2-O-α-L-rhamonopyranosyl-D-glucopyranose | 2781-65-9

• 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-rhamonopyranosyl-D-glucopyranose
• 英文别名: 2-O-α-L-rhamnopyranosyl-D-glucopyranose；2-O-α-L-rhamnopyranosyl-D-glucose；neohesperidoside；neohesperidose；Rha(a1-2)Glc；(2S,3R,4R,5R,6S)-2-methyl-6-[(3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 2781-65-9
• 化学式: C₁₂H₂₂O₁₀
• 分子量: 326.301
• InChiKey: VSRVRBXGIRFARR-SLVHYYSXSA-N

物化性质

• 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

• 作为反应物：
  描述：

  2-O-α-L-rhamonopyranosyl-D-glucopyranose 在 McIlvaine buffer 、 α-L-rhamnosidase 作用下， 以 水 为溶剂， 反应 24.0h， 生成 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Kamiya, Shintaro; Esaki, Sachiko; Tanaka, Reiko, Agricultural and Biological Chemistry, 1985, vol. 49, # 1, p. 55 - 62

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranose 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 palladium(II) hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-O-α-L-rhamonopyranosyl-D-glucopyranose
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x

文献信息

• NOVEL POLYPHENOL COMPOUND
  申请人：NOMURA Kenzo

  公开号：US20110237533A1

  公开（公告）日：2011-09-29

  Compounds represented by formula (I) wherein the symbols are as defined in the description, exhibit a lipase inhibitory activity, and are useful for foods, drinks, and the like.

  式(I)所代表的化合物，在符号如描述中所定义的情况下，表现出脂肪酶抑制活性，并且对于食品、饮料等具有用途。
• Kim, Youn Chul; Higuchi, Ryuichi; Komori, Tetsuya, Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580
  作者：Kim, Youn Chul、Higuchi, Ryuichi、Komori, Tetsuya

  DOI：——

  日期：——
• POLYMORPH
  申请人：Oncology Research International Limited

  公开号：EP2935308A1

  公开（公告）日：2015-10-28
• [EN] POLYMORPH<br/>[FR] POLYMORPHE
  申请人：ONCOLOGY RES INT LTD

  公开号：WO2014094032A9

  公开（公告）日：2017-02-02

  [EN] The present invention relates to a new polymorphic form of the compound diosgenyl α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside (compound (I)) and pharmaceutical compositions containing this polymorph
  [FR] La présente invention concerne un nouveau polymorphe du composé diosgenyl α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside (composé (I)) et des compositions pharmaceutiques contenant ce polymorphe.
• Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure
  作者：Kazuaki Yamasaki、Ryogo Hishiki、Eisuke Kato、Jun Kawabata

  DOI：10.1021/ml100171x

  日期：2011.1.13

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.