(4-[(4′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate) | 73255-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-[(4′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate)
• 英文别名: 4-[(4'-O-acetyl-α-L-rhamnosyloxy)benzyl] isothiocyanate；4-(4'-O-acetyl-α-L-rhamnopyranosyloxy)benzyl isothiocyanate；4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate；[(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl] acetate
• CAS: 73255-41-1
• 化学式: C₁₆H₁₉NO₆S
• 分子量: 353.396
• InChiKey: WVUZLAMBBZISKM-QOYUQHOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 葡糖硫苷酶(-20℃) 作用下， 生成 (4-[(4′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate)
  参考文献：
  名称：

  Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro

  摘要：

  Moringa (Moringa oleifera Lam.) is an edible plant used as both a food and medicine throughout the tropics. A moringa concentrate (MC), made by extracting fresh leaves with water, utilized naturally occurring myrosinase to convert four moringa glucosinolates into moringa isothiocyanates. Optimum conditions maximizing MC yield, 4-[(α-L-rhamnosyloxy)benzyl]isothiocyanate, and 4-[(4'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate content were established (1:5 fresh leaf weight to water ratio at room temperature). The optimized MC contained 1.66% isothiocyanates and 3.82% total polyphenols. 4-[(4'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate exhibited 80% stability at 37°C for 30 days. MC, and both of the isothiocyanates described above significantly decreased gene expression and production of inflammatory markers in RAW macrophages. Specifically, both attenuated expression of iNOS and IL-1β and production of nitric oxide and TNFα at 1 and 5 μM. These results suggest a potential for stable and concentrated moringa isothiocyanates, delivered in MC as a food-grade product, to alleviate low-grade inflammation associated with chronic diseases.

  DOI：

  10.1016/j.phytochem.2014.03.028

文献信息

• PRODUCING ISOTHIOCYANATES FROM CALLUS SUSPENSION CULTURES
  申请人：Perpetuum CropScience BVBA

  公开号：EP3707993A1

  公开（公告）日：2020-09-16

  The present invention provides a method of producing isothiocyanates, The method comprises forming, in a semisolid or solid callus induction medium, compact callus aggregates from cells obtained from explant material of a plant of a Brassicales plant species. The method comprises transferring cells from the callus aggregates, e.g. transferring the callus aggregates, to a suspension culture in a liquid medium in a shake flask, the liquid medium containing at least one elicitor and/or adsorbent. The method comprises transferring, after culturing in the shake flask, cells from the suspension culture to a further suspension culture in a bioreactor containing the at least one elicitor and/or adsorbent. The method comprises extracting and/or purifying of at least one isothiocyanate from cells obtained from the bioreactor.

  本发明提供了一种生产异硫氰酸酯的方法，该方法包括在半固体或固体胼胝体诱导培养基中，从十字花科植物的外植体材料中获得的细胞形成紧密的胼胝体聚集体。该方法包括将胼胝体聚集体中的细胞，例如将胼胝体聚集体转移到摇瓶中液体培养基的悬浮培养中，液体培养基中含有至少一种诱导剂和/或吸附剂。该方法包括在摇瓶中培养后，将悬浮培养物中的细胞转移到生物反应器中的另一个悬浮培养物中，该悬浮培养物中含有至少一种激发剂和/或吸附剂。该方法包括从生物反应器中获得的细胞中提取和/或纯化至少一种异硫氰酸酯。
• Treatment of helicobacter with isothiocyanates
  申请人：——

  公开号：US20020151505A1

  公开（公告）日：2002-10-17

  The present invention relates to methods of preventing or inhibiting the growth of Helicobacter through the use of a composition that comprises a glucosinolate, an isothiocyanate or a derivative or metabolite thereof. The present invention also relates to methods of preventing or treating persistent chronic gastritis, ulcers and/or stomach cancer in subjects at risk for, or in need of treatment thereof.

  本发明涉及通过使用包含葡萄糖苷酸盐、异硫氰酸盐或其衍生物或代谢物的组合物来预防或抑制螺旋杆菌生长的方法。本发明还涉及预防或治疗有患病风险或需要治疗的受试者的顽固性慢性胃炎、溃疡和/或胃癌的方法。
• Treatment of helicobacter with isothocyanates
  申请人：——

  公开号：US20040180843A1

  公开（公告）日：2004-09-16

  The present invention relates to methods of preventing or inhibiting the growth of Helicobacter through the use of a composition that comprises a glucosinolate, an isothiocyanate or a derivative or metabolite thereof. The present invention also relates to methods of preventing or treating persistent chronic gastritis, ulcers and/or stomach cancer in subjects at risk for, or in need of treatment thereof.

  本发明涉及通过使用包含葡萄糖苷酸盐、异硫氰酸盐或其衍生物或代谢物的组合物来预防或抑制螺旋杆菌生长的方法。本发明还涉及预防或治疗有患病风险或需要治疗的受试者的顽固性慢性胃炎、溃疡和/或胃癌的方法。
• Method of extraction of isothiocyanates into oil from glucosinolate-containing plants and method of producing products with oil containing isothiocyanates extracted from glucosinolate-containing plants
  申请人：Fahey W. Jed

  公开号：US20060127996A1

  公开（公告）日：2006-06-15

  A method of extraction of isothiocyanates into the oil from glucosinolate-containing plants. A method of preparing products including pharmaceutical compositions, food or drink products, supplements or additives, skin or hair products, and agricultural products which contain isothiocyanate oil extracted from glucosinolate-containing plants.

  一种从含葡萄糖苷酸的植物中提取异硫氰酸酯油的方法。一种制备含有从含葡萄糖苷酸植物中提取的异硫氰酸盐油的产品的方法，这些产品包括药物组合物、食品或饮料产品、补充剂或添加剂、皮肤或头发产品以及农产品。
• TREATMENT OF HELICOBACTER WITH ISOTHIOCYANATES
  申请人：Fahey, Jed W.

  公开号：EP1313377B1

  公开（公告）日：2015-01-21