2-O-α-L-rhamnopyranosyl-β-D-glucopyranose | 19949-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-α-L-rhamnopyranosyl-β-D-glucopyranose
• 英文别名: β-2-O-alpha-L-rhamnopyranosyl-D-glucopyranose；4',5,7-trihydroxyflavone 7-rhamnoglucoside；naringin；Neohesperidose; 2-O-α-L-Rhamnopyranosyl-D-glucopyranose；Neohesperidose；Norhesperidose；2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose；(2S,3R,4R,5R,6S)-2-methyl-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 19949-48-5
• 化学式: C₁₂H₂₂O₁₀
• mdl: MFCD00064919
• 分子量: 326.301
• InChiKey: VSRVRBXGIRFARR-OUEGHFHCSA-N

物化性质

• 熔点：
  191-192 °C
• 沸点：
  633.9±55.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  柚皮苷 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 2-O-α-L-rhamnopyranosyl-β-D-glucopyranose 、 (S)-柚皮素
  参考文献：
  名称：

  Chemical composition and biological activity of Citrus jambhiri Lush

  摘要：

  The fresh peel of Citrus jambhiri was extracted with aqueous methanol and the residue was fractionated using light petroleum, chloroform and ethyl acetate. The constituents of the extracts were separated by column chromatography employing solvents of different polarity. The chemical structure of the isolated compounds was then identified by MS and NMR. Column chromatography of the petroleum fraction resulted in the isolation of nobiletin, 5-O-demethylnobiletin, tangeretin, 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone, 3,5,6,7,8,3',4'-heptamethoxyflavone, and a mixture of beta-sitosterol and stigmasterol. The chloroform fraction afforded 6-demethoxynobiletin, 5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone, limonin and nomilin. The flavonoid glycosides naringin, hesperidin and neohesperidin were isolated from the ethyl acetate fraction. The chemical structure of the isolated compounds was established by MS and NMR (APT, COSY, HSQC, HMBC, and NOESY). LC-ESI-MS analysis of the ethyl acetate fraction afforded eight flavonoid glycosides, while the dichloromethane fraction of the defatted seeds contained seven limonoid aglycones. The chloroform fraction exerted the strongest DPPH* free radical scavenging activity in comparison to other fractions. The petroleum fraction showed a significant inhibition of lipoxygenase indicating an anti-inflammatory action (IC50 29 +/- 1 mu g/mL). Some of the isolated polymethoxyflavones exhibited strong cytotoxicity against COS7, HeLa and Caco-2 cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2010.12.129

文献信息

• A straightforward access to neohesperidose from naringin by acetolysis. Comparative behaviour of some flavonoid neohesperidosides and rutinosides under acetolysis
  作者：Guy Lewin

  DOI：10.1016/j.tet.2013.12.064

  日期：2014.2

  semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state

  分三步进行新橙皮苷的简单半合成，从柚皮中的主要类黄酮柚皮苷开始，总产率为43％。另外，比较了两对类黄酮7- O-鼠李糖苷（新橙皮苷苷柚皮苷和rhoifolin；芦丁苷橙皮苷和薯os皂苷）在相同的乙酰分解条件下的行为。结果证明了糖苷配基（黄酮或黄酮）的氧化态以及二糖部分的性质对反应过程的关键影响。
• Method for Biotechnological Production of Dihydrochalcones
  申请人：Symrise AG

  公开号：US20140045233A1

  公开（公告）日：2014-02-13

  A method for production of a dihydrochalcone, especially of phloretin, using a transgenic microorganism, containing a nucleic acid section (a), comprising or consisting of a gene coding for a bacterial chalcone isomerase, and/or a nucleic acid section (a′), comprising or consisting of a gene coding for a plant chalcone isomerase, and a nucleic acid section (b), comprising or consisting of a gene coding for a bacterial enoate reductase, corresponding transgenic microorganisms, containing a nucleic acid section (a), comprising or consisting of a gene coding for a bacterial chalcone isomerase, and/or a nucleic acid section (a′), comprising or consisting of a gene coding for a plant chalcone isomerase, and/or a nucleic acid section (b), comprising or consisting of a gene coding for a bacterial enoate reductase, and host cells, containing one or more identical or different such vectors.

  一种利用转基因微生物生产二氢黄酮的方法，特别是花瘤素的方法，其中所述转基因微生物包含核酸片段(a)，包括或仅包括编码细菌查尔酮异构酶的基因，和/或核酸片段(a')，包括或仅包括编码植物查尔酮异构酶的基因，以及核酸片段(b)，包括或仅包括编码细菌烯酸还原酶的基因，所述转基因微生物，包含核酸片段(a)，包括或仅包括编码细菌查尔酮异构酶的基因，和/或核酸片段(a')，包括或仅包括编码植物查尔酮异构酶的基因，和/或核酸片段(b)，包括或仅包括编码细菌烯酸还原酶的基因，以及包含一个或多个相同或不同的这样的载体的宿主细胞。
• Oleanene-type triterpene glycosides as masking agents
  申请人：Symrise AG

  公开号：EP2559346A1

  公开（公告）日：2013-02-20

  The present invention relates to the use of certain oleanene-type triterpene glycosides of formula (I) and/or physiologically acceptable salts thereof wherein M is hydrogen or hydroxyl, preferably hydroxyl, and A is a carbohydrate moiety, preferably an oligosaccharide moiety, for modifying (i.e. modulating) or masking (i.e. reducing or suppressing) unpleasant taste impressions, in particular bitter and/or astringent taste impressions and to a corresponding method for modulating or masking an unpleasant taste of a substance or substance mixture. The present invention also relates to compositions, in particular orally consumable compositions, comprising (a) one or more compounds of formula (I) or a physiologically acceptable salt thereof, and (b) one or more substances with unpleasant taste, in particular bitter and/or astringent taste.

  本发明涉及式 (I) 的某些齐墩果烯型三萜苷和/或其生理上可接受的盐的用途 其中 M 是氢或羟基，最好是羟基，以及 A 是碳水化合物分子，最好是寡糖分子、 用于改变（即调节）或掩盖（即减少或抑制）不愉快的味道印象，特别是苦味和/或涩味印象，以及用于调节或掩盖物质或物质混合物的不愉快味道的相应方法。 本发明还涉及组合物，特别是口服组合物，包括(a)一种或多种式(I)化合物或其生理上可接受的盐，和(b)一种或多种具有令人不快的味道，特别是苦味和/或涩味的物质。
• Rhamnosyl-tranferase gene and uses thereof
  申请人：Gressel Jonathan

  公开号：US20050089882A1

  公开（公告）日：2005-04-28

  An isolated polynucleotide comprising a nucleotide sequence encoding a polypeptide having a flavanone-7-O-glucoside-2″-O-rhamnosyl-transferase catalytic activity and its uses.

  一种分离的多核苷酸，包含编码具有黄酮-7-O-葡萄糖苷-2″-O-鼠李糖基转移酶催化活性的多肽的核苷酸序列及其用途。
• SURFACE STERILISATION BY MISTING WITH A BIOFLAVANOID SOLUTION COMPRISING NARINGIN AND NEOHESPERIDIN
  申请人：Citrox Biosciences Limited

  公开号：EP2393356B1

  公开（公告）日：2014-12-03