Flavonoid pigments in chalkhill blue (Lysandra coridon Poda) and other lycaenid butterflies

Nine flavonoids, namely, kaempferol, kaempferol 7-rharanoside, kaempferol 3-rhamnoside, kaempferol 3-glucoside, kaempferol 3-glucoside, 7-rhamnoside, quercetin 3-glucoside, quercetin 3,7-diglucoside, isorhamnetin 3-glucoside, and isorhamnetin 3,7-diglucoside, have been identified in the body and wings of the chalkhill blue butterflyLysandra coridon Poda. Flavonoids have also been found in 15 of a further 17 lycaenid species examined. Analysis of the two-dimensional paper chromatographic flavonoid patterns and aglycone results has shown that the flavonoid content ofL. coridon and the other lycaenids is dependent on the flavonoid content of the larval diet. Differences in the flavonoid patterns ofL. coridon and its leguminous larval food plantsHippocrepis comosa, Anthyllis vulneraria, andLotus corniculatus, indicate that the ingested flavonoids are metabolized byL. coridon or its gut flora before sequestration. Despite the presence of fiavones, glycoflavones, and isoflavones in the larval food plant species, only flavonols are sequestered by the lycaenid species examined. The relationship between lycaenid butterflies and their larval food plants, and the possible role(s) of flavonoids in lycaenids has been discussed. Interactions between ants, plants, flavonoids, and myrmecophilous lycaenids have also been considered.     

Comparative polyphenolic antioxidant profile and quality of traditional apple cultivars as affected by cold storage

‘Kathista’ and ‘Lortiko’ are regarded as traditional and highly appreciated apple cultivars in Cyprus, yet their postharvest behaviour and phytochemical content are largely unknown. Such fruits were examined for their qualitative traits, phenolic composition and antioxidant capacity after harvest or short, intermediate or extended cold storage and additional ripening at room temperature (RT), using ‘Gala’ as reference cultivar. Total phenolic content was dependent on cultivar and length of cold storage, while hydroxycinnamic acids were always at higher levels compared to total flavonols for all the examined cultivars. No clear trends regarding the influence of cold storage or RT maintenance on fruit antioxidant properties were evident. Overall, quality attributes and polyphenolic content of the traditional apple cultivars were comparable with ‘Gala’ at harvest; thus, they can be considered a good source of nutraceuticals as summer apple cultivars. However, extended cold storage deteriorates fruit behaviour and antioxidant capacity, particularly in ‘Lortiko’ fruit.     

Impact of postharvest methyl jasmonate treatment on the volatile composition and flavonol content of strawberries

BACKGROUND: Although strawberry aroma is very complex, certain compounds have been described as main contributors, i.e. furanones, aldehydes, alcohols, sulfur compounds and particularly methyl and ethyl esters. In addition, strawberries possess potent antioxidant activity because of their high content of phenolic compounds. Among them, flavonols are highlighted as important antioxidant compounds in strawberry. The objective of this study was to assess the effect of methyl jasmonate (MJ) on the composition of the major contributors to aroma and on the content of certain flavonols in strawberry fruits. RESULTS: The levels of all studied volatile compounds were significantly affected by MJ treatment, though the individual effect differed according to the specific compound considered. Most of them increased significantly (P < 0.05), except methyl butanoate, which always showed higher levels in untreated strawberries. In contrast to aroma compounds, the change in the concentration of flavonols (i.e. myricetin, quercetin and kaempferol) was not significant in MJ‐treated strawberries. Considering the health‐promoting activity of these compounds, further investigations on the experimental conditions related to the treatment are required to control flavonol bioformation by means of MJ. CONCLUSION: The exogenous application of MJ vapour to strawberry enhances, in general, the production of the most relevant aroma‐active compounds. On the contrary, MJ treatment does not appear to influence the levels of myricetin, quercetin and kaempferol. Thus postharvest MJ treatment is proposed as an approach to obtain improved strawberry fruits in terms of sensory quality and health‐promoting properties. Copyright © 2010 Society of Chemical Industry     

Electron spin resonance (ESR) spectroscopic assessment of the contribution of quercetin and other flavonols to the antioxidant capacity of red wines

Health benefits of red wine have been ascribed in part to the antioxidant properties of quercetin and other flavonols. Red wines, however, contain many other polyphenolic compounds with antioxidant potential. The present study has assessed the antioxidant capacity of seven red wines using electron spin resonance spectrometry to measure their ability to donate hydrogen atoms to a stable Fremy's radical. Antioxidant capacity of the wines was strongly related to the total phenol content (r = 0.872, P < 0.01) but less so to total flavonol content (r = 0.651, P < 0.10). The only flavonols detected in the wines by HPLC with post‐column derivatisation were the aglycones and conjugated forms of quercetin and myricetin. These accounted for less than 2% of total phenolic content when expressed as gallic acid equivalents. Although these flavonols showed marked ability to quench Fremy's radical, they contributed less than 1.5% to the total antioxidant capacity of the wines. Consequently, quercetin is not a major antioxidant in red wine. The antioxidant activity of other polyphenols may be of greater importance in contributing to the reputed health benefits of moderate wine consumption. © 1999 Society of Chemical Industry     

中国野生刺葡萄冬剪枝条多酚类物质含量及其抗氧化活性研究

为探讨中国野生刺葡萄冬剪枝条的多酚类物质含量及其抗氧化活性,以7种中国野生刺葡萄冬剪枝条为研究对象,利用超声波辅助传统有机溶剂提取法提取多酚物质。分别测定粗提液中总酚、总黄酮、原花色素的含量,采用体外抗氧化活性法测定其DPPH自由基清除能力、羟自由基清除率、铜离子还原力和总还原力,并分析其相关性。结果表明:枝条中总酚、总黄酮、总原花色素含量(以干基计)分别为24.68～32.76、51.03～72.63、36.69～44.41mg/g。DPPH自由基清除率、羟自由基清除率、铜离子还原力和总还原力分别为23.62～28.02mg/g、31.51%～36.11%、47.19～73.28mg/g和39.76～53.80mg/g。中国野生刺葡萄枝条具有较高的酚类物质含量和抗氧化性能,其中还原力与总酚、总黄酮、原花色素含量有较高的相关性(R2>0.9),是具有良好开发前景的天然抗氧化剂及生物药品基料。     

Rapid Detection of Antioxidant Flavonoids in Azalea (Rhododendron mucronulatum) Flowers using On-line HPLC-ABTS+ System and Preparative Isolation of Three Flavonoids by Centrifugal Partition Chromatography

High-performance liquid chromatography coupled to an on-line ABTS⁺-based assay (on-line HPLC-ABTS⁺) system was used to determine the principle antioxidants in azalea flowers. Three flavonoids, myricetin, quercetin, and kaempferol, recovered in ethyl acetate extracts of azalea flowers were determined to have antioxidant activities. These three flavonoids were isolated and purified by successive centrifugal partition chromatography (CPC) using two different biphasic solvent systems, consisting of n-hexane-ethyl acetate-methanol-water (3:5:3:5 or 4:5:4:5, v/v). A total of 46.2 mg of myricetin, 28.9 mg of quercetin, and 10.6 mg of kaempferol with purities of 97.0%, 95.4%, and 93.9%, respectively, were purified from 500 mg of ethyl acetate soluble material from azalea flowers. The structures were identified by their retention time, UV spectra, and ESI-MS in the positive ion mode and were confirmed by NMR experiments.     

Synthesis of flavonols and expression of flavonol synthase genes in the developing grape berries of Shiraz and Chardonnay (Vitis vinifera L.)

Flavonols were determined in Shiraz and Chardonnay grapes throughout berry development. The predominant flavonols were quercetin-3-glycosides with trace amounts of kaempferol-3-glycosides detected in Shiraz flowers but not in developing berries. Flavonols were present in the skin of ripening grapes but were not detected in seeds or flesh. Flavonols were also present in buds, tendrils, inflorescences, anthers and leaves. The concentration of flavonols in flowers (mg/g fresh weight) was high and decreased between flowering and berry set then remained relatively constant through berry development. The total amount of flavonols in berries (mg/berry) was low until pre-veraison then increased during berry development, particularly before veraison, the onset of ripening, in Chardonnay and during ripening in Shiraz. Two cDNA fragments with homology to genes encoding the enzyme flavonol synthase (FLS) were isolated from Shiraz flowers. In the overlapping region of the two cDNAs, they had 80% sequence identity at the nucleotide level and both had high homology to FLS genes from other plants. VvFLS1 was expressed in leaves, tendrils, pedicels, buds and inflorescences as well as in developing grapes. Expression was highest between flowering and fruit set then declined, increasing again during ripening coincident with the increase in flavonols per berry. Expression of VvFLS2 was much lower than for VvFLS1 and did not change during berry development. The results indicate that two distinct periods of flavonol synthesis occur in grapes, the first around flowering and the second during ripening of the developing berries.     

烟草中异源表达番茄HQT基因对多酚物质合成的影响

羟基肉桂酰辅酶A：奎尼酸羟基肉桂酰转移酶（Hydroxycinnamoyl-CoA：quinate hydroxycinnamoyl transferase,HQT）是催化茄科植物咖啡酰奎尼酸生物合成最后一步的关键酶。为培育富含多酚物质的烟草,提高烟草品质,通过克隆番茄HQT基因,构建P35S：：SlHQT超量表达载体,在野生型三生烟草（SS）中异源表达,利用高效液相色谱技术（HPLC）及液质联用（LC-MS/MS）技术对转基因烟草叶片中一咖啡酰奎尼酸及黄酮醇含量进行检测,探究SlHQT基因对三生烟草一咖啡酰奎尼酸及黄酮醇物质合成的影响。结果显示,转SlHQT烟草叶片中一咖啡酰奎尼酸总含量最高可提高14.98倍,芦丁和山奈酚芸香糖苷含量最高可分别提高11.47和9.32倍,且生长表型与野生型烟草没有明显差异;转SlHQT基因烟草叶片中有4种（1-CQA,3-CQA,4-CQA,5-CQA）一咖啡酰奎尼酸,野生型烟草叶片中只检测到3种（3-CQA,4-CQA,5-CQA）。SlHQT基因在烟草中的异源表达促进了1-CQA的生物合成且提高了一咖啡酰奎尼酸总含量,同时增加了黄酮醇的生物合成。     

A review of the antioxidant potential of medicinal plant species

Some researchers suggest that two-thirds of the world's plant species have medicinal value; in particular, many medicinal plants have great antioxidant potential. Antioxidants reduce the oxidative stress in cells and are therefore useful in the treatment of many human diseases, including cancer, cardiovascular diseases and inflammatory diseases. This paper reviews the antioxidant potential of extracts from the stems, roots, bark, leaves, fruits and seeds of several important medicinal species. Synthetic antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxylanisole (BHA) are currently used as food additives, and many plant species have similar antioxidant potentials as these synthetics. These species include Diospyros abyssinica, Pistacia lentiscus, Geranium sanguineum L., Sargentodoxa cuneata Rehd. Et Wils, Polyalthia cerasoides (Roxb.) Bedd, Crataeva nurvala Buch-Ham., Acacia auriculiformis A. Cunn, Teucrium polium L., Dracocephalum moldavica L., Urtica dioica L., Ficus microcarpa L. fil., Bidens pilosa Linn. Radiata, Leea indica, the Lamiaceae species, Uncaria tomentosa (Willd.) DC, Salvia officinalis L., Momordica Charantia L., Rheum ribes L., and Pelargonium endlicherianum. The literature reveals that these natural antioxidants represent a potentially side effect-free alternative to synthetic antioxidants in the food processing industry and for use in preventive medicine.