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.     

Hot-pressurized fluid extraction of flavonoids and phenolic acids from Brazilian propolis and their cytotoxic assay in vitro

This work has examined the hot-pressurized fluid extraction of seven flavonoids, caffeic acid phenethyl ester and four phenolic acids from Brazilian propolis lumps generating, during the process, fat- and water-soluble extracts. The solid content of water-soluble extract obtained by hot-pressurized water in the presence of 29% natural surfactant was 35.2 mg/mL and was 44% greater than that obtained without natural surfactant. Furthermore the amount of the seven flavonoids and caffeic acid phenethyl ester in the fat-soluble extract exceeded those in the water-soluble sample while, on the other hand, the amount of the four phenolic acids in the water-soluble extract was more than those in the fat-soluble extract. Our findings show that the total solid content and the amount of these 12 active compounds produced by the emulsified hot-pressurized water are 36% and 7% higher, respectively, than those produced by emulsified water at atmospheric pressure. The EC₅₀ value of the free radical scavenging activity of 1,1-diphenyl-2-picrylhydrazyl of the emulsified hot-pressurized water extract was the lowest, and presented the strongest anti-oxidation ability among all the extracts. In vitro cytotoxicity indicated that the water-soluble extract strongly suppressed the growth of leukemia (HL-60, U937), lung cancer (A549, CH27) and liver cancer (Hep G2, Hep 3B) cells in a concentration-dependent behavior.     

超声波法提取仙人掌中黄酮类化合物的初步探讨

采用超声波萃取法,研究仙人掌黄酮类化合物的提取方法.通过实验确定了乙醇的体积分数、料液比及超声时间的最佳参数.结果表明,乙醇体积分数80%.革取时间20min,料液比为1:10的提取效果最佳;最优条件下提取的黄酮含量为323.81 mg./100g,加标回收率为97.7%.该法与常规溶剂提取法相比,具有提取温度低,产品得率高,氧化损耗小等特点.     

Floral nectar phenolics as biochemical markers for the botanical origin of heather honey

In order to find out biochemical markers for the botanical origin of heather (Erica) honey, the phenolic metabolites present in heather floral nectar, collected from the honey-stomach of bees gathering nectar from these flowers, were analysed. The flavonoid fraction of nectar contained four main flavonoids. Two of them were quercetin and kaempferol 3-rhamnosides, and the other two were tentatively identified as myricetin 3-methyl ether and isorhamnetin 3-rhamnosides. Since the natural glycosides are hydrolysed by bee enzymes to render the corresponding aglycones, which are the metabolites detected in honey, acid hydrolysis of the nectar glycosides was achieved. The aglycones quercetin, myricetin 3-methyl ether, kaempferol and isorhamnetin were identified, as well as the gallic acid derivative ellagic acid. The analysis of Portuguese heather honey samples showed that ellagic acid was present in all the samples in significant amounts ranging between 100 g and 600 g per 100 g honey. The other nectar-derived flavonoids were also present, although some of them in very variable amounts. Ellagic acid and myricetin 3-methyl ether, which have not been detected in any of the monofloral honey samples investigated so far, with the only exception being a French honey sample of the botanically relatedCalluna (Ericaceae) which also contained ellagic acid, seem to be the most useful potential markers for the floral origin of heather honey. However, more detailed and extensive investigations are needed to prove the utility of these markers.     

响应面法优化超声波提取迎春花总黄酮工艺的研究

首次研究利用响应面法优化迎春花总黄酮的提取工艺,在单因素试验基础上,利用中心组合设计响应面试验,考察了超声波提取温度、液料比、提取时间对总黄酮提取率的影响,并建立回归模型.优化后的工艺参数为:提取温度55℃,液料比50 1 mL/g,超声时间25 min,在此条件下总黄酮提取率为16.03%.与传统溶剂浸提法相比,提取时间大大缩短且节约了能耗.     

The Potential Toxic Side Effects of Flavonoids

Flavonoids are a class of phytochemical molecules abundant in many plants, fruits, vegetables, and leaves. Flavonoids possess a series of significant biological activities, including anticancer, antioxidant, antiviral, and antiinflammatory properties. They become an important source of dietary supplements and natural health products. Though many studies confirmed the safety of flavonoids, the potential toxicity of flavonoids is still a remarkable field of research to be explored. The enthusiasm for flavonoids expressed by the public has sometimes overlooked their toxicity and also consumed the flavonoids exceeding the body requirements. The current review focused on the potential toxicity of flavonoids to make the public consume flavonoids with caution. This review summarizes the current toxicity which has been reported in vivo and in vitro experiments. The toxicity involves carcinogenicity and mutation, liver and kidney toxicity, and the influence on the thyroid and reproductive function and intestinal flora disorders. The mechanism of toxicity is fully complicated, and current evidence indicates that natural flavonoid glycosides act on different targets with different doses in vivo and in vitro experiments. Though most kinds of flavonoids are considered safe, flavonoids proposed as food supplements need to be assessed their tolerable upper intake level as there have been reports of toxic flavonoids.     

Pressurised hot water extraction with on-line particle formation by supercritical fluid technology

In this work, an on-line process for pressurised hot water extraction (PHWE) of antioxidants from plants as well as drying of the extract in one step by particle formation based on the use of supercritical carbon dioxide (SC-CO₂) has been developed. This process has been called WEPO®, water extraction and particle formation on-line. With this process, dried extracts from onion with the same composition of quercetin derivatives as non-dried extracts have been obtained as a fine powder with spherical particles from 250 nm to 4 μm in diameter. The major compounds present in the extract were quercetin-3,4′-diglucoside, quercetin-4′-glucoside and quercetin. An auxiliary inert gas (hot N₂) was used to enhance the drying process. Parameters such as temperature (120 °C), SC-CO₂ and N₂ pressures (80 and 12.5 bar, respectively) and flow rate of SC-CO₂ (10 ml/min), have been settled by trial-and-error in order to achieve a fine and constant spray formation. Water content, size and morphology, antioxidant capacity and quercetin content of the particles were studied to evaluate the efficiency of the WEPO process. Results were compared with the ones from extracts obtained by continuous flow PHWE followed by freeze-drying. Results showed that both processes gave similar results in terms of antioxidant capacity, concentration of quercetin derivatives and water content, while only WEPO was able to produce defined spherical particles smaller than 4 μm.     

Oxygen species scavenger activities and phenolic contents of four West African plants

In West Africa, Alchornea cordifolia, Baphia nitida, Cassia occidentalis and Boerhavia diffusa leaves are used in food and drinks, as well as in traditional medicine, to treat rheumatic ailments which incur oxidative stress. First, these plants were evaluated for their antioxidant properties through a scavenger effect on reactive oxygen species (ROS), such as hydrogen peroxide and hypochlorous acid. All of them showed dose-dependent antioxidant activity. The values obtained were comparable to those of antioxidant pharmacological substances: N-acetylcysteine and Mesna. Second, rates of total phenolic, flavonoid and proanthocyanidin contents were evaluated. The highest rates were to be found in the most active extracts, indicating that antioxidant activity could be influenced by these phytochemical groups.The results of our study confirm the traditional use of these plants in inflammatory diseases, and demonstrate that they could contribute, through their phenolic contents, to attenuating tissue damage due to ROS. These plants can also be beneficial for health as a source of antioxidants when they are included in food and drinks.     

Unexploited Thapsia garganica,Orlaya maritima,and Retama raetam Seeds: Potential Sources of Unsaturated Fatty Acid and Natural Antioxidants

Total lipid contents, fatty acid compositions, phenolic profiles and antioxidants activities of seeds from Thapsia garganica, Orlaya maritima, and Retama raetam were investigated. The oil values were more than 26 %, except seeds of R. raetam (ca. 3 %). Unsaturated fatty acids accounted for the majority of the fatty acids (more than 75 %). Oleic and linoleic acid were the predominant fatty acids. Total phenolic compounds (24–104 mg GAE g^?1 DR), total flavonoids (4–102 mg QE g^?1g DR), total tannins (28–85 mg GAE g^?1 DR) and condensed tannins (0.62–131 mg CE g^?1 DR) were also determined. The antioxidant activities using different assays were evaluated. The predominant detected classes were the phenolic acids (42–85 %) and the flavonoids (11–48 %). The major phenolic acids were caffeic, trans‐4‐hydroxy‐3‐methoxycinnamic, p‐coumaric, and gallic acid. The predominant flavonoids were quercetin, luteolin, naringin, apigenin, and kaempferol. This study brings attention to the medicinal importance of these species as a source of oil and antioxidant molecules.     

Germination as a process to increase the polyphenol content and antioxidant activity of lupin seeds (Lupinus angustifolius L.)

In this work, the effect of germination of lupin seeds (Lupinus angustifolius L., c.v. Zapatón) on bioactive phenolic compounds as well as on the antioxidant activity was studied. Phenolic compounds were analysed by HPLC-PAD-ESI/MS. The antioxidant activity was determined by spectrophotometry, evaluating the free radical scavenging activity of the samples. Germination produced significant changes in flavonoids and non-flavonoid phenolic compounds. In the analysed samples, isoflavones, flavones and dihydroflavonols in free and conjugated forms were identified. The results obtained indicate that germination modifies the quantitative and qualitative polyphenolic composition of lupin (Lupinus angustifolius L.) seeds during the different days of the process, with a significant increase of flavonoids. An increase in the antioxidant activity was also observed as a consequence of the process. Germination was shown to be a good process to increase the phenolic content of lupin seeds as well as their antioxidant activity.