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芜菁(油菜)硫代葡萄糖苷的腈衍生物会对牛产生肝毒性或胆管毒性吗?

Could nitrile derivatives of turnip (Brassica rapa) glucosinolates be hepato- or cholangiotoxic in cattle?

作者信息

Collett Mark G, Stegelmeier Bryan L, Tapper Brian A

机构信息

Institute of Veterinary, Animal and Biomedical Sciences, Massey University , Palmerston North 4442, New Zealand.

出版信息

J Agric Food Chem. 2014 Jul 30;62(30):7370-5. doi: 10.1021/jf500526u. Epub 2014 Apr 11.

Abstract

Turnip (Brassica rapa ssp. rapa) and rape (Brassica napus ssp. biennis) and other brassica forage crops are regarded as "safe" feed for cattle during late summer and fall in the North Island of New Zealand when high Pithomyces chartarum spore counts in pastures frequently lead to sporidesmin toxicity (facial eczema). Sporadic acute severe cases of turnip photosensitization in dairy cows characteristically exhibit high γ-glutamyl transferase and glutamate dehydrogenase serum enzyme activities that mimic those seen in facial eczema. The two diseases can, however, be distinguished by histopathology of the liver, where lesions, in particular those affecting small bile ducts, differ. To date, the hepato-/cholangiotoxic phytochemical causing liver damage in turnip photosensitization in cattle is unknown. Of the hydrolysis products of the various glucosinolate secondary compounds found in high concentrations in turnip and rape, work has shown that nitriles and epithionitriles can be hepatotoxic (and nephro- or pancreatotoxic) in rats. These derivatives include β-hydroxy-thiiranepropanenitrile and 3-hydroxy-4-pentenenitrile from progoitrin; thiiranepropanenitrile and 4-pentenenitrile from gluconapin; thiiranebutanenitrile and 5-hexenenitrile from glucobrassicanapin; phenyl-3-propanenitrile from gluconasturtiin; and indole-3-acetonitrile from glucobrassicin. This perspective explores the possibility of the preferential formation of such derivatives, especially the epithionitriles, in acidic conditions in the bovine rumen, followed by absorption, hepatotoxicity, and secondary photosensitization.

摘要

芜菁(芜菁甘蓝亚种)、油菜(甘蓝型油菜二年生亚种)以及其他十字花科饲料作物,在新西兰北岛的夏末和秋季被视为牛的“安全”饲料,此时牧场中高球孢霉孢子计数常常导致孢霉毒素中毒(面部湿疹)。奶牛偶发性急性芜菁光敏症的特征是血清γ-谷氨酰转移酶和谷氨酸脱氢酶活性升高,与面部湿疹所见相似。然而,这两种疾病可通过肝脏组织病理学加以区分,其病变,尤其是影响小胆管的病变有所不同。迄今为止,导致牛芜菁光敏症肝损伤的肝/胆管毒性植物化学物质尚不清楚。在芜菁和油菜中大量存在的各种硫代葡萄糖苷次生化合物的水解产物中,研究表明腈类和环硫腈类在大鼠中可能具有肝毒性(以及肾毒性或胰腺毒性)。这些衍生物包括来自丙硫氧嘧啶的β-羟基-硫杂环丙烷丙腈和3-羟基-4-戊烯腈;来自硫代葡萄糖苷的硫杂环丙烷丙腈和4-戊烯腈;来自葡糖芸苔素的硫杂环丁烷腈和5-己烯腈;来自葡萄糖异硫氰酸酯的苯基-3-丙腈;以及来自葡糖硫苷的吲哚-3-乙腈。本文探讨了在牛瘤胃酸性条件下优先形成此类衍生物,尤其是环硫腈类,随后被吸收、产生肝毒性并引发继发性光敏症的可能性。

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