(2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-β-D-galactopyranosyl 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)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-β-D-galactopyranosyl glycerol
• 英文别名: 1-O-linolenoyl-2-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol；1,2,di-O-α-linolenoyl-3-O-β-galactopyranosyl-sn-glycerol；(2S)-1,2-di-O-linolenoyl-3-O-β-D-galactopyranosyl glycerol；1,2-O-dilinolenoyl-3-O-(β-D-galactopyranosyl)glycerol；glycerol 1,2-dilinolenyl-3-O-β-D-galactopyranoside；glycerol 1,2-dilinolenyl-3-O-β-D-galactopyanoside；1,2-Di-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol；[2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• 化学式: C₄₅H₇₄O₁₀
• 分子量: 775.077
• InChiKey: QUZHZFAQJATMCA-VLTMIGNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  55
• 可旋转键数：
  35
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-β-D-galactopyranosyl glycerol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 口服葡萄糖
  参考文献：
  名称：

  Chemical constituents and antibacterial activity of Melastoma malabathricum L.

  摘要：

  The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2 alpha-hydroxyursolic acid (2), asiatic acid (3), beta-sitosterol 3-O-beta-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-beta-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-alpha-L-rhamnopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), kaempferol 3-O-beta-D-galactopyranoside (9), kaempferol 3-O-(2 '',6 ''-di-O-E-p-coumaryl)-beta-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.

  DOI：

  10.1080/14786419.2010.538395
• 作为产物：
  描述：

  [2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate 在 水 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到(2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-β-D-galactopyranosyl glycerol
  参考文献：
  名称：

  An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids

  摘要：

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.030

文献信息

• Chemoenzymatic synthesis and antimicrobial activity evaluation of monogalactosyl diglycerides
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Luciana Gabrielli Favretto、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.ejmech.2007.03.012

  日期：2008.1

  examined for antimicrobial activity against Gram positive, Gram negative bacteria and fungi. The study of their in vitro antimicrobial activity confirms the significant activity of some monogalactosyl diacylglycerol analogues and establishes for the galactose series that the 1,2-disubstitution and the octanoyl chain are the proper structural features for the maximum activity.

  制备具有中等至长脂肪酸酰基链的单半乳糖甘油二酯，并检查其对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。对它们的体外抗菌活性的研究证实了某些单半乳糖基二酰基甘油类似物的显着活性，并为半乳糖系列确定了1,2-二取代基和辛酰基链是最大活性的适当结构特征。
• Process for preparing a crassocephalum crepidioides extract, extract prepared thereby and use of the extract
  申请人：DEVELOPMENT CENTER FOR BIOTECHNOLOGY

  公开号：US10980853B2

  公开（公告）日：2021-04-20

  The present invention provides a process for the preparation of a Crassocephalum crepidioides extract, and the extract prepared thereby. The present invention further relates to a pharmaceutical composition/combination comprising the Crassocephalum crepidioides extract. The use of the extract and the composition/combination comprising the extract in the prevention or treatment of cancer is also provided.

  本发明提供了一种制备 Crassocephalum crepidioides 提取物的工艺，以及由此制备的提取物。本发明还涉及一种药物组合物/复方制剂，其中包含糙叶牛樟芝提取物。本发明还提供了该提取物和包含该提取物的组合物/复合物在预防或治疗癌症中的用途。
• Glycolipids and pharmaceutical compositions thereof for use in therapy
  申请人：THE UNIVERSITY OF NOTTINGHAM

  公开号：US11248016B2

  公开（公告）日：2022-02-15

  The invention may provide, in part, compounds for use as antiproliferative, chemotherapeutic, antiviral, cell sensitising 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 disorder 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、亨廷顿病和帕金森病。
• Use of glycosides of mono- and diacylglycerol as anti-inflammatory agents
  申请人：——

  公开号：US20030139350A1

  公开（公告）日：2003-07-24

  Glycosides of diacylglycerol, e.g. 3-&bgr;-D-galactopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate (GOPO), which was isolated from extracts of rose-hips by activity guided fractionation, can be used as an oral anti-inflammatory agent for the treatment of inflammatory diseases such as arthritis and osteoarthrosis. 1

  二酰甘油的糖苷，例如通过活性引导分馏从玫瑰果提取物中分离出的 3-&bgr;-D-半乳糖吡喃氧基-2-（十八碳-9Z,12Z,15Z-三烯酰氧基）丙基十八碳-9Z,12Z,15Z-三烯酸酯（GOPO），可用作口服消炎药，用于治疗关节炎和骨关节病等炎症性疾病。 1
• Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase
  作者：Francesca Cateni、Paolo Bonivento、Giuseppe Procida、Marina Zacchigna、Giuditta Scialino、Elena Banfi

  DOI：10.1016/j.bmcl.2007.01.019

  日期：2007.4

  Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaccae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains. (c) 2007 Elsevier Ltd. All rights reserved.