Oleoside dimethyl ester | 30164-95-5

• 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
• 英文名称: Oleoside dimethyl ester
• 英文别名: methyl (4S,5E,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• CAS: 30164-95-5
• 化学式: C₁₈H₂₆O₁₁
• 分子量: 418.398
• InChiKey: KYVUMEGNMQDSHO-PVCIXGPPSA-N

物化性质

• 沸点：
  600.1±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Oleoside dimethyl ester 在 sodium hydroxide 、 乙醇-D1 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 48.0h， 生成 oleoside <11-OC2H3>methyl ester
  参考文献：
  名称：

  Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors

  摘要：

  Several deuterium-labelled secoiridoids have been prepared and tested as possible precursors for the iridoids in Fraxinus excelsior, Syringa josikaea and S. vulgaris. Oleoside Ii-methyl ester was an efficient precursor for the oleosides, whereas secologanin-type iridoids gave only significant incorporation in 5. josikaea. In this plant low incorporations into the oleosides were also seen for kingiside and 8-epi-kingiside. The major pathway to the oleosides therefore seems to proceed via a direct ring fission of ketologanin to oleoside 11-methyl ester. A Baeyer-Villiger-like mechanism which explains the different compounds found in the plants is proposed, and the taxonomy of the Oleaceae is discussed. Due to the unique presence of the usual pathway leading to secologanin and its congeners in Fontanesia, the Oleaceae is considered to be a member of the Gentiananae rather than Scrophulariales/Lamianae.

  DOI：

  10.1016/0031-9422(95)00211-o
• 作为产物：
  描述：

  橄榄苦甙 在 吡啶 、 2,4,6-三氯苯甲酰氯 、 二乙胺 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.17h， 生成 Oleoside dimethyl ester
  参考文献：
  名称：

  橄榄苦苷的新半合成类似物在体外和体内显示出改善的抗癌活性

  摘要：

  橄榄苦苷是存在于橄榄果实和叶子中的一种糖基化的类花生油。由于橄榄苦苷具有广泛的生物学活性，包括抗癌特性，因此在过去的20年中受到了科学的关注。富含橄榄苦苷的橄榄叶提取物对一系列人类癌细胞系的有希望的抗增殖活性，促使我们着手合成橄榄苦苷的51个类似物。在对雌激素受体阴性乳腺癌细胞株SKBR3进行初步筛选后，显示7种类似物显示出明显的细胞毒性，并进一步针对6种其他实体肿瘤衍生和白血病细胞株进行了测试。选择具有最有前途的抗肿瘤活性的类似物（24）进行更详细的研究。24在接近其最大抑制浓度一半的浓度下进行测试时，对健康献血者的外周血单核细胞无毒。在荷黑素瘤小鼠体内给予24只可导致肿瘤大小以剂量依赖性方式减少，并诱导抗黑素瘤反应性免疫反应。我们的结果表明，从橄榄苦苷的初始结构中出现的类似物24代表了有希望的进一步优化的先导结构。

  DOI：

  10.1016/j.ejmech.2017.05.029

文献信息

• Secoiridoid Glucosides from the Twigs of &lt;i&gt;Syringa oblata&lt;/i&gt; var. &lt;i&gt;dilatata&lt;/i&gt; and Their Neuroprotective and Cytotoxic Activities
  作者：Kyoung Jin Park、Won Se Suh、Lalita Subedi、Sun Yeou Kim、Sang Un Choi、Kang Ro Lee

  DOI：10.1248/cpb.c16-00804

  日期：——

  Phytochemical investigation of the twigs of Syringa oblata var. diatata led to the isolation of two new secoiridoid glucosides, dilatioside A–B (1–2), along with thirteen known ones (3–15). The structures were determined by spectroscopic methods including one and two dimensional (1- and 2D-) NMR techniques, high resolution (HR)-FAB-MS, and chemical methods. The isolated compounds (1–15) were tested for the induction of nerve growth factor (NGF) secretion in a C6 rat glioma cell line and their cytotoxicity against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, HCT15) in vitro using a sulforhodamine B bioassay. Compounds 5, 7, 8, 10, and 14 were found to induce upregulation of NGF secretion without causing significant cell toxicity.

  Diatata 变种的小枝进行了植物化学研究，分离出了两种新的琥珀苷--地拉地苷 A-B (1-2)，以及 13 种已知的琥珀苷 (3-15)。这些化合物的结构是通过光谱方法（包括一维和二维核磁共振技术）、高分辨率（HR）-FAB-MS 和化学方法确定的。利用磺基罗丹明 B 生物测定法测试了分离出的化合物（1-15）在 C6 大鼠胶质瘤细胞系中诱导神经生长因子（NGF）分泌的情况，以及它们在体外对四种人类癌细胞系（A549、SK-OV-3、SK-MEL-2 和 HCT15）的细胞毒性。结果发现，化合物 5、7、8、10 和 14 能诱导 NGF 分泌上调，但不会对细胞造成明显毒性。
• Five trimeric secoiridoid glucosides from Jasminum polyanthum
  作者：Yukiko Takenaka、Takao Tanahashi、Naotaka Nagakura

  DOI：10.1016/s0031-9422(97)00890-x

  日期：1998.5

  Investigation of the crude drug “Ye su xin”, the dried flowers of Jasminum polyanthum, has led to the isolation of five new secoiridoid glucosides, oleopolyanthosides A and B, and jaspolyoleosides A, B, and C. The structures of the new compounds were elucidated by spectroscopic and chemical means.

  对茉莉花干花原料药“野素心”的考察，分离出5个新的类环烯醚萜苷、油多苷A、B、油多苷A、B、C。新化合物的结构为通过光谱和化学方法阐明。
• Oligomeric secoiridoid glucosides from Jasminum abyssinicum☆
  作者：F GALLO、G PALAZZINO、E FEDERICI、R IURILLI、F MONACHE、K CHIFUNDERA、C GALEFFI

  DOI：10.1016/j.phytochem.2005.11.007

  日期：2006.3

  From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations

  从收集在刚果的 Jasminum abyssinicum (Oleaceae) 的根皮中分离出一种名为 craigosides AC 的树低聚二环环烯醚萜苷。这三种化合物是具有环戊烷类单萜的具有环戊烷骨架的酯，分别用三个、两个和两个油苷 11-甲酯单元酯化。通过光谱方法和化学相关性阐明了结构。
• A secoiridoid glucoside from Fraxinus insularis
  作者：Takao Tanahashi、Atsuko Shimada、Naotaka Nagakura、Kenichiro Inoue、Hiroshi Kuwajima、Kiyokazu Takaishi、Chen Cheng-Chang

  DOI：10.1016/0031-9422(93)85527-x

  日期：1993.5

  Abstract A new secoiridoid glucoside, insularoside, was isolated from Fraxinus insularis . The structural elucidation of insularoside by spectroscopic and chemical studies is described. The biogenesis of this glucoside is also briefly discussed.

  摘要 从岛叶白蜡中分离得到了一种新的类环烯醚萜苷，岛叶苷。描述了通过光谱和化学研究对岛叶糖苷的结构阐明。还简要讨论了这种糖苷的生物发生。
• Syringoleosides A–H, Secoiridoids from <i>Syringa dilatata</i> Flowers and Their Inhibition of NO Production in LPS-Induced RAW 264.7 Cells
  作者：Jung Eun Gwag、Yeong-Geun Lee、Hyoung-Geun Kim、Dong-Sung Lee、Dae Young Lee、Nam-In Baek

  DOI：10.1021/acs.jnatprod.0c00490

  日期：2020.9.25

  Repeated column chromatography of Syringa dilatata flowers, a native shrub to Korea, led to the isolation of eight new oleoside-type secoiridoids, syringoleosides A-H (1-8), as well as five known secoiridoids (9-13). The new chemical structures were identified through spectroscopic data analysis, as well as the application of chemical methods. Compounds 1, 2, 6, 7, 11, and 13 showed suppression effects on NO production in LPS-induced RAW 264.7 cells, with IC50 values ranging from 32.5 +/- 9.8 to 65.7 +/- 11.0 mu M, and no visible toxicity. The content of the major secoiridoids in S. dilatata flowers, compounds 1, 4, 5, 8, 9, 12, and 13, were determined through HPLC analysis.