyclic product 3-methyl-2(5H)-furanone. Furanones are known to possess antimicrobial properties indicating that rhodiocyanoside A may have evolved to serve as a phytoanticipin that following beta-glucosidase activation and cyclization of the aglycone formed, give rise to a potent defense compound. (C) 2012 Elsevier Ltd. All rights reserved.
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