Mustard: chemistry and potential as a nutraceutical ingredient.
The current term "functional foods" or "nutraceuticals" are used frequently to describe those foods or food ingredients which not only have important functional properties but also exhibit beneficial physiological effects in humans. Mustard products contain a wide range of such active components including isothiocyanates, phenolics, dithiolthiones and dietary fibre. For example, isothiocyanates of essential mustard oil exert pharmacological as well as toxic properties by their goitrogenic, antibacterial, antifungal and antiprotozoal activities. They are cytotoxic and also capable of inducing chromosome abnormalities and neoplasia as well as blocking chemical carcinogenesis. The mucilage from yellow mustard does not only stabilize prepared mustard products, but also is able to reduce glycemic index in both normal people and diabetic patients. This review intends to cover the basic chemistry and functionality of mustard components and the potential of mustard products as a "functional food" or "nutraceutical ingredient".
Mustard and Mustard Products
Mustard has been consumed by humans as a condiment for about 3000 years. The original use of mustard was to mask the taste of degraded perishables. Today, mustard is the largest volume spice in international trade, accounting for 160,000 tons per year; Canada is one of the major contributors to the world trade market of mustard . The spiciness of mustard is caused by a group of compounds called isothiocyanates. When mustard seeds are crushed and exposed to liquids, an enzyme called myrosinase (thioglucoside glucohydrolase, EC 188.8.131.52) hydrolyses glucosinolates to release isothiocyanates. The differences in mustard flavour are due to the structural changes of the released isothiocyanates. For example, oriental and brown mustard release a volatile compound, ally isothiocyanate (AIT), which produces a sharp taste sensation and pungent aroma similar to horseradish. Yellow mustard releases a non-volatile compound, 4-hydroxybenzyl isothiocyanate (PHBIT), which elicits a hot mouth feel in condiments.
Traditional mustard products include mustard flour, ground mustard and prepared mustard. Mustard flour is a fine powder derived from the endosperm or interior portion of the seed. Three species of mustard seeds commonly ground into flour are yellow mustard (Sinapis alba), and the oriental and brown mustards (Brassica juncea). Oriental and brown mustard flour both possess a volatile oil responsible for their pungency. In contrast, yellow mustard flour contains a non-volatile oil which produces a sharp taste. Commercially, mustard flour is made from either straight yellow or oriental mustard seeds or a blend of the two. Mustard flour is generally retailed directly or sold to industry as ingredient for such products as salad dressings, mayonnaise, barbecue sauces, pickles and processed meats. Ground mustard, a powder made by grinding whole yellow mustard seeds, is used primarily in the meat industry as an emulsifier, water binder and inexpensive bulking agent. It is also used in seasonings for frankfurters, bologna, salami and lunch loaf. Ground mustard is also used in salad dressings, pickled products and condiments. The water binding and emulsifying properties of ground mustard is largely attributed to the mucilaginous material present in yellow mustard bran. The amount of ground mustard added to processed meat was limited, at one time, to its hot flavour. This problem, however, was resolved by the introduction of a deheating process to deactivate myrosinase under controlled temperature conditions. Prepared mustard is a smooth paste usually composed of ground mustard and/or mustard flour with salt, vinegar, with or without sugar and/or dextrose, spices or other condiments. For example, Dijon mustard is a paste made from sifted or sieved products of which the total dry matter (including salt and sugar) must not be less than 28%. There are other popular prepared mustard products such as French and German mustards in North America and Europe. Yellow mustard bran used to be a by-product in the preparation of mustard flour. The situation has recently changed because the bran is often found to be in higher demand than the flour because of its emulsifying and stabilizing properties. Yellow mustard bran contained about 25-30% water-soluble mucilage which exhibited unique rheological and interfacial properties. These properties were responsible for the stabilizing, emulsifying, water binding and fat absorbing properties of yellow mustard bran and bran-containing products.
Chemistry and Functionality of Mustard Components
Mustard seeds are composed of protein (23-30%), fixed oil (2936%), carbohydrate (12-18%) together with minor constituents including minerals (4%), essential oil (glucosinolates, 0.8-2.3%), phytin (2-3%) as well as phenolic compounds and dithiolthiones. Processed mustard flour is usually enriched with fixed oil (3042%) and protein (30-35%). In contrast, bran products contain much less oil and protein (7 and 13-16%, respectively), but are rich in dietary fibre (15%). This section describes the chemistry and functionality of these components.
The high level of glucosinolates is desirable in mustard as they are the precursors of flavour components. When mustard seeds are crushed and exposed to liquids, such as water, vinegar or grape juice, the enzyme myrosinase (thioglucoside glucohydrolase, EC 184.108.40.206) hydrolyses glucosinolates to isothiocyanates according to the following mechanism shown in Figure 1. These enzyme produced isothiocyanates give the hot spicy flavour of prepared mustard products. In addition to the flavour characteristics, mustard isothiocyanates also exhibit biological activities which might be used for health care of humans.
Mustard oil was reported over half a century ago to exhibit antifungal activity [2,3,4]. The more aromatic PHBIT appeared to be far more fungiotoxic than the aliphatic ITs. The antifungal effectiveness of AIT was demonstrated over the past 30 years by Zsolnia  and Hejrnanskowa  and more recently by Tsunoda . Evidence accrued to-date points to AIT and other volatile isothiocyanates being specifically effective against the germination and growth of several fruit pathogens . In the vapour phase, AIT from brown mustard proved a potent antifungal agent when included in modified atmosphere packaging of different food samples . AIT was particularly effective against mycotoxin producing molds such as Aspergillus flavus, Penicillium citrinum and Fusarium graminearum.
Mustard oil has been shown to inhibit the growth of several yeasts. A recent study showed AIT in mustard oil exerted lethal effects on Neurospora yeast in mustard seed . AIT also inhibited the growth of yeast when added to fruit juices at a concentration of 1%. This may explain why the Romans used mustard oil to prevent fermentation of fruit juices or finished wines .
The antibacterial activity of ITs differed substantially and in some cases was strain specific. For example, benzyl (BIT), [Beta]-phenylethyl (PEIT), m-methoxylbenzyl (MTBIT) and p-methoxybenzvl (PMBIT) isothiocyanates were all found to be more effective against Staphylococcus aureus compared to a series of aliphatic ITs. AIT and phenyl isothiocyanate (PIT), however, were both found to be ineffective against Streptococcus pyrogenes, Streptococcus aureus or three gram-negative bacteria at levels that severely inhibited the growth of yeasts and fungi . A recent study by Delaquis and Mazza  showed the effect of vaporised AIT on food born pathogens was dose dependent. The growth of microorganisms was inhibited at concentrations above 500ng/ml. The log number of killed bacteria was proportional to the AIT concentration for Salmonella typhimurium and Listeria monocytogenes, but almost unchanged for Eschrichia coli. Some ITs, such as BIT, exhibit antibiotic activity in vitro, and are sold as pharmaceuticals for the treatment of infections of the respiratory and urinary tracts [12-15].
The ability of ITCs to block carcinogenesis was recognized over 35 years ago [16,17]. In long-term feeding studies, [Alpha]-naphthyl-ITC significantly reduced (in a dose-dependent manner) formation of liver tumours in male Wistar rats. [Beta]-Napthyl-IT also blocked hepatic tumour formation in rats fed the carcinogen 4-dimethylaminobenzene. Both of these ITs had profound effects on hepatic enzymes that metabolize xenobiotics [18,19]. These findings laid the groundwork for subsequent studies on the turnout blocking activities of ITs which were usually administered for only short periods of time.
Aromatic ITCs appear to exert anticarcinogenic activities against a variety of animal cancers including mammary, forestomach and lung tumours as well as tumours of the esophagus [20,21]. Single doses of PIT, PEIT and BIT markedly reduced the incidence and multiplicity of mammary tumours in female Sprague Dawley rats. When BIT was administered by gavage 2 hr prior to a single dose of carcinogen, the average number of rats bearing tumours was reduced from 77% to 8%, while the number of tumours per animal dropped from 1.6 to 0.08 . BIT inhibited benzo[[Alpha]]pyrene-induced turnout development in the lung and forestomach and N-nitrosodiethylamine-induced neoplasms in the forestomach of A/J mice. PEIT showed significant inhibitory effects against lung tumours induced by nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) but had no effect against benzo[[Alpha]]pyrene-induced lung tumour in A/J mice [23,24]. Since both NNK and benzo[[Alpha]]-pyrene are important tobacco carcinogens and lung cancer is attributed to tobacco usage, ITs may be a more effective chemoprotective agents for prevention of lung cancers. Jiao and co-workers  suggested that lipophilicity and low reactivity of ITs were important factors for inhibiting NNK-induced lung cancers.
PEIT has also been shown to inhibit esophageal tumours in rats induced by asymmetrical nitrosamine. Male F344 rats treated with N-nitrosobenzylmethylamine (0.5 mg/Kg s.c. once per week for 15 weeks) developed 100% esophageal tumours at the end of the 25-week assay period with turnout multiplicity of 11.5/animal. In experimental groups fed PElT (3[micro]mole/g of diet) tumour incidence was only 13% while the average turnout multiplicity was negligible (0.1/animal). At higher doses of PElT (6[micro]mole/g of diet) no tumours were observed . PElT appeared to block the formation of both preneoplastic and neoplastic lesions in the esophagus. The amount of glucosinolates in mustard seeds are much higher than their corresponding hydrolysis products, isothiocyanates. However, there are only limited number studies on the tumour-blocking effects of glucosinolates. For example, administration of large single doses of glucobrassicin (indoylmethyl glucosinolate) or glucotropaeolin (benzyl glucosinolate) 4 hr prior to benzo[[Alpha]]pyrene substantially reduced both the incidence (75% to 25-38%) and multiplicity (1.35 to 0.5-0.69 tumour/animal) of mammary tumours. However, administration of these glucosinolates or glucosinalbin (4-hydroxybenzyl glucosinolate) produced some reduction in multiplicity but did not effect the incidence of forestomach tumours and pulmonary adenomas in mice treated with benzo[[Alpha]]pyrene . The overall effect of glucosinolates may be due to their hydrolysis products as tumour-blocking activity appears to be related to the extent of glucosinolate hydrolysis.
It is evident that ITCs exhibit a broad range of anticarcinogenic activities against the development of liver, mammary gland, forestomach and esophagus tumours. They are widely distributed in plants consumed by man so that it is important to understand the mechanism of anticarcinogenic activity to maximise the benefits from these compounds. ITs may inhibit carcinogenesis by neutralization of carcinogens or by suppressing proliferation activity of neoplastic cells. These compounds could prevent carcinogens from reaching their target site or weaken the effects of genetic modification that occur during the early stages of neoplastic transformations as well as inhibit key enzymes involved in the regulation of cell division .
Proteins and Oil of Mustard Proteins
The large amount of protein of around 30% for whole mustard seeds and flours appears satisfactory, for growth and development. Compared to most oilseed meals, mustard protein contained higher amounts of lysine and sulfur amino acids, with the exception of soybean. Manufacturing protein concentrates from mustard seeds requires inactivation of the enzyme myrosinase to prevent formation of isothiocyanates. The latter are responsible for the hot flavour of unheated mustard. Commercially, yellow mustard seeds are processed to produce a deheated ground mustard flour which is used extensively in processed meats. Only a maximum of 1% ground mustard was permitted to be added to processed meat products until the early 1990s. The current levels permitted in sausages and other processed meats is 5% while still labelled as "spice" or "mustard." It is believed that the water-soluble portion of the proteins in mustard contributed partially to the emulsification properties of mustard products.
Niazi and co-workers  prepared a mustard protein concentrate by enzymic treatment of mustard meal followed by steeping in 4% NaCl solution at pH 5. This method eliminated glucosinolates as well as 85.7% of phytate with the resulting concentrate containing 53.1% protein, 6.1% crude fibre, 5.8% ash and 0.4% phytate. Nutritional assessment of the mustard protein concentrate by rat bioassay showed it compared favourably with casein with a PER (Protein Efficiency Ratio) of 2.4; NPU (Net Protein Utilization) 68.5%; TD (Total Digestibity) of 87.0% and a BV (Biological Value) of 78.4%.
Mustard oil is used as an edible oil in India. The content of fixed oil in Brassica juncea seeds (32-36%) is significantly higher compared to Sinapis alba seeds (29%). Erucic acid, accounting for 18-51% of the total fatty acids, is the major fatty acid in mustard oils. Sinapis alba seeds tend to be higher in monounsaturated fatty acids (oleic and erucic acids) and lower in polyunsaturated fatty acids (linoleic and linolenic acids). It is worth noting that mustard oil also contains 9-15% of essential fatty acid, omega-3 fatty acids; it is much higher than most of the commonly used vegetables oils (canola, 10.5%, soybean, 7.8% and corn, 1.5%).
Erucic acid (C22:1), a long chain monounsaturated fatty acid, has a higher fire and smoke point (217 [degrees] C). This property permits erucic acid to withstand high temperatures and remain liquid at room temperature . Oils containing high levels of erucic acid, such as crambe and industrial rapeseed, have found extensive uses as lubricants or in lubricant formulations . High erucic acid oils have found clinical applications in the treatment of a rare children's disease known as adrenoleukidystrophy. Non-edible uses of high erucic acid oils are based on the industrial applications of erucic acid and its cleavage products. These include the hydrogenated derivative behenic acid, erucyl and behenyl alcohols and their esters, amides and amine derivatives.
erucic acid: C[H.sub.3][(C[H.sub.2]).sub.7]CH=CH[(C[H.sub.2]).sub.11]COOH behenic acid: [H.sub.3][(C[H.sub.2]).sub.7]C[H.sub.2]C[H.sub.2][(C[H.sub.2]).sub.11]COOH
These compounds are used in industry as slip, softening and release agents: emulsifiers; processing aids: antistatic agents; stabilisers; and corrosion inhibitors. Behenic acid and esters are also used to enhance the performance of pharmaceuticals, cosmetics, fabric softeners and hair conditioners.
Erucamide, the amide derivative of erucic acid, is a processing aid and antiblock agent in plastic films by lubricating and forming a thin layer on the surface of the plastic.
erucamide: [H.sub.3][(C[H.sub.2]).sub.7]CH = CH[(C[H.sub.2]).sub.11]CON[H.sub.2]
In addition to these applications, oxidative products of erucic acid are used in the production of plastics, resins and nylons. These include brassylic acid, a 13-carbon dicarboxylic acid and perlagonic acid. Brassylic acid is used in the preparation of long chain nylons and used in automative parts and products [7,8].
pelargonic acid: C[H.sub.3][(C[H.sub.2]).sub.7]COOH brassylic acid: OOC[(C[H.sub.2]).sub.11]COOH
Based on the extensive applications of erucic acid, those mustard species with high levels of this acid could be grown to meet industrial demands.
Dithiolthiones, Phenolics and Phytin in Mustards Dithiolthiones
Many spices used in foods are also recognized for their medicinal properties . Brown mustard seeds or Brassica nigra, a common condiment used in India was recently examined for its antimutagenic properties by Polassa and co-workers  using benzo[[Alpha]]pyrene, a potential carcinogen. Rats injected with the carcinogen were fed diets containing 1 to 10% mustard seeds for up to one month with 24 hr urine samples collected for examination of mutagens. A diet containing 1% mustard exhibited a strong antimutagenic effect which did not change in diets containing up to 10% mustard seeds. These researchers attributed this effect to the presence of sulfur-containing compounds, dithiolthiones in mustard. These compounds were thought to be partly responsible for the anticarcinogenic properties of diets high in vegetables . Dithiolthiones exert their effect by increasing tissue levels of glutathione and detoxifying enzymes such as glutathione transferase . A diet containing 10% mustard was shown by Polassa et al  to elevate glutathione-S-transferase in rat liver. The ability of 1% mustard diets to significantly inhibit the mutagenicity of benzo[[Alpha]]pyrene in vivo is important as mustard is only consumed in small quantities in our diet. Dithiolthiones, the active principle of mustard or the Brassica genus, are used as antichistomal drugs for humans . The structure of oltiraz, a typical dithiolthione is shown in Figure 2. The specific levels of dithiolthiones in mustard, however, are unknown and require further examination.
Concern over the toxicity of synthetic antioxidants has resulted in a search for natural antioxidants in foods . The latter include phenolic compounds, tocopherols, phospholipids and amino acids . Oilseeds in general, are rich in phenolic compounds that retard oxidation of the oil. Koslowska and coworkers  reported the presence of phenolic acids in rapeseed and mustard in which sinapic acid isomers were the predominant forms present. Recent research by Saleemi et al  compared the antioxidant properties of low-pungency ground mustard seed (LPGMS) with synthetic antioxidants butylated hydroxytoluene (BHT) and tertiary-butyl hydroquinone (TBHQ) on the stability of comminuted pork. The addition of 1.5% and 2.0% LPGMS was as effective as 200 ppm of BHT or 30 ppm of TBHQ in controlling oxidative rancidity as measured by TBA. Further work by these researchers  showed that an 85% methanolic extract from LPGMS exhibited the strongest antioxidant activity due to the presence of much higher levels of phenolics compared to either water or 10% methanolic extracts. In addition, to antioxidant activity, LPGMS also enhanced cook yield without exerting a detrimental effect on the colour quality of the treated meat samples .
Phytin or phytate accounts for approximately 2-3% of mustard seeds. It is considered an antinutrient because its structure confers strong chelation properties. While phytate is generally considered undesirable in foods, it nevertheless has found wide industrial applications particularly outside the United States . Labelled phytates, for example, have been used in medicine as imaging agents for organ scintigraphy [42-45]. The cariostatic properties of phytate led to a number of patents in which it is incorporated in commercial oral care products such as dentrifices, mouth rinses, dental cements and cleaning agents for dentures . The very chelating properties associated with phytate are also responsible for its strong anticorrosive properties. The patent literature is filled with phytate-containing coating materials for metals and alloys which not only inhibit corrosion but also improves paint adhesion . The industrial and medical applications of phytate suggests mustard could be a good source of this compound.
Yellow Mustard Mucilage (IAMB) Occurrence and Extraction
All mustard seeds contain mucilage, but only yellow mustard mucilage is significant because of its high yield and functionality [46-54]. Since the mucilage is deposited in the epidermal lamer of the testy [55,56], it is relatively easy to extract. A typical extraction procedure includes mixing yellow mustard seed or bran with water, stirring under room or elevated temperature for a period of time of 1 to 24 hr. The viscous extract was filtered through muslin or louvers of cheese cloth, or centrifuged to separate the seeds/bran from the liquid solution/dispersion. The mucilage can be precipitated by pouring the aqueous extract into 2 to 4 volume of 95% alcohol. The precipitated mucilage is usually washed with alcohol 2 to 3 times then dried under vacuum or freeze dried. The prepared mucilage is a snow-white fibrous product corresponding in yield of about 2-5% of the dry seed.
Using whole yellow mustard seeds as a source of mucilage is not economically feasible as there are no practical applications for the seeds following extraction of mucilage. In North America, a number of food companies currently process mustard meats as food ingredients with the bran as a by-product. Since mucilage is deposited mainly in the epidermal layer of the seed coat, extraction of mucilage from yellow mustard bran appeared to be a better way of producing the gum. The reported yield of mucilage obtained from the bran varied from 15-25% depending on the extraction conditions [57-58]. The extraction process generally involved defatting the bran with a mixture of hexade, ethanol and water. The defatted, dried bran was then water extracted (1:20 ratio) and separated by centrifugation with the mucilage precipitated with 2 volumes of 95% ethanol and then dried (freeze-fried or under vacuum).
Heterogeneity and Structures of Yellow Mustard Mucilage
Yellow mustard mucilage is a complex mixture of polysaccharides containing six neutral sugars and two uronic acids. Yellow mustard mucilage was first reported to be composed of cellulose (50%) together with acidic polysaccharides which yielded arabinose, galactose, rhamnose, galacturonic and glycuronic acids on hydrolysis, as well as containing methoxyl groups . The most recent study suggested that the crude mucilage contained 80.4% carbohydrates, 4.4% protein and 15% ash . Dialysis reduced the ash content to 4.8% with a corresponding increase in carbohydrates from 80.4 to 91.1%. Of the monosaccharides, glucose (23.5%) was the predominant neutral sugar followed by galactose (13.8%), rhamnose (3.2%), arabinose (3.0%) and xylose (1.8%) together with 14.7% galacturonic acid and 4-methyl-glucuronic acid. Using selective precipitation and anion chromatography, IAMB was fractionated into ten fractions. Of which, two theologically responsible fractions were identified and characterized. One is a neutral polysaccharide typical of cellulose-like structures. Some of the hydroxyl groups at C2, 3 and 6 were occasionally substituted by ether groups (ethyl and propyl). The ethyl group was randomly distributed in the C2, 3 and 6 positions while the propyl ether was predominant at the 6 position . These ether groups along the cellulose-like backbone chain may act as "kinks" which can alter the conformational regularity of the 1,4-linked b-D-glucose backbone chain and favour the solubilization of the polymer in an aqueous medium. Alternatively, for steric reasons, these groups will hinder interchain associations among the cellulose chains, thus enhancing solubility of the polysaccharide.
The second fraction was a pectic polysaccharide composed of 2,4-linked and 2-linked L-rhamnose, 6-linked D-galactose, a terminal non-reducing D-glucuronic acid and 4-linked D-galacturonic acid . An average repeating unit was proposed for the pectic polysaccharide based on evidence of methylation analysis and 2D NMR spectroscopy as seen in Figure 3.
Functional Properties: The consistency of prepared mustard products, such as salad dressings and food pastes is attributed to the presence of mucilage . In general, the mucilage appeared similar to xanthan gum by: (1). exhibiting shear thinning flow behaviour at concentrations above 0.3%; (2). exhibiting weak-gel properties; and (3). interacting synergistically with galactomannans. When IAMB was mixed with galactomannans such as locust bean gum (LBG), guar gum and fenugreek gum, the viscosities of the mixed systems were significantly increased and the mixed system formed gels at ratios of one part of galactomannans to 5 to 9 parts of IAMB . IAMB also exhibited interfacial activity as it reduces the surface tension of water . Increasing the mucilage concentration up to 0.05% substantially reduced surface tension. Further addition of mucilage decreased surface tension only slightly. The water soluble fraction of IAMB exhibited the greatest reduction in surface tension compared to crude mucilage and the insoluble fraction. A practical application of the interfacial activity of IAMB is to stabilize emulsions of commercial interests. A study compared IAMB with commonly used gums including locust bean gum, guar gum, CMC, xanthan, tracacanth and propylene glycol alginate. A favourable comparison was observed between 0.25% IAMB, 0.5% guar gum and 0.5% CMC. In addition, 0.75% IAMB compared favourably with both 0.5% CMC and xanthan gum.
Physiological Properties: IAMB is a water soluble dietary fibre which may exert physiological effects like the other soluble dietary fibre does. A study by Begin and co-workers  examined the effect of IAMB and other soluble fibres on glycemia, insulinaemia and gastrointestinal function m the rat. They found that YMM, guar gum, oat [Beta]-glucan and carboxy-methylcellulose all significantly decreased postprandial insulin levels at 45 min, indicating a slow down in glucose absorption. It is believed that IAMB decreased insulinemia primarily by delaying gastric emptying, while the other fibres increased intestinal contents and consequently decreased absorption. Viscosity was considered a major contributory factor to the improved insulin status at peak time. Since viscosity of IAMB increases at acid pH, it exerts a stronger gastric effect compared to the other fibres examined. Incorporating mustard fibre into white bread at levels not affecting palatability had a modest but significant effect in reducing the glycemic index of the bread in both normal and diabetic human volunteers . A significant reduction in percent peak rise in postprandial blood glucose was also observed. Although there is no studies reported on the effect of IAMB blood cholesterol, a positive response may be anticipated for IAMB in reducing blood cholesterol as Wood and co-workers  demonstrated the ability of dietary fibres to reduce blood cholesterol and insulin response was highly viscosity dependent.
Mustard products have been accepted as condiments in human diet for many years. The new functionalities described in this review for mustard components may suggest considerable potential as a source of nutraceutical ingredient. As a functional food, mustard provides components that exhibit both functional and health-related properties which will make our food both attractive and healthful. For more detailed information on yellow mustard products and functionality the readers are referred to a recent chapter .
1. Hemmingway, J.S., 'Mustard and Condiment Products', Encyclopedia of Food Science and Technology and Nutrition, Academic Press, New York, pp. 3178-3182, 1993.
2. Hoffman, C. and Evans, A.C., 'The Use of Spices as Preservatives', J. Ind. Eng. Chem., 3:835-838, 1911.
3. Blum, H.B. and Fabian, F.W, 'Spice Oils and Their Components for Controlling Microbial Surface Growth', Fruit Prod. J., 22:326-329, 1943.
4. Zsolnai, T., 'Die antimikrobielle wirkung von thiocyanatee und isothiocyanates', Arzneimittel Forschung, 16:870-876, 1966.
5. Hejmankova, N., Leiferlova, L. and Lisa, M., 'Study on Antifungal Effects of Allylisothiocyanate', Acta Univer. Palackianan Olomucensis (Fac. Med.) 89:9-16.
6. Tsunoda, K., 'Effect of Gaseous Treatment with Allylisothiocyanate on the Control of Microbial Growth on a Wood Surface', J. Anmtibact. Antifung. Agents, 22:145-148, 1994.
7. Mari, M., Iori, R., Leoni, O. and Marchi, A., 'In vitro Activity of Glucosinolate Derived Isothiocyanates Against Postharvest Fruit Pathogens', Ann. Appl. Bio., 123:155-164, 1993.
8. Isshiki, K., Tokuora, K., Mori, R. and Chiba, S., 'Preliminary Examination of Allyliusothiocyanate Vapor for Food Preservation', Biosci. Biotech. Biochem., 55:1476-1477. 1992.
9. Webb, A.H. and Tanner, F.W., 'Effect of Spices and Flavoring Materials on Growth of Yeasts', Food Res., 10:273-282, 1946.
10. Tressler, K.D. and Joslyn, M.A., The Chemistry and Technology of Fruits and Vegetable Juice Production, Avi Pub. Co. Inc., New York, pp. 204-205, 1954.
11. Delaquis, P.J. and Mazza, G., 'Antimicrobial Properties of Isothiocyanates in Food Preservation', Food Technol., 11:73-84, 1995.
12. Massier, J., 'Uber Erfahrungen mit einem pflanzlichen Antibiotikum in der Urologie', Die Medizinische Welt., 1964:2390-2393.
13. Bergmann, M., Lipsky, H. and Glawogger, F. 'Ein Antibiotikum aus der Kapuzinerkresse bei Harnwegsinfektionen', Medizinische Klinik., 61:1469-1472, 1996.
14. Borowski, J., 'Infekt-Behandlung in der taglichen Praxis', Die Medizinische Welt., 17 (N.F.):2431-2433, 1966.
15. Ebbinghaus, K.D., 'Zur Langzeithandlung der Pyelonphritis', Die Medizinische Welt 17(N.F.):58-61, 1966.
16. Sassaki, S., 'Inhibitory Effects by [Alpha]-naphthyl-isothiocyanate on Development of Hepatoma in Rats Treated with 3'-methyl-4-dimethyl-aminobenzene', J. Nara Med. Assoc., 14:101-105, 1963.
17. Sidranksky, H., Ito, N. and Verney, E., 'Influence of [Beta]-naphthylisothiocyanate on Development of Hepatoma in Rats Treated with 3'-methyl-4-dimethyl-aminoazobenzene', J. Nara Med. Assoc., 37:677-686, 1966.
18. Leonard, T.B., Popp, J.A., Graichen, M.E. and Dent, J.G., 'Naphthylisothiocyanate Induced Alterations in Hepatic Drug Metabolizing Enzymes and Liver Morphology. Implications Concerning Anticarcinogenesis', Carcinogenesis Lond., 2:473-482.
19. Leonard, T.B., Popp, J.A., Graichen, M.E. and Dent, J.G., 'Naphthylisothiocyanate Induced Alterations in Hepatic Drug Metabolism and Liver Morphology, Toxicol. Appl. Pharmacol., 60:527-534, 1981.
20. Morse, M.A., et al, 'Inhibition of 4-(methylnitrosamino)-1(3-pyridyl)-1-butazone-induced DNA Adduct Formation and Tumorigenicity in the Lung of F344 Rats by Dietary Phenethyl Isothiocyanate', Cancer Res., 49: 549-553, 1989.
21. Zhang, Y. and Talalay, P., 'Anticarcinogenic Activities of Organic Isothiocyanates: Chemistry and Mechanisms', Cancer Res., 54:1976-1981, 1994.
22. Wattenberg, L.W., 'Inhibition of Carcinogen-induced Neoplasia by Sodium Cyanate, tert-butyl Isothiocyanate and Benzyl Isothiocyanate Administered Subsequent to Carcinogen Exposure', Cancer Res., 41:2991-2994, 1981.
23. Wattenberg, L.W., Inhibition of Carcinogenic Effects of Polycyclic Hydrocarbons by Benzyl Isothiocyanate and Related Compounds', J. Natl. Cancer Inst., 58:395-398, 1978.
24. Wattenberg, L.W., Inhibitory Effect of Benzyl Isothiocyanate Administered Shortly Before Diethylnitrosamines or Benzo[[Alpha]]pyrene on Pulmonary and Forestomach Neoplasis in A/J Mice', Carcinogenesis (Lond.), 8:1971-1973, 1987.
25. Jiano, D., et al, Structure-activity Relationships of Isothiocyanates as Mechanism-based Inhibitors of 4(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced Lung Tumorigenesis in A/J Mice', Cancer Res., 54:4327-4333, 1994.
26. Stoner, G.D. et al, 1991. 'Inhibitory Effects of Phenylethyl Isothiocyanate on N-nitrosobenzyl-methylamine Carcinogenesis in the Rat Esophagus', Cancer Res., 51:2063-2068, 1991.
27. Wattenberg, L.W., Hanley, A.B., Barany,G., Sparmins, V.L., Lam, L.K.T. and Fenwick, G.R., 'Inhibition of Carcinogenesis by Some Minor Dietary Constituents', in Diet, Nutrition and Cancer, Y.Hayashi et al (eds.), Tokyo, Japan Science Society, Press., pp. 193-203, 1986.
28. Niazi, A.H.K., Khan, A.D. and Shah, F.H., 'Nutritional Quality of Mustard Protein Concentrate', Pakistan J. Scientific and Industrial Res., 32:546-548, 1989.
29. Nieschlag, H.J., Hagemann, J.W., Wolff, I.A, Palm, W.E. and Witnauer, L.P., 'Brassylic Acid Esters as Plasticizers for Poly(vinylchloride)', Industrial & Engineering Chemistry, Product, 6:201-204, 1967.
30. Van Dyne, D.L., Blase, MG. and Carlson, K.D., Industrial Feedstocks and Products from High Erucic Acid Oil: Crambe and Industrial Rapeseed, University of Missouri, Columbia, 1990.
31. Pruthi, J.S., Spices and Condiments, National Book Trust, New Delhi, 1976.
32. Polasa, J.A., Kumar, P.U. and Krishnaswamy, K., 'Effect of Brassica nigra on benzo[[Alpha]]pyrene Mutagenicity', Food Chem. Toxic., 32:777-781, 1994.
33. Ansher, S.S., Dolan, P. and Bueding, E., 'Chemoprotective Effects of Two Dithiolthiones and of Butylhydroxyanisole Against C[Cl.sub.4] and Acetaminophen Toxicity', Hepatology, 3:932-935, 1983.
34. Ansher, S.S., Dolan, P. and Bueding, E., 'Biochemical Effects of Dithiolthiones', Food Chem. Toxic., 24:405-415, 1986.
35. Ansher, S.S., 'The Chemotherapy of Schistomiasis', Ann. Rev. Pharmacol. and Toxicol., 25:485-508, 1985.
36. Barlow, S.M., 'Technological Aspects of Antioxidants Used as Food Additives', in Food Antioxidants, Hudson, B.J.F. ed., Elsevier, London. pp. 253-307, 1990.
37. Dugan, L.R., 'Natural Antioxidants', in Autoxidation in Food and Biological Systems, editors, Simic, M.G. and Karel, M., Plenum Press, New York. pp. 261-282, 1980.
38. Kozlowska, K., Rotkiewicz, D.A. and Zadernowski, R., 'Phenolic Acids in Rapeseed and Mustard', J. Amer. Oil Chem. Soc., 60:1119-1123, 1983.
39. Saleemi, Z.O., Janitha, P.K., Wanasundara, P.D. and Shahidi, F., 'Effects of Low Pungency Ground Mustard Seed on Oxidative Stability, Cooking Yield and Color Characteristics of Comminuted Pork', J. Agric. Food Chem., 60:1861-1867, 1993.
40. Shahidi, F., Wanasundara, P.D. and Amarowiczy, R. 'Natural Antioxidants From Low-pungency Mustard Flour', Food Res. Internat., 27:489-493, 1996.
41. Graf, E., 'Application of Phytic Acid', J. Amer. Oil Chem. Soc, 60:1861-1867, 1983.
42. Alavi, A., Staum, M.M., Shesol, B.F. and Bloch, P.H., 'Technetium-99m Stannous Phytate as an Imaging Agent for Lymph Nodes', J. Nucl. Med., 19:422-426, 1978.
43. Campbell, J., Bellen, J.C., Baker, R.J. and Cook, D.J., 'Technetium-99m Calcium Phytate: Optimization of Calcium Content for Liver and Spleen Scintography', J. Nucl. Med., 22:157-160, 1981.
44. Isitman, A.T., Manoli, M., Schmidt, G.H. and Holmes, R.A., 'Assessment of Alveolar Deposition and Pulmonary Clearance of Radiopharmaceuticals After Nebulization', Amer. J. Roentgenol. Radium Ther. Nucl. Med., 120:776-781, 1974.
45. Sewatkar, A.B., Noronha, O.P.D, Ganstra, R.D. and Glenn, H., Radiopharmaceutics of Technetium-99m Labeled Phytate', J. Nucl. Med., 14:46-51, 1975.
46. Cui, W., Eskin, N.A.M. and Biliaderis, C.G., 'Chemical and Physical Properties of Yellow Mustard (Sinapis alba) Mucilage', Food Chem., 46:169-176, 1993.
47. Weber, F.E., Taillie, S.A. and Stauffer, K.R., Functional Characteristics of Mustard Mucilage', J. Food Sci., 39:461-466, 1974.
48. Cui, W., Eskin, N.A.M. and Biliaderis, C.G., 'Water-soluble Yellow Mustard (Sinapis alba L.) Polysaccharides: Partial Characterization, Molecular Size Distribution and Rheological Properties', Carbohydr. Polym., 20: 215-225, 1993.
49. Cui, W., Eskin, N.A.M. and Biliaderis, C.G, 'Fractionation, Structural Analysis and Rheological Properties of Water-soluble Yellow Mustard (Sinapis alba L.) Polysaccharides', J. Agric. Food Chem., 42:657-664, 1994.
50. Cui, W., Eskin, N.A.M. and Biliaderis, C.G., 'Yellow Mustard Mucilage: Chemical Structure and Rheological Properties', Food Hydrocolloids, 8:203-214, 1994.
51. Cui, W., Eskin, N.A.M. and Biliaderis, C.G., 'NMR Characterization of a 1,4-linked [Beta]-D-glucan Having Ether Groups from Yellow Mustard (Sinapis alba L.) Mucilage', Carbohydr. Polym., 27:117-122, 1995.
52. Cui, W., Eskin, N.A.M., Biliaderis, C.G. and Marat, K., 'NMR Characterization of a 4-O-methyl-D-glucuronic Acid Containing rhamno- galacturonan from Yellow Mustard (Sinapis alba L.) Mucilage', Carbohydr. Res., 292:173-183, 1996.
53. Cui, W., Eskin, N.A.M., Biliaderis, C.G. and Mazza, C.G., 'Synergistic Interactions Between Yellow Mustard Polysaccharides and Galactomannans,' Carbohydr. Polym., 27:123-127, 1995.
54. Cui, W., and Eskin, N.A.M., 'Interaction Between Yellow Mustard Gum and Locust Bean Gum: Impact on a Salad Cream Product', in Gums and Stabilisers for the Food Industry 8, Phillips, G.O., Williams, P.A. and Wedlock, D.J. (eds.), IRL Press at Oxford University. pp. 161-170, 1996.
55. Vaughan, J.G., The Structure and Utilization of Oilseeds, Chapman and Hall Ltd. London. pp.55-57, 1970.
56. Siddiqui, I.R., Yiu, S.H., Jones, J.D. and Kalab, M., 'Mucilage in Yellow Mustard (Brassica hirta) Seeds', Food Microstructure, 5:157-162, 1986.
57. Vose, J.R., 1974. 'Chemical and Physical Studies of Mustard and Rapeseed Coats', Cereal Chem., 51:658-665, 1974.
58. Hirst, E.L., Rees, D.A. and Richardson, N.G., 'Seed Polysaccharides and Their Role in Germination', Biochem. J., 95:453-458, 1965.
59. Bailey, K. and Norris, F.W., 'The Nature and Composition of the Mucilage From Seeds of White Mustard (Brassica alba)', Biochem. J., 26:1609-1623, 1932.
60. Begin, F., Vachon, C., Jones, J., Wood, P.J. and Savoie, L., 'Effect of Dietary Fibers on Glycemia and Insulinemia and on Gastrointestinal Function in Rats', Can. J. Physiol. Pharmacol., 67:1265-1271, 1988.
61. Jenkins, A.L., Jenkins, D.J.A., Ferrari, F., Collier, G., Rao, A.V., Samuels, S., Jones, J.D., Wong, G.S. and Josse, R.G., 'Effect of Mustard Seed Fiber on Carbohydrate Tolerance', J. Clin. Nutr. Gastrenterol., 2:81-86, 1987.
62. Wood, J.P., 'Physicochemical Characteristics and Physiological Properties of Oat (1 [approaches] 3)(1 [approaches] 4)-[Beta]-D-glucan', Oat Bran, Wood, P.J. (ed.). Am. Assoc. Cereal Chem, St. Paul, MN. pp. 83-112, 1993.
63. Cui, W. and Eskin, N.A.M, 'Processing and Functional Properties of Mustard Products and Components', in Processing and Evaluation of Functional Foods, Mazza, G. ed., Technomic Publishing Co., lancaster, PA. In press, 1997.
W. (Steve) Cui is a Research Scientist specializing in Carbohydrate Chemistry and Rheology with the Food Processing and Quality Improvement Program (FPQIP), Agriculture and Agri-Food Canada, Guelph, ON. He obtained a BSc Chemistry at Peking University, China in 1983, a MSc Chemical Engineering at Wuxi Institute of Light Industry, China in 1986 and a PhD Carbohydrate Chemistry and Rheology at University of Manitoba, Canada in 1993. Before joining the FPQIP in 1997, he was a NSERC visiting fellow at the Centre for Food and Animal Research, Agriculture and Agri-Food Canada and worked as a Research Associate at the University of Manitoba, and two Research Stations, Agriculture and Agri-Food Canada (Morden, MB and Summerland, BC, respectively). Cui is a member of American Association of Cereal Chemists and The Society of Rheology. He has authored and co-authored 24 scientific papers, reviews and book chapters.
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|Publication:||Canadian Chemical News|
|Date:||Nov 1, 1997|
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