西红花苷IV | 57710-64-2

• 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IV
• 英文名称: trans-crocetin di(β-D-glucosyl) ester
• 英文别名: crocetin-di-(β-D-glucosyl) ester；crocin-3；crocin-2'；trans-2-gg-crocin；crocetin di(β-D-glucopyranosyl) ester；dicrocin；bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• CAS: 57710-64-2
• 化学式: C₃₂H₄₄O₁₄
• 分子量: 652.693
• InChiKey: QBZWPZHDUZGTLS-IIDMIUPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  233
• 氢给体数：
  8
• 氢受体数：
  14

制备方法与用途

藏红花苷IV（双色藏红花苷）是一种藏红花苷，属于类胡萝卜素色素，展现出强烈的抗氧化活性[1]。

反应信息

• 作为反应物：
  描述：

  西红花苷IV 、 UDP-glucose 生成 西红花苷Ⅱ 、 氢(+1)阳离子 、 UDP
  参考文献：
  名称：

  UGT75L6 and UGT94E5 mediate sequential glucosylation of crocetin to crocin inGardenia jasminoides

  摘要：

  Crocin is an apocarotenoid glycosyl ester accumulating in fruits of Gardenia jasminoides and used as a food coloring and nutraceutical. For the first time, the two glucosyltransferases UGT75L6 and UGT94E5 that sequentially mediate the final glucosylation steps in crocin biosynthesis in G. jasminoides have been identified and functionally characterized. UGT75L6 preferentially glucosylates the carboxyl group of crocetin yielding crocetin glucosyl esters, while UGT94E5 glucosylates the 6′ hydroxyl group of the glucose moiety of crocetin glucosyl esters. The expression pattern of neither UGT75L6 nor UGT94E5 correlated with the pattern of crocin accumulation in G. jasminoides.

  DOI：

  10.1016/j.febslet.2012.03.003
• 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'.
• Glucosylation of the saffron apocarotenoid crocetin by a glucosyltransferase isolated from Crocus sativus stigmas
  作者：Angela Rubio Moraga、Pedro Fern�ndez Nohales、Jos� Antonio Fern�ndez P�rez、Lourdes G�mez-G�mez

  DOI：10.1007/s00425-004-1299-1

  日期：2004.10

  Saffron, the dry stigma of Crocus sativus L., is considered to be the world's most expensive spice. Three major apocarotenoids-ocrocin, crocetin and picrocrocin-are responsible for the colour and bitter taste of saffron. The final step in the biosynthesis of the 20-carbon esterified carotenoid crocin is the transformation of the insoluble crocetin into a soluble and stable storage form by glucosylation. These glucosylation reactions are catalysed by glucosyltransferases (GTases) that play a crucial role in natural-product biosynthesis. Using degenerate primers designed to match the plant secondary product GTase (PSPG) box we cloned two cDNAs, UGTCs2 and UGTCs3, from C. sativus stigmas that encode putative polypeptides of 460 and 475 amino acids, respectively. These genes were expressed differentially in saffron tissues. UGTCs2 was mainly expressed in fully developed stigmas, whereas UGTCs3 was mainly expressed in stamens. The UGTCs2 transcript was not detected in the stigma tissue of a Crocus species that does not synthesize crocin, while UGTCs3 and other structural genes for carotenoid biosynthesis were expressed in the stigma of all tested Crocus species. To identify the biochemical function of UGTCs2, the isolated cDNA was expressed in Escherichia coli cells. The recombinant protein UGTCs2 had glucosylation activity against crocetin, crocetin beta-D-glucosyl ester and crocetin beta-D-gentibiosyl ester. These results might suggest that the isolated clone UGTCs2 codes for a saffron crocetin GTase.