咖啡酸苯乙酯 | 104594-70-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 咖啡酸苯乙酯
• 中文别名: 咖啡酸β-苯乙醇酯；3,4-二羟基-反式-肉桂酸苯乙酯；2-苯乙基-3-(3,4-二羟苯基)-2-丙烯酸酯
• 英文名称: caffeic acid phenethylester
• 英文别名: CAPE；caffeic acid phenylethyl ester；phenethyl caffeate；phenylethyl caffeate；3,4-dihydroxycinnamic acid phenethyl ester；2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 104594-70-9
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: SWUARLUWKZWEBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129℃
• 沸点：
  498.6±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)
• 溶解度：
  溶于乙酸乙酯，浓度为50mg/ml。溶于DMSO和乙醇。
• 最大波长(λmax)：
  323nm(lit.)
• LogP：
  3.734 (est)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918290000
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  UD3334375
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封储存，存放在阴凉干燥的库房中。最佳冷藏温度为-20°C。

SDS

Phenethyl Caffeate Revision number: 5.3
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Phenethyl Caffeate

Revision number: 5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Phenethyl Caffeate
Percent: >98.0%(HPLC)
CAS Number: 104594-70-9
Synonyms: Caffeic Acid Phenethyl Ester , Phenethyl 3,4-Dihydroxycinnamate , 3,4-
Dihydroxycinnamic Acid Phenethyl Ester , CAPE
Chemical Formula: C17H16O4
Phenethyl Caffeate

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a freezer.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
White - Pale yellow
Colour:
Phenethyl Caffeate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Odour: No data available
pH: No data available
Melting point/freezing point:129°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: dni-hmn-hla 5 umol/L
dnd-hmn-lym 0.5 umol/L/18H
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available
RTECS Number: UD3334375

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Phenethyl Caffeate

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Section 14. TRANSPORT INFORMATION
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

咖啡酸苯乙酯（CPAE）是蜂胶的主要活性组分之一，对疱疹病毒具有抑制效果。蜂胶中其他被抑制的病毒包括腺病毒和流感病毒。

蜂胶中的CAPE、槲皮素、异戊二烯酯、鼠李素、高良素以及甙类、多糖类等物质均具有抗癌活性，能够抑制肿瘤细胞增生，并对癌细胞产生一定的毒杀作用。特别是CAPE 对肿瘤细胞有特定的杀伤力，Jeng等人认为它参与了诱导自然细胞死亡的过程，并对恶性病变组织具有细胞毒性作用。微量的CAPE 就可以改善由肿瘤因子 (12-0-十四酰拂波醇-13-乙酸酯) 引起的炎症反应。

咖啡酸苯乙酯结构中含有儿茶酚基团，为清除自由基提供了一种常见模式，并且有两个邻位酚羟基使苯环上的电子密度增加，容易自动氧化而呈色。不同地区蜂胶的化学成分有所差异，因此CAPE 的含量也有所不同。研究表明，产自中国的蜂胶中CAPE 含量较高，达到 15～25 mg/g；而巴西蜂胶则不含CAPE。

实验室通过以咖啡酸和β-溴乙基苯为原料，并使用磷酸钾作为催化剂合成咖啡酸苯乙酯，其产率可达60%。以上信息由Chemicalbook编辑整理。

生物活性

咖啡酸苯乙酯（CAFE）是一种强效的特异性NF-κB 活化抑制剂，能够表现出抗氧化、免疫调节和抗炎活动。

靶点

Target	Value
NF-κB

体外研究

咖啡酸苯乙酯可通过抑制p65的入核转运来抑制佛波酯、神经酰胺、强心酸过氧化氢等诱导的NF-kB 激活。在多种肿瘤细胞系中，它表现出抗增殖活性，对26-L5、B16-BL6恶性瘤、人类HT-1080的EC50分别为 1.76 μM、3.16 μM 和13.7 μM、44.0 μM。此外，它通过抑制ROS 形成和半胱氨酸天冬氨酸蛋白酶活性发挥抗凋亡作用，并通过抑制NF-kB信号通路来减弱LPS诱导的炎症反应及HSCs细胞对细胞因子的敏感性。

体内研究

在C57BL/6 和 BALB/c 小鼠中，腹腔内注射10毫克/千克咖啡酸苯乙酯能够抑制肺细胞癌、结肠癌和黑色素瘤的增长以及肿瘤血管新生。动物体内（5, 10, 20 mg/kg）的咖啡酸苯乙酯通过减少胸腺重量及胸腺和脾脏的孔性而具有免疫调节作用。

用途

1. 抗氧化作用
2. 抗炎作用
3. 抗肿瘤作用

用于含量测定、鉴定以及药理实验等。

反应信息

• 作为反应物：
  描述：

  咖啡酸苯乙酯 在 bis(acetylacetonato)manganese(II) 、 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以51%的产率得到bis(2-phenylethyl) 6,9,10-trihydroxybenzo[kl]xanthene-1,2-dicarboxylate
  参考文献：
  名称：

  自然和“???非自然”的仿生合成???? 由咖啡酸酯的氧化偶联产生的木脂素

  摘要：

  金属介导的咖啡酸酯氧化偶联已被用于二聚木脂素和新木脂素的仿生合成。苯乙酯和咖啡酸甲酯用作底物，MnO2、Mn(OAc)3 和Ag2O 用作氧化偶联剂。锰介导的反应产生了不寻常的苯并 [kl] 呫吨木脂素 6 和 15 作为主要产物，伴随着少量的芳基二氢萘木脂素 (±)-7 和 (±)-16。当使用 Ag2O 时，新木脂素 (±)-17 是主要产物。这种仿生途径也用于获得天然苯并[kl]呫吨木脂素rufescidride (9) 和mongolicumin A (10)。还进行了偶联反应的计算研究。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900804
• 作为产物：
  描述：

  咖啡酸 在 氯化亚砜 、 盐酸胍 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 咖啡酸苯乙酯
  参考文献：
  名称：

  咖啡酸苯乙酯及其相关丙酸、乙酸和苯甲酸类似物的合成和抗自由基/抗氧化活性。

  摘要：

  咖啡酸苯乙酯 (CAPE) 是一种从蜂胶中分离出来的生物活性成分。合成了一系列 CAPE 类似物并分析了它们的抗自由基/抗氧化作用。双键和共轭体系的存在对抗氧化作用的影响用从3-(3,4-二羟基苯基)丙酸获得的类似物进行评价。那些从 2-(3,4-二羟基苯基) 乙酸和 3,4-二羟基苯甲酸获得的物质可以评估羰基和芳族体系之间存在两个碳的影响。

  DOI：

  10.3390/molecules171214637

文献信息

• Structure–activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties
  作者：Riho Taguchi、Koki Hatayama、Tomohito Takahashi、Takafumi Hayashi、Yuki Sato、Daisuke Sato、Kiminori Ohta、Hiroto Nakano、Chigusa Seki、Yasuyuki Endo、Kiyotaka Tokuraku、Koji Uwai

  DOI：10.1016/j.ejmech.2017.07.026

  日期：2017.9

  disease. Rosmarinic acid, which is one of the main aggregation inhibitors derived from Lamiaceae, was employed as a lead compound and its 25 derivatives were synthesized. In this study, the structure–activity relations of rosmarinic acid derivatives for the amyloid-β aggregation inhibitory effect (MSHTS assay), antioxidant properties, and xanthine oxidase inhibition were evaluated. Among the tested compounds

  淀粉样β聚集抑制剂有望成为阿尔茨海默氏病的治疗剂或预防剂。迷迭香酸是衍生自唇形科的主要聚集抑制剂之一，被用作前导化合物，并合成了其25种衍生物。在这项研究中，评价了迷迭香酸衍生物对淀粉样β聚集抑制作用（MSHTS分析），抗氧化剂特性和黄嘌呤氧化酶抑制的构效关系。在测试的化合物中，化合物16d和19被发现是最有效的淀粉样蛋白聚集抑制剂。SAR揭示了在分子的一侧存在酚羟基的必要性以及整个分子的亲脂性。这些结构特性的重要性也受到对接模拟的支持。
• Caffeic Acid Esters Are Effective Bactericidal Compounds Against Paenibacillus larvae by Altering Intracellular Oxidant and Antioxidant Levels
  作者：William Collins、Noah Lowen、David J. Blake

  DOI：10.3390/biom9080312

  日期：——

  activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 µg/mL when used individually, and a MIC and MBC of 31.25 µg/mL for each compound

  American Foulbrood（AFB）是一种致命的细菌性疾病，会影响and和幼虫蜜蜂。AFB是由形成内生孢子的幼虫Paenibacillus幼虫（PL）引起的。蜂胶含有多种有机化合物，是蜜蜂觅食的产物，是一种主要来自树木中植物性植物的树脂物质。蜂胶中常见的几种咖啡酸酯类化合物已显示出对PL的抗菌活性。在这项研究中，合成，纯化，光谱分析六种不同的咖啡酸酯，并测试它们对PL的活性，以确定最小抑菌浓度（MIC）和最小杀菌浓度（MBC）。咖啡酸异丙烯基酯（CAIE），咖啡酸苄基酯（CABE），单独使用的MIC和MBC为125 µg / mL，而咖啡酸苯乙酯（CAPE）则最能有效抑制PL生长并杀死PL细胞，当使用CAIE时，每种化合物的MIC和MBC分别为31.25 µg / mL CABE和CAPE结合使用可防止PL。这些化合物通过杀菌作用抑制细菌的生长，这种作用显示出细胞被杀死，但在18
• Inhibitory Effects of Caffeic Acid Ester Analogues on Free Radicals and Human Liver Microsome CYP1A2 Activities
  作者：Churdsak Jaikang、Chaiyavat Chaiyasut、Paitoon Narongchai、Kanokporn Niwatananun、Siripun Narongchai、Winthana Kusirisin

  DOI：10.2174/157340611794859316

  日期：2011.3.1

  Ethyl caffeate (EC), octyl caffeate(OC), benzyl caffeate(BC) and phenethyl caffeate(PC) were synthesized and evaluated for scavenging of superoxide anion, nitric oxide radical and 1,1-diphenyl-1-picrylhydrazyl radical(DPPH). Antioxidant activity was investigated with reducing power method. Pooled human liver microsome was used for investigating the effects on cytochrome P450 1A2 (CYP1A2) catalytic activities by using phenacetin as a substrate. Dixon and Cornish- Bowden plots were used for enzyme kinetic analysis. The EC, OC, BC and PC potentially inhibited superoxide anion, nitric oxide and DPPH radicals. IC50 values of superoxide anion scavenging of EC, OC, BC and PC were 16.42, 79.83, 123.69 and 123.69 μg/ml, respectively. EC was more potent than OC and BC in terms of nitric oxide radical scavenger: IC50 values of EC, OC and BC were 24.16, 37.34 and 52.64 μg/ml, respectively. In addition, the IC50 values of EC, OC, BC and PC on DPPH radical scavenging were 70.00, 184.56, 285.34 and 866.54 μg/ ml, respectively. The IC50 values of EC, OC, BC and PC on phenacetin O-deethylation were 124.98, 111.86, 156.68 and 31.05 μg/ml, respectively. Enzyme kinetics showed that the type of inhibition mechanism was mixed-type. The result of this study shows that caffeic acid ester analogues potentially scavenge free radicals and inhibit catalytic activity of CYP1A2. This may lead to important implications in the prevention of CYP1A2-mediated chemical carcinogenesis.

  合成了乙基咖啡酸酯（EC）、辛基咖啡酸酯（OC）、苄基咖啡酸酯（BC）和苯乙基咖啡酸酯（PC），并评估了它们对超氧阴离子、氮氧自由基和1,1-二苯基-1-苦味唑自由基（DPPH）的清除能力。采用还原力法研究抗氧化活性。使用人类肝微粒体进行研究，以探讨对细胞色素P450 1A2（CYP1A2）催化活性的影响，使用对乙酰氨基酚作为底物。采用Dixon和Cornish-Bowden绘图法进行酶动力学分析。结果表明，EC、OC、BC和PC对超氧阴离子、氮氧和DPPH自由基具有潜在的抑制作用。EC、OC、BC和PC对超氧阴离子清除的IC50值分别为16.42、79.83、123.69和123.69 μg/ml。在氮氧自由基清除方面，EC的活性优于OC和BC，其IC50值分别为24.16、37.34和52.64 μg/ml。此外，EC、OC、BC和PC对DPPH自由基清除的IC50值分别为70.00、184.56、285.34和866.54 μg/ml。EC、OC、BC和PC对对乙酰氨基酚O-去乙基化的IC50值分别为124.98、111.86、156.68和31.05 μg/ml。酶动力学分析表明抑制机制为混合型抑制。该研究结果表明，咖啡酸酯类类化合物可能对自由基具有清除作用，并抑制CYP1A2的催化活性。这可能对预防CYP1A2介导的化学致癌有重要意义。
• Protective Effect of Caffeic Acid Derivatives on tert-Butyl Hydroperoxide-Induced Oxidative Hepato-Toxicity and Mitochondrial Dysfunction in HepG2 Cells
  作者：Tzung-Hsun Tsai、Chun-Hsien Yu、Yu-Ping Chang、Yu-Ting Lin、Ching-Jang Huang、Yueh-Hsiung Kuo、Po-Jung Tsai

  DOI：10.3390/molecules22050702

  日期：——

  Oxidative stress results in structural and functional abnormalities in the liver and is thought to be a crucial factor in liver diseases. The aim of this study was to investigate the cytoprotective and antioxidant effects of caffeic acid (CA) derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative stress in HepG2 cells. Nine CA derivatives were synthesized, including N-phenylethyl caffeamide (PECA), N-(3-florophen)methyl caffeamide (FMCA), N-(4-methoxy-phen)methyl caffeamide (MPMCA), N-heptyl caffeamide (HCA), N-octyl caffeamide (OCA), octyl caffeate (CAOE), phenpropyl caffeate (CAPPE), phenethyl caffeate (CAPE), and phenmethyl caffeate (CAPME). The results showed that CA and its derivatives significantly inhibited t-BHP-induced cell death of HepG2 cells. The rank order of potency of the CA derivatives for cytoprotection was CAOE > HCA > OCA > FMCA > CAPPE > CAPME > CAPE > PECA > MPMCA > CA. Their cytoprotective activity was associated with lipophilicity. The antioxidant effect of these compounds was supported by the reduction in the levels of thiobarbituric acid reactive substrates, a biomarker of lipid peroxidation, in HepG2 cells. Pre-treatment of CA derivatives significantly prevented the depletion of glutathione, the most important water-soluble antioxidant in hepatocytes. Pre-treatment of CA derivatives before t-BHP exposure maintained mitochondrial oxygen consumption rate and ATP content in the injured HepG2 cells. CA derivatives except OCA and HCA significantly suppressed t-BHP-induced hypoxia-inducible factor-1α (HIF-1α) protein level. In addition, all of these CA derivatives markedly increased the nuclear factor erythroid 2-related factor 2 (Nrf2) accumulation in the nucleus, indicating that their cytoprotection may be mediated by the activation of Nrf2. Our results suggest that CA derivatives might be a hepatoprotective agent against oxidative stress.

  氧化应激导致肝脏结构和功能异常，被认为是肝脏疾病的一个关键因素。本研究的目的是探讨咖啡酸（CA）衍生物在特丁基过氧化氢（t-BHP）诱导的肝HepG2细胞氧化应激中的细胞保护和抗氧化作用。合成了九种CA衍生物，包括N-苯乙基咖啡酰胺（PECA）、N-(3-氟苯)甲基咖啡酰胺（FMCA）、N-(4-甲氧基苯)甲基咖啡酰胺（MPMCA）、N-庚基咖啡酰胺（HCA）、N-辛基咖啡酰胺（OCA）、辛基咖啡酸酯（CAOE）、苯丙基咖啡酸酯（CAPPE）、苯乙基咖啡酸酯（CAPE）和苯甲基咖啡酸酯（CAPME）。结果显示，CA及其衍生物显著抑制了t-BHP诱导的HepG2细胞死亡。CA衍生物的细胞保护效力的排列顺序为CAOE > HCA > OCA > FMCA > CAPPE > CAPME > CAPE > PECA > MPMCA > CA。它们的细胞保护活性与脂溶性相关。这些化合物的抗氧化效果得到了支持，因为它们降低了HepG2细胞中硫代巴比妥酸反应底物的水平，这是脂质过氧化的生物标志物。CA衍生物的预处理显著防止了谷胱甘肽的耗竭，谷胱甘肽是肝细胞中最重要的水溶性抗氧化剂。CA衍生物在t-BHP暴露前的预处理保持了受损HepG2细胞的线粒体氧气消耗率和ATP含量。除OCA和HCA外，CA衍生物显著抑制了t-BHP诱导的缺氧诱导因子-1α（HIF-1α）蛋白水平。此外，所有这些CA衍生物显著增加了核因子红细胞2相关因子2（Nrf2）在细胞核中的积累，表明它们的细胞保护可能是通过激活Nrf2介导的。我们的结果表明，CA衍生物可能是对抗氧化应激的肝保护剂。
• Novel benzoxanthene lignans that favorably modulate lipid mediator biosynthesis: A promising pharmacological strategy for anti-inflammatory therapy
  作者：Jana Gerstmeier、Christian Kretzer、Simone Di Micco、Laura Miek、Hannah Butschek、Vincenza Cantone、Rossella Bilancia、Roberta Rizza、Fabiana Troisi、Nunzio Cardullo、Corrado Tringali、Armando Ialenti、Antonietta Rossi、Giuseppe Bifulco、Oliver Werz、Simona Pace

  DOI：10.1016/j.bcp.2019.03.003

  日期：2019.7

  effects. Here, we report on the discovery and characterization of the two novel benzoxanthene lignans 1 and 2 that modulate select LM biosynthetic enzymes enabling the switch from pro-inflammatory LT to SPM biosynthesis as potential pharmacological strategy to intervene with inflammation. In cell-free assays, compound 1 and 2 inhibit microsomal prostaglandin E2 synthase-1 and leukotriene C4 synthase (IC50 ∼ 0

  脂质介体（LM）包括促炎性前列腺素（PG）和白三烯（LT），还包括在健康和疾病中显示出关键生物活性的专门的促解析介体（SPM）。对诸如骨关节炎和类风湿性关节炎之类的炎性疾病的药理干预通常使用抗炎药，其可以抑制PG和LT的形成，但是其有效性和副作用有限。在这里，我们报道了两种新型苯并氧杂蒽木脂素1和2的发现和表征，它们可以调节选择的LM生物合成酶，从而使从促炎性LT转变为SPM生物合成成为潜在的干预炎症的药理策略。在无细胞试验中，化合物1和2抑制微粒体前列腺素E2合酶-1和白三烯C4合酶（IC50〜0.6-3。4 µM）并有效干扰5-脂氧合酶（5-LOX），这是LT生物合成中的关键酶（IC50 = 0.04和0.09 µM）。在人类嗜中性粒细胞，单核细胞以及M1和M2巨噬细胞中，化合物1和2有效抑制LT生物合成（IC50 <1 µM），同时升高15-LOX衍生的LM（包括SPM）。在酵母聚糖