(2S)-1-O-(9Z,12Z,15Z-octadecyltrienoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(β-D-galactopyranose-6-1-α-D-galactopyranose)-sn-glycerol | 87584-96-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-1-O-(9Z,12Z,15Z-octadecyltrienoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(β-D-galactopyranose-6-1-α-D-galactopyranose)-sn-glycerol
• 英文别名: (2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-[β-D-galactopyranosyl-(1"→6')-O-β-D-galactopyranosyl]glycerol；(2S)-3-O-[α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol；(2S)-3-O-α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol；(2S)-1-O-linolenoyl-2-O-linolenoyl-3-O-[α-D-galactopyranosyl-(1''->6')-β-D-galactopyranosyl]glycerol；(2S)-3-O-(α-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl)-1,2-di-O-linolenoyl-sn-glycerol；(2S)-1,2-di-O-linolenoyl-3-O-(α-galactopyranosyl-(1->6)-O-β-galactopyranosyl)glycerol；Dgdg；[(2S)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 87584-96-1；106927-47-3；125410-84-6；127515-98-4；63142-69-8
• 化学式: C₅₁H₈₄O₁₅
• 分子量: 937.219
• InChiKey: KDYAPQVYJXUQNY-OPHDRXFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  66
• 可旋转键数：
  38
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-(9Z,12Z,15Z-octadecyltrienoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(β-D-galactopyranose-6-1-α-D-galactopyranose)-sn-glycerol 在 甲醇 、 sodium methylate 作用下， 生成 Γ-十八碳三烯酸
  参考文献：
  名称：

  Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi

  摘要：

  Bioassay guided fractionation of ethanolic extract of the leaves of Bauhinia racemosa led to the isolation of galactolipid and catechin class of the compounds (1-7) from the most active n-butanol fraction (F4). Among the active galactolipids, 1 emerged as the lead molecule which was active on both forms of lymphatic filarial parasite, Brugia malayi. It was found to be better than the standard drug ivermectin and diethylcarbamazine (DEC) in terms of dose and efficacy. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.057
• 作为产物：
  描述：

  (2S)-3-O-(2,3-di-O-allyl-4,6-di-O-allyloxycarbonyl-α-D-galactopyranosyl-(1→6)-2,3-di-O-allyl-4-O-allyloxycarbonyl-β-D-galactopyranosyl)-1,2-di-O-linolenoyl-sn-glycerol 在 C₁₈H₁₆NO₂Ru^(1-)*F₆P⁽¹⁺⁾ 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 15.0h， 以46%的产率得到(2S)-1-O-(9Z,12Z,15Z-octadecyltrienoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(β-D-galactopyranose-6-1-α-D-galactopyranose)-sn-glycerol
  参考文献：
  名称：

  聚合合成二半乳糖基二酰基甘油

  摘要：

  已经完成了具有半乳糖-半乳糖α（1→6）-键和半乳糖-甘油β-键以及含有多种脂肪酸的二酰基甘油的高效二聚半乳糖基二酰基甘油（DGDG）的聚合化学合成。为了实现简洁的合成，我们选择使用烯丙基保护基作为永久保护基。作为关键步骤，我们还以高收率获得了各自键的α-和β-选择性糖基化。

  DOI：

  10.1021/acs.orglett.7b03043

文献信息

• Novel Galactolipids from the Leaves of Ipomoea batatas L.: Characterization by Liquid Chromatography Coupled with Electrospray Ionization–Quadrupole Time-of-Flight Tandem Mass Spectrometry
  作者：Assunta Napolitano、Virginia Carbone、Paola Saggese、Kinya Takagaki、Cosimo Pizza

  DOI：10.1021/jf071331z

  日期：2007.12.1

  Sixteen novel and ten known galactolipids have been isolated and characterized from the leaves of Ipomoea batatas L. (sweet potato) using an analytical method based on high-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry. Using this technique, the structures and regiochemistries of the fatty acyl groups and the positions of the

  使用高效液相色谱和电喷雾电离-四极杆飞行时间串联质谱联用的分析方法，从番薯叶中分​​离并鉴定了十六种新型半乳糖脂和十种已知的半乳糖脂。使用这种技术，确定了脂肪酰基的结构和区域化学以及酰基链上双键的位置。通过分析一维和二维核磁共振谱来鉴定糖部分。通过气相色谱-质谱法确定了多不饱和脂肪酸双键的位置，并在某些情况下确定了它们的几何形状。这是甘薯叶中半乳糖脂的首次报道。
• Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase
  作者：Rie Tanaka、Yuichi Sakano、Akito Nagatsu、Masaaki Shibuya、Yutaka Ebizuka、Yukihiro Goda

  DOI：10.1016/j.bmcl.2004.10.013

  日期：2005.1

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Galactolipids from Bauhinia racemosa as a new class of antifilarial agents against human lymphatic filarial parasite, Brugia malayi
  作者：Koneni V. Sashidhara、Suriya P. Singh、Sweta Misra、Jyoti Gupta、Shailja Misra-Bhattacharya

  DOI：10.1016/j.ejmech.2012.01.057

  日期：2012.4

  Bioassay guided fractionation of ethanolic extract of the leaves of Bauhinia racemosa led to the isolation of galactolipid and catechin class of the compounds (1-7) from the most active n-butanol fraction (F4). Among the active galactolipids, 1 emerged as the lead molecule which was active on both forms of lymphatic filarial parasite, Brugia malayi. It was found to be better than the standard drug ivermectin and diethylcarbamazine (DEC) in terms of dose and efficacy. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Convergent Synthesis of Digalactosyl Diacylglycerols
  作者：Shinsuke Inuki、Junichiro Kishi、Emi Kashiwabara、Toshihiko Aiba、Yukari Fujimoto

  DOI：10.1021/acs.orglett.7b03043

  日期：2017.12.15

  diacylglycerols (DGDGs), which have both a galactose–galactose α(1→6)-linkage and a galactose–glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with

  已经完成了具有半乳糖-半乳糖α（1→6）-键和半乳糖-甘油β-键以及含有多种脂肪酸的二酰基甘油的高效二聚半乳糖基二酰基甘油（DGDG）的聚合化学合成。为了实现简洁的合成，我们选择使用烯丙基保护基作为永久保护基。作为关键步骤，我们还以高收率获得了各自键的α-和β-选择性糖基化。