4-methylsulfinylbutyl glucosinolate | 1432982-77-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylsulfinylbutyl glucosinolate
• 英文别名: glucoraphanin；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z)-5-methylsulfinyl-N-sulfooxypentanimidothioate
• CAS: 1432982-77-8；21414-41-5
• 化学式: C₁₂H₂₃NO₁₀S₃
• 分子量: 437.513
• InChiKey: GMMLNKINDDUDCF-BYNGITTOSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  26
• 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：
  236
• 氢给体数：
  5
• 氢受体数：
  13

制备方法与用途

简介

萝卜硫苷是西兰花提取物的一个有效成分，也是萝卜硫素的前体药物。在体内，萝卜硫苷可以转化为萝卜硫素，从而发挥抗癌和抗氧化的功效。

功效与作用

萝卜硫苷是一种主要存在于西兰花种子和芽苗中的天然活性产物，经黑芥子酶或肠道微生物的作用后可转化为萝卜硫素（Sulforaphane）。萝卜硫素是目前发现的Nrf2最强激活剂之一，可通过激活Nrf2开启解毒、抗氧化、抗炎等多种细胞保护作用。

生物活性

Glucoraphanin 是一种存在于十字花科蔬菜中的硫代葡萄糖苷，它是 Nrf2 诱导剂 sulforaphane 的前体。Sulforaphane 具有抗氧化、抗炎和抗癌的作用。

体内研究

在高脂饮食（HFD）喂养的小鼠中，Glucoraphanin 可以减少体重增加并提高能量消耗。它还能改善胰岛素敏感性和葡萄糖耐受性。然而，在 Nrf2 缺陷小鼠中，Glucoraphanin 并未表现出抗肥胖和改善胰岛素敏感性的效果。Glucoraphanin 能够阻止高脂饮食引起的白色脂肪组织 Ucp1 蛋白水平的下降（仅限野生型小鼠）。它还能减轻高脂饮食引起的小鼠肝脏脂肪变性和氧化应激，抑制肝部和脂肪组织中巨噬细胞的促炎激活，并减少高脂饮食喂养小鼠肠道微生物组中的 LPS 水平和变形菌门的比例。另外，含有 0.1% Glucoraphanin 的饲料能显著减轻受压小鼠的社会回避时间缩短现象，在 1% 蔗糖偏好测试（SPT）中，0.1% Glucoraphanin 的喂养也能显著改善受压小鼠对蔗糖的偏好。

化学性质

类白色结晶粉末，可溶于甲醇、乙醇、DMSO 等有机溶剂，来源于莱菔子。

用途

抗癌抗氧化。可用于含量测定、鉴定及药理实验等。

反应信息

• 作为反应物：
  描述：

  4-methylsulfinylbutyl glucosinolate 在 phosphate buffer 、 葡糖硫苷酶(-20℃) 作用下， 生成 莱菔硫烷
  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
• 作为产物：
  描述：

  glucoerucin 在 双氧水 作用下， 生成 4-methylsulfinylbutyl glucosinolate
  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

• ISOTHIOCYNATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIONS CONTAINING SAME
  申请人：Rajski Scott R.

  公开号：US20130116203A1

  公开（公告）日：2013-05-09

  The present invention provides glucosinolate and isothiocyanate compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.

  本发明提供了葡萄糖苷和异硫氰酸酯化合物以及相关的合成这些化合物和类似物的方法。在某些实施例中，这些葡萄糖苷和异硫氰酸酯化合物可用作化学预防和/或化疗剂。
• Stabilized sulforaphane
  申请人：Dagan Ido Dov

  公开号：US20080176942A1

  公开（公告）日：2008-07-24

  A method of stabilizing sulforaphane is provided. The method includes contacting sulforaphane, or an analog thereof, and a cyclodextrin to form a complex between the sulforaphane, or analog thereof, and the cyclodextrin.

  提供了一种稳定硫代异硫氰酸酯的方法。该方法包括将硫代异硫氰酸酯或其类似物与环糊精接触，以形成硫代异硫氰酸酯或其类似物与环糊精之间的复合物。
• [EN] METHOD OF SYNTHESISING SULFORAPHANE<br/>[FR] PROCÉDÉ DE SYNTHÈSE DU SULFORAPHANE
  申请人：PHARMAGRA LABS INC

  公开号：WO2013179057A1

  公开（公告）日：2013-12-05

  The present invention relates to a method of synthesising sulforaphane by reacting a compound of formula (A) with an oxidizing agent in an aqueous solvent and in the presence of a catalyst. The invention further provides a method of synthesising a stabilised complex of sulforaphane and cyclodextrin by mixing the sulforaphane prepared by the methodology defined herein with cyclodextrin in an aqueous solvent.

  本发明涉及一种通过在水溶剂中，在催化剂存在下，将公式（A）化合物与氧化剂反应合成硫代芥的方法。本发明还提供了一种通过将本文所定义的方法制备的硫代芥与环糊精在水溶剂中混合制备稳定复合物的方法。
• Biosynthetic Engineering of Glucosinolates
  申请人：Geu-Flores Fernando

  公开号：US20110016582A1

  公开（公告）日：2011-01-20

  The invention provides methods and materials, such as newly characterised genes, and novel processes, for converting a host from a phenotype whereby the host is unable to carry out glucosinolate (GSL) biosynthesis or chain elongation from an amino acid GSL-precursor to a phenotype whereby the host carries out said biosynthesis or elongation.

  本发明提供了一种将宿主从无法进行葡萄糖硫酸盐（GSL）生物合成或链延伸的表型转化为能够进行上述生物合成或延伸的表型的方法和材料，例如新鉴定的基因和新型工艺。
• Administration of 3H-1, 2-dithiole-3-thione, anethole dithiolethione, sulforaphane, phenethyl isothiocyanate, 6-(methylsulfinyl)hexyl isothiocyanate and allyl isothiocyanate for the treatment of canities
  申请人：Commo Stephane

  公开号：US20080027129A1

  公开（公告）日：2008-01-31

  At least one compound selected from among 3H-1,2-dithiole-3-thione, anethole dithiolethione, sulforaphane, phenethyl isothiocyanate, 6-(methylsulfinyl)hexyl isothiocyanate and allyl isothiocyanate and derivatives and mixtures thereof, and admixtures thereof with other active agents selected from among active agents for combating desquamative conditions of the scalp, plant extracts having propigmenting activity and active agents that slow hair loss and/or promote hair regrowth, are useful for preventing and/or limiting and/or stopping the development of canities.

  至少选择一种化合物，包括3H-1,2-二硫代-3-硫酮，茴香二硫代乙硫醚，芥子硫醇，苯乙基异硫氰酸酯，6-(甲硫基)己基异硫氰酸酯和丙烯基异硫氰酸酯及其衍生物和混合物，以及与其他用于对抗头皮脱屑症状的活性剂，具有促进色素沉积活性的植物提取物和减缓脱发和/或促进头发再生的活性剂混合使用，可用于预防和/或限制和/或阻止白发的发展。