585-95-5
Chemical Structure
Progoitrin
- CAS No.: 585-95-5
- Formula:C11H19NO10S2
- Molecular Weight:389.40
IUPAC Name: ((((Z)-3-phenyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)propylidene)amino)oxy)sulfonic acid
InChIKey: MYHSVHWQEVDFQT-ZLKQMKLXSA-N
SMILES: C=C[C@H](O)C/C(S[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO)=N/OS(=O)(O)=O
Biological Activity: Progoitrin is a sulfur-containing glucosinolate, as well as a naturally occurring orally active thioglycoside. Progoitrin acts as a hepatotoxin and antithyroid agent. Progoitrin is quantitatively converted to goitrin in vivo, including via a gastrointestinal hydrolysis pathway that does not require exogenous myrosinase, thereby blocking the organification of iodine in the thyroid gland and inhibiting the uptake and accumulation of radioactive iodine. Progoitrin can be used in studies related to Graves' disease[1][2][3].
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Progoitrin | Progoitrin is a sulfur-containing glucosinolate, as well as a naturally occurring orally active thioglycoside. Progoitrin acts as a hepatotoxin and antithyroid agent. Progoitrin is quantitatively converted to goitrin in vivo, including via a gastrointestinal hydrolysis pathway that does not require exogenous myrosinase, thereby blocking the organification of iodine in the thyroid gland and inhibiting the uptake and accumulation of radioactive iodine. Progoitrin can be used in studies related to Graves' disease. | |||||||||||||||||||||
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- [1]. Collett MG, et al. Hepatotoxicity of Two Progoitrin-Derived Nitriles in New Zealand White Rabbits. Toxins (Basel). 2020;12(11):695. Published 2020 Nov 2. [Content Brief]
- [2]. GREER MA, et al. Antithyroid activity elicited by the ingestion of pure progoitrin, a naturally occurring thioglycoside of the turnip family. J Clin Invest. 1959 Sep;38(9):1465-74. [Content Brief]
- [3]. Liu Z, et al. Reducing progoitrin and enriching glucoraphanin in Brassica napus seeds through silencing of the GSL-ALK gene family. Plant Mol Biol. 2012;79(1-2):179-189. [Content Brief]
Keywords
