西红花苷E | 58050-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 西红花苷E
• 英文名称: crocetin mono(β-D-glucosyl) ester
• 英文别名: crocin-5；beta-D-glucosyl crocetin；(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadeca-2,4,6,8,10,12,14-heptaenoic acid
• CAS: 58050-17-2
• 化学式: C₂₆H₃₄O₉
• 分子量: 490.551
• InChiKey: ZVGODNZUEWDIPM-YXRLTKITSA-N

物化性质

• 沸点：
  743.9±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

制备方法与用途

西红花酸β-D-吡喃葡萄糖苷是来自专利CN 105935363 A中提取的藏红花色素的活性成分。

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 藏红花酸 在 glycosyltransferase from Bacillus subtilis 168 作用下， 以 aq. buffer 为溶剂， 生成 西红花苷E 、 西红花苷IV
  参考文献：
  名称：

  通过枯草芽孢杆菌168中的微生物糖基转移酶从Crocetin中高效合成番红花

  摘要：

  藏红花是在番红花（一种著名的“植物金”）中发现的最重要的活性成分。crocetin的糖基转移酶催化糖基化是生物合成crocros的最后一步，并有助于其结构多样性。现在缺乏对番红花素具有活性的有效糖基转移酶阻碍了番红花的生物合成。在这项研究中，基于对目标植物来源的UGT75L6和Cs-GT2的PSPG序列和N端基序的综合分析，成功地开发了两种微生物糖基转移酶（Bs-GT和Bc-GTA）。枯草芽孢杆菌的Bs-GT168是一种比Bc-GTA具有更高的对藏红花糖基化活性的酶。首次报道了微生物GT（Bs-GT）催化从藏红花素高效合成藏红花素，其分子转化率为81.9％，从而产生了476.8 mg / L藏花红素。Bs-GT对藏红花糖基的羧基进行糖基化反应，专门生成了重要的稀有藏红花色素crocin-5和crocin-3。

  DOI：

  10.1021/acs.jafc.8b04274

文献信息

• Regulated preparation of Crocin-1 or Crocin-2′ Triggered by the Cosolvent DMSO Using Bs-GT/At-SuSy One-Pot Reaction
  作者：Feng Liu、Fangyu Ding、Wenming Shao、Bingfang He、Guangji Wang

  DOI：10.1021/acs.jafc.9b05000

  日期：2019.11.13

  Crocins are the primary coloring ingredients of saffron. The low-glycosylated members of this compound family, such as crocin-1 (crocetin mono-glucosyl ester) and crocin-2' (crocetin di-glucosyl ester), are rarely distributed in nature and attracting interest for their therapeutic uses. In the present study, a one-pot reaction system was used for efficient preparation of crocin-1 and crocin-2' with in situ regeneration of UDP-Glc by coupling Bs-GT with At-SuSy, a sucrose synthase from Arabidopsis thaliana. Noticeably, DMSO was used as a cosolvent and resulted in improvement of the solubility of the substrate crocetin and regulation of the selectivity of glycosylation. With periodic addition of crocetin, the biosynthesis of crocin-2' was performed with a high yield of 3.25 g/L in 2% DMSO aqueous solution, whereas crocin-1 (2.12 g/L) was selectively obtained in a 10% DMSO aqueous solution. The present study provided a simple approach for the biosynthesis of crocin-1 and crocin-2'.
• METHODS AND MATERIALS FOR RECOMBINANT PRODUCTION OF SAFFRON COMPOUNDS
  申请人：Evolva SA

  公开号：EP2742131B1

  公开（公告）日：2018-11-28
• Methods and Materials for Recombinant Production of Saffron Compounds
  申请人：EVOLVA SA

  公开号：US20170306376A1

  公开（公告）日：2017-10-26

  Recombinant microorganisms, plants, and plant cells are disclosed that have been engineered to express a zeaxanthin cleavage dioxygenase alone or in combination with recombinant genes encoding UDP-glycosyltransferases (UGTs). Such microorganisms, plants, or plant cells can produce compounds from saffron such as crocetin, crocetin dialdehyde, crocin, or picrocrocin.