C8-C10 methylsulfinylalkyl glucosinolates (GLs), and C8-C10 methylsulfonylalkyl GLs were identified in the seed of Arabis turrita L. by HPLC-MS/ESI analysis of intact GLs. Enzymatic (with myrosinase) and non-enzymatic (thermal at 100°C, and chemical at different pH) hydrolyses were performed and the volatile isolates were analyzed by GC-MS. Only the enzymatic and chemical (pH 10) degradations produced volatiles which are originating from GL degradation. GC-MS analysis showed the presence of long-chain olefinic isothiocyanates (ITCs) along with other the long-chain thiofunctionalized GL breakdown products.
NikolićT. Flora Croatica Database, On-Line (http://hirc.botanic.hr/fcd), Department of Botany, Faculty of Science, University of Zagreb, Zagreb, 2012.
2.
BennettRN, MellonFA, KroonPA. (2004) Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry. Journal of Agricultural and Food Chemistry, 52, 428–438;
3.
FaheyJW, ZalcmannAT, TalalayP. (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry, 56, 5–51;
4.
AgerbirkN, OlsenCE. (2012) Glucosinolate structures in evolution. Phytochemistry, 77, 16–45;
5.
SongsakT, LockwoodGB. (2002) Glucosinolates of seven medicinal plants from Thailand. Fitoterapia, 73, 209–216;
6.
VaughnSF, BerhowMA. (2005) Glucosinolate hydrolysis products from various plant sources: pH effects, isolation, and purification. Industrial Crops and Products, 21, 193–202.
7.
DaxenbichlerME, SpencerGF, CarlsonDG, RoseGB, BrinkerAM, PowellRG (1991). Glucosinolate composition of seeds from 297 species of wild plants, Phytochemistry, 30, 2623–2638;
8.
ColeRA. (1976) Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae. Phytochemistry, 15, 759–762.
9.
ChiangWCK, PusateriDJ, LeitzREA. (1998) Gas chromatography/mass spectrometry method for the determination of sulforaphane and sulforaphane nitrile in broccoli. Journal of Agricultural and Food Chemistry, 46, 1018–1021;
10.
BlaževićI, MastelićJ. (2009) Glucosinolate degradation products and other bound and free volatiles in the leaves and roots of radish (Raphanus sativus L.). Food Chemistry, 113, 96–102;
11.
BlaževićI, RadonićA, SkočibušićM, De NicolaGR, MontautS, IoriR, RollinP, MastelićJ, ZekićM, MaravićA. (2011) Glucosinolate profiling and antimicrobial screening of Aurinia leucadea (Brassicaceae). Chemistry and Biodiversity, 8, 2310–2321;
12.
BlaževićI, MastelićJ. (2008) Free and bound volatiles of garlic mustard (Alliaria petiolata). Croatica Chemica Acta, 8, 607–613;
13.
MastelićJ, BlaževićI, JerkovićI. (2006) Free and bound sulphur containing and other volatile compounds from evergreen candytuft (Iberis sempervirens L.). Croatica Chemica Acta, 79, 591–597;
14.
RadonićA, BlaževićI, MastelićJ, ZekićM, SkočibušićM, MaravićA. (2011) Phytochemical analysis and antimicrobial activity of Cardaria draba (L.) Desv. volatiles. Chemistry and Biodiversity, 8, 1170–1181;
15.
BlaževićI, RadonićA, MastelićJ, ZekićM, SkočibušićM, MaravićA. (2010) Hedge mustard (Sisymbrium officinale): Chemical diversity of volatiles and their antimicrobial activity. Chemistry and Biodiversity, 7, 2023–2034;
16.
MastelićJ, BlaževićI, KosalecI. (2010) Chemical composition and antimicrobial activity of volatiles from Degenia velebitica, a European stenoendemic plant of the Brassicaceae family. Chemistry and Biodiversity, 7, 2755–2765;
17.
BlaževićI, BurčulF, RuščićM, MastelićJ. (2013) Glucosinolates, volatile constituents, and acetylcholinesterase inhibitory activity of Alyssoides utriculata. Chemistry of Natural Compounds, 49, 374–378;
18.
BlaževićI, De NicolaGR, MontautS, RollinP. (2013) Glucosinolates in two endemic plants of the Aurinia genus and their chemotaxonomic significance. Natural Product Communications, 8, 1463–1466.
19.
ChevolleauS, GascN, RollinP, TulliezJ. (1997) Enzymatic, chemical and thermal breakdown of 3H-labeled glucobrassicin, the parent indole glucosinolate. Journal of Agricultural and Food Chemistry, 45, 4290–4296;
20.
HanschenFS, LamyE., SchreinerM, RohnS. (2014) Reactivity and stability of glucosinolates and their breakdown products Angewandte Chemie - International Edition, 53, 11430–11450;
21.
HanschenFS, RohnS, MewisI, SchreinerM, KrohLW. (2012) Influence of the chemical structure on the thermal degradation of the glucosinolates in broccoli sprouts. Food Chemistry, 130, 1–8;
22.
HanschenFS, PlatzS, MewisI, SchreinerM, RohnS, KrohLW. (2012) Thermally induced degradation of sulfur-containing aliphatic glucosinolates in broccoli sprouts (Brassica oleracea var. italica) and model systems. Journal of Agricultural and Food Chemistry, 60, 2231–2241.
23.
EttlingerMG, LundeenAJ. (1956) The structures of sinigrin and sinalbin: an enzymic rearrangement. Journal of the American Chemical Society, 78, 4172–4173;
24.
OlsenO, SørensenH. (1980) Glucosinolates and amines in Reseda media. Phytochemistry, 19, 1783–1787;
25.
OlsenO, SørensenH. (1979). Isolation of glucosinolates and the identification of O-(alpha-L-rhamnopyranosyloxy)benzylglucosinolate from Reseda odorata. Phytochemistry, 18, 1547–1552;
26.
BonesAM, RossiterJT. (2006) The enzymic and chemically induced decomposition of glucosinolates, Phytochemistry, 67, 1053–1067;
27.
FriisP, LarsenPO, OlsenCE. (1977) Base-catalyzed Neber-type rearrangement of glucosinolates [1-(β-D-glucosylthio)-N-(sulphonate-oxy)alkylideneamines. Journal of the Chemical Society, Perkin Transactions, 1, 661–665;
28.
BlaževićI, MalešT, RuščićM. (2014) Glucosinolates of Lunaria annua: thermal, enzymatic, and chemical degradation. Chemistry of Natural Compounds, 49, 1154–1157.
29.
ZrybkoCL, FukudaEK, RosenRT. (1997) Determination of glucosinolates in domestic and wild mustard by high-performance liquid chromatography with confirmation by electrospray mass spectrometry and photodiode-array detection. Journal of Chromatogaphy A, 767, 43–52.
30.
AdamsRP. (1995) Identification of essential oil components by gas chromatography/mass spectroscopy, Allured Publishing Corp., Carol Stream, IL, 469 pp.
31.
BerhowMA, PolatU, GlinskiJA, GlenskM, VaughnSF, IsbellT, Ayala-DiazI, MarekL, GardnerC. (2013) Optimized analysis and quantification of glucosinolates from Camelina sativa seeds by reverse-phase liquid chromatography. Industrial Crops and Products, 43, 119–125.