glucoerucin | 21973-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: glucoerucin
• 英文别名: 4-Methylthiobutyl glucosinolate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z)-5-methylsulfanyl-N-sulfooxypentanimidothioate
• CAS: 21973-56-8
• 化学式: C₁₂H₂₃NO₉S₃
• 分子量: 421.514
• InChiKey: GKUMMDFLKGFCKH-AHMUMSBHSA-N

物化性质

• 密度：
  1.68±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  153-154°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  225
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  glucoerucin 在 phosphate buffer 、 葡糖硫苷酶(-20℃) 作用下， 以82%的产率得到三芥子酸甘油酯
  参考文献：
  名称：

  Direct Antioxidant Activity of Purified Glucoerucin, the Dietary Secondary Metabolite Contained in Rocket (Eruca sativa Mill.) Seeds and Sprouts

  摘要：

  Rocket (Eruca sativa Mill. or Eruca vesicaria L.) is widely distributed all over the world and is usually consumed fresh (leafs or sprouts) for its typical spicy taste. Nevertheless, it is mentioned in traditional pharmacopoeia and ancient literature for several therapeutic properties, and it does contain a number of health promoting agents including carotenoids, vitamin C, fibers, flavonoids, and glucosinolates (GLs). The latter phytochemicals have recently gained attention as being the precursors of isothiocyanates (ITCs), which are released by myrosinase hydrolysis during cutting, chewing, or processing of the vegetable. ITCs are recognized as potent inducers of phase II enzymes (e.g., glutathione transferases, NAD(P)H:quinone reductase, epoxide hydrolase, etc.), which are important in the detoxification of electrophiles and protection against oxidative stress. The major GL found in rocket seeds is glucoerucin, GER (108 +/- 5 mu mol g(-1) d.w.) that represents 95% of total GLs. The content is largely conserved in sprouts (79% of total GLs), and GER is still present to some extent in adult leaves. Unlike other GLs (e.g., glucoraphanin, the bio-precursor of sulforaphane), GER possesses good direct as well as indirect antioxidant activity. GER (and its metabolite erucin, ERN) effectively decomposes hydrogen peroxide and alkyl hydroperoxides with second-order rate constants of k(2) = 6.9 +/- 0.1 x 10(-2) M-1 s(-1) and 4.5 +/- 0.2 x 10(-3) M-1 s(-), respectively, in water at 37 degrees C, thereby acting as a peroxide-scavenging preventive antioxidant. Interestingly, upon removal of H2O2 or hydroperoxides, ERN is converted into sulforaphane, the most effective inducer of phase 11 enzymes among ITCs. On the other hand, ERN (and conceivably GER), like other ITCs, does not possess any chain-breaking antioxidant activity, being unable to protect styrene from its thermally (37 degrees C) initiated autoxidation in the presence of AMVN. The mechanism and relevance of the antioxidant activity of GER and ERN are discussed.

  DOI：

  10.1021/jf047945a

文献信息

• Cancer chemoprotective food products
  申请人：THE JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE

  公开号：EP1219180A1

  公开（公告）日：2002-07-03

  Vegetable sources of cancer chemoprotective agents have been identified which are extraordinarily rich in glucosinolates, metabolic precursors or isothiocyanates. The vegetable sources are used to provide a dietary means of reducing the level of carcinogens in mammals.

  癌症化学保护剂的蔬菜来源已经确定，它们含有特别丰富的葡萄糖苷酸盐、代谢前体或异硫氰酸酯。这些蔬菜来源可作为降低哺乳动物体内致癌物质水平的膳食手段。
• Enteric-coated glucosinolates and beta-thioglucosidases
  申请人：Kraft Foods Holdings, Inc.

  公开号：EP2065034A2

  公开（公告）日：2009-06-03

  The present invention relates to a particulate composition comprising enteric-coated glucosinolate and beta-thioglucosidase particles. The present invention further provides a method of converting glucosinolate to isothiocyanate in the small intestine comprising orally administering to a subject an enteric-coated chemoprotectant precursor composition comprising enteric-coated glucosinolate and beta-thioglucosidase particles. In another aspect, uncoated glucosinolate and beta-thioglucosidase particles may be provided in an enteric-coated capsule. Preferably, the glucosinolate is glucoraphanin and the beta-thioglucosidase is myrosinase. The enteric coating targets the compound for release in the small intestine where beta-thiaglucosidase enzyme converts glucosinolate to chemoprotectant isothiocyanate.

  本发明涉及一种微粒组合物，该组合物由肠包衣葡萄糖苷酸和β-硫代葡萄糖苷酶微粒组成。本发明进一步提供了一种在小肠中将葡萄糖苷酸转化为异硫氰酸酯的方法，该方法包括向受试者口服肠溶化学保护剂前体组合物，该组合物包含肠溶葡萄糖苷酸和β-硫代葡萄糖苷酶颗粒。另一方面，未包衣的葡萄糖苷酸和β-巯基葡萄糖苷酶颗粒可以装在肠溶胶囊中。葡萄糖苷酸最好是葡萄糖醛酸，β-巯基葡萄糖苷酶最好是酪氨酸酶。肠溶衣可将化合物靶向释放到小肠中，在小肠中，β-硫代葡萄糖苷酶将葡萄糖苷酸转化为化学保护剂异硫氰酸酯。
• Electrostatic protein/glucosinolate complexes
  申请人：Nestec S.A.

  公开号：EP2229823A1

  公开（公告）日：2010-09-22

  The present invention relates to the field of electrostatic complexes. Embodiments of the present invention relate to food-grade electrostatic complexes containing at least one milk protein and at least one glucosinolate and to the uses of such complexes, e.g., to reduce the perceived bitterness of glucosinolates and/or to form and stabilize emulsions and/or foams.

  本发明涉及静电络合物领域。本发明的实施方案涉及含有至少一种牛奶蛋白和至少一种葡萄糖苷酸的食品级静电络合物，以及此类络合物的用途，例如，降低葡萄糖苷酸的苦味和/或形成并稳定乳液和/或泡沫。
• ELEVATED RESISTANCE TO INSECTS AND PLANT PATHOGENS WITHOUT COMPROMISING SEED PRODUCTION
  申请人：Board of Trustees of Michigan State University

  公开号：EP3812464A1

  公开（公告）日：2021-04-28

  Described herein are modified plants, plant cells, and plant seeds that have at least one mutant loss-of-function JAZ gene and at least one loss-of-function cdk8 gene. Such plants are highly resistant to pests and environmental stress and have restored growth and increased seed yield compared to plant lines with a jazD genetic background.

  本文描述的是改良植物、植物细胞和植物种子，它们具有至少一个功能缺失的突变 JAZ 基因和至少一个功能缺失的 cdk8 基因。与具有 jazD 遗传背景的植物品系相比，这些植物对害虫和环境胁迫具有很强的抗性，并能恢复生长和提高种子产量。
• LIGHT SOURCE FOR PLANT CULTIVATION
  申请人：Seoul Viosys Co., Ltd.

  公开号：EP3841870A1

  公开（公告）日：2021-06-30

  A light source of a plant cultivation is turned on or turned off depending on a light period and a dark period of a plant, and the light source of the plant cultivation is turned on in the light period and emits a light having a spectrum with a plurality of peaks to the plant to increase a content of a predetermined substance in the plant.

  根据植物的光照期和黑暗期开启或关闭植物栽培的光源，在光照期开启植物栽培的光源，并向植物发射具有多个峰值的光谱的光，以增加植物中预定物质的含量。