Glucosinolates of Sisymbrium officinale and S. orientale

Abstract

Glucosinolates (GSLs) from Sysimbrium officinale and S. orientale were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS. Eight GSLs were identified in S. officinale, including Val-derived (glucoputranjivin) and Trp-derived (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin) as the major ones followed by Leu-derived (Isobutyl GSL), Ile-derived (glucocochlearin) and Phe/Tyr-derived (glucosinalbin). Different S. orientale plant parts contained six GSLs, with Met-derived (progoitrin, epiprogoitrin, and gluconapin) and homoPhe-derived (gluconasturtiin) as the major ones, followed by glucosinalbin and neoglucobrassicin. GSL breakdown products obtained by hydrodistillation (HD) and microwave-assisted distillation from S. officinale, as well as isopropyl isothiocyanate, as the major volatile in both isolates, were tested for their cytotoxic activity using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Generally, all volatile isolates showed similar activity toward the three cancer cell lines. The best activity was shown by isopropyl isothiocyanate at a concentration of 100 µg/mL after 72 h of incubation, with 53.18% for MDA-MB-231, 56.61% for A549, and 60.02% for the T24 cell line.

Glucosinolates in Wild-Growing Reseda spp. from Croatia

“…The m / z 318 signal in MS 2 ( Figure S4A ) may correspond to two isomers, desulfoglucocochlearin ( d61 ) and isobutyl dGSL ( d62 ). This GSL was previously identified in Sisymbrium officinale at the same retention time (t R = 5.30 min), which is consistent with this study [ 37 ].…”

“…In addition to having different retention times, d109 and d110 vary in their MS 2 spectra [ 6 ]. Figure S4B shows the MS 2 spectra of d109 at collision energies of 20 and 30 V. Typical thioglucosidic bond fragmentation results in [anhydroglucose + Na] + at m / z 185 (type a ) and [M-162 + Na] + at m / z 219 (type b ), while the type c fragment results from loss of an anhydroglucose, [M-162 + Na] + [ 37 ]. Fragments from the elimination of anhydrorhamnose, anhydroglucose, and thioglucose (fragment h ) were observed, with the characteristic fragment m / z 334 resulting from the loss of glucose ( m / z 180).…”

“…GSLs were extracted from different plant parts, as previously reported [ 37 ]. To inactivate the endogenous myrosinase, the plant material was ground into a fine powder, and 100 mg was extracted for 5 min at 80 °C in 2 mL MeOH/H 2 O (70:30 v / v ).…”

Glucosinolates and Cytotoxic Activity of Collard Volatiles Obtained Using Microwave-Assisted Extraction

“…All these GSLs were previously reported in the leaves of kales and collard. The indole ring of 43 is hydroxylated by CYP81Fs in positions 4 or 1, and IGMTs convert hydroxyl groups into methoxy groups [ 24 , 25 , 26 , 27 , 28 , 29 , 30 ].…”

“…Volatile extracts from Brassicaceae plants containing isothiocyanates demonstrated activity against various human cancer cell lines, such as: bladder UM-UC-3 ( Lepidium latifolium , L. graminifolium ); bladder T24 ( Armoracia rusticana , Sysimbrium officinale ); glioblastoma LN229 ( L. latifolium , L. graminifolium ); lung A549 ( A. rusticana , Lunaria annua , S. officinale , Lobularia lybica ); breast MDA-MB-231 ( L. annua , S. officinale ); breast MCF-7 ( L. lybica ); hepatic HUH-7 ( L. lybica ); colon HCT116 ( L. lybica , Tropaeolum majus ), cervical HeLa; and osteosarcoma U2OS ( T. majus ) [ 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. The chemical reactivity of the isothiocyanate group, which can easily bind to protein, appears to be primarily responsible for the biological activity of these compounds.…”