Extraction and Characterization of Glucosinolates and Isothiocyanates from Rape Seed Meal

被引:9
作者
Ishikawa, Shota [1 ]
Maruyama, Atsushi [1 ]
Yamamoto, Yukihiro [1 ]
Hara, Setsuko [1 ]
机构
[1] Seikei Univ, Fac Sci & Technol, Musashino, Tokyo 1808633, Japan
关键词
rape seed meal; glucosinolate; isothiocyanate; myrosinase; BRASSICA; 3-BUTENYL;
D O I
10.5650/jos.ess13170
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
While some isothiocyanate (ITCs) are attractive targets for the agricultural and pharmaceutical industries, the presence of goitrin and ITCs has hampered the widespread utilization of rapeseed meal. ITCs are the products of the myrosinase-mediated hydrolysis of glucosinolate (GSLs). As such, a study was conducted in order to gain a better understanding into the identity of the GSLs contained in rapeseed meal. Extraction of the GSLs was carried out with 20% ethanol, affording 3.0% GSL content. The resulting GSL extracts were purified via silica gel column chromatography resulting in the isolation of main three pure GLSs (GSL A, B, and C) and a final GSL content of 39.8%. The indirect-identification of the GSLs in rapeseed meal was also carried out via GC/MS analysis of ITCs. The GSLs, progoitrin and gluconapin, were present in the highest concentration in these extracts. Interestingly, only goitrin was produced when GSL A was the substrate for the defatted rapeseed meal mediated hydrolysis reaction. This indicates GSL A is a progoitrin. Conversely, 3-butenyl ITC was produced only when GSL B was used as substrate, indicating GSL B is gluconapin. These results will be helpful for opening the doors for the use of rapeseed meal in the agricultural or pharmaceutical sectors.
引用
收藏
页码:303 / 308
页数:6
相关论文
共 16 条
[1]   Effect of cruciferous vegetables on lung cancer in patients stratified by genetic status: a mendelian randomisation approach [J].
Brennan, P ;
Hsu, CC ;
Moullan, N ;
Szeszenia-Dabrowska, N ;
Lissowska, J ;
Zaridze, D ;
Rudnai, P ;
Fabianova, E ;
Mates, D ;
Bencko, V ;
Foretova, L ;
Janout, V ;
Gemignani, F ;
Chabrier, A ;
Hall, J ;
Hung, RJ ;
Boffetta, P ;
Canzian, F .
LANCET, 2005, 366 (9496) :1558-1560
[2]  
Enami RH., 2011, J FISH AQUAT SCI, V6, P22
[3]   THE STRUCTURES OF SINIGRIN AND SINALBIN - AN ENZYMATIC REARRANGEMENT [J].
ETTLINGER, MG ;
LUNDEEN, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :4172-4173
[4]  
Fowke JH, 2003, CANCER RES, V63, P3980
[5]   Inhibition of carcinogenesis by isothiocyanates [J].
Hecht, SS .
DRUG METABOLISM REVIEWS, 2000, 32 (3-4) :395-411
[6]   PRELIMINARY EXAMINATION OF ALLYL ISOTHIOCYANATE VAPOR FOR FOOD PRESERVATION [J].
ISSHIKI, K ;
TOKUOKA, K ;
MORI, R ;
CHIBA, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (09) :1476-1477
[7]   Evaluation of Antibacterial Activity of 3-Butenyl, 4-Pentenyl, 2-Phenylethyl, and Benzyl Isothiocyanate in Brassica Vegetables [J].
Jang, Miran ;
Hong, Eunyoung ;
Kim, Gun-Hee .
JOURNAL OF FOOD SCIENCE, 2010, 75 (07) :M412-M416
[8]  
KAWAKISHI S, 1985, NIPPON SHOKUHIN KOGY, V32, P836
[9]   PRELIMINARY-OBSERVATIONS ON THE EFFECT OF DIETARY BRUSSELS-SPROUTS ON THYROID-FUNCTION [J].
MCMILLAN, M ;
SPINKS, EA ;
FENWICK, GR .
HUMAN TOXICOLOGY, 1986, 5 (01) :15-19
[10]   TRPA1 Contributes to the Acute Inflammatory Response and Mediates Carrageenan-Induced Paw Edema in the Mouse [J].
Moilanen, Lauri J. ;
Laavola, Mirka ;
Kukkonen, Meiju ;
Korhonen, Riku ;
Leppanen, Tiina ;
Hogestatt, Edward D. ;
Zygmunt, Peter M. ;
Nieminen, Riina M. ;
Moilanen, Eeva .
SCIENTIFIC REPORTS, 2012, 2