leoligin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: leoligin
• 英文别名: [(2S,3R,4R)-4-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)tetrahydrofuran-3-yl]methyl (2Z)-2-methylbut-2-enoate；[(2S,3R,4R)-2-(3,4-dimethoxyphenyl)-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl]methyl (Z)-2-methylbut-2-enoate
• 化学式: C₂₇H₃₄O₇
• 分子量: 470.563
• InChiKey: ZODXGUUEHGOUMO-HRPHUONDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 在 4-二甲氨基吡啶 、 二氯二茂钛 、 lithium aluminium tetrahydride 、 三溴化磷 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 leoligin
  参考文献：
  名称：

  PHARMACEUTICAL COMPOSITIONS COMPRISING LIGNANS AND THEIR DERIVATIVES FOR TREATING HYPERPLASTIC DISEASES

  摘要：

  公开号：

  EP2320887B8

文献信息

• Design and Synthesis of a Compound Library Exploiting 5-Methoxyleoligin as Potential Cholesterol Efflux Promoter
  作者：Thomas Linder、Sophie Geyrhofer、Eleni Papaplioura、Limei Wang、Atanas G. Atanasov、Hermann Stuppner、Verena M. Dirsch、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.3390/molecules25030662

  日期：——

  5-methoxyleoligin which can be readily used to prepare a novel compound library of related analogs. The target 5-methoxyleoligin was synthesized exploiting a recently disclosed modular route, which allows also rapid synthesis of analogous compounds. All obtained products were tested towards macrophage cholesterol efflux enhancement and the performance was compared to the parent compound leoligin. It was found that

  5-Methoxyleoligin 和 leoligin 是源自雪绒花 (Leontopodium nivale ssp. alpinum) 的天然木脂素，具有强大的促血管生成和促动脉生成活性。巨噬细胞的胆固醇流出与胆固醇逆向转运有关，从而抑制心血管疾病的发展。在这项研究中，我们开发了一种模块化和立体选择性的 5-甲氧基油氨酸全合成方法，可以很容易地用于制备相关类似物的新型化合物库。目标 5-methoxyleoligin 是利用最近公开的模块化路线合成的，该路线还允许快速合成类似的化合物。所有获得的产品都针对巨噬细胞胆固醇流出增强进行了测试，并将其性能与母体化合物 leoligin 进行了比较。
• Characterization of a Structural Leoligin Analog as Farnesoid X Receptor Agonist and Modulator of Cholesterol Transport
  作者：Angela Ladurner、Thomas Linder、Limei Wang、Verena Hiebl、Daniela Schuster、Michael Schnürch、Marko D. Mihovilovic、Atanas G. Atanasov、Verena M. Dirsch

  DOI：10.1055/a-1171-8357

  日期：2020.10

  receptor-activating compounds. The most active one being LT-141A, with an EC50 of 6 µM and an Emax of 4.1-fold. This analog did not activate the G protein-coupled bile acid receptor, TGR5, and the metabolic nuclear receptors retinoid X receptor α, liver X receptors α/β, and peroxisome proliferator-activated receptors β/γ. Investigation of different farnesoid X receptor target genes characterized LT-141A as selective

  配体激活的法尼醇 X 受体是开发针对代谢综合征相关疾病的药物的新兴治疗靶点。在这种情况下，选择性胆汁酸受体调节剂代表了药物开发的新概念。选择性胆汁酸受体调节剂以靶基因或组织特异性方式起作用，因此被认为不太可能引起不需要的副作用。基于 leoligin，一种来自高山植物 Leontopodium nivale ssp 的木脂素型次生植物代谢物。alpinum，在硅药效团模型中在法尼醇 X 受体中筛选了 168 种合成的结构类似物。生成了 56 个虚拟点击。这些命中在基于细胞的法尼醇 X 受体反式激活试验中进行了测试，并产生了 7 种法尼醇 X 受体激活化合物。最活跃的是LT-141A，EC50 为 6 µM，Emax 为 4.1 倍。该类似物不激活 G 蛋白偶联胆汁酸受体 TGR5 和代谢核受体类视黄醇 X 受体 α、肝脏 X 受体 α/β 和过氧化物酶体增殖物激活受体 β/γ。不同法尼醇 X
• Use of extracts and constituents of leontopodium as enhancers of cholinergic function
  申请人：Leopold-Franzens-Universität Innsbruck

  公开号：EP1792623A1

  公开（公告）日：2007-06-06

  The present invention relates to the use of a plant extract from at least one Leontopodium species for the preparation of a medicament for the treatment of diseases which can be modulated by the selective inhibition of the enzyme acetylcholinesterase and/or increase of acetylcholine concentration at the cholinergic synapse.

  本发明涉及使用至少一种Leontopodium物种的植物提取物制备药物，用于治疗可通过选择性抑制乙酰胆碱酯酶和/或增加胆碱能突触处的乙酰胆碱浓度来调节的疾病。
• LEOLIGIN-DERIVATE ALS GLATTMUSKELZELLEN-PROLIFERATIONSHEMMER
  申请人：Technische Universität Wien

  公开号：EP3160462A1

  公开（公告）日：2017-05-03
• PHARMACEUTICAL COMPOSITIONS COMPRISING LIGNANS AND THEIR DERIVATIVES FOR THE MEDICAL MANAGEMENT OF ANGIOGENESIS AND HYPOVASCULARITY
  申请人：Bernhard David

  公开号：US20130053438A1

  公开（公告）日：2013-02-28

  The present invention relates to a pharmaceutical composition for stimulating angiogenesis and/or the treatment or prevention of hypovascularity and/or the prevention and/or treatment of an angiogenic disorder/disease, whereby the composition comprises specific compounds which may be obtained from Leontopodium alpinum Cass, (Edelweiss). These compounds relate to lignan compounds as shown in herein disclosed formula I. A preferred compound in this context is leologin—IUPAC name [(2S,3R,4R)-4-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)tetxahydrofuran-3-yl]methyl (2Z)-2-methylbut-2-enoat], and even more particularly 5-methoxy-leoligin (IUPAC name: [(25,3R,4R)-4-(3,4-dimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3-yl]methyl-(2Z)-2-methylbut-2-enoat) and derivatives thereof. Corresponding means and methods in respect of medical uses of these compounds are described. The compounds provided herein may particularly be useful in the treatment of wound healing, in particular traumatic wounds (like, but not limited to surface and skin wounds), non-diabetic retinopathy, vascular obliteration. The compounds derived from Leontopodium alpinum Cass. (Edelweiss) as described herein are also useful in the re-vascularization of tissue after amputation as well during or after transplantation of tissues or organs. These compounds are also useful in the medical intervention of arterio- and veno-microvasculopathy of blood vessels, in particular retinal microvasculopathy, arterio- and veno-microangiopathy that preferably cannot be treated by surgery, in ischemic diseases or ischemic disorders or in the treatment or prevention of necrosis/necrotic events, in particular of ischemic diseases or necrosis/necrotic events that cannot be treated by surgery. These compounds may also be used in the treatment or prevention of stable angina abdominalis, vascular dementia, impotence or penile dysfunction and the like and they may be employed in the reactivation of necrotisising tissue or in the reactivation of hibernating tissue.