Glucosinolates sulfonated oxime moiety and side chain derived

Glucosinolates or sulfur-containing glucosides and their hydrolytic products found in all Brassica vegetables responsible for their characteristics of mustard-like taste, hot and pungent odor and unique health benefits.  Glucosinolates also commonly named as mustard oil glucosinolates.  GSLs belongs to a relatively small but diverse group of secondary metabolites with vary structural subgroups.  This secondary metabolite structure containing the ?-D-thioglucose group, a sulfonated oxime moiety and side chain derived from methionine, an aromatic or branched amino acids (Mahn, A., & Reyes, A., 2012).


This compound had gained renewed interest in recent years due to the chemoprotective and anticarcinogenic properties of isothiocyanates, major hydrolysis products of glucosinolates (Yuan, G., Sun, B., Yuan, J., & Wang, Q.,2009).  Isothiocyanates also called mustard oils because responsible for the hot taste.  GSLs are also reported to be involved in plant defense against pest and disease indoles (Hui, Y. H. & Evranuz, E. O., 2015).  The higher amount of glucosinolates shows more resistant the plant towards pest and disease infection.

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Most abundant glucosinolates found in Brassica genus are aliphatic glucosinolates and their concentration varies among different groups of Brassicaceae.  Predominant GSLs found in broccoli are 4-methylsulfinylbutyl glucosinolate, glucoraphanin with 80.5%, 3-indolylmethyl glucosinolate, glucobrassicin7.8%, 4-methioxi-glucobrassicin with 3.8%, 1-methoxy-glucobrassicin with 3.8% and 3-butenyl glucosinolate, gluconapin (Yuan, G., Sun, B., Yuan, J., & Wang, Q., 2009, Mahn, A., & Reyes, A., 2012).Glucosinolates are not directly bioactive but their hydrolysis products are thought to be powerful in anticarcinogenic properties.  As broccoli cut, plant tissues damaged and myrosinase enzymes released.  Glucosinolates then hydrolyzed to unstable aglycone that further stabilized by spontaneous conversion into variety bioactive products including active isothiocyanates, ITCs, less active thiocyanates or nitriles.Amount of glucosinolate correspond to isothiocyanates are differ among Brassica vegetable. For examples 40%, 36% and 0% isothiocyanates found in cabbage, broccoli and cabbage turnip respectively.  The main isothiocyanates in broccoli are 1-isothiocyanato-4-(methyl-sulfinyl) butane, sulforaphane, SFN.  Isothiocyanates also named as mustard oil because it is responsible for hot taste.  Broccoli also reported being the best source of sulforaphane so far.  Sulforaphane comes from the result of glucosinolate glucoraphanin hydrolysis by myrosinase.  The sulforaphane has been demonstrated in the cancer-protective effect where the anticarcinogenic properties attribute to modify detoxification routes.  Besides that, sulforaphane concentration in broccoli strongly depends on processing and time period since harvested. Phenolic compoundsPhenolic compounds are secondary metabolites composed of aromatic rings substituted with several hydroxyl groups and classified as flavonoids, phenolic acids, stilbenes and lignans based on structure.  The group has more than 8000 compounds that occur widely in plants.  Major classes of phenolic compounds in Brassica vegetables are flavonoids, anthocyanins, and phenolic acids. Phenolic compounds are one of the most important groups that possessing the antioxidant capacity, provide protection against fungal disease and ultraviolet light.  This compounds also provide bitter or astringent taste and in some cases, provide aroma and color.  Phenolics in vegetables found to be either free form or conjugated form.  Polyphenolic contents among Brassica vegetables are differed for examples Chinese cabbage contains 1189 ±125 µg/g, broccoli has 822 ± 89 µg/g, cauliflower have 278 ±15µg/g and white cabbage with 153 ± 21 µg/g on a fresh-weight basis (Hui, Y. H., & Evranuz, O., 2015).  Broccoli also possessed the highest total phenolic compounds compared to other types of vegetables.Flavonoids are also polyphenolic compounds which consist of 15 carbons with two aromatic rings connected by the three-carbon bridge.  Among the flavonoids, flavonols are the most widespread throughout the plant kingdom.  Main flavonols found in Brassica vegetables are kaempferol, quercetin, isorhamnetin and myricetin also their O-glycosides.  Major flavonols found in broccoli florets are kaempferol-3-O-sophoroside and quercetin while minor flavonols in broccoli are isoquercitrin, kaempferol-3-O-glucoside, and kaempferol diglucoside.  Among the flavonoids, anthocyanins are the most important group of colored pigments and possessed antioxidant activity also other useful biological properties.  Anthocyanins are involved in protecting plants against excessive light and attract pollinating insects.  Hui, Y. H., and Evranuz, O. (2015) in the book entitled Handbook of vegetable preservation and processing explained that phenolic acids are nonflavonoid phenolics derived from benzoic and cinnamic acids. The most common cinnamic acids in Brassica vegetables are p-coumaric, sinapic and ferulic acids.  They are found in conjugation with sugar or other hydroxycinnamic acids.  The hydroxycinnamic acids are the most abundant phenolic acid presented in Brassica vegetables.  Kale, cabbage, broccoli, and cauliflower has been reported to have significant levels of hydroxycinnamic acids.


Lignans are another group of phenolic compounds which also found in Brassica vegetables.  Lignans possessed antioxidant, cancer-preventive and antiestrogenic properties by exhibit antimicrobial and antifungal activities.  Common lignans identified in Brassicaceae are lariciresinol and pinoresinol.  However, secoicolariciresinol and matairesinol are other lignans found in Brassica vegetables.  About 8µg/100g and 38µg/100g of secoicolariciresinol dry-weight basis found in white cabbage and broccoli respectively.  On the other hand, matairesinol found in kale.Green leafy of Brassica vegetables known to have rich in carotenes especially lutein and ?-carotene.  “Broccoli: Description and History”, (2018) ranked broccoli at the sixteenth place of best vitamin A source in the form of carotenoids.  Carotenoids are the precursor to vitamin A.  Carotenoids that found in dark green leafy vegetables responsible in the prevention of oxidative stress consequences.  Besides that, carotenes are well recognized in promoting healthy eyes.  Beta-carotene has vitamin A activity while zeaxanthin belongs to carotenoids of the xanthophyll class.Cruciferae
vegetables are known to have a high content of vitamin C and E.  Cruciferous such as broccoli, cauliflower,
and cabbage are reported as a better source of vitamin C than a banana, apple
and raspberry (Hui, Y. H., & Evranuz, O., 2015).  According to “Broccoli: Description and History”, (2018), among
100 of good foods, broccoli is ranked third best source of vitamin C and tenth
best source of vitamin E.  Vitamin C
including ascorbic acids has many biological activities inside the body by
acting as an enzyme cofactor, radical scavenger and donor or acceptor in
electron transport at the plasma membrane. 
Vitamin E including tocopherols and tocotrienols are important
lipophilic antioxidant in both humans and animals.  Vitamin E is recognized as a cure for an age-related
disease and cardiovascular disease. 
Alpha-tocopherol is the predominant tocopherol in Cruciferous except for
cauliflower containing gamma-tocopherol. Minerals Generally,
cruciferous vegetables are rich in minerals including calcium and iron.  Cauliflower, broccoli, and kale been reported
to have high mineral contents.  However,
broccoli has the capability to accumulate selenium, Se that found in soil which
then enhancing health-promoting benefits (Mahn,
A., & Reyes, A., 2012). 
Selenium is bioactive compound and may act directly or indirectly as a cellular
antioxidant.  The antioxidant effect that
selenium exerted mainly due to an active site formed to protect cells from
oxidative damage. Selenium compound, se-methyl-selenocysteine (SMSeC) at doses
between 1 and 3mg Se/kg proved to be a powerful chemoprotective agent by
excreting its anticarcinogenic properties (Mahn,
A., & Reyes, A., 2012).  Broccoli can
take up SMSeC to a concentration of 2.8mmol/g dry weight or even higher if
planted in Se-enriched medium (Mahn, A., & Reyes, A., 2012). 2.1.2 Health benefit of broccoli consumptionTraditionally,
vegetables are used not only as food and for nutrition, but also for therapy of
diseases since they contain pharmacological active substances (Herr, Ingrid, and Markus W.
Büchler, 2010).  For example,
an onion was recommended for application in treating inflamed wounds during
1500 B.C. by Egyptians.  Besides that,
diversion in brassica genus plants is very important in the ancient world where
cabbage is served more as medicament than aliment. Broccoli
is an edible green plant belongs to the group of Brassica oleraceae species. 
This green plant is listed in top ten healthiest food in the world, it is
shown that consumption of this vegetable is compromising with significant
benefit in human health.  Constituents
present in broccoli are known to possess antioxidant benefits, anticarcinogenic
properties and reducing the risk of diabetes (Ravikumar, C., 2015). 
Besides that, broccoli also improves bowel function and
anti-inflammatory benefits (Anandharamakrishnan,
C., 2015). Antioxidant benefitAntioxidant
in vegetables is mainly from vitamin including tocopherol, carotenoid and
ascorbic acid, minerals and other phytonutrients.  However, broccoli which containing SFN known
to be a powerful antioxidant.  SFN is
contrary to standard antioxidant where SFN works indirectly due to its ability
to make cells create a diverse group of enzymes then block selected chemicals
from becoming carcinogens. Apart
from SFN, polyphenols in broccoli also act as a potent antioxidant as they
protect the cell against oxidative stress by donating an electron to free
radicals.  Polyphenols possessed ideal
structural chemistry for free radical scavenging activities and showed to be
more effective antioxidants than vitamin E and C on the molar basis.  Polyphenols also act as chelators of metal
ions by preventing the metal catalyzed formation of initiating radical species.
Cancer preventionBroccoli plays a major role in treating several
cancers that occur in different parts of the body.  Cancer is a multistep process that results in
uncontrolled cell division (Ravikumar, C., 2015).  ITCs are well-known class of cancer chemo
preventive agents.  ITCs suppress tumor
growth by inducing cycle arrest that leading to apoptosis, inhibit the size,
multiplicity, and progression of bladder cancer, prevent the prostate
carcinogenesis process. Sulforaphane from broccoli been reported in
demonstrating the inhibition of Helicobacter
pylori which associated with an increase in the risk of gastric cancer (Herr, Ingrid, & Markus W. Büchler, 2010).  The purified SFN act by inhibit the growth
and kill strains of H. pylori in the
test tube and tissue culture.  In a study
about the consumption of broccoli in 48 patients who infected by H. pylori shows a reduction in gastritis.
However, the parameters increased again to the original value when broccoli
consumption is stopped (Herr, Ingrid, and Markus W. Büchler, 2010. Selenium-enriched broccoli compared to normal
broccoli is found to be superior and induced apoptosis of prostate cancer,
inhibit proliferation and reduce prostate-specific antigen secretion.  Selenium-enriched broccoli also used as an
alternative selenium source for prostate cancer prevention and therapy.  The high Se-broccoli is protective against
chemically induced mammary or colon cancer. Broccoli
is also an excellent source of indole-3-cabinol, a chemical which boosts DNA
repair in cells and appears to block the cancer cells from growing (Shivale,
N., Shahm S., Sampat, K. & Deshpande, K., 2015).  Indole-3-carbinol,
hydrolysis product of the glucosinolate glucobrassicin together with SFN from
broccoli seen to be useful for cancer prevention.  The success has been proved in National
Cancer Institute clinical trials against breast cancer and respiratory
papilloma (Jeffery, E. H. et al, 2003). Apart
from ITCs, SFN and indole-3-carbinol, beta-carotene, lycopene and lutein also
show to give a response in inducing cancer cells division.  They have been reported to provide protection
against uterine, prostate, breast, colorectal and lung cancer (Hui, Y. H.,
& Evranuz, O., 2015).
Diabetes risk reductionDiabetes
is a disease involving problems with the hormone insulin.  People suffer with diabetes need to manage
their disease to stay healthy since there is no cure.  Broccoli reported in one of the few
vegetables that claimed to possess antidiabetic potency.  This plant has shown the beneficial
hypoglycemic influence in both animals and humans experiment (Ravikumar, C., 2015).  Flavonoid-rich in broccoli have
anti-inflammatory and antioxidant effects to protect against diabetes. Besides
that, SFN also has potential in inducing some peroxide proliferators which
activate the receptors that contributed to glucose homeostasis in hyperglycemic
and oxidative conditions as well as preventing nephropathy (Ravikumar, C., 2015).  Dr. Anders Rosengren and his team conducted a
study on 97 patients suffering from type 2 diabetes and SFN extract from
broccoli reported that majority of patients are doing well but 37 of them still
have poor blood sugar control.
Anti-inflammatory benefitIn
general, constipation is not usually dangerous but causing person to have painful
and experiencing abdominal cramping as well bloating.  Institute of Medicine recommends both male
and female within 19 to 50 years old should consume 38g and 25g of fiber in
daily diet.  The fiber found in broccoli
and other vegetables reported to help in keeping stool run smoothly through the
colon.  Fiber in broccoli contains both
soluble and insoluble fiber. 2.2
Spray DryingThe University
of Guelph discussed spray drying in the book entitled The Dairy Science and
Technology and stated that spray drying is the process which nearly complete
removal of water to a level less than 5%. 
Drying process takes place within a matter of seconds at high
temperature, approximately 200°C.  Spray dryer that widely used is a type of air
convection dryer. (2017) indicated that process steps in
spray drying are strongly depend on material properties, equipment design and
setting of operating parameters.  These
factors influence final product quality, especially in moisture residues,
particle size and powder morphology. 
Usually, the optimization of these variables achieved by try and error