(+)-oleuropeic acid | 22155-73-3

• 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: (+)-oleuropeic acid
• 英文别名: (4R)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carboxylic acid
• CAS: 22155-73-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BFYWJELXORKNFO-QMMMGPOBSA-N

物化性质

• 沸点：
  319.6±25.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  undulatoside A 、 (+)-oleuropeic acid 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以56%的产率得到cypellocarpin C
  参考文献：
  名称：

  Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

  摘要：

  Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K-1 and K-2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.029
• 作为产物：
  描述：

  6-O-[(R)-oleuropeoyl]-1-O-[2-(1-hydroxy-4-oxocyclohexyl)ethyl]-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以0.6 mg的产率得到(+)-oleuropeic acid
  参考文献：
  名称：

  Quinoid glycosides from Forsythia suspensa

  摘要：

  Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded 10 compounds, including quinoid glycosides, lignan glycosides, phenylethanoid glycoside and allylbenzene glycoside together with 13 known ones. Their structures were established based on extensive spectroscopic data analyses, including IR, UV, HRESIMS, 1D NMR and 2D NMR. Absolute configurations were determined by ECD calculation method and chemical degradation. In addition, all compounds were evaluated for their antiviral activity against influenza A (H1N1) virus and several were further evaluated against respiratory syncytial virus (RSV) in vitro. Among them, two previously known compounds showed significant activities against RSV with EC50 values of 3.43 and 6.72 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.04.010

文献信息

• Eucalmaidins A−E, (+)-Oleuropeic Acid Derivatives from the Fresh Leaves of <i>Eucalyptus maideni</i>
  作者：Li-Wen Tian、Ying-Jun Zhang、Yi-Fei Wang、Chi-Choi Lai、Chong-Ren Yang

  DOI：10.1021/np900290s

  日期：2009.9.25

  (+)-oleuropeic acid derivatives, eucalmaidins A−E (1−5), together with 12 known compounds (6−17), were isolated from the fresh leaves of Eucalyptus maideni. Structures of the new compounds were determined on the basis of spectroscopic analyses (HSQC, HMBC, and 1H−1H COSY), chemical degradation, and enzymatic hydrolysis. Of the tested compounds, only quercetin showed slight anti-herpes simplex virus 1 (HSV-1) activity

  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。
• Biotransformation of α-terpineol by <i>Alternaria alternata</i>
  作者：Rui-Feng Mei、Ya-Xian Shi、Wei-He Duan、Hao Ding、Xiao-Ran Zhang、Le Cai、Zhong-Tao Ding

  DOI：10.1039/c9ra08042b

  日期：——

  α-Terpineol (1), the main volatile constituent in some traditional Chinese medicines, has been reported to be metabolized to 4R-oleuropeic acid by the larvae of common cutworms. The present study verified that α-terpineol could be converted to 4R-oleuropeic acid (2) and (1S,2R,4R)-p-menthane-1,2,8-triol (3) by Alternaria alternata fermentation. Using shortened fermentation times, 7-hydroxy-α-terpineol

  α-松油醇( 1 )是一些中药中的主要挥发性成分，据报道，地老虎幼虫将α-松油醇(1)代谢为4R-油橄榄酸。本研究证实α-萜品醇可以通过链格孢发酵转化为4R-橄榄酸( 2 )和( 1S , 2R , 4R )-p-薄荷烷-1,2,8-三醇( 3 ) 。通过缩短发酵时间，7-羟基-α-萜品醇（ 2a ）被鉴定为氧化中间体，这与之前研究提出的假设一致。细胞色素 P450 酶也被证实可以催化这种生物转化。这是首次通过微生物发酵生物转化α-萜品醇的研究。
• Elsholblanosides A−D, Four New Oleuropeic Acid Derivatives Isolated from <i>Elsholtzia blanda</i> and Their Inhibition of NO Production in LPS‐activated RAW264.7 Cells
  作者：Duong Thi Dung、Do Thi Trang、Pham Hai yen、Nguyen Huy Hoang、Bui Huu Tai、Phan Van Kiem

  DOI：10.1002/cbdv.202300785

  日期：2023.8

  afforded four new oleuropeic acid derivatives (1–4), named as elsholblanosides A−D, respectively, together with 11 known compounds (5–15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1–4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33 μM, compared

  香薷地上部分的植物化学调查。提供了四种新的橄榄酸衍生物 ( 1 – 4 )，分别命名为 elsholblanosides A−D，以及 11 种已知化合物 ( 5 – 15 )。它们的结构是根据 HR-ESI-MS、1D 和 2D NMR 以及 ECD 光谱的广泛分析确定的。化合物1-4和14在LPS激活的RAW264.7细胞中表现出中等程度的NO产生抑制作用，其IC 50值范围为23.2至86.33 μM ，而阳性对照化合物地塞米松的IC 50值为16.9 μM。
• 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.
• Quinoid glycosides from Forsythia suspensa
  作者：Chang Li、Yi Dai、Shu-Xiang Zhang、Ying-Hui Duan、Ming-Li Liu、Liu-Yuan Chen、Xin-Sheng Yao

  DOI：10.1016/j.phytochem.2014.04.010

  日期：2014.8

  Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded 10 compounds, including quinoid glycosides, lignan glycosides, phenylethanoid glycoside and allylbenzene glycoside together with 13 known ones. Their structures were established based on extensive spectroscopic data analyses, including IR, UV, HRESIMS, 1D NMR and 2D NMR. Absolute configurations were determined by ECD calculation method and chemical degradation. In addition, all compounds were evaluated for their antiviral activity against influenza A (H1N1) virus and several were further evaluated against respiratory syncytial virus (RSV) in vitro. Among them, two previously known compounds showed significant activities against RSV with EC50 values of 3.43 and 6.72 mu M. (C) 2014 Elsevier Ltd. All rights reserved.