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Glycosidic Conjugates of C13 Norisoprenoids, Monoterpenoids, and Cucurbates in Boronia megastigma (Nees)


Cooper, CM and Davies, NW and Motti, C and Menary, RC, Glycosidic Conjugates of C13 Norisoprenoids, Monoterpenoids, and Cucurbates in Boronia megastigma (Nees), Journal of Agricultural and Food Chemistry, 59, (6) pp. 2610-2617. ISSN 0021-8561 (2011) [Refereed Article]

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Copyright 2011 American Chemical Society

DOI: doi:10.1021/jf104051t


Analysis of a methanolic extract of marc from Boronia megastigma (Nees) using LC-MS (APCI, nominal mass)provided strong evidence for the presence of both glycosides and malonyl glycosides of methyl cucurbates, C13 norisoprenoids including megastigmanes, and monoterpene alcohols. Subsequent fractionation of an extract from the marc using XAD-2 and LH 20 chromatography followed by LC-UV/MS-SPE-NMR and accurate mass LC-MS resulted in the isolation and identification of (1R,4R,5R)-3,3,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohexyl -D-glucopyranoside (3-hydroxy-5,6-dihydro--ionone--Dglucopyranoside); 3,7-dimethylocta-1,5-diene-3,7-diol-3-O--D-glucopyranoside; and a methyl {(1R)-3-(-D-glucopyranosyloxy)- 2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate stereoisomer (a methyl cucurbate--D-glucopyranoside); and provided evidence for 3,7-dimethylocta-1,5-diene-3,7-diol-3-O-(60-O-malonyl)--D-glucopyranoside in boronia flowers.

Item Details

Item Type:Refereed Article
Research Division:Agricultural, Veterinary and Food Sciences
Research Group:Horticultural production
Research Field:Post harvest horticultural technologies (incl. transportation and storage)
Objective Division:Plant Production and Plant Primary Products
Objective Group:Horticultural crops
Objective Field:Horticultural crops not elsewhere classified
UTAS Author:Cooper, CM (Dr Christopher Cooper)
UTAS Author:Davies, NW (Associate Professor Noel Davies)
UTAS Author:Menary, RC (Professor Robert Menary)
ID Code:65080
Year Published:2011
Web of Science® Times Cited:5
Deposited By:Agricultural Science
Deposited On:2010-09-29
Last Modified:2012-09-19

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