Swerosid Aglucon | 15215-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: Swerosid Aglucon
• 英文别名: Sweroside aglycone；(3R,4R,4aS)-4-ethenyl-3-hydroxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• CAS: 15215-11-9
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: HBAKFDGYROBYSH-BKPPORCPSA-N

物化性质

• 沸点：
  361.3±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Swerosid Aglucon 、 乙酸酐 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 以31 mg的产率得到
  参考文献：
  名称：

  Transformation of naturally-occurring 1,9-trans-9,5-cis sweroside to all trans sweroside during acetylation of sweroside aglycone

  摘要：

  From the rootstock of Scabiosa columbaria L. loganin and sweroside were isolated. Sweroside showed moderate antibacterial activity. Pure sweroside was converted to the sweroside aglycone 1-acetoxy derivative (DABCO/Ac2O) after hydrolysis of the glucose unit. X-ray crystallography of the monoacetate showed unambiguously that it had been transformed to a new seco-iridoid having the novel trans diaxial configuration for the protons on C-1, C-9 and C-5. The mechanism for the rearrangement is discussed. (C) 2001 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0031-9422(00)00460-x
• 作为产物：
  描述：

  獐牙菜苷 在 β-glucosidase from almonds 、 水 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 Swerosid Aglucon
  参考文献：
  名称：

  忍冬花芽中的两种新的β-羟基氨基酸偶联的类脂环素：分离，结构解析，半合成和生物学活性

  摘要：

  摘要从忍冬（Lonicera japonic a）的花蕾水提物中分离出了两种新的β-羟基氨基酸偶联的类香豆素，分别称为丝氨酸二硒精（1）和苏糖二硒精（2）。通过光谱数据分析确定了它们的不常见结构（包括绝对构型），并通过同时存在的secologanin（3）和secologanic酸（4）的半合成证实了它们的结构。化合物1和2对杏仁的β-葡萄糖苷酶和黑曲霉的橙皮苷酶均具有抗药性，它们还对由血小板活化因子诱导的大鼠多形核白细胞中的葡萄糖醛酸苷酶释放具有抑制作用，抑制率分别为（34.9±3.1）％和分别为（53.6±2.6）％。

  DOI：

  10.1016/j.cclet.2014.05.037

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。
• Two new β-hydroxy amino acid-coupled secoiridoids from the flower buds of Lonicera japonica: Isolation, structure elucidation, semisynthesis, and biological activities
  作者：Wei-Xia Song、Yong-Chun Yang、Jian-Gong Shi

  DOI：10.1016/j.cclet.2014.05.037

  日期：2014.9

  were isolated from an aqueous extract of the flower buds of Lonicera japonic a. Their uncommon structures including absolute configurations were determined by spectroscopic data analysis, and confirmed by semisynthesis from the co-occurring secologanin ( 3 ) and secologanic acid ( 4 ). Compounds 1 and 2 exhibited resistant activity against β -glucosidase from almonds and hesperidinase from Aspergillus

  摘要从忍冬（Lonicera japonic a）的花蕾水提物中分离出了两种新的β-羟基氨基酸偶联的类香豆素，分别称为丝氨酸二硒精（1）和苏糖二硒精（2）。通过光谱数据分析确定了它们的不常见结构（包括绝对构型），并通过同时存在的secologanin（3）和secologanic酸（4）的半合成证实了它们的结构。化合物1和2对杏仁的β-葡萄糖苷酶和黑曲霉的橙皮苷酶均具有抗药性，它们还对由血小板活化因子诱导的大鼠多形核白细胞中的葡萄糖醛酸苷酶释放具有抑制作用，抑制率分别为（34.9±3.1）％和分别为（53.6±2.6）％。
• Transformation of naturally-occurring 1,9-trans-9,5-cis sweroside to all trans sweroside during acetylation of sweroside aglycone
  作者：Marion M. Horn、Siegfried E. Drewes、Nicola J. Brown、Orde Q. Munro、J.J.Marion Meyer、Abbey D.M. Mathekga

  DOI：10.1016/s0031-9422(00)00460-x

  日期：2001.5

  From the rootstock of Scabiosa columbaria L. loganin and sweroside were isolated. Sweroside showed moderate antibacterial activity. Pure sweroside was converted to the sweroside aglycone 1-acetoxy derivative (DABCO/Ac2O) after hydrolysis of the glucose unit. X-ray crystallography of the monoacetate showed unambiguously that it had been transformed to a new seco-iridoid having the novel trans diaxial configuration for the protons on C-1, C-9 and C-5. The mechanism for the rearrangement is discussed. (C) 2001 Elsevier Science Ltd. All lights reserved.