Sesquiterpenoids from the Root Bark of Acanthopanax leucorrhizus and Their Biological Activities

Three furoeremophilane‐type sesquiterpenoids, including one new, 1α‐acetoxy‐6β‐(benzoyloxy)‐10β‐hydroxy‐9‐oxofuroeremophilane ( 1 ), and two known, 1β,6β‐diacetoxy‐9‐oxofuroeremophilane ( 2 ) and (6α)‐furoeremophilan‐14,6‐olide ( 3 ), were isolated from the root bark of Acanthopanax leucorrhizus from China. Their structures were elucidated on the basis of comprehensive spectroscopic analyses, including IR, HR‐ESI‐MS, 1D‐ and 2D‐NMR experiments. A preliminary bioassay revealed that compound 1 exhibits weak cytotoxicities against the human tumor cell lines MCF‐7 and SMMC‐7721 with the IC₅₀ values of 75.12±1.69 and 168.36±2.01 μg/ml, respectively. Compound 1 and 2 showed moderate activities against Escherichia coli with the MIC values of 32 and 64 μg/ml, respectively.     

Microwave Assisted-extraction of Flavonols from Acanthopanax Senticosus Harms and High-performance Liquid Chromatography Analysis

Flavonols were extracted from Acanthopanax Senticosus Harms by Soxhlet extraction(SE),atmospheric pressure microwave-assisted extraction(AMAE) and pressurized microwave-assisted extraction(PMAE).The influences of experimental conditions,such as concentration of ethanol in the eluent,microwave irradiation time,etc.on the extraction yield were studied.Four flavonols(hyperin,rutin,quercitrin and quercetin) in the extracts were determined quantitatively by HPLC method.The experimental results demonstrate the ad...     

多种气相色谱联用技术分析陕西刺五加茎挥发油的化学成分

采用气相色谱/四极杆质谱(GC/qMS)、气相色谱/正交加速飞行时间质谱(GC/oaTOFMS)和气相色谱/傅里叶变换红外光谱(GC/FTIR)联用技术,对一种陕西产刺五加Acanthopanax senticosus (Rupr. et Maxim.) Harms茎挥发油的化学成分进行了分析。基于GC/qMS谱库的检索功能,结合GC/FTIR在结构鉴别上的优势和GC/oaTOFMS对质谱碎片离子精确的质量测定功能,成功地实现了对68个色谱组分的定性分析。与使用单一的联用技术(例如GC/qMS)相比,利用多种色谱联用技术在定性分析上的互补性,可以明显提高对组成复杂的挥发油类样品分析的可靠性。     

Three new compounds from the leaves of Acanthopanax senticosus Harms

<正>Three new compounds named(2E)-prenyl benzoate-4-O-α-L-arabinopyranosyl(1→6)β-D-glucopyranoside(1),7-methoxy-8- O-β-D-glucopyranosyl coumarin(2),and 3,4'-dihydroxy-3'-methoxy benzenepentanoic acid(3) were isolated from the leaves of Acanthopanax senticosus Harms.The structures of new compounds were determined by means of 2D NMR experiments and chemical methods.     

A Green Method of Extracting and Recovering Flavonoids from Acanthopanax senticosus Using Deep Eutectic Solvents

In recent years, green extraction of bioactive compounds from herbal medicines has generated widespread interest. Deep eutectic solvents (DES) have widely replaced traditional organic solvents in the extraction process. In this study, the efficiencies of eight DESs in extracting flavonoids from Acanthopanax senticosus (AS) were compared. Response surface methodology (RSM) was employed to optimize the independent variable including ultrasonic power, water content, solid-liquid ratio, extraction temperature, and extraction time. DES composed of glycerol and levulinic acid (1:1) was chosen as the most suitable extraction medium. Optimal conditions were ultrasonic power of 500 W, water content of 28%, solid-liquid ratio of 1:18 g·mL⁻¹, extraction temperature of 55 °C, and extraction time of 73 min. The extraction yield of total flavonoids reached 23.928 ± 0.071 mg·g⁻¹, which was 40.7% higher compared with ultrasonic-assisted ethanol extraction. Macroporous resin (D-101, HPD-600, S-8 and AB-8) was used to recover flavonoids from extracts. The AB-8 resin showed higher adsorption/desorption performance, with a recovery rate of total flavonoids of up to 71.56 ± 0.256%. In addition, DES solvent could efficiently be reused twice. In summary, ultrasonic-assisted DES combined with the macroporous resin enrichment method is exceptionally effective in recovering flavonoids from AS, and provides a promising environmentally friendly and recyclable strategy for flavonoid extraction from natural plant sources.     

刺五加寡糖的电喷雾多级串联质谱研究

采用小柱层析法从刺五加中分离得到刺五加寡糖类系列化合物(刺五加二糖刺五加六糖).实验结果表明,在正离子模式下的ESI-MS谱中,此类化合物呈现出特征的加合离子峰簇[M+Na]⁺/[M+K]⁺或[M+H₂O+Na]⁺/[M+H₂O+K]⁺,可以确定其分子量;在负离子模式下的ESI-MS谱中,刺五加寡糖易形成[M-H]^-/[M+nH₂O-H]^-(n<3).还利用电喷雾多级串联质谱(ESI-MSⁿ)对刺五加三糖进行了系统的研究,推断出刺五加三糖的组成与结构.     

Quantitative determination of 15 bioactive triterpenoid saponins in different parts of Acanthopanax henryi by HPLC with charged aerosol detection and confirmation by LC–ESI‐TOF‐MS

Triterpenoid saponins are difficult to analyze using high‐performance liquid chromatography coupled to UV/vis spectrophotometry due to their lack of chromophores. This study describes the first analytical method for the determination of 15 triterpenoid saponins from the leaves, stems, root bark, and fruits of Acanthopanax henryi, using a high‐performance liquid chromatography with charged aerosol detection coupled with electrospray ionization mass spectrometry method. The separation was carried out on a Kinetex XB‐C18 column with an acetonitrile/water gradient as the mobile phase, followed by charged aerosol detection. The operating conditions of charged aerosol detection were set at 24 kPa for nitrogen pressure and 100 pA for the detection range. Liquid chromatography with electrospray ionization mass spectrometry is described for the identification of compounds in plant samples. The electrospray ionization mass spectrometry method involved the use of the [M + Na]⁺ and [M + NH₄]⁺ ions for compounds 1 – 15 in the positive ion mode with an extracted ion chromatogram. The developed method was fully validated in terms of linearity, sensitivity, precision, repeatability, and recovery, then subsequently applied to evaluate the quality of A. henryi.     

Characterization of the multiple components of Acanthopanax Senticosus stem by ultra high performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

Acanthopanax Senticosus Harms. has been used widely in traditional Chinese medicine for the treatment of chronic bronchitis, neurasthenia, hypertension and ischemic heart disease. However, the in vivo constituents of the stem of Acanthopanax Senticosus remain unknown. In this paper, ultra high performance liquid chromatography with electrospray ionization quadrupole time‐of‐flight mass spectrometry and the MarkerLynx^TM software combined with multiple data processing approach were used to study the constituents in vitro and in vivo. The aqueous extract from the Acanthopanax Senticosus stem and the compositions in rat serum after intragastric administration were completely analyzed. Consequently, 115 compounds in the aqueous extract from Acanthopanax Senticosus stem and 41 compounds absorbed into blood were characterized. Of the 115 compounds in vitro, 54 were reported for first time, including sinapyl alcohol, sinapyl alcohol diglucoside, and 1‐O‐sinapoyl‐β‐d ‐glucose. In the 41 compounds in vivo, 7 were prototype components and 34 were metabolites which were from 21 components of aqueous extract from Acanthopanax Senticosus stem, and the metabolic pathways of the metabolites were elucidated for first time. The results narrowed the range of screening the active components and provided a basis for the study of action mechanism and pharmacology.     

ICP-AES测定刺五加中的微量元素

采用高压消解罐对样品进行处理,将化学计量学应用于ICP-AES测定种植刺五加、野生刺五加、五加皮、白参和西洋参中Na、Mg、Se、Pb、K、Fe、Ca、Sr微量元素的含量。该方法操作简单、快速、灵敏度高,回收率在95.54%—100.8%之间,相对标准偏差小于0.0470%。实验结果表明,5种物质中均含有人体所需的大量微量元素,而且对比种植刺五加和野生刺五加发现,野生刺五加的营养价值优于种植刺五加。从微量元素含量的角度上,刺五加和人参不具有相似性。     

UPLC-MS/MS结合多探针底物方法研究刺五加叶中黄酮苷类成分对CYP450活性的影响

利用超高效液相色谱-串联质谱联用(UPLC-MS/MS)的多反应监测(MRM)技术结合多探针底物方法, 研究了刺五加叶中的主要黄酮苷类化合物槲皮苷、金丝桃苷及芦丁对肝细胞色素P450酶(CYP450)亚型CYP1A2, CYP2C, CYP2E1, CYP2D和CYP3A活性的影响. 结果表明, 3种化合物对各CYP亚型酶均有抑制作用, 其中金丝桃苷和槲皮苷对CYP1A2催化的非那西丁的O-脱乙基反应抑制的IC₅₀值分别为46.53和49.75 μmol/L, 金丝桃苷和芦丁对CYP2E1催化的氯唑沙宗的6-羟基化反应抑制的IC₅₀值分别为99.87和86.36 μmol/L. 机理性抑制实验结果表明, 3种化合物对2种亚型酶的抑制作用是随着预孵时间延长而增强的机理性抑制.