Antiplatelet Effect and Selective Binding to Cyclooxygenase (COX) by Molecular Docking Analysis of Flavonoids and Lignans

The known flavonoids ginkgetin (1), taiwanhomoflavone A (2), taiwanhomoflavone B (3), and taiwanhomoflavone C (4) and eight known lignans: justicidin B (9), justicidin C (10), justicidin D (11), chinensinaphthol methyl ether (12), procumphthalide A (13), procumbenoside A (15), and ciliatosides A (16) and B (17) were isolated from Cephalotaxus wilsoniana and Justicia species, respectively. The antiplatelet effects of the above constituents on human platelet-rich plasma (PRP) were evaluated. Of the compounds tested on human PRP, compounds 1, 4, 9, and 11 showed inhibition of secondary aggregation induced by adrenaline. Compound 1 had an inhibitory effect on cyclooxygenase-1 (COX-1). Molecular docking studies revealed that 1 and the related compounds apigenin (5), cycloheterophyllin (6), broussoflavone F (7), and quercetin (8) were docked near the gate of active site of COX-1. It indicated that the antiplatelet effect of 1, 4, 9, and 11 is partially owed to suppression of COX-1 activity and reduced thromboxane formation. Flavonoids, 1, 5, 6, 7, and 8 may block the gate of the active site of COX-1 and interfere the conversion of arachidonic acid to prostaglandin (PG) H₂ in the COX-1 active site.     

高效液相色谱法测定南、北五味子中木脂素含量

建立了用高效液相色谱法测定南、北五味子中5种木脂素成分(五味子醇甲、五味子醇乙、五味子酯甲、五味子甲素和五味子乙素)的分析方法。以甲醇和水为流动相,采用梯度洗脱,对21个不同产地的南、北五味子样本进行了色谱分离,并利用标准物质、保留时间和紫外光谱对木脂素进行定性。结果表明,样品中各组分的色谱峰基本达到基线分离,该方法重复性好、灵敏度高,为评价南、北五味子中的木脂素活性成分提供了一种可靠的分析方法。     

牛蒡子化学成分研究

研究牛蒡子的化学成分。利用各种色谱技术进行分离、纯化,通过波谱解析结合理化性质鉴定化合物的结构。从牛蒡子中分离得到六种化合物,根据理化性质和光谱数据分别鉴定为牛蒡子苷元、邻苯二甲酸二异丁酯、9,12,15-十八碳三烯酸、二十六烷酸、亚油酸乙酯、十八烷酸甘油酯。     

五味子木脂素超声循环提取工艺条件的优化

采用超声循环提取的方法从五味子中提取五味子醇甲等木脂素类有效成分,考察溶剂、超声时间、超声功率、液固比和温度对提取工艺的影响．结果表明采用85％的乙醇作为提取溶剂,在单因素实验的基础上通过正交实验得出最佳工艺条件：超声功率500W,超声时间10min,温度30℃,液固比20,五味子木脂素提取率达到80．84％．     

Hydrogenolysis of Hydroxymatairesinol Over Carbon-Supported Palladium Catalysts

The natural lignan hydroxymatairesinol was hydrogenolysed to a potential anticarcinogenic substance matairesinol over different carbon-supported palladium catalysts. The reaction was conducted in 2-propanol at 70 °C under hydrogen flow in a stirred glass reactor. The catalysts were characterised by N₂-physisorption, CO pulse chemisorption and pH measurement of aqueous catalyst slurries. The most active catalyst (Degussa-Hüls) gave yields of matairesinol over 90% in 4 h. It was concluded that the acidity of the catalyst had a profound influence on the reaction rate.     

Sesame lignans enhance the thermal stability of edible vegetable oils

The effect of sesame lignans on the thermal and storage stability of edible vegetable oils (soybean-SBO, sunflower-SFO and ricebran-RBO) was studied by (i) determining the total free radical scavenging activity (RSA) using DPPH, (ii) % total tocol retention, (iii) lignan profile and (iv) PUFA composition. The order of RSA and retention of total tocols of oils heated up to 120 min at frying temperature (FT) were RBO = SBO > SFO and RBO > SBO > SFO, respectively. Heating SBO or SFO at FT after addition of 1.2% lignans increased RSA of SBO to a greater extent than that of SFO, and increased retention of total tocols only in SBO. However, addition of lignans did not further increase the RSA of RBO. Heating oils with added lignans, increased sesamol and decreased sesamolin while sesamin was relatively resistant to heat. These findings suggest that sesame lignans may have potential application as natural antioxidants in the edible oil and food industry.     

Processing of rye bran influences both the fermentation of dietary fibre and the bioconversion of lignans by human faecal flora in vitro

Plant lignans are converted to mammalian forms, enterodiol and enterolactone, in the colon. Enhanced plasma or urinary enterolactone levels have been associated with lowered risk of cardiovascular diseases and breast cancer. Processed rye bran and its fractions were compared to ascertain the fermentation rates of fermentable carbohydrates and the bioconversion of lignans. Rye bran was extruded and treated with a food‐grade xylanase. Part of the xylanase‐treated rye bran was separated into a soluble rye bran extract and an insoluble residue, and a part of the xylanase‐treated rye bran was freeze‐dried without separation. All the samples were digested by pepsin and pancreatin and subsequently fermented with a human faecal inoculum in vitro. The consumption of carbohydrates, the productions of short‐chain fatty acids (SCFA), enterodiol and enterolactone were followed as a function of time. The soluble rye bran extract showed the fastest fermentation rate and the highest extent of fermentation determined as the consumption of neutral sugar residues (arabinose, xylose and glucose), the production of SCFA and the formation of enterodiol and enterolactone. Xylanase treatment enhanced the fermentation rate of extruded rye bran. An even a higher fermentation rate was observed for rye bran extract containing soluble carbohydrates. The amount of enterolactone precursors in rye seemed to be too low for enterolactone formation using an amount of substrate suitable for carbohydrate fermentation. However, xylanase treatment enhanced the availability of plant lignans from rye bran, as enterodiol formation was increased by the use of xylanase. Copyright © 2005 Society of Chemical Industry     

Inhibition of potato cyst nematode hatch by lignans fromBupleurum salicifolium (Unbelliferae)

A series of lignans fromBupleurum salicifolium Soland (Umbelliferae) were tested for nematostatic activity on the cysts and freed secondstage juveniles of the potato cyst nematodesGlobodera rostochiensis andG. pallida. None of the six lignans tested—bursehernin, matairesinol, syringaresinol, the novel product buplerol, guayarol, and a derivative, nortrachelogenin triacetate—showed nematicidal activity in an in vitro analysis with second-stage juveniles, but significant differences were noted when the lignans were assayed for nematostatic activity as cyst hatching inhibitors. Bursehernin and matairesinol showed the greatest activity, at concentrations of 50 ppm. This is the first known instance of a natural product inhibiting the hatch of the nematodeG. pallida. The HID (hatching inhibiting dose) of bursehernin was estimated, and some conclusions were drawn about the structure-activity relationships of the lignans under study.     

固相萃取高效液相色谱法同时测定五仁醇浸膏中的5种木脂素

建立了五仁醇浸膏中5种木质素（五味子醇甲、五味子醇乙、五味子脂甲、五味子甲素和五味子乙素）的快速检测方法,并采用固相萃取高效液相色谱法对其进行了检测.结果显示：五味子醇甲、五味子醇乙、五味子脂甲、五味子甲素和五味子乙素进样量分别在0.048 8-2.44、0.040 8-2.04、0.049 6-2.48、0.036 0-1.80和0.048 0-2.40μg范围内具有良好的线性关系（R^2≤0.999 8）;平均加样回收率分别为101.24%、99.52%、103.72%、98.66%和98.08%,RSD≤1.62%.实验表明,固相萃取-高效液相色谱法具有简便、准确、稳定、灵敏度高、重现性好等优点,可用于五仁醇浸膏的质量控制.     

木脂素的生物合成及其微生物法生产的研究进展

木脂素是一类分布于植物中的次级代谢产物,由两分子苯丙素衍生物聚合而成。木脂素具有抗细菌、抗病毒和抗真菌活性,被广泛用于药物和食品中。目前,木脂素的生产主要依赖于植物提取。植物生长周期长、木脂素含量低等问题,限制了木脂素的商业应用。随着木脂素合成路径和关键酶的不断解析,木脂素的生物催化合成过程受到了越来越多的关注。本文总结了典型木脂素的生物活性、生物合成路径和微生物法生产的研究进展,可以为深入研究木脂素的微生物合成提供参考。