[글루코시놀레이트 표준물질(Reference Substances)] Glucosinolates_Phyproof PhytoLab - 코아사이언스

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Glucosinolates

As one of the leading manufacturers internationally, PhytoLab offers over 1,400 extensively documented herbal reference substances of all classes of natural compounds. Our portfolio currently includes a total of 25 glucosinolates and one glucosinolate-derived goitrogenic degradation product. Most of our glucosinolates and related compounds are certified as primary reference standards.

Occurrence and properties

Glucosinolates are secondary plant metabolites that occur in a wide variety of plants mainly from the families of the Brassicaceae (e.g. horseradish (Armoracia rusticana), radish (Raphanus sativus), wasabi (Eutrema japonicum), black mustard (Brassica nigra), white mustard (Sinapis alba), broccoli (Brassica oleracea var. italica), rapeseed (Brassica napus), maca (Lepidium meyenii), crambe (Crambe abyssinica), stonecrop (Alyssum argenteum), false flax (Camelina sativa), winter cress (Barbarea vulgaris), water cress (Nasturtium officinale), hoary alyssum (Berteroa incana), wallflower (Cheiranthus cheiri), rocket (Eruca sativa), dame’s violet (Hesperis matronalis), bitter candytuft (Iberis amara) and woad (Isatis tinctoria)), the Capparaceae (e.g. capers (Capparis spinosa)) and the Caricaceae (e.g. papaya (Carica papaya)), but also from the Euphorbiaceae, the Tropaeolaceae (e.g. garden nasturtium (Tropaeolum majus)), the Cleomaceae (e.g. spiny spider flower (Cleome spinosa)), the Limnanthaceae (e.g. Douglas’ meadowfoam (Limnanthes douglasii)) and the Moringaceae (e.g. drumstick tree (Moringa oleifera)).

Besides being responsible for the pungent and bitter taste of these plants, the glucosinolates and their hydrolysis products also protect plants against herbivores and have been shown to have antimicrobial, antiviral, antifungal and anticarcinogenic properties. Due to their antimicrobial properties, herbal medicinal products containing nasturtium herb and horseradish root are used in the treatment of sinusitis, bronchitis and urinary tract infections. The German Commission E published a monograph on horseradish (Armoraciae rusticanae radix) in 1988.

Structure of glucosinolates and derived compounds

General structure of glucosinolates

 

All glucosinolates are composed of a central carbon that is bound via a sulfur atom to a glucose, and via a nitrogen atom to a sulfate group. Furthermore, a substance-specific side chain (its structure depending on the amino acid involved in the initial phase of the glucosinolate biosynthesis) is bound to the central carbon atom. As the sulfate group is negatively charged, glucosinolates are most often isolated in the form of their potassium salts. Biosynthesis of glucosinolates that bear an alkyl or a sulfur-containing side chain (such as thiomethyl-, sulfinyl- or sulfonyl groups) starts most frequently from methionine (such as epiprogoitrin, glucoalyssin, glucoarabin, glucoberteroin, glucobrassicanapin, glucocamelinin, glucocapparin, glucocheirolin, glucoerucin, glucohesperin, glucoiberin, gluconapin, glucoraphanin, glucoraphasatin, glucoraphenin, 11-methylsulfinylundecylglucosinolate, progoitrin and sinigrin). The biosynthesis of glucosinolates with a phenyl or benzyl ring in the core structure starts from either phenylalanine or tyrosine (e.g. glucobarbarin, glucolimnanthin, glucomoringin, gluconasturtiin, glucotropaeolin and sinalbin), while indolyl-containing side chains as in glucobrassicin originate from the amino acid tryptophane.

Upon contact with the enzyme myrosinase and water (myrosinase is kept in a separate compartment in the cell, but can be released e.g. during cutting or chewing), the glucose moiety is cleaved. The remaining molecule can then undergo various spontaneous reactions, usually resulting in the corresponding isothiocyanate. Depending on the reaction conditions also thiocyanates, nitriles or oxazolidine 2-thiones such as the goitrin can be formed.

Structure of DL-Goitrin

 

Glucosinolates: side chain structure and derived isothiocyanates

Glucosinolate	Side chain R	Corresponding isothiocyanate
Epiprogoitrin	CH2=CH–CHOH–CH2–	2(S)-Hydroxy 3-butenylisothiocyanate
Glucoalyssin	CH3–SO–(CH2)5-	5-(Methylsulfinyl)pentylisothiocyanate
Glucoarabin	CH3–SO–(CH2)9-	9-(Methylsulfinyl)nonylisothiocyanate
Glucobarbarin	C6H5–CHOH–CH2–	2(S)-Hydroxy 2-phenylethylisothiocyanate
Glucoberteroin	CH3–S–(CH2)5–	5-(Methylthio)pentylisothiocyanate
Glucobrassicanapin	CH2=CH2–(CH2)3–	4-Pentenylisothiocyanate
Glucobrassicin	3-Indolylmethyl-	3-Indolylmethylisothiocyanate
Glucocamelinin	CH3–SO–(CH2)10-	10-(Methylsulfinyl)decylisothiocyanate
Glucocapparin	CH3–	Methylisothiocyanate
Glucocheirolin	CH3–SO2–(CH2)3–	3-(Methylsulfonyl)propylisothiocyanate
Glucoerucin	CH3–S–(CH2)4–	4-(Methylthio)butylisothiocyanate
Glucohesperin	CH3–SO–(CH2)6-	6-(Methylsulfinyl)hexylisothiocyanate
Glucoiberin	CH3–SO–(CH2)3–	3-(Methylsulfinyl)propylisothiocyanate
Glucolimnanthin	OCH3-C6H5–CH2–	3-Methoxybenzylisothiocyanate
Glucomoringin	4-O-Rhamnosy-C6H4–CH2–	4-(Rhamnosyloxy)benzylisothiocyanate
Gluconapin	CH=CH–(CH2)2–	3-Butenylisothiocyanate
Gluconasturtiin	C6H5–(CH2)2–	2-Phenylethylisothiocyanate
Glucoraphanin	CH3–SO–(CH2)4–	Sulforaphane
Glucoraphasatin	CH3–S–CH=CH–(CH2)2–	4-(Methylthio)-3-butenylisothiocyanate
Glucoraphenin	CH3–SO–CH=CH–(CH2)2–	Sulforaphene
Glucotropaeolin	C6H5–CH2–	Benzylisothiocyanate
11-Methylsulfinylundecyl-glucosinolate	CH3–SO–(CH2)11-	11-(Methylsulfinyl)undecylisothiocyanate
Progoitrin	CH2=CH–CHOH–CH2–	2(R)-Hydroxy-3-butenylisothiocyanate
Sinalbin	4-OH-C6H4–CH2–	4-Hydroxybenzylisothiocyanate
Sinigrin	CH2=CH–CH2–	Allylisothiocyanate

Recommendation

For a reliable quantitative analysis of glucosinolates and their degradation products well characterized reference substances are essential. Currently we offer 25 glucosinolates and 1 goitrogen, all of them supplied together with a comprehensive certificate of analysis. Due to the negative charge of the glucosinolate core structure the counter ion has to be taken into account. For all glucosinolates characterized as primary reference standard, potassium was determined quantitatively and considered as an impurity in the calculation of the absolute content, which therefore refers to the pure glucosinolate only.

 

Related 26 products

 

Epiprogoitrin potassium salt

89657

 

 

Glucoalyssin potassium salt

85742

 

Glucoarabin potassium salt

85743

 

Glucobarbarin potassium salt

89684

 

Glucoberteroin potassium salt

83241

 

Glucobrassicanapin potassium salt

83242

 

Glucobrassicin potassium salt

80593

 

Glucocamelinin potassium salt

85744

 

Glucocapparin potassium salt

85745

 

Glucocheirolin potassium salt

89685

 

Glucoerucin potassium salt

89686

 

Glucohesperin potassium salt

85746

 

Glucoiberin potassium salt

89687

 

Glucolimnanthin potassium salt

85747

 

Glucomoringin potassium salt

85748

Gluconapin potassium salt

89688

 

Gluconasturtiin potassium salt

89689

 

Glucoraphanin potassium salt

89215

 

Glucoraphasatin potassium salt

84216

 

Glucoraphenin potassium salt

89690

 

Glucotropaeolin potassium salt

89216

 

DL-Goitrin

85696

11-Methylsulfinylundecylglucosinolate (K-salt)

85758

 

 

Progoitrin potassium salt

89765

 

Sinalbin potassium salt

89793

 

Sinigrin potassium salt

89279

 

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