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Influence of Heat Treatments on Sulforaphane in Italian Brassica

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Influence of Heat Treatments on Sulforaphane in Italian Brassica L AVORO ORIGINALE L.F. DI CESARE1, Influence of heat treatments on C. MIGLIORI1,D.VISCARDI1, sulforaphane in italian brassica cultivars V. FERRARI2 PROGRESS IN NUTRITION Summary VOL. 11,N.2, 100-109, 2009 Organic isothiocyanates (ITCs), and particularly sulforaphane, are wi- dely studied as potential inhibitors carcinogenesis in animal models in- TITOLO cluding cancer of lung, esophagus, forestomach, colon, mammary glands Influenza dei trattamenti and pancreas. Sulforaphane, enzymatic breakdown product of glucora- termici sul sulforafane nelle phanin, was extracted by solvent from vegetable homogenates and quali- cultivar di brassica coltivate in quantitatively analysed by GC/MS. This method, modified from VanEt- Italia ten procedure, was used to evaluate sulforaphane in fresh and cooked (microwave, boiling water, steam, pan cooking) broccoli, cauliflower KEY WORDS (“Romanesco”, “verde di Macerata”, “violetto di Catania”, “Jesino” and Broccoli, cauliflowers, cabbage, commercial hybrid) and white cabbage. The highest content in sulfora- cooking methods (microwave, phane was noted in the raw broccoli, respect of the other examinated boiling water, steam, pan cooking), fresh brassica cultivars. When all these samples were cooked, the reten- sulforaphane; GC/MS analysis tion of sulforaphane, the most potent activator of phase II enzymes among all ITCs, were higher in the microwave cooked samples (61- PAROLE CHIAVE 86%), little lower in the boiling water (38-74%) and strongly lower in Broccoli, cavolfiore, cavolo, metodi the steam (18-52%) and pan cooking (14-48%). The microwave seems di cottura (microonde, acqua to be the most efficient cooking method for all these vegetables because bollente, vapore, frittura), it shows the highest retention in sulforaphane. sulforafane, analisi GC/MS Riassunto Gli isotiocianati, ed in particolare il sulforafane, sono largamente studiati in quanto hanno la capacità di inibire alcune forme tumorali che interes- sano la lingua, esofago, stomaco, colon, ghiandole mammarie e pancreas, in animali da laboratorio e nell’uomo. Il sulforafane, prodotto di idrolisi enzimatica delle glucorafanina, è stato estratto con solventi dai vegetali 1 C.R.A.- I.A.A.- Unità di Ricerca omogeneizzati ed analizzato quali-quantitativamente per via GC/MS. per i Processi dell’Industria Questo metodo, ottenuto in seguito a modifiche di quello originale di Agroalimentare, Milano 2 C.R.A.- O.R.A.- Unità di Ricerca VanEtten, è stato usato per la determinazione del sulforafane nei cam- per l’Orticoltura, Stella di pioni freschi e cotti (microonde, acqua bollente, vapore, frittura) di broc- Monsampolo del Tronto (AP) colo, cavolfiore (“Romanesco”, “verde di Macerata”, “violetto di Catania”, “Jesino” ed un ibrido commerciale) e cavolo-cappuccio bianco. Nei cam- Indirizzo per corrispondenza: pioni freschi di broccolo è stato accertato il più alto contenuto in sulfora- Dr. Luigi Di Cesare Tel. 02/239557215; fane, rispetto alle altre cultivar allo stato fresco. Quando tutti i campioni e-mail: [email protected] sono stati cotti, la ritenzione percentuale del sulforafane, il più potente 100 PROGRESS IN NUTRITION 2/2009 attivatore degli enzimi della fase II tra tutti gli isotiocianati, è stata più elevata nei campioni cotti con microonde (61-86 %), un po’ più bassa nella cottura in acqua bollente (38-74 %) ed ancora più bassa nella cottu- ra a vapore (18-52 %) e frittura (14-48 %). Le microonde si sono dimo- strate il più efficiente sistema di cottura per questi vegetali, poiché esso mostra le più alte ritenzioni in sulforafane per tutti i vegetali presi in esa- me. Introduction gregated from glucosinolates and is prevention. These ITCs are potent released after cellular damage. inhibitors of tumorigenesis in va- The natural organic isothiocyana- Myrosynase catalyzes at pH=7 the rious animal models (10, 11, 12). tes (ITCs) are synthesized and following reaction (4, 5) (Fig. 1). The dual action of ITCs is to in- stored as glucosinolates (β-thio- It has long been known that ITCs hibit phase I enzymes that are re- glucoside N-hydroxy sulfates) in have different biological effects sponsible for the bioactivation of cruciferous vegetables consumed due to their chemical reactivity (2, carcinogenesis, reducing the pro- by humans, such as broccoli, cab- 6, 7). More recently, ITCs such as duction of electrophilic interme- bage, cauliflower, radish, turnip 4-methylsulfinylbutyl NCS or sul- diates (13) and to enhance the ac- and watercress (1-3). foraphane, 3-methylsulfinylpropyl tivity of phase II enzymes such as The glucosinolates are hydrolyzeed NCS, 3(methylthio)propyl NCS, glutathione transferases, epoxide to isothiocyanates by myrosinase 2-phenylethyl NCS, allyl NCS hydrolases, NAD(P)H: quinone (β-thioglucoside glucohydrolase; and methyl NCS (8, 9), have been reductases and glucoronosyl trans- EC 3,2. 3-1), that is normally se- studied for their effects in cancer ferases, that increase the detoxifi- cation and clearance of carcino- Figura 1 - Production of isothiocyanates from glucosinolates gens (14-16). The effects on phase I and II enzymes, and consequently a re- duced cancer risk, have been de- monstrated in humans that consu- me a large quantity of cruciferous vegetables (12, 17-22). Recent works have also shown that ITCs act as suppressing agents during the promotion of neoplastic process and as signal transduction pathways within the cell, induce apoptosis and inhibit cell grown (23-26). 101 VOLUME 11 A large number of brassica vegeta- glucosinolates in four type of portu- hybrid (Brassica oleracea var. bles are consumed after cooking guese cabbage and in one hybrid of Botrytis) were grown in the and the amounts of glucosinolates, white cabbage before and after co- C.R.A.-ISOR, Monsampolo del and consequently of the corrispec- oking for 5-10 min in boiling water. Tronto (AP) fields. tive isothiocyanates, are usually re- Analysis of fresh cabbage, cooked Broccoli (Brassica oleracea var. Ita- duced in the cooked vegetables leaves and cooking water showed lica) and white cabbage (Brassica (27). that the glucosinolates content of oleracea var. Capitata) were pur- Jiao et al (28) determined the con- cabbages was reduced by more than chased at the Milan general horti- tent in total isothiocyanates in 102 50%. Almost all of this loss was ac- cultural market. cooked vegetables consumed in counted as intact glucosinolates in The heads of broccoli and cauli- Singapore. They used an HPLC the cooking water. Even in Italy a flowers were decored to florets be- method to quantify the cyclic pro- lot of papers were published about fore using. The heads of white ducts of ITCs and 1,2-benzenedi- the content of glucosinolates in cabbage were cut as a wedge with thiol after treatment of vegetable fresh crucifers (31-33). the edge parallel to the core. Than juices with myrosinase. The con- The aim of this paper is to evalua- the samples were cut into 3-5 cm tent of total ITCs in 9 type of cru- te the influence of different heat cube before using. ciferous vegetables ranged bet- treatments (microwave, boiling ween 4.9 µmol 100 g-1 d.m. in water, steam and pan cooking) on Cooking methods bokchoi and 81.3 µmol 100 g-1 the sulforaphane content in some d.m. in watercress. brassica cultivar (broccoli, cabbage, a) Microwave: 300 g of each sam- Wennberg et al (29) studied the cauliflower) that are frequently ple were cooked in 1L special effect of blanching and treatment consumed in Italy. glass becker, containing 800 mL with white vinegar on glucosinola- In the present research, to deter- of water with 0.3% of NaCl, co- tes of white cabbage (cv Heckla, minate the sulforaphane content vered by a Petri glass. Microwa- Predikant). Glucosinolates content in the brassica samples it was used ve power applied was 900-1000 decreased substancially in both a GC/MS procedure, modifying watt for 5-6 min for all samples. blanched cultivars, although the the original method of VanEtten b) Boiling water: 300 g of samples total loss was higher in Predikant (34, 35). Sulforaphane was also were cooked for 6-8 min in (74%) than in Heckla (50%). The determined with a similar proce- 1300 mL of boiling water with individual glucosinolates were ef- dures by Chang et al (36) and 0.3% of NaCl for all samples. fected to different degrees (15- Omary et al (37). c) Steam: 300 g of each sample 91%). During souring with acetic were cooked in a steam cooker acid, total content of glucosinolate Multigourmet (Braun) for 20- was not effected in Heckla but Material and methods 25 min, for all sample. In the was further reduced in Predikant. lying container were put 1500 A substantial increase in 4-me- Plant source mL of water. thoxyglucobrassicin was noted in d) Pan cooking: 300 g of each both cultivars. Cauliflower “Romanesco”, “verde sample were cooked in steel pan Rosa et al (30) measured the con- di Macerata”, “violetto di Cata- with 15-20 g of olive oil and 3 centrations of individual and total nia”, “Jesino” and commercial g of NaCl for 18-22 min. 102 PROGRESS IN NUTRITION 2/2009 For all the sample, all the tests we- Figure 2 - GC/MS chromatogram of sulforaphane obtained from hydrolysis re repeated three times. of glucoraphanin prepared according to Rochfort et al (31). The mass-spec- Isolation and purification of glu- trum of sulforaphane was in agreement with previously published by Spencer coraphanin from broccoli seeds. at al (39) Glucoraphanin was prepared from broccoli seeds with boiling water, purified and concentrated by SPE and preparative scale HPLC, ac- cording to Rochfort et al (38), using method 3 for the concentra- tion of the glucoraphanin. To evaluate the purity of glucora- phanin, the aqueous fraction was submitted to modified method, following described, for determi- nation of relative breakdown sul- foraphane, that was quali-quanti- tatively analysed by GC/MS. The chromatogram in figure 2 shows that the substance content in the fraction with 22-25 min of reten- thiocyanate by GC/MS was per- The combined filtrates were redu- tion time is glucoraphanin, becau- formed according to VanEtten et ced to about 10 mL under vacuum se its breakdown product is sulfo- al (34, 35).
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