西红花苷Ⅱ | 55750-84-0

• 物质功能分类: 生物化工 - 提取物
• 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Ⅱ
• 中文别名: 西红花苷II
• 英文名称: crocin-2
• 英文别名: crocin II；trans-crocin 2；trans-crocetin (β-D-glucosyl) (β-D-gentiobiosyl) ester；trans-crocin-3；Crocetin gentiobiosylglucosyl ester；1-O-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 16-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• CAS: 55750-84-0
• 化学式: C₃₈H₅₄O₁₉
• 分子量: 814.835
• InChiKey: CZSBHMFVVLYIQQ-DRVLGOCHSA-N

物化性质

• 沸点：
  1032.1±65.0 °C(Predicted)
• 密度：
  1.47
• 溶解度：
  溶于甲醇和碱性水溶液

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  312
• 氢给体数：
  11
• 氢受体数：
  19

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Crocin II是从栀子（Gardenia jasminoides）的果实中分离出来的，具备抗氧化、抗癌和抗抑郁作用。它能抑制NO产生，IC50值为31.1 μM，并且能够抑制iNOS和COX-2的蛋白质及m-RNA的表达。

靶点

IC50: 31.3 μM (NO production)

化学性质

Crocin II是一种红色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于西红花。

用途

Crocin II具有中枢降压和防治动脉粥样硬化的作用。

反应信息

• 作为反应物：
  描述：

  西红花苷Ⅱ 、 乙酸酐 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Novel Glycosidic Constituents from Saffron

  摘要：

  The methanolic extract of saffron was prefractionated with the aid of multilayer coil countercurrent chromatography (MLCCC). After subsequent purification of certain fractions by high-performance liquid chromatography, the following glycoconjugates were isolated and identified on the basis of their spectral (UV, MS, NMR) data: the beta-n-glucosides of (4R)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (5), (4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (6), and (4S)-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone (7), as well. as the beta-D-gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid (4). In addition to these new natural products, known saffron constituents, i.e., the di-beta-D-gentiobiosyl and beta-D-gentiobiosyl-beta-D-glucopyranosyl esters of crocetin, have also been isolated and separated using MECCC.

  DOI：

  10.1021/jf960861k
• 作为产物：
  描述：

  beta-D-gentiobiosyl crocetin(1-) 、 UDP-glucose 生成 西红花苷Ⅱ 、 UDP
  参考文献：
  名称：

  Glucosylation of the saffron apocarotenoid crocetin by a glucosyltransferase isolated from Crocus sativus stigmas

  摘要：

  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.

  DOI：

  10.1007/s00425-004-1299-1

文献信息

• Compositions containing enriched natural crocin and/or crocetin, and their therapeutic or nutraceutical uses
  申请人：Gao Song

  公开号：US10842805B2

  公开（公告）日：2020-11-24

  The invention relates to unique compositions containing enriched and purified natural crocin and/or crocetin for prevention and/or treatment of cancers and other conditions and diseases. Compositions comprise mainly enriched or purified natural crocin or crocetin or combination of both and possible other active phytochemicals. A composition is used as functional food, drink, dietary supplement, or therapeutic dosage to a human orally or through other appropriate way (parenteral, percutaneous, rectal, mucosal, intranasal or topical administration). A method of natural crocin and crocetin enriching and purification is revealed.

  本发明涉及含有富集和纯化的天然羊角霉素和/或羊胎素的独特组合物，用于预防和/或治疗癌症及其他病症和疾病。组合物主要包括富集或纯化的天然巴豆素或巴豆黄素或二者的组合以及可能的其他活性植物化学物质。组合物可作为功能性食品、饮料、膳食补充剂或治疗剂量，口服或通过其他适当方式（肠外、经皮、直肠、粘膜、鼻内或局部给药）给人服用。揭示了一种富集和提纯天然巴豆素和藏红花素的方法。
• 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.
• Compositions Containing Enriched Natural Crocin and/or Crocetin, and Their Therapeutic or Nutraceutical Uses
  申请人：Gao Song

  公开号：US20140141082A1

  公开（公告）日：2014-05-22

  The invention relates to unique compositions containing enriched and purified natural crocin and/or crocetin for prevention and/or treatment of cancers and other conditions and diseases. Compositions comprise mainly enriched or purified natural crocin or crocetin or combination of both and possible other active phytochemicals. A composition is used as functional food, drink, dietary supplement, or therapeutic dosage to a human orally or through other appropriate way (parenteral, percutaneous, rectal, mucosal, intranasal or topical administration). A method of natural crocin and crocetin enriching and purification is revealed.
• US9211298B2
  申请人：——

  公开号：US9211298B2

  公开（公告）日：2015-12-15
• Novel Glycosidic Constituents from Saffron
  作者：Markus Straubinger、Magnus Jezussek、Reiner Waibel、Peter Winterhalter

  DOI：10.1021/jf960861k

  日期：1997.5.1

  The methanolic extract of saffron was prefractionated with the aid of multilayer coil countercurrent chromatography (MLCCC). After subsequent purification of certain fractions by high-performance liquid chromatography, the following glycoconjugates were isolated and identified on the basis of their spectral (UV, MS, NMR) data: the beta-n-glucosides of (4R)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (5), (4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (6), and (4S)-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone (7), as well. as the beta-D-gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid (4). In addition to these new natural products, known saffron constituents, i.e., the di-beta-D-gentiobiosyl and beta-D-gentiobiosyl-beta-D-glucopyranosyl esters of crocetin, have also been isolated and separated using MECCC.