Influence of Cabbage (Brassica oleracea) Accession and Growing Conditions on Myrosinase Activity, Glucosinolates and Their Hydrolysis Products

Glucosinolates are secondary plant metabolites present in Brassica vegetables. The endogenous enzyme myrosinase is responsible for the hydrolysis of glucosinolates, yielding a variety of compounds, including health-promoting isothiocyanates. The influence of cabbage accession and growing conditions on myrosinase activity, glucosinolates (GSL) and their hydrolysis products (GHPs) of 18 gene-bank cabbage accessions was studied. Growing conditions, cabbage morphotype and accession all significantly affected myrosinase activity and concentration of glucosinolates and their hydrolysis products. In general, cabbages grown in the field with lower growth temperatures had significantly higher myrosinase activity than glasshouse samples. Profile and concentration of glucosinolates and their hydrolysis products differed across the accessions studied. Aliphatic glucosinolates accounted for more than 60 % of total glucosinolates in most of the samples assessed. Nitriles and epithionitriles were the most abundant hydrolysis products formed. The results obtained showed that consumption of raw cabbages might reduce the amount of beneficial hydrolysis products available to the consumer, as more nitriles were produced from hydrolysis compared to beneficial isothiocyanates. However, red and white cabbages contained high concentrations of glucoraphanin and its isothiocyanate, sulforaphane. This implies that careful selection of accessions with ample concentrations of certain glucosinolates can improve the health benefits derived from raw cabbage consumption.

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EFFECTS OF ASCORBIC ACID AND FERUM IONS CONCENTRATION ON THE HYDROLYSIS OF GLUCOSINOLATE AND MYROSINASE ACTIVITY IN THE WATERCRESS (Nasturtium officinale sp.)

Jurnal Teknologi ◽

10.11113/jt.v78.5092 ◽

2016 ◽

Vol 78 (8) ◽

Cited By ~ 1

Author(s):

Syamimi Mohd Zul ◽

Noumie Surugau

Keyword(s):

Ascorbic Acid ◽

Enzymatic Hydrolysis ◽

Hydrolysis Product ◽

Carcinogenic Activity ◽

Nasturtium Officinale ◽

Hydrolysis Products ◽

Low Concentrations ◽

Health Promoting ◽

Hydrolysis Of ◽

Myrosinase Activity

Watercress (Nasturtium officinale sp.) from the Brassicae family contains phenethyl glucosinolates (gluconasturtiin) as the main glucosinolate (GLS). The enzymatic hydrolysis products by naturally-occuring myrosinase produced phenethyl isothicyanate (PEITC) which reported to possess anti-carcinogenic activity. Depending on several factors, its counterpart, phenethyl nitrile (PEN) can also be formed as hydrolysis product. This study investigated the effects of adding ascorbic acid and Fe2+ ions at different concentration on the hydrolysis of gluconasturtiin. Hydrolysis products were extracted using dichloromethane and analyzed semi-quantitatively by using GCMS. The results showed that PEITC increased at the low concentration of ascorbic acid (up to 0.06M). Similarly, addition of up to 0.06M Fe2+ ions increased PEITC; higher than 0.06M inhibits the formation of PEITC. Interestingly, similar trend for the production of PEN was detected. This study also investigated myrosinase activity both by exogenous and endogenous methods at different concentrations of ascorbic acid and Fe2+ ions using standard sinigrin as subsrat. Overall, the myrosinase activity was more active at the low concentrations of ascorbic acid. Also, the exogenous method is more efficient than endogenous. This study proved that the presence of reducing agents such as ascorbic acid and Fe2+ ions during the preparation of watercress as food would affect the production of the health-promoting PEITC.

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The Impact of Domestic Cooking Methods on Myrosinase Stability, Glucosinolates and Their Hydrolysis Products in Different Cabbage (Brassica oleracea) Accessions

Foods ◽

10.3390/foods10122908 ◽

2021 ◽

Vol 10 (12) ◽

pp. 2908

Author(s):

Omobolanle O. Oloyede ◽

Carol Wagstaff ◽

Lisa Methven

Keyword(s):

Brassica Oleracea ◽

Residual Activity ◽

Cooking Methods ◽

Hydrolysis Products ◽

Brassica Vegetables ◽

Glucosinolate Concentration ◽

Health Promoting ◽

The Impact ◽

Myrosinase Activity

Glucosinolate hydrolysis products are responsible for the health-promoting properties of Brassica vegetables. The impact of domestic cooking on the myrosinase stability, glucosinolates and hydrolysis products in 18 cabbage accession was investigated. Cabbages were steamed, microwaved, and stir-fried before analysis. Cooking significantly affected myrosinase stability and glucosinolate concentrations within and between cabbage morphotypes. Myrosinase was most stable after stir-frying, with up to 65% residual activity. Steaming and microwaving resulted in over 90% loss of myrosinase activity in some accessions. Stir-frying resulted in the greatest decrease in glucosinolate concentration, resulting in up to 70% loss. Steamed cabbages retained the highest glucosinolates after cooking (up to 97%). The profile and abundance of glucosinolate hydrolysis products detected varied across all cooking methods studied. Cooking reduced the amounts of nitriles and epithionitriles formed compared to raw samples. Steaming led to a significant increase in the concentration of beneficial isothiocyanates present in the cabbage and a significantly lower level of nitriles compared to other samples. Microwaving led to a reduction in the concentrations of both nitriles and isothiocyanates when compared to other cooking methods and raw cabbage. The results obtained help provide information on the optimal cooking methods for cabbage, suggesting that steaming may be the best approach to maximising beneficial isothiocyanate production.

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Advanced Analytical Methods for Phenolics in Fruits

Journal of Food Quality ◽

10.1155/2018/3836064 ◽

2018 ◽

Vol 2018 ◽

pp. 1-6 ◽

Cited By ~ 5

Author(s):

Nesibe Ebru Kafkas ◽

Müberra Kosar ◽

Ayşe Tülin Öz ◽

Alyson E. Mitchell

Keyword(s):

Phenolic Compounds ◽

Value Added ◽

Biological Tissues ◽

Carbon Chain ◽

Polyphenolic Compounds ◽

Hydroxyl Groups ◽

Plant Metabolites ◽

Secondary Plant Metabolites ◽

Extraction Separation ◽

Health Promoting

Phenolic compounds are a group of secondary plant metabolites, many with health-promoting properties that are present in all parts of plants. They have an aromatic structure, including either one or more hydroxyl groups giving them the ability to stabilize free radicals and protect biological tissues against damage related to reactive oxygen species. Phenolic compounds are concentrated in the fruit of plants, and therefore, the fruit can be an important dietary source of these phytochemicals, which exist as monomers, or bound to one another. Polyphenolic compounds are classified into different subclasses based upon the number of phenol ring systems that they contain, saturation, and length of the carbon chain that bind the rings to one another. The phenolic acids present in fruit tissues protect the plant against disease, infections, UV radiation, and insect damage. For this reason, the beneficiary effects of phenolic compounds are continually being investigated for their health-promoting properties and for meeting increased consumer demand for healthy nutritious food. Due to the functional properties of polyphenolic compounds, there is increased interest on improving extraction, separation, and quantification techniques of these valuable bioactive compounds, so they can be used as value-added ingredients in foods, pharmaceuticals, and cosmetics. This review provides information on the most advanced methods available for the analysis of phenolics in fruits.

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Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production

Molecules ◽

10.3390/molecules24040796 ◽

2019 ◽

Vol 24 (4) ◽

pp. 796 ◽

Cited By ~ 30

Author(s):

Kathrin Kohnen-Johannsen ◽

Oliver Kayser

Keyword(s):

Tropane Alkaloids ◽

Structural Diversity ◽

Basic Structure ◽

In Planta ◽

Plant Metabolites ◽

Comprehensive Overview ◽

Secondary Plant Metabolites ◽

Pharmaceutical Therapy ◽

High Concentrations ◽

Microbial Biosynthesis

Tropane alkaloids (TA) are valuable secondary plant metabolites which are mostly found in high concentrations in the Solanaceae and Erythroxylaceae families. The TAs, which are characterized by their unique bicyclic tropane ring system, can be divided into three major groups: hyoscyamine and scopolamine, cocaine and calystegines. Although all TAs have the same basic structure, they differ immensely in their biological, chemical and pharmacological properties. Scopolamine, also known as hyoscine, has the largest legitimate market as a pharmacological agent due to its treatment of nausea, vomiting, motion sickness, as well as smooth muscle spasms while cocaine is the 2nd most frequently consumed illicit drug globally. This review provides a comprehensive overview of TAs, highlighting their structural diversity, use in pharmaceutical therapy from both historical and modern perspectives, natural biosynthesis in planta and emerging production possibilities using tissue culture and microbial biosynthesis of these compounds.

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Seasonal Variation of Glucosinolate Hydrolysis Products in Commercial White and Red Cabbages (Brassica oleracea var. capitata)

Foods ◽

10.3390/foods9111682 ◽

2020 ◽

Vol 9 (11) ◽

pp. 1682

Author(s):

Nicole S. Wermter ◽

Sascha Rohn ◽

Franziska S. Hanschen

Keyword(s):

Seasonal Variation ◽

Hydrolysis Product ◽

Red Cabbage ◽

Beneficial Effects ◽

Hydrolysis Products ◽

Food Retailers ◽

Brassica Vegetables ◽

Health Promoting ◽

First Time ◽

Excellent Source

Brassica vegetables contain glucosinolates, which are well-known for their potential to form health-promoting isothiocyanates. Among those crucifers, white and red cabbage are commonly consumed vegetables, exhibiting different glucosinolate and hydrolysis profiles thereof. Regarding the health beneficial effects from these vegetables, more information, especially concerning the seasonal variation of glucosinolate profiles and the formation of their bioactive hydrolysis products in commercial cabbages, is needed. In this study, glucosinolates and glucosinolate hydrolysis product profiles in red and white cabbages from three different food retailers were monitored over six different sampling dates across the selling season in autumn. For the first time, it was shown that, while glucosinolate profiles were similar in each cabbage variety, glucosinolate hydrolysis product profiles and hydrolysis behavior varied considerably over the season. The highest total isothiocyanate concentrations were observed in conventional red (1.66 μmol/g FW) and organic white (0.93 μmol/g FW) cabbages purchased at the first sampling date in September. Here, red cabbage was with up to 1.06 μmol/g FW of 4-(methylsulfinyl)butyl isothiocyanate (sulforaphane), an excellent source for this health-promoting isothiocyanate. Cabbages purchased 11 weeks later in autumn released lower levels of isothiocyanates, but mainly nitriles and epithionitriles. The results indicate that commercial cabbages purchased in early autumn could be healthier options than those purchased later in the year.

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ANALYSIS OF FLAVONES C-GLYCOSIDES AND AND STEPWISE HYDROLYSIS OF THEIR ACETATES IN THE LEAVES OF RUBUS CHAMAEMORUS L.

chemistry of plant raw material ◽

10.14258/jcprm.2021029185 ◽

2021 ◽

pp. 257-265

Author(s):

Andrey Kennet Whaley ◽

Anastasiya Olegovna Ponkratova ◽

Anastasiya Andreyevna Orlova ◽

Evgeni Borisovich Serebryakov ◽

Stanislav Ivanovich Selivanov ◽

...

Keyword(s):

Biological Activity ◽

Hplc Analysis ◽

Higher Plants ◽

Two Dimensional ◽

Cardiotonic Activity ◽

Hydrolysis Products ◽

Rubus Chamaemorus ◽

Growing Conditions ◽

First Time ◽

Hydrolysis Of

The C-glycoside embinin and its mono- and diacetate derivatives have immunotropic and cardiotonic activity, which makes the search for plants that contain them interesting. Embinin and its acetate derivatives were previously isolated only from some plants of the genus Iris, the habitat and growing conditions of which are very different from those of the genus Rubus. As a result of the study, the structure of seven C-glycosides, embinin derivatives, isolated from the leaves of Rubus chamaemorus L. (Rosaceae) was established. Using HR-ESI-MS, HPLC-MS, as well as one- and two-dimensional NMR spectroscopy, the structure of three substances isolated in individual form was established: embinin (1) and its diacetyl derivatives – 2''',3'''-diacetylembinin (5) and 3''',4'''-diacetylembinin (7). The method of stepwise hydrolysis of C-glycoside acetate residues proposed in this study, followed by HPLC analysis of the resulting hydrolysis products, made it possible to establish the structure of minor flavone C-glycosides contained in the leaves of Rubus chamaemorus L.: 2'''-acetylembinin (2), 3'''-acetylembinin (3), 4'''-acetylembinin (4) and 2''',4'''-diacetylembinin (6). All these compounds were found in the leaves of Rubus chamaemorus L. for the first time. The C-glycosides - embinin and its acetate derivatives are rare metabolites of higher plants, the presence of which is determined by the peculiarity of their physiology, and the biological activity determines the prospects for medical use.

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Bioactive Phenolics and Polyphenols: Current Advances and Future Trends

International Journal of Molecular Sciences ◽

10.3390/ijms21176142 ◽

2020 ◽

Vol 21 (17) ◽

pp. 6142

Author(s):

Daniel A. Jacobo-Velázquez ◽

Luis Cisneros-Zevallos

Keyword(s):

Phenolic Compounds ◽

Future Trends ◽

Plant Metabolites ◽

Secondary Plant Metabolites ◽

Health Promoting ◽

Secondary Plant

Phenolic compounds are secondary plant metabolites with remarkable health-promoting properties [...]

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Importance of Genotype on Carotenoid and Chlorophyll Levels in Broccoli Heads

HortScience ◽

10.21273/hortsci.44.5.1248 ◽

2009 ◽

Vol 44 (5) ◽

pp. 1248-1253 ◽

Cited By ~ 12

Author(s):

Mark W. Farnham ◽

Dean A. Kopsell

Keyword(s):

The United States ◽

Dry Mass ◽

The Other ◽

Genotypic Differences ◽

Plant Metabolites ◽

Positive Health ◽

Secondary Plant Metabolites ◽

Genotype Effect ◽

Health Promoting ◽

Carotenoid Profile

Carotenoids are secondary plant metabolites in vegetables known to be essential in the human diet and reported to confer various positive health-promoting effects when consumed. Brassica oleracea L. vegetables like kale, cabbage, and broccoli are recognized as excellent sources of dietary carotenoids. Broccoli has emerged as the most important B. oleracea crop in the United States and it likely supplies more carotenoids to the U.S. diet than the other crops of this species. However, very little is known about the general carotenoid profile of this important vegetable or the levels of specific carotenoids and how they might vary among genotypes. Thus, the objectives of this study were to assess carotenoid profiles of different inbred broccoli heads; to assess chlorophyll concentrations measured simultaneously during carotenoid assays; to determine the relative effects of genotype versus environment in influencing head carotenoid levels; and to examine phenotypic correlations between carotenoid levels and other traits. Results show lutein to be the most abundant carotenoid in broccoli heads ranging from 65.3 to 139.6 μg·g−1 dry mass (DM) among nine inbreds tested in three environments. Genotype had a highly significant effect on lutein levels in broccoli heads and the ratio of σ2 g/σ2 p for this carotenoid was 0.84. Violaxanthin also exhibited a significant genotype effect, but it was found at lower levels (17.9 to 35.4 μg·g−1 DM) than lutein. β-carotene and neoxanthin were detected at levels similar to violaxanthin, but genotypic differences were not detected when all environments were compared. This was also true for antheraxanthin, which was detectable in all genotypes at lower levels (mean of 13.3 μg·g−1 DM) than the other carotenoids. Significant genotypic differences were observed for both chlorophyll a and b among the studied inbreds; however, no environment or genotype-by-environment effects were observed with these compounds. Results indicated that most carotenoids measured were positively and significantly correlated with one another, indicating that higher levels of one carotenoid were typically associated with higher levels of others. This study emphasizes the relative importance of lutein in broccoli heads and the key role that genotype plays with this compound, ultimately indicating that breeding cultivars with increased levels of this particular carotenoid may be feasible.

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Chemoprofiling as Breeding Tool for Pharmaceutical Use of Salix

Frontiers in Plant Science ◽

10.3389/fpls.2021.579820 ◽

2021 ◽

Vol 12 ◽

Author(s):

Nadja Förster ◽

Kyriaki Antoniadou ◽

Matthias Zander ◽

Sebastian Baur ◽

Verena Karolin Mittermeier-Kleßinger ◽

...

Keyword(s):

Phenolic Compounds ◽

Metabolite Profile ◽

Targeted Metabolomics ◽

Plant Metabolites ◽

Secondary Plant Metabolites ◽

Health Promoting ◽

Willow Bark ◽

Intraspecific Hybrids ◽

Metabolomics Analysis ◽

Intraspecific Crossing

Willow bark is traditionally used for pharmaceutical purposes. Evaluation is so far based on the salicylate content, however, health promoting effects of extracts might be attributed to the interaction of those salicylates with other compounds, which support and complement their action. So far, only S. purpurea, S. daphnoides, and S. fragilis are included in pharmaceutical extracts. Crossing with other species could result in a more diverse secondary metabolite profile with higher pharmacological value. With the help of targeted inter- and intraspecific crossing, new chemotypes were generated, whereby nine different Salix genotypes (S. alba, S. daphnoides, S. humboldtiana, S. lasiandra, S. nigra, S. pentandra, S. purpurea, S. x rubens, S. viminalis) were included in the study. Based on substances known for their health promoting potential and characteristic for Salix (selected phenolic compounds including salicylates), a targeted metabolomics analysis and clustering of 92 generated Salix clones was performed revealing four different cluster/chemoprofiles. In more specific, one group is formed by S. daphnoides clones and inter- and intraspecific hybrids, a second group by S. viminalis clones and inter- and intraspecific hybrids, a third group generally formed by S. alba, S. pentandra, S. x rubens, and S. lasiandra clones and hybrids, and a fourth group by S. purpurea clones and inter- and intraspecific hybrids. Clustering on the basis of the selected phenolic compounds can be used for identifying Salix clones with a different compound profile. New combinations of secondary plant metabolites offer the chance to identify Salix crosses with improved effects on human health.

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Impact of Food-Derived Bioactive Compounds on Intestinal Immunity

Biomolecules ◽

10.3390/biom11121901 ◽

2021 ◽

Vol 11 (12) ◽

pp. 1901

Author(s):

Christian Zimmermann ◽

Anika E. Wagner

Keyword(s):

Immune System ◽

Bioactive Compounds ◽

Intestinal Barrier ◽

Immune Homeostasis ◽

Intestinal Immunity ◽

Plant Metabolites ◽

Food Ingredients ◽

Secondary Plant Metabolites ◽

Bowel Diseases ◽

Health Promoting

The gastrointestinal system is responsible for the digestion and the absorption of nutrients. At the same time, it is essentially involved in the maintenance of immune homeostasis. The strongest antigen contact in an organism takes place in the digestive system showing the importance of a host to develop mechanisms allowing to discriminate between harmful and harmless antigens. An efficient intestinal barrier and the presence of a large and complex part of the immune system in the gut support the host to implement this task. The continuous ingestion of harmless antigens via the diet requires an efficient immune response to reliably identify them as safe. However, in some cases the immune system accidentally identifies harmless antigens as dangerous leading to various diseases such as celiac disease, inflammatory bowel diseases and allergies. It has been shown that the intestinal immune function can be affected by bioactive compounds derived from the diet. The present review provides an overview on the mucosal immune reactions in the gut and how bioactive food ingredients including secondary plant metabolites and probiotics mediate its health promoting effects with regard to the intestinal immune homeostasis.

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