Sinalbin: Difference between revisions

Revision as of 23:33, 11 December 2024

Sinalbin

Sinalbin is a glucosinolate compound found in certain plants, particularly in the seeds of white mustard (Sinapis alba). It is responsible for the characteristic pungent taste of mustard and has been studied for its potential health benefits and role in plant defense mechanisms.

Chemical Structure

Sinalbin is a type of glucosinolate, which are sulfur-containing compounds found in the Brassicaceae family. The chemical structure of sinalbin includes a glucose molecule, a sulfate group, and a side chain derived from the amino acid phenylalanine. Upon hydrolysis by the enzyme myrosinase, sinalbin is converted into 4-hydroxybenzyl isothiocyanate, which is responsible for its pungent flavor.

Occurrence

Sinalbin is predominantly found in the seeds of the white mustard plant (Sinapis alba). Unlike sinigrin, another glucosinolate found in black mustard and other cruciferous vegetables, sinalbin is less common and contributes to the milder flavor of white mustard compared to black mustard.

Biological Role

In plants, glucosinolates like sinalbin serve as a defense mechanism against herbivores and pathogens. When plant tissue is damaged, myrosinase enzymes come into contact with glucosinolates, leading to the production of isothiocyanates and other compounds that deter herbivory and inhibit microbial growth.

Health Implications

Research has suggested that glucosinolates and their hydrolysis products may have potential health benefits, including anti-cancer properties. Isothiocyanates, such as those derived from sinalbin, have been studied for their ability to induce phase II detoxification enzymes, inhibit carcinogen activation, and promote apoptosis in cancer cells.

Uses

Sinalbin is primarily used in the food industry as a flavoring agent in mustard condiments. The mild pungency of white mustard seeds makes them suitable for use in various culinary applications, including salad dressings, sauces, and pickling.

Also see

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-{{chembox
+Sinalbin
-| verifiedrevid = 439550668
-|ImageFile=Sinalbin structure.png
-|ImageSize=200px
-|IUPACName= [(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]
--(4-hydroxyphenyl)-''N''-sulfooxyethanimidothioate
-|IUPACName_hidden = yes
-|OtherNames=Glucosinalbin; 4-Hydroxybenzyl glucosinolate; Glucosinalbate
-|Section1= {{Chembox Identifiers
-|  CASNo_Ref = {{cascite|correct|??}}
-| CASNo=19253-84-0
-|  PubChem=656568
-|  SMILES=O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](S/C(CC2=CC=C(O)C=C2)=N\OS(O)(=O)=O)[C@@H]1O
-  }}
-|Section2= {{Chembox Properties
-|  C=14 | H=19 | N=1 | O=10 | S=2
-|  Appearance=
-|  Density=
-|  MeltingPt=
-|  BoilingPt=
-|  Solubility=
-  }}
-|Section3= {{Chembox Hazards
-|  MainHazards=
-|  FlashPt=
-|  Autoignition=
-  }}
-}}
-== Sinalbin ==
+'''Sinalbin''' is a glucosinolate compound found in certain plants, particularly in the seeds of white mustard (''Sinapis alba''). It is responsible for the characteristic pungent taste of mustard and has been studied for its potential health benefits and role in plant defense mechanisms.
-[[File:Sinalbin structure.svg|thumb|Sinalbin_structure]]
+==Chemical Structure==
+Sinalbin is a type of [[glucosinolate]], which are sulfur-containing compounds found in the Brassicaceae family. The chemical structure of sinalbin includes a glucose molecule, a sulfate group, and a side chain derived from the amino acid phenylalanine. Upon hydrolysis by the enzyme myrosinase, sinalbin is converted into 4-hydroxybenzyl isothiocyanate, which is responsible for its pungent flavor.
-'''Sinalbin''' is a glucosinolate, a group of natural compounds found predominantly in plants, particularly those of the Brassica genus such as white mustard (''Sinapis alba''). Glucosinolates like sinalbin play vital roles in plant defense against herbivores and have been the subject of various nutritional and pharmacological studies due to their potential health benefits for humans<ref>Traka, M. H., & Mithen, R. F. (2009). Glucosinolates, isothiocyanates and human health. Phytochemistry reviews, 8(1), 269-282.</ref>.
+==Occurrence==
+Sinalbin is predominantly found in the seeds of the white mustard plant (''Sinapis alba''). Unlike [[sinigrin]], another glucosinolate found in black mustard and other cruciferous vegetables, sinalbin is less common and contributes to the milder flavor of white mustard compared to black mustard.
-== Chemical Characteristics ==
+==Biological Role==
-Sinalbin, chemically distinguished as a β-thioglucoside N-hydroxysulphate, undergoes enzymatic hydrolysis by myrosinase, a process that yields 4-hydroxybenzyl isothiocyanate<ref>Bones, A. M., & Rossiter, J. T. (2006). The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry, 67(11), 1053-1067.</ref>. This resultant compound has been identified as the primary component responsible for the pungent aroma associated with crushed mustard seeds.
+In plants, glucosinolates like sinalbin serve as a defense mechanism against herbivores and pathogens. When plant tissue is damaged, myrosinase enzymes come into contact with glucosinolates, leading to the production of isothiocyanates and other compounds that deter herbivory and inhibit microbial growth.
-== Biological Significance and Applications ==
+==Health Implications==
-In plants, glucosinolates like sinalbin play a defensive role. When plant cells are damaged (for instance, during herbivore consumption), myrosinase enzymes come into contact with glucosinolates, catalyzing their hydrolysis and producing isothiocyanates. These compounds are deterrents to many herbivores and also possess antimicrobial properties<ref>Textor, S., & Gershenzon, J. (2009). Herbivore induction of the glucosinolate-myrosinase defense system: major trends, biochemical bases and ecological significance. Phytochemistry Reviews, 8(1), 149-170.</ref>.
+Research has suggested that glucosinolates and their hydrolysis products may have potential health benefits, including anti-cancer properties. Isothiocyanates, such as those derived from sinalbin, have been studied for their ability to induce phase II detoxification enzymes, inhibit carcinogen activation, and promote apoptosis in cancer cells.
-For humans, the hydrolytic products of glucosinolates have garnered interest for their potential health benefits. Studies suggest a possible correlation between dietary intake of glucosinolate-rich foods and a reduced risk of certain cancers<ref>Halkier, B. A., & Gershenzon, J. (2006). Biology and biochemistry of glucosinolates. Annual review of plant biology, 57, 303-333.</ref>. Research on sinalbin and other glucosinolates is ongoing, with investigations delving into their antioxidant, anti-inflammatory, and chemopreventive properties.
+==Uses==
+Sinalbin is primarily used in the food industry as a flavoring agent in mustard condiments. The mild pungency of white mustard seeds makes them suitable for use in various culinary applications, including salad dressings, sauces, and pickling.
-== Dietary Sources and Processing ==
+==Also see==
-White mustard seeds are the principal dietary source of sinalbin. The processing of mustard, such as cooking or fermenting, can alter the glucosinolate content, with implications for both flavor and potential health benefits<ref>Shahidi, F., & Ambigaipalan, P. (2015). Phenolics and polyphenolics in foods, beverages and spices: Antioxidant activity and health effects–A review. Journal of functional foods, 18, 820-897.</ref>.
+* [[Glucosinolate]]
+* [[Sinigrin]]
+* [[Myrosinase]]
+* [[Isothiocyanate]]
+* [[Brassicaceae]]
-== Conclusion ==
+{{Reflist}}
-Sinalbin, with its significance in plant defense and potential implications for human health, underscores the fascinating interplay between plant biochemistry and human nutrition. As research continues, our understanding of this compound and its myriad effects will only deepen.
-== References ==
-<references />
-{{stub}}
-[[Category:Pungent flavors]]
-[[Category:Nutrition]]
 [[Category:Glucosinolates]]
+[[Category:Plant defense compounds]]
+[[Category:Mustard]]