水仙苷 | 604-80-8

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 水仙苷
• 中文别名: 异鼠李素-3-O-芸香糖苷；水仙甙异鼠李素-3-O-β-D-芸香糖苷异鼠李素-3-O-芸香糖苷；水仙甙；异鼠李素-3-O-β-D-芸香糖苷；异鼠李素-3-O-Β-D-芸香糖苷；水仙甙；异鼠李素-3-O-β-D-芸香糖苷；异鼠李素-3-O-芸香糖苷
• 英文名称: narcissin
• 英文别名: Isorhamnetin 3-O-rutinoside；5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one；3'-methoxy-3-(6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy)-4',5,7-trihydroxyflavone；quercetin 3'-O-methyl-3-O-β-D-glucopyranosyl-[(1->6)-α-L-rhamnopyranoside]；3'-O-methylquercetin 3-O-α-L-rhamnopyranosyl-(1->6)-O-β-D-glucopyranoside；3'-O-methylquercetin 3-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside
• CAS: 604-80-8
• 化学式: C₂₈H₃₂O₁₆
• 分子量: 624.552
• InChiKey: UIDGLYUNOUKLBM-GEBJFKNCSA-N

物化性质

• 熔点：
  182-184°C
• 沸点：
  953.1±65.0 °C(Predicted)
• 密度：
  1.74
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  255
• 氢给体数：
  9
• 氢受体数：
  16

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃

制备方法与用途

生物活性方面，Narcissin（Narcissoside）是从布渣叶、槐米以及秋水仙Colchicum autumnale和甘草中分离出的一种黄连糖苷。它能够清除ONOO- 和 SIN-1衍生的ONOO-，其IC50值分别为3.5 μM和9.6 μM，并且具有抗氧化活性。

在化学性质上，Narcissin是一种黄色结晶粉末，可以溶于甲醇、乙醇及DMSO等有机溶剂。

在用途方面，Narcissin常用于含量测定、鉴定以及药理实验中。其药理作用包括抗氧化和抗自由基活性。

反应信息

• 作为反应物：
  描述：

  水仙苷 在 三氟乙酸 作用下， 反应 0.5h， 生成 异鼠李素
  参考文献：
  名称：

  Hydrolyzed Flavonoids from Cyrtosperma johnstonii with Superior Antioxidant, Antiproliferative, and Anti-Inflammatory Potential for Cancer Prevention

  摘要：

  Cyrtosperma johnstonii is one of the most interesting traditional medicines for cancer treatment. This study aimed to compare and combine the biological activities related to cancer prevention of the flavonoid glycosides rutin (RT) and isorhamnetin-3-o-rutinoside (IRR) and their hydrolysis products quercetin (QT) and isorhamnetin (IR) from C.johnstonii extract. ABTS and MTT assays were used to determine antioxidant activity and cytotoxicity against various cancer cells, as well as normal cells. Anti-inflammatory activities were measured by ELISA. The results showed that the antioxidant activities of the compounds decreased in the order of QT > IR > RT > IRR, while most leukemia cell lines were sensitive to QT and IR with low toxicity towards PBMCs. The reduction of IL-6 and IL-10 secretion by QT and IR was higher than that induced by RT and IRR. The combination of hydrolysis products (QT and IR) possessed a strong synergism in antioxidant, antiproliferative and anti-inflammatory effects, whereas the combination of flavonoid glycosides and their hydrolysis products revealed antagonism. These results suggest that the potential of the combination of hydrolyzed flavonoids from C. johnstonii can be considered as natural compounds for the prevention of cancer.

  DOI：

  10.3390/molecules27103226
• 作为产物：
  描述：

  isorhamnetin 3-O-2^G-rhamnopyranosylrutinoside-7-O-α-L-rhamnopyranoside 在 hesperidinase 、 葡萄糖 作用下， 以 二甲基亚砜 为溶剂， 反应 21.0h， 生成 异鼠李素-3-O-葡萄糖苷 、 香蒲新苷 、 水仙苷
  参考文献：
  名称：

  Flavonoid and benzophenone glycosides from Coleogyne ramosissima

  摘要：

  A benzophenone glucoside and two flavonol glycosides were isolated together with 27 known polyphenols from the aerial parts of Coleogyne ramosissima, and their structures were elucidated by spectroscopic and chemical methods as iriflophenone 2-O-beta-glucogyranoside, isorhamnetin 3-O-2(G)-rhamnopyranosylrutinoside-7-O-alpha-rhamnopyranoside and limocitrin 3-O-rutinoside-7-O-beta-glucopylanoside, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00192-8

文献信息

• Flavonoids and anthocyans from Alhagi pseudoalhagi
  作者：E. N. Novruzov、G. A. Abdullaeva、L. A. Shamsizade、N. Sh. Mustafaev

  DOI：10.1007/s10600-009-9287-0

  日期：2009.3

  the aerial part of the plant contained 2.95% flavonoids (per dry weight) [8]. Pure flavonoids were isolated from ground air-dried aerial part by exhaustive extraction with ethanol on a water bath at 70°C. The extract was filtered and condensed in vacuo to a small volume. The evaporated extract was diluted with water and treated successively with CHCl3, ether, EtOAc, and n-BuOH. The ether extract contained

  植物 Alhagi pseudoalhagi 的研究相对较少。已在其地上部分观察到酸性硫脂酰化聚半内酯、鞣剂 [1]、儿茶素和原花青素 [2]。研究发现，由跑步者制备的酊剂具有利尿、溶石 [3]、低氮、抗氧化 [4] 和利胆活性 [5]。在此，我们提供了有关阿塞拜疆共和国生长的 A. pseudoalhagi (Fabaceae Lindl.) 花的地上部分类黄酮成分以及花青素的定性成分和定量含量的数据 [6]。在萌芽期间（2007 年 6 月）在巴库（拉玛那）附近收集材料。分光光度法 [7] 表明植物地上部分含有 2.95% 的黄酮类化合物（每干重）[8]。通过在 70°C 水浴上用乙醇彻底提取，从地面风干的地上部分中分离出纯黄酮类化合物。过滤提取物并真空浓缩至小体积。蒸发的萃取液用水稀释并依次用CHCl 3 、乙醚、EtOAc和n-BuOH处理。乙醚提取物含有两种化合物；乙酸乙酯，3；BuOH，2。醚提取物的制备纸色谱
• Chemical Composition and Biological Activity of Salicornia fruticosa L.
  作者：Rasha Elatif、Manal Shabana、lamyaa fawzy、Ragaa Mansour、Hanem Awad、Mahmed sharaf

  DOI：10.21608/ejchem.2019.18470.2139

  日期：2019.10.31

  major flavonoids were isolated and identified from the cytotoxic methanolic extract. The isolated compounds were identified, as quercetin 3',4'-dimethyl ether (1), isorhamnetin (2), isorhamnetin 3-O-rhamnoside (3), isorhamnetin 3-O-glucoside (4), isorhamnetin 3-O-rutinoside (5), isorhamnetin 3-O-neohesperidoside (6), isorhamnetin 3-O-rhamnosyl(1-2)arabinoside (7), by chromatographic analysis, chemical and

  摘要多年以来，植物一直被用作治疗许多疾病和病症的传统医学来源。他们被认为是具有抗氧化和抗癌活性的极好的植物化学物质来源。本研究的目的是调查化学成分和确定金缕梅（Chenopodiaceae）甲醇提取物的抗癌活性。金黄色葡萄球菌被证明是异鼠李素及其糖苷的来源，并显示出抗癌活性。从细胞毒性甲醇提取物中分离并鉴定了七个主要类黄酮。分离出的化合物经鉴定为槲皮素3'，4'-二甲醚（1），异鼠李素（2），异鼠李素3-O-鼠李糖苷（3），异鼠李素3-O-葡萄糖苷（4），异鼠李素3-O-芸香糖苷（5），异鼠李素3-O-新橙皮苷（6），异鼠李素3-O-鼠李糖基（1-2）阿拉伯糖苷（7），通过色谱分析，化学和光谱工具（酸水解，UV，1H和13C NMR）。化合物1和3-7首次从所研究的植物中分离出来。通过MTT分析评价甲醇提取物对HCT-116，HepG2，A549和MCF-7人癌细胞的细胞毒性活性，结果表明
• Purification and characterization of a flavonol 3-O-β-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench
  作者：Andreas Baumgertel、Rudi Grimm、Wilhelm Eisenbeiß、Wolfgang Kreis

  DOI：10.1016/s0031-9422(03)00418-7

  日期：2003.9

  A flavonol-3-O-beta-heterodisaccharide glycosidase (FHG I) was isolated from dried aerial tissues of Fagopyrum esculentum Moench (Fagopyri herba). It has a specific enzyme activity of ca. 3.5 nkat mg(-1) protein in buffered extracts when rutin (quercetin-3-O-rutinoside) was used as substrate and an optimal enzyme activity was seen at around pH 4.8 and 30 degreesC. FHG I was purified about 156-fold to apparent homogeneity by hydrophobic interaction, anion exchange and size exclusion chromatographic steps. The apparent molecular mass of FHG I was 74.5 +/- 2 kDa as determined by SDS-PAGE and it is a monomeric glycoprotein with a carbohydrate content of 23%. The isoelectric point as determined by isoelectric focusing was 5.7 and the energy of activation was 32 kJ mol(-1). FHG I exhibits a high substrate specificity, preferring flavonol 3-O-glycosides comprising the disaccharide rutinose. The K-m and V-max values for the natural substrate rutin were calculated to be 0.561 muM and 745 nkat mg(-1) protein, respectively. Two oligopeptide fragments obtained after enzymatic digestion of FHG I were sequenced and showed similarities to sequences of beta-glucohydrolases from other plant species. Polyclonal antibodies were raised and their specificities determined. Another flavonol 3-O-beta-hcterodisaccharide glycosidase (FHG II) could also be detected in buckwheat herb, having a molecular irlass of 85.3 +/- 2 kDa and an isoelectric point between pH 6.0 and 6.5. (C) 2003 Elsevier Ltd. All rights reserved.
• Flavonoids from Camelina sylvestris Seeds
  作者：V. A. Kurkin、K. S. Pavlenko

  DOI：10.1007/s10600-014-1008-7

  日期：2014.7
• ——
  作者：A. A. Yuldashev、M. P. Yuldashev、V. N. Abdullabekova

  DOI：10.1023/a:1020400615593

  日期：——