demethyloleuropein | 52077-55-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: demethyloleuropein
• 英文别名: oleuropein；(4S,5E,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
• CAS: 52077-55-1
• 化学式: C₂₄H₃₀O₁₃
• 分子量: 526.494
• InChiKey: HKVGJQVJNQRJPO-VTDDDATNSA-N

物化性质

• 沸点：
  803.9±65.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

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：

  demethyloleuropein 在 重水 、 erbium(III) triflate 作用下， 反应 4.0h， 生成 3,4-DHPEA-EDA-D₂
  参考文献：
  名称：

  Biomimetic synthesis and antioxidant evaluation of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate]

  摘要：

  Phenolic compounds present in extra virgin olive oil have attracted considerable recent attention. Many of them, show specific anti-inflammatory and anti-tumor activities. In this work we describe the biomimetic synthesis of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate], starting from natural demethyloleuropein present in olive tissues. A comparison between 3,4-DHPEA-EDA (6) and oleuropein (1), oleuropein aglycone (4) and hydroxytyrosol ORAC(FL) values was undertaken. Published by Elsevier Ltd.

  DOI：

  10.1016/j.foodchem.2014.04.015
• 作为产物：
  描述：

  橄榄苦甙 在 吡啶 、 4-二甲氨基吡啶 、 水 、 一水合肼 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 demethyloleuropein
  参考文献：
  名称：

  [EN] PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES
  [FR] PROCÉDÉ DE PRODUCTION D'OLÉOCANTHAL, D'OLÉACEINE ET DE LEURS ANALOGUES

  摘要：

  根据公式(I)，从欧洲橄榄叶苷开始生产化合物的方法，例如欧力坎醇或欧力酮。该方法提供了欧力坎醇、欧力酮及其类似物所需立体化学结构的二醛核心。此外，通过在酯化步骤中改变醇基的结构，该方法可用于生产大量结构多样的产物。

  公开号：

  WO2021121925A1

文献信息

• Absolute Method for the Assay of Oleuropein in Olive Oils by Atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry
  作者：Antonio De Nino、Leonardo Di Donna、Fabio Mazzotti、Enzo Muzzalupo、Enzo Perri、Giovanni Sindona、Antonio Tagarelli

  DOI：10.1021/ac050545h

  日期：2005.9.1

  Oleuropein (OLP, 1), the active ingredient present (i) in food integrators extracted from olive leaves, (ii) in table olives, and (iii) in extra virgin olive oils is a nutraceutical whose health benefits have been widely documented. A new analytical method for its assay, which is based on the utilization of atmospheric pressure chemical ionization tandem mass spectrometry and on the use of a synthetic labeled analogue, the 4-trideuteriocarboxyoleuropein (2), as an internal standard, is presented. The results obtained with extra virgin olive oils from different cultivars and different Italian regions are discussed.

  橄榄苦苷（OLP，1），作为一种活性成分，存在于（i）从橄榄叶中提取的食品补充剂，（ii）餐桌橄榄，以及（iii）特级初榨橄榄油中，是一种健康营养品，其健康益处已被广泛记录。本文提出了一种新颖的分析方法，用于检验橄榄苦苷，该方法基于大气压化学电离串联质谱的应用，以及使用合成标记类比物4-三氘羧基橄榄苦苷（2）作为内标。本研究讨论了来自不同品种和不同意大利地区的特级初榨橄榄油所获得的结果。
• ANALOGUES OF OLEUROPEIN AND OLEACEIN AND USES THEREOF
  申请人：Attica Sciences Ltd.

  公开号：US20220110962A1

  公开（公告）日：2022-04-14

  Analogues of oleuropein and oleacein and pharmaceutically acceptable salts thereof and processes for the preparation of these compounds are disclosed. The invention further relates to use of oleuropein and oleacein analogues for the treatment of inflammatory disorders, cardiometabolic disorders, and cancer.

  本发明公开了欧洲橄榄苦苷和欧洲橄榄苦酸及其药学上可接受的盐的类似物，以及制备这些化合物的方法。本发明还涉及使用欧洲橄榄苦苷和欧洲橄榄苦酸类似物治疗炎症性疾病、心脏代谢性疾病和癌症的方法。
• 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。
• Cytomimetic formulations and methods of manufacturing the same
  申请人：MITANI GROUP, INC.

  公开号：US10342757B2

  公开（公告）日：2019-07-09

  A cytomimetic formulation is provided comprising at least two of: (a) a fermented truffle extract; (b) a plurality of hyaluronic acids of different molecular weight, ranging from 50 KDa up to 2000 KDa; (c) an olive leaf extract in a mineral-containing water; and (d) a fermented grape must. The formulations mimic the skin cytoplasmic environment and create optimal conditions for cellular growth and skin rejuvenation. Methods of use and processes for manufacturing thereof are also provided.

  本发明提供了一种细胞模拟配方，至少包含以下两种成分：(a) 发酵松露提取物；(b) 不同分子量的多种透明质酸，分子量从 50 KDa 到 2000 KDa 不等；(c) 含矿物质水中的橄榄叶提取物；(d) 发酵葡萄汁。这些制剂模拟皮肤细胞质环境，为细胞生长和皮肤年轻化创造最佳条件。此外，还提供了使用方法及其制造工艺。
• 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。