(2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol

• 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-linoleoyl-2-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol
• 英文别名: 2S-1-O-linolenoyl-2-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol；(2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-beta-D-galactopyranosyl-sn-glycerol；1-18:2-2-18:2-Monogalactosyldiacylglycerol；[(2S)-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
• 化学式: C₄₅H₇₈O₁₀
• 分子量: 779.108
• InChiKey: BROOMPUVDPTGEG-RHNBIRJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  55
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol 在 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 亚油酸甲酯
  参考文献：
  名称：

  番薯叶的新型半乳糖脂：通过液相色谱与电喷雾电离-四极杆飞行时间串联质谱联用进行表征。

  摘要：

  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。

  DOI：

  10.1021/jf071331z
• 作为产物：
  描述：

  (2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl-(9Z,12Z)-octadeca-9,12-dienoate 、 uridine 5'-(α-D-galactopyranosyl diphosphate) 生成 (2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol 、 氢(+1)阳离子 、 UDP
  参考文献：
  名称：

  Two types of MGDG synthase genes, found widely in both 16:3 and 18:3 plants, differentially mediate galactolipid syntheses in photosynthetic and nonphotosynthetic tissues in Arabidopsis thaliana

  摘要：

  在拟南芥中，单半乳糖二酰基甘油（MGDG）由由多基因家族的MGDG合成酶合成，由两种不同的酶组成，其N-末端不同：A型（atMGD1）和B型（atMGD2和atMGD3）。本文比较了B型同工酶与已知坐落在质体包膜内膜的A型酶。16：3和18：3植物中A和B型的出现表明，两种类型并不是原核和真核甘油脂生物合成途径的专门同工酶。atMGD1基因在绿色组织和植物发育过程中丰富表达，并编码最活跃的酶。其成熟多肽在转运肽剪切后在拟南芥叶绿体的包膜中被免疫检测到。因此，atMGD1可能专门用于大量生产所需的MGDG，以扩展内包膜膜并建立类囊体网络。在拟南芥叶片中绿色荧光蛋白融合的瞬时表达和体外进口实验表明，B型前体由于不同的机制被定位到质体中。非规范寻址肽参与了B型前体的定位，其加工无法评估，可能定位于外包膜膜，从而有助于膜的扩张。B型酶的表达在非绿色组织，即花序（atMGD2）和根（atMGD3）中更高，它们可能影响MGDG中真核结构的突出性。此外，在缺磷条件下，B型酶的表达得到增强。

  DOI：

  10.1073/pnas.181331498

文献信息

• Glycolipids and pharmaceutical compositions thereof for use in therapy
  申请人：THE UNIVERSITY OF NOTTINGHAM

  公开号：US10428102B2

  公开（公告）日：2019-10-01

  The invention may provide, in part, compounds for use as antiproliferative, chemotherapeutic, antiviral, cell sensitizing or adjuvant agents, and pharmaceutical compositions including the compounds. The compounds may be for use in treating diseases and disorders related to cell proliferation such as cancer, or in treating diseases and disorders which are linked to aberrant control of protein synthesis, such as cancer, viral infection, muscle wasting, autistic spectrum disorders, Alzheimer's disease, Huntingdon's disease and Parkinson's disease.

  本发明可部分提供用作抗增殖剂、化疗剂、抗病毒剂、细胞增敏剂或佐剂的化合物，以及包括这些化合物的药物组合物。这些化合物可用于治疗与细胞增殖有关的疾病和紊乱，如癌症，或用于治疗与蛋白质合成异常控制有关的疾病和紊乱，如癌症、病毒感染、肌肉萎缩、自闭症谱系障碍、阿尔茨海默病、亨廷顿氏病和帕金森氏病。
• GLYCOLIPIDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR USE IN THERAPY
  申请人：THE UNIVERSITY OF NOTTINGHAM

  公开号：US20170275323A1

  公开（公告）日：2017-09-28

  A compound of Formula I: R1-L1-C(A)(A′)-CH 2 , -L2-R2 or a pharmaceutically acceptable salt thereof, for use in medicine, for example in the treatment of a disease or condition selected from the group comprising cancer, autistic spectrum disorders. Alzheimer's disease, Parkinson's disease, Huntingdon's disease, muscle wasting and viral infection, wherein: R1 is selected from a carbohydrate group or derivative thereof, hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; L1 is a linking group; L2 is a linking group; R2 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; A is selected from hydrogen and a C1-C6 alkyl group: A′ is selected from hydrogen, a C3-C6 alkyl group, and L3-R3; wherein L3 is a linking group; and R3 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; and wherein if A′ is not L3-R3, then R2 is a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group; and wherein if A′ is L3-R3, then one or both of R2 and R3 are a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group.
• 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。
• Two types of MGDG synthase genes, found widely in both 16:3 and 18:3 plants, differentially mediate galactolipid syntheses in photosynthetic and nonphotosynthetic tissues in <i>Arabidopsis thaliana</i>
  作者：Koichiro Awai、Eric Maréchal、Maryse A. Block、Delphine Brun、Tatsuru Masuda、Hiroshi Shimada、Ken-ichiro Takamiya、Hiroyuki Ohta、Jacques Joyard

  DOI：10.1073/pnas.181331498

  日期：2001.9.11

  In Arabidopsis , monogalactosyldiacylglycerol (MGDG) is synthesized by a multigenic family of MGDG synthases consisting of two types of enzymes differing in their N-terminal portion: type A (atMGD1) and type B (atMGD2 and atMGD3). The present paper compares type B isoforms with the enzymes of type A that are known to sit in the inner membrane of plastid envelope. The occurrence of types A and B in 16:3 and 18:3 plants shows that both types are not specialized isoforms for the prokaryotic and eukaryotic glycerolipid biosynthetic pathways. Type A atMGD1 gene is abundantly expressed in green tissues and along plant development and encodes the most active enzyme. Its mature polypeptide is immunodetected in the envelope of chloroplasts from Arabidopsis leaves after cleavage of its transit peptide. atMGD1 is therefore likely devoted to the massive production of MGDG required to expand the inner envelope membrane and build up the thylakoids network. Transient expression of green fluorescent protein fusions in Arabidopsis leaves and in vitro import experiments show that type B precursors are targeted to plastids, owing to a different mechanism. Noncanonical addressing peptides, whose processing could not be assessed, are involved in the targeting of type B precursors, possibly to the outer envelope membrane where they might contribute to membrane expansion. Expression of type B enzymes was higher in nongreen tissues, i.e., in inflorescence ( atMGD2 ) and roots ( atMGD3 ), where they conceivably influence the eukaryotic structure prominence in MGDG. In addition, their expression of type B enzymes is enhanced under phosphate deprivation.

  在拟南芥中，单半乳糖二酰基甘油（MGDG）由由多基因家族的MGDG合成酶合成，由两种不同的酶组成，其N-末端不同：A型（atMGD1）和B型（atMGD2和atMGD3）。本文比较了B型同工酶与已知坐落在质体包膜内膜的A型酶。16：3和18：3植物中A和B型的出现表明，两种类型并不是原核和真核甘油脂生物合成途径的专门同工酶。atMGD1基因在绿色组织和植物发育过程中丰富表达，并编码最活跃的酶。其成熟多肽在转运肽剪切后在拟南芥叶绿体的包膜中被免疫检测到。因此，atMGD1可能专门用于大量生产所需的MGDG，以扩展内包膜膜并建立类囊体网络。在拟南芥叶片中绿色荧光蛋白融合的瞬时表达和体外进口实验表明，B型前体由于不同的机制被定位到质体中。非规范寻址肽参与了B型前体的定位，其加工无法评估，可能定位于外包膜膜，从而有助于膜的扩张。B型酶的表达在非绿色组织，即花序（atMGD2）和根（atMGD3）中更高，它们可能影响MGDG中真核结构的突出性。此外，在缺磷条件下，B型酶的表达得到增强。