萝卜硫苷 | 21414-41-5

• 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
• 中文名称: 萝卜硫苷
• 中文别名: 硫代葡萄糖苷；萝卜硫素；萝卜苷
• 英文名称: 4-(methylsulfinyl)butyl-glucosinolate
• 英文别名: 4-methylsulfinyl-n-butylglucosinolate；4-Methylsulphinylbutyl glucosinolate；4-methylsulfinylbutyl glucosinolate；glucoraphanin；GRA；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] 5-methylsulfinyl-N-sulfooxy-pentanimidothioate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 5-methylsulfinyl-N-sulfooxypentanimidothioate
• CAS: 21414-41-5
• 化学式: C₁₂H₂₃NO₁₀S₃
• 分子量: 437.513
• InChiKey: GMMLNKINDDUDCF-SISVVIKZSA-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

安全信息

• 海关编码：
  2932999099
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

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：

  萝卜硫苷 在 葡糖硫苷酶(-20℃) 、 水 作用下， 生成 莱菔硫烷
  参考文献：
  名称：

  Cytotoxic and Antioxidant Activity of 4-Methylthio-3-butenyl Isothiocyanate from Raphanus sativus L. (Kaiware Daikon) Sprouts

  摘要：

  There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis, release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase 11 detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p < 0 05) increased Bax and decreased Bcl2 protein expression, as well as producing caspase-9 and PARP-1 cleavage after 3 days of exposure in the three cancer cell lines. GRH-ITC treatment was shown to have no toxicity with regard to normal human lymphocytes (-15 +/- 5%) in comparison with SFN (complete growth inhibition). GRH and GRH-ITC were able to quench the 2,2-diphenyl-1-picrylhydrazyl radical, with second-order rate constants of 14.0 +/- 2.8 and 43.1 +/- 9.5 M-1 s(-1), respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant alpha-tocopherol was 425 +/- 40 M-1 s(-1). GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37 degrees C, with rate constants of 1.9 +/- 0.3 x 10(-2) and 9.5 +/- 0.3 x 10(-4) M-1 s(-1) (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cylotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.

  DOI：

  10.1021/jf073123c
• 作为产物：
  描述：

  芝麻菜苷 在 双氧水 作用下， 以 甲醇 为溶剂， 以100%的产率得到萝卜硫苷
  参考文献：
  名称：

  Cytotoxic and Antioxidant Activity of 4-Methylthio-3-butenyl Isothiocyanate from Raphanus sativus L. (Kaiware Daikon) Sprouts

  摘要：

  There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis, release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase 11 detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p < 0 05) increased Bax and decreased Bcl2 protein expression, as well as producing caspase-9 and PARP-1 cleavage after 3 days of exposure in the three cancer cell lines. GRH-ITC treatment was shown to have no toxicity with regard to normal human lymphocytes (-15 +/- 5%) in comparison with SFN (complete growth inhibition). GRH and GRH-ITC were able to quench the 2,2-diphenyl-1-picrylhydrazyl radical, with second-order rate constants of 14.0 +/- 2.8 and 43.1 +/- 9.5 M-1 s(-1), respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant alpha-tocopherol was 425 +/- 40 M-1 s(-1). GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37 degrees C, with rate constants of 1.9 +/- 0.3 x 10(-2) and 9.5 +/- 0.3 x 10(-4) M-1 s(-1) (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cylotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.

  DOI：

  10.1021/jf073123c

文献信息

• Cytotoxic and Antioxidant Activity of 4-Methylthio-3-butenyl Isothiocyanate from Raphanus sativus L. (Kaiware Daikon) Sprouts
  作者：Alessio Papi、Marina Orlandi、Giovanna Bartolini、Jessica Barillari、Renato Iori、Moreno Paolini、Fiammetta Ferroni、Maria Grazia Fumo、Gian Franco Pedulli、Luca Valgimigli

  DOI：10.1021/jf073123c

  日期：2008.2

  There is high current interest in the chemopreventive potential of Brassica vegetables (cruciferae), particularly due to their content in glucosinolates (GL), which upon myrosinase hydrolysis, release the corresponding isythiocyanates (ITC). Some ITCs, such as sulforaphane (SFN) from broccoli (Brassica oleacea italica), have been found to possess anticancer activity through induction of apoptosis in selected cell lines, as well as indirect antioxidant activity through induction of phase 11 detoxifying enzymes. Japanese daikon (Raphanus sativus L.) is possibly the vegetable with the highest per capita consumption within the Brassicaceae family. Thanks to a recently improved gram scale production process, it was possible to prepare sufficient amounts of the GL glucoraphasatin (GRH) as well as the corresponding ITC 4-methylthio-3-butenyl isothiocyanate (GRH-ITC) from its sprouts. This paper reports a study on the cytotoxic and apoptotic activities of GRH-ITC compared with the oxidized counterpart 4-methylsulfinyl-3-butenyl isothiocyanate (GRE-ITC) on three human colon carcinoma cell lines (LoVo, HCT-116, and HT-29) together with a detailed kinetic investigation of the direct antioxidant/radical scavenging ability of GRH and GRH-ITC. Both GRH-ITC and GRE-ITC reduced cell proliferation in a dose-dependent manner and induced apoptosis in the three cancer cell lines. The compounds significantly (p < 0 05) increased Bax and decreased Bcl2 protein expression, as well as producing caspase-9 and PARP-1 cleavage after 3 days of exposure in the three cancer cell lines. GRH-ITC treatment was shown to have no toxicity with regard to normal human lymphocytes (-15 +/- 5%) in comparison with SFN (complete growth inhibition). GRH and GRH-ITC were able to quench the 2,2-diphenyl-1-picrylhydrazyl radical, with second-order rate constants of 14.0 +/- 2.8 and 43.1 +/- 9.5 M-1 s(-1), respectively (at 298 K in methanol), whereas the corresponding value measured here for the reference antioxidant alpha-tocopherol was 425 +/- 40 M-1 s(-1). GRH reacted with H2O2 and tert-butyl hydroperoxide in water (pH 7.4) at 37 degrees C, with rate constants of 1.9 +/- 0.3 x 10(-2) and 9.5 +/- 0.3 x 10(-4) M-1 s(-1) (paralleling recently developed synthetic antioxidants) being quantitatively (>97%) converted to GRE. It is demonstrated that GRH-ITC has interesting antioxidant/radical scavenging properties, associated with a selective cylotoxic/apoptotic activity toward three human colon carcinoma cell lines, and very limited toxicity on normal human T-lymphocytes.