demethyl oleuropein

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: demethyl oleuropein
• 英文别名: (4S,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
• 化学式: C₂₄H₃₀O₁₃
• 分子量: 526.494
• InChiKey: HKVGJQVJNQRJPO-LRPGRGPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  demethyl oleuropein 在 erbium(III) triflate 作用下， 生成 oleacein
  参考文献：
  名称：

  Hydrolases-mediated transformation of oleuropein into demethyloleuropein

  摘要：

  Phenolic compounds present in extra virgin olive oil have recently attracted considerable attention due to their pharmacological activities. Among them oleacein (3,4-DHPEA-EDA), structurally related to oleochantal (4HPEA-EDA), is one of the most studied. 3,4-DHPEA-EDA has been synthesized through decarboxylation of demethyloleuropein catalyzed by Er(OTf)(3). Demethyloleuropein is extracted from black olives drupes in very limited amounts and only in particular periods of the year. The availability of demethyloleuropein could be increased by a selective hydrolysis of the methyl ester moiety of oleuropein, a secoiridoid present in large amount in olive leaves. In this work we describe a new enzymatic method for carrying out a selective hydrolysis of oleuropein via the screening of a panel of hydrolases (lipases, esterases and proteases). Among all the enzymes tested the best results was obtained using alpha-chymotrypsyn from bovine pancreas as biocatalyst, thus revealing a classic example of catalytic enzyme promiscuity.

  DOI：

  10.1016/j.bioorg.2018.12.005
• 作为产物：
  描述：

  oleuropein 在 α-chymotrypsyn from bovine pancreas 作用下， 以 aq. phosphate buffer 为溶剂， 反应 72.0h， 以35%的产率得到demethyl oleuropein
  参考文献：
  名称：

  Hydrolases-mediated transformation of oleuropein into demethyloleuropein

  摘要：

  Phenolic compounds present in extra virgin olive oil have recently attracted considerable attention due to their pharmacological activities. Among them oleacein (3,4-DHPEA-EDA), structurally related to oleochantal (4HPEA-EDA), is one of the most studied. 3,4-DHPEA-EDA has been synthesized through decarboxylation of demethyloleuropein catalyzed by Er(OTf)(3). Demethyloleuropein is extracted from black olives drupes in very limited amounts and only in particular periods of the year. The availability of demethyloleuropein could be increased by a selective hydrolysis of the methyl ester moiety of oleuropein, a secoiridoid present in large amount in olive leaves. In this work we describe a new enzymatic method for carrying out a selective hydrolysis of oleuropein via the screening of a panel of hydrolases (lipases, esterases and proteases). Among all the enzymes tested the best results was obtained using alpha-chymotrypsyn from bovine pancreas as biocatalyst, thus revealing a classic example of catalytic enzyme promiscuity.

  DOI：

  10.1016/j.bioorg.2018.12.005

文献信息

• A METHOD FOR TREATING PETROLEUM OR NATURAL GAS
  申请人：Tesch, Rainer

  公开号：EP3339399A1

  公开（公告）日：2018-06-27

  A method for treating petroleum, petroleum fraction, or natural gas, the process comprising: adding a) a first component which is selected from material, particularly roots, of a plant of the genus Glycyrrhiza, and/or an arbuscular mycorrhizal fungi, and b) a second component which is selected from a plant material or -ingredient comprising plastids, algae and/or cyanobacteria, to the petroleum, petroleum fraction, or natural gas.

  一种处理石油、石油馏分或天然气的方法，该工艺包括 添加 a) 第一种成分，选自甘草属植物的材料，特别是根，和/或丛枝菌根真菌，以及 b) 第二种成分，选自植物材料或由质体、藻类和/或蓝藻组成的成分、 石油、石油馏分或天然气。
• Treatment and prevention of bone and joint disorders
  申请人：Summit Innovation Labs, LLC

  公开号：US11039636B2

  公开（公告）日：2021-06-22

  The invention encompasses compositions and methods for effectively treating and/or preventing the development and/or progression of osteoporosis and related disorders such as osteoarthritis and rheumatoid arthritis, and for promoting overall bone and joint health. This is accomplished by addressing multiple key mechanisms that lead to such disorders. The invention includes compositions comprising a combination of agents having biological activities that effectively suppress, regulate or interfere with the various key biochemical processes and mechanisms that increase the risk for development and/or progression of osteoporosis. The present compositions and methods simultaneously promote bone formation and reduce bone resorption by (a) stimulating osteoblast formation and osteogenesis; (b) suppressing adipocyte differentiation; (c) inhibiting osteoclast formation; and (d) increasing apoptosis of osteoclasts. The inventive compositions used for administration to human and other mammalian subjects having or at risk for development of osteoporosis comprise (1) at least one agent capable of modulating expression and/or activity of one or more of peroxisome activated protein receptor gamma (PPAR-γ), CAAT/enhancer binding protein-α (C/EBPα) and Sterol Regulatory Element-Binding Protein (SREBP-1); (2) at least one agent that activates expression and/or activity of one or more of the osteogenic transcription factors (Runx2/Cbfα1, Dlx5, Osterix, Msx2); (3) at least one agent that activates expression and/or activity of one or more of bone morphogenetic proteins (BMPs: BMP 2 and 4), alkaline phosphatase (ALP), and osteocalcin; (4) at least one agent capable of activating Wnt/β-catenin signaling pathway; (5) at least one agent that inhibits the activity of pro-oxidants including reactive nitrogen species and reactive oxygen species (ROS); (6) at least one agent that suppresses one or more of inflammatory mediators including interleukins IL-1α, IL-1β, IL-6, NF-κB, TNF-α, matrix metalloproteinases (MMPs) and prostaglandin E2 (PGE2); and (7) at least one agent that induces the expression of and/or activates one or more of adenosine monophosphate-activated protein kinase (AMPK), sirtuin (SIRT1) and adiponectin (AP).

  本发明包括用于有效治疗和/或预防骨质疏松症及骨关节炎和类风湿性关节炎等相关疾病的发展和/或恶化，以及促进整体骨骼和关节健康的组合物和方法。这是通过解决导致此类疾病的多种关键机制来实现的。本发明包括由多种制剂组合而成的组合物，这些制剂具有生物活性，可有效抑制、调节或干扰增加骨质疏松症发生和/或发展风险的各种关键生化过程和机制。本发明的组合物和方法通过(a)刺激成骨细胞形成和成骨；(b)抑制脂肪细胞分化；(c)抑制破骨细胞形成；(d)增加破骨细胞的凋亡，同时促进骨形成和减少骨吸收。本发明组合物用于对具有骨质疏松症或有骨质疏松症发病风险的人类和其他哺乳动物施用，包括 (1) 至少一种能够调节过氧化物酶体激活蛋白受体γ（PPAR-γ）、CAAT/增强子结合蛋白-α（C/EBPα）和甾醇调节元件结合蛋白（SREBP-1）中的一种或多种表达和/或活性的制剂；(2) 至少一种能激活一种或多种成骨转录因子（Runx2/Cbfα1、Dlx5、Osterix、Msx2）表达和/或活性的制剂； (3) 至少一种能激活一种或多种骨形态发生蛋白（BMPs：(4) 至少一种能激活 Wnt/β-catenin 信号通路的制剂；(5) 至少一种能抑制促氧化剂（包括活性氮和活性氧）活性的制剂；(6) 至少一种抑制一种或多种炎症介质的制剂，包括白细胞介素 IL-1α、IL-1β、IL-6、NF-κB、TNF-α、基质金属蛋白酶（MMPs）和前列腺素 E2（PGE2）；(7) 至少一种能诱导和/或激活单磷酸腺苷激活蛋白激酶（AMPK）、sirtuin（SIRT1）和脂联素（AP）中的一种或多种的表达的制剂。
• Treatment and prevention of diabetes and obesity
  申请人：Summit Innovation Labs, LLC

  公开号：US11357250B2

  公开（公告）日：2022-06-14

  The invention encompasses compositions and methods for effectively treating and/or preventing diabetes and/or obesity. This is accomplished by totally addressing the multiple mechanisms that lead to such conditions. The invention includes compositions comprising a combination of agents that effectively suppress, regulate or interfere with the various biochemical processes and mechanisms that lead to diabetes and obesity. The inventive compositions used for administration to human and other mammalian subjects comprise (1) at least one agent capable of modulating expression and/or activity of one or more of peroxisome activated protein receptor gamma (PPAR-γ), CAAT/enhancer binding protein-α (C/EBPα) and Sterol Regulatory Element-Binding Protein (SREBP-1); (2) at least one agent capable of activating Wnt/β-catenin pathway; (3) at least one agent capable of activating the adenosine monophosphate-activated protein kinase (AMPK) signaling pathway; (4) at least one agent that inhibits the activity of pro-oxidants including reactive nitrogen species and reactive oxygen species (ROS); (5) at least one agent that suppresses one or more of inflammatory mediators including interleukins IL-1α, IL-1β, IL-6, NF-κB, TNF-α, matrix metalloproteinases (MMPs) and prostaglandin E2 (PGE2); (6) at least one agent capable of enhancing glucose transporter (GLUT4) and/or inhibiting glucose transporter GLUT2; (7) at least one agent that induces the expression of and/or activates adiponectin and (8) at least one agent that induces the expression of and/or activates sirtuin (SIRT1). The active agents for use herein are natural materials such as phytonutrients, vitamins and minerals. Compositions with combinations of such natural agents have the ability to prevent, reduce or treat diabetes and obesity by (a) clearing glucose and fatty acids from blood, (b) reducing the number of adipose cells and fat storage, (c) interfering with fat, glucose, and cholesterol biosynthesis, and (d) promoting fat and glucose oxidation. Since the present compositions are aimed toward normalizing metabolism and energy expenditure and managing oxidative stress and inflammation, they are also beneficial in relation to physical activity, in particular performance, endurance, fatigue and recovery during intensive and continuous exercise/exertion.

  本发明包括有效治疗和/或预防糖尿病和/或肥胖症的组合物和方法。这是通过彻底解决导致此类病症的多种机制来实现的。本发明包括由多种制剂组合而成的组合物，这些制剂能有效抑制、调节或干扰导致糖尿病和肥胖症的各种生化过程和机制。用于给人类和其他哺乳动物施用的本发明组合物包括：(1) 至少一种能够调节过氧化物酶活化蛋白受体γ（PPAR-γ）、CAAT/增强子结合蛋白-α（C/EBPα）和甾醇调节元件结合蛋白（SREBP-1）中一种或多种的表达和/或活性的制剂；(2) 至少一种能激活 Wnt/β-catenin 通路的制剂； (3) 至少一种能激活单磷酸腺苷激活蛋白激酶（AMPK）信号通路的制剂；(4) 至少一种能抑制促氧化剂活性的制剂，包括活性氮和活性氧（ROS）； (5) 至少一种能抑制一种或多种炎症介质的制剂，包括白细胞介素 IL-1α、IL-1β、IL-6、NF-κB、TNF-α、基质金属蛋白酶（MMPs）和前列腺素 E2（PGE2）；(6) 至少一种能增强葡萄糖转运体（GLUT4）和/或抑制葡萄糖转运体 GLUT2 的制剂； (7) 至少一种能诱导脂肪连素表达和/或激活脂肪连素的制剂；以及 (8) 至少一种能诱导 sirtuin（SIRT1）表达和/或激活 sirtuin（SIRT1）的制剂。本文使用的活性剂是天然材料，如植物营养素、维生素和矿物质。含有此类天然制剂组合的复合物能够通过以下方式预防、减少或治疗糖尿病和肥胖症：(a) 清除血液中的葡萄糖和脂肪酸；(b) 减少脂肪细胞的数量和脂肪储存；(c) 干扰脂肪、葡萄糖和胆固醇的生物合成；(d) 促进脂肪和葡萄糖的氧化。 由于目前的组合物旨在使新陈代谢和能量消耗正常化，并控制氧化应激和炎症，因此它们也有益于体育活动，特别是在高强度和持续运动/剧烈运动期间的表现、耐力、疲劳和恢复。
• USE OF OLEUROPEIN AND DERIVATIVES IN THE TREATMENT OF TYPE 2 DIABETES MELLITUS AND PATHOLOGIES ASSOCIATED WITH PROTEIN AGGREGATION PHENOMENA
  申请人：Universita' Degli Studi di Firenze

  公开号：EP2285388B1

  公开（公告）日：2014-03-26
• COMPOSITIONS COMPRISING OLEUROPEINS AND FLAVANOIDS AND THEIR USE
  申请人：Phyto Innovative Products Ltd

  公开号：EP2635120A1

  公开（公告）日：2013-09-11