桃叶珊瑚甙元 | 64274-28-8

• 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: 桃叶珊瑚甙元
• 中文别名: 桃叶珊瑚苷元
• 英文名称: aucubigenin
• 英文别名: Aucubigenen；(1R,4aR,5S,7aS)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1,5-diol
• CAS: 64274-28-8
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: BACWCXKATFIVFS-JQCXWYLXSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  442.7±45.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  桃叶珊瑚甙元 在 硼氘化钠 、 重水 作用下， 生成 Deuteroisoeucommiol
  参考文献：
  名称：

  异环己醇的部分合成，一种新的环戊烯类四醇

  摘要：

  通过NaBH 4还原augubigenin 4a的半缩醛部分，可以制备出eucommiol 1的环戊烯-四醇异构体isoeucommiol 3。已经通过使用NaBD 4研究了这种减少的机理。

  DOI：

  10.1016/0040-4020(77)80033-1
• 作为产物：
  描述：

  桃叶珊瑚苷（杜仲甙） 在 β-glucosidase 、 水 作用下， 生成 桃叶珊瑚甙元
  参考文献：
  名称：

  Determination of Antibacterial Activity of Aucubigenin and Aucubin

  摘要：

  由于之前的报告相互矛盾，我们采用敏感的标准微孔稀释法和自动分光光度法，与纸片扩散法相比，重新研究了褐藻苷元和褐藻素的抗菌活性。微孔稀释法比纸片扩散法更准确。结果表明，杜鹃黄素没有抗菌活性，而杜鹃甙元对所有受试细菌都有显著的抗菌活性。褐藻甙元对金黄色葡萄球菌尤其有效，其 MIC 值和 MBC 值分别为 0.0313 毫克/毫升和 0.0625 毫克/毫升。

  DOI：

  10.14233/ajchem.2014.15833

文献信息

• Studies on iridoid-related compounds. IV Antitumor activity of iridoid aglycones.
  作者：KYOKO ISHIGURO、MASAE YAMAKI、SHUZO TAKAGI、YOSHIAKI IKEDA、KIYOTAKA KAWAKAMI、KEIZO ITO、TAKASHI NOSE

  DOI：10.1248/cpb.34.2375

  日期：——

  An extensive study has been made on the antitumor activity of several iridoid glycosides and their aglycones in mice bearing the experimental tumor leukemia P388. Most of the aglycones were found to be active. Among them, scadoside methyl ester aglycone (SMEH) showed the most potent activity, and it was furhter tested against several kinds of experimental tumor. None of the glucosides showed any activity. Our observations suggest that the hemiacetal structure of iridoid aglycones plays a significant role in the antitumor activity, as in the case of the antimicrobial activity reported previously.

  对几种环烯醚萜苷及其糖苷在实验性肿瘤白血病P388小鼠体内的抗肿瘤活性进行了广泛研究。大多数糖苷被发现具有活性。其中，scadoside methyl ester aglycone (SMEH)表现出最强活性，并进一步对几种实验性肿瘤进行了测试。这些苷类均未显示出任何活性。我们的观察表明，环烯醚萜苷半缩醛结构在抗肿瘤活性中起着重要作用，正如先前报道的抗菌活性一样。
• Centrifugal partition chromatography: an efficient tool to access highly polar and unstable synthetic compounds on a large scale
  作者：Dean Marković、Cédric Barboux、Ysé Salle de Chou、Judith Bettach、Raphaël Grougnet、Brigitte Deguin

  DOI：10.1039/c4ra12141d

  日期：——

  compounds with chemical value, significantly simplifying the reaction work-up. From Aucuba japonica Thunb., an abundant natural terpenoid, aucubin, was isolated. Its reduced derivatives and corresponding unstable aglucons were purified by CPC. The latter chiral synthons were obtained under protecting group free conditions using eco-friendly, non-chlorinated solvents and without silica gel.

  离心分配色谱法（CPC）是一种适用于纯化具有化学价值的合成化合物的有效方法，可大大简化反应过程。从Aucuba japonica Thunb。中分离了丰富的天然萜类化合物aucubin。通过CPC纯化其还原的衍生物和相应的不稳定的苷元。后者的手性合成子是在无保护基的条件下使用环保，无氯的溶剂，且没有硅胶而获得的。
• Crystal Structure and Characterization of Iridoid Related Compound Isoeucommiol
  作者：Yang Li、Ye Zhao、Guo-Ping Yang、Min-Juan Wang、Yong-Min Zhang、Wen-Ji Sun

  DOI：10.1007/s10870-010-9857-9

  日期：2011.2

  A single crystal of iridoid related compound isoeucommiol was obtained through NaBH4 reduction of aucubigenin which was formed by enzymatic hydrolysis of aucubin. Its structure and stereochemistry were determined by X-ray diffraction. The crystal adopts an envelope conformation, presenting a triclinic system, space group P1 with Z = 1, unit cell dimensions a = 5.4158(13) Å, b = 6.5251(15) Å, and c = 7

  通过NaBH4还原桃红甙元酶水解形成的桃红甙元，得到环烯醚萜类化合物异丁香酚单晶。其结构和立体化学通过 X 射线衍射确定。该晶体采用包络构象，呈三斜晶系，空间群 P1，Z = 1，晶胞尺寸 a = 5.4158(13) Å，b = 6.5251(15) Å，c = 7.1555(17) Å。此外，在晶格中可以观察到广泛的分子间O-H···O氢键网络。图解摘要通过NaBH4还原桃红豆碱，得到异丁香酚单晶，并通过X射线衍射确定其结构和立体化学。
• X-ray crystal structure of iridoid glucoside aucubin and its aglycone
  作者：Yang Li、Ye Zhao、Yong-min Zhang、Min-juan Wang、Wen-ji Sun

  DOI：10.1016/j.carres.2009.08.021

  日期：2009.11

  X-ray diffraction analyses of iridoid glycoside aucubin (1) and its aglycone aucubigenin (2) are reported. it was found that crystals of 1 are orthorhombic, with P2(1)2(1)2(1) space group, both cyclopentane ring and pyran ring adopt envelope conformations, and the Glc moiety is in the C-4(1), conformation. Crystals of 2 are monoclinic, with space group P2(1), the cyclopentane and pyran rings also adopt the envelope conformation. The absolute configurations of 1 and 2 were also determined. Intensive O-H center dot center dot center dot O hydrogen bonds in both crystal lattices were observed. (C) 2009 Elsevier Ltd. All rights reserved.
• Determination of Antibacterial Activity of Aucubigenin and Aucubin
  作者：Yang Li、Lei Chen、Guijun Han、Junhui Zhou、Ye Zhao

  DOI：10.14233/ajchem.2014.15833

  日期：——

  Because of the previously conflicted reports, the aucubigenin and aucubin have been reinvestigated for their antibacterial activities by a sensitive standardized micro-well dilution with automated spectrophotometric method, compared with paper disc diffusion method. The micro-well dilution assay was more accurate than paper disc diffusion method. The results showed that aucubin exhibited no antibacterial activity, while aucubigenin showed remarkable antibacterial activity against all of the tested bacteria. Aucubigenin was particularly more effective against Staphylococcus aureus with MIC value of 0.0313 mg/mL and MBC value of 0.0625 mg/mL, respectively.

  由于之前的报告相互矛盾，我们采用敏感的标准微孔稀释法和自动分光光度法，与纸片扩散法相比，重新研究了褐藻苷元和褐藻素的抗菌活性。微孔稀释法比纸片扩散法更准确。结果表明，杜鹃黄素没有抗菌活性，而杜鹃甙元对所有受试细菌都有显著的抗菌活性。褐藻甙元对金黄色葡萄球菌尤其有效，其 MIC 值和 MBC 值分别为 0.0313 毫克/毫升和 0.0625 毫克/毫升。