(R)-methyl oleuropeic acid methyl ester

• 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: (R)-methyl oleuropeic acid methyl ester
• 英文别名: (+)-(R)-oleuropeic acid methyl ester；(+)-(R)-oleuropeic acid methylester；(+)-oleuropeic acid methyl ester；methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carboxylate
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: HOXYDQOHVVZOJV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  eucalmaidin B 、 sodium methylate 以 甲醇 为溶剂， 反应 12.0h， 生成 (R)-methyl oleuropeic acid methyl ester
  参考文献：
  名称：

  来自麦加桉树新鲜叶子的真花青素A-E，（+）-油酸衍生物

  摘要：

  五个新的（+） - oleuropeic酸衍生物，eucalmaidins A-E（1 - 5），加上12种已知化合物（6 - 17），从新鲜叶中分离直杆蓝桉。在光谱分析（HSQC，HMBC和1 H- 1 H COSY），化学降解和酶水解的基础上确定了新化合物的结构。在测试的化合物中，只有槲皮素在体外显示出轻微的抗单纯疱疹病毒1（HSV-1）活性。

  DOI：

  10.1021/np900290s

文献信息

• New Acylated Phenolic Glycosides with ROS-Scavenging Activity from <i>Psidium guajava</i> Leaves
  作者：Yuanyuan Li、Dongli Li、Qi An、Hang Ma、Yu Mu、Wenjun Qiao、Zengguang Zhang、Jingsheng Zhang、Xueshi Huang、Liya Li

  DOI：10.1021/acs.jafc.9b04318

  日期：2019.10.9

  functional foods against multiple chronic metabolism disorders. In the course of finding novel polyphenols with antioxidative activities from guava leaf, 11 acylated phenolic glycosides (1–11), including 5 new oleuropeic acid-conjugated phenolic glycosides, named guajanosides A–E (1, 2, and 5–7), along with 17 known meroterpenoides (12–28), were isolated and identified. Their structures were determined by

  据报道，活性氧和随后的氧化应激在慢性代谢疾病中起重要作用。植物来源的多酚，尤其是食物来源的酚类，由于其潜在的抗氧化应激相关疾病的用途而备受关注。的叶番石榴（被称为番石榴）被认为是多酚的一个很好的资源，其产品在日本市售抗多种慢性代谢紊乱的功能性食品。在寻找新的多酚与来自番石榴叶抗氧化活性的过程中，11酰化酚苷（1 - 11），包括5个新oleuropeic酸缀合酚苷，名为guajanosides A-E（1，2，和5 – 7），以及17种已知的甲氧萜类化合物（12 – 28）被分离出来并被鉴定出来。通过光谱数据分析，化学降解和酸水解来确定它们的结构。化合物1，2，和5 - 11中显示强效的活性氧物质清除活性脂多糖刺激的RAW 264.7巨噬细胞。免疫印迹表明化合物6显着增加了核因子-类胡萝卜素2相关因子2（Nrf2），NAD（P）H醌脱氢酶1（NQO1）和谷氨酸-半胱氨酸连接酶催化亚基的表达
• Pheonolic Compounds from the Fruits of Viburnum sargentii Koehne
  作者：Yang Xie、Jing Wang、Yan-Mei Geng、Zhi Zhang、Yan-Fei Qu、Guang-Shu Wang

  DOI：10.3390/molecules200814377

  日期：——

  Seven phenolic compounds were isolated from the fruits of Viburnum sargentii Koehne by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as (−)-Epicatechin (1), 5,7,4′-trihydroxy-flavonoid-8-C-β-D-glucopyranoside (2), 1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-α-L-rhamnopyranoxypropyl)-2-methoxyphenoxy]-1,3-propane-diol (erythro) (3), 1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-α-L-rhamnopyranoxypropyl)-2-methoxyphenoxy]-1,3-propanediol (threo) (4), (R)-4-hydroxylphenol O-(6-O-oleuropeoyl)-β-D-glucopyranoside (5), (R)-3-methoxy-4-hydroxylphenol O-(6-O-oleuropeoyl)-β-D-glucopyranoside (6), quercetin-3-O-rutinoside (7). Compounds 5 and 6 are new monoterpene phenolic glycosides, compounds 1, 3 and 4 were isolated from the Viburnum genus for the first time, and compounds 2 and 7 from the Viburnum sargentii Koehne for the first time. Compounds 1–7 were also assayed for their antioxidant activities with DPPH free radicals.

  采用硅胶柱色谱和制备型高效液相色谱法从Viburnum sargentii Koehne果实中分离得到7种酚类化合物。根据化学和光谱方法，其结构被鉴定为(−)-表儿茶素(1)、5,7,4′-三羟基-黄酮-8-C-β-D-吡喃葡萄糖苷(2)、1-( 4-羟基-3-甲氧基苯基)-2-[4-(3-α-L-鼠李吡喃氧基丙基)-2-甲氧基苯氧基]-1,3-丙二醇(赤式)(3), 1-(4-羟基- 3-甲氧基苯基)-2-[4-(3-α-L-鼠李吡喃氧基丙基)-2-甲氧基苯氧基]-1,3-丙二醇(苏式)(4),(R)-4-羟基苯酚O-(6-O -橄榄酰基)-β-D-吡喃葡萄糖苷 (5)、(R)-3-甲氧基-4-羟基苯酚 O-(6-O-橄榄酰基)-β-D-吡喃葡萄糖苷 (6)、槲皮素-3-O-芸香苷（7）。化合物5和6为新的单萜酚苷，化合物1、3和4为首次从荚莲属植物中分离得到，化合物2和7为首次从荚莲属植物中分离得到。还利用 DPPH 自由基测定了化合物 1-7 的抗氧化活性。
• Cypellocarpins A−C, Phenol Glycosides Esterified with Oleuropeic Acid, from <i>Eucalyptus cypellocarpa</i>
  作者：Hideyuki Ito、Mayuko Koreishi、Harukuni Tokuda、Hoyoku Nishino、Takashi Yoshida

  DOI：10.1021/np0001981

  日期：2000.9.1

  Three new phenol glycosides acylated with (+)-oleuropeic acid, cypellocarpins A (1), B (2), and C (3), along with seven known compounds, were isolated from the dried leaves of Eucalyptus cypellocarpa. Structures of the new compounds were determined on the basis of spectroscopic methods, including 2D NMR experiments and chemical degradation. These new compounds and a known related glucoside (7) showed

  从桉树干燥后的干叶中分离出三种新的被（+）-油酸酸酰化的苯酚糖苷，cycarpellocarpins A（1），B（2）和C（3），以及七个已知化合物。根据光谱方法，包括2D NMR实验和化学降解，确定了新化合物的结构。这些新化合物和已知的相关葡萄糖苷（7）在短期生物测定中显示出强大的体外抗肿瘤促进活性，评估了12-O-十四烷酰佛波醇13-乙酸酯（TPA）对爱泼斯坦-巴尔病毒早期抗原激活的抑制作用）。这些化合物还抑制一氧化氮和TPA在小鼠皮肤上引起的体内两阶段癌变。
• Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus
  作者：Tatsuya Hasegawa、Fumihide Takano、Takanobu Takata、Masato Niiyama、Tomihisa Ohta

  DOI：10.1016/j.phytochem.2007.08.030

  日期：2008.2

  Two monoterpene glycosides, conjugated with gallic acid [globulusin A (1) and B (2)], together with four known compounds, cypellocarpin A (3), eucaglobulin (4), cuniloside (5) and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranoside (6), were isolated from hot-water extracts of the leaves of Eucalyptus globulus. The structures of compounds 1 and 2 were determined by 1D, 2D NMR and MS spectroscopic analyses. The absolute stereochemistry of 1 was determined by correlating the spectroscopic data with those of synthetic compound 6 with a known configuration. Globulusin A (1) and B (2), cypellocarpin A (3) and eucaglobulin (4), scavenged DPPH free radicals and globulusin A (1) showed a higher antioxidant activity than the other tested compounds, with an IC(50) of 3.8 mu M. Globulusin A (1) and eucaglobulin (4) concentration-dependently suppressed inflammatory cytokine production, tumor-necrosis factor-alpha and interleukin-1 beta in cultured human mycloma THP-1 cells co-stimulated with phorbol myristate acetate. These compounds also inhibited melanogenesis in cultured murine melanoma B16F1 cells, without any significant cytotoxicity. These results suggested that globulusin A (1) and eucaglobulin (4), which were isolated as antioxidants from E globulus, also had anti-inflammatory as well as anti-melanogenesis activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Non-volatile components of the essential oil secretory cavities of Eucalyptus leaves: Discovery of two glucose monoterpene esters, cuniloside B and froggattiside A
  作者：Jason Q.D. Goodger、Benjamin Cao、Inneke Jayadi、Spencer J. Williams、Ian E. Woodrow

  DOI：10.1016/j.phytochem.2009.06.004

  日期：2009.6

  The essential oils extracted from the embedded foliar secretory cavities of many Eucalyptus species are of economic value as pharmaceuticals and fragrance additives. Recent studies have indicated that Eucalyptus secretory cavities may not be exclusively involved in the biosynthesis and storage of essential oils. Therefore, we selected three species upon which to perform an examination of the contents of foliar secretory cavities: Eucalyptus froggattii, E. polybractea and E. globulus. This paper describes the isolation and structural characterization of two non-volatile glucose monoterpene esters, which we have named cuniloside B and froggattiside A, from within the secretory cavities of these species, and shows the presence of these compounds in solvent extracts of the leaves from two other species of Eucalyptus. Both compounds were found in high proportions relative to the essential oils extracted from the leaves. We propose that many other carbohydrate monoterpene esters previously isolated from bulk leaf extracts of various Eucalyptus species may also be localized within the non-volatile fraction of foliar secretory cavities. (C) 2009 Elsevier Ltd. All rights reserved.