Anthocyanins in berries of Maqui (Aristotelia chilensis (Mol.) Stuntz)

The anthocyanin composition of berries of Maqui [Aristotelia chilensis (Mol.) Stuntz] was determined by HPLC with photodiode array and MS detection. Eight pigments corresponding to the 3-glucosides, 3,5-diglucosides, 3-sambubiosides and 3-sambubioside-5-glucosides of delphinidin and cyanidin were identified, the principal anthocyanin being delphinidin 3-sambubioside-5-glucoside (34% of total anthocyanins). The average total anthocyanin content was 137.6 +/- 0.4mg/100g of fresh fruit (211.9 +/- 0.6 mg/100g of dry fruit). The relative high anthocyanin content and the important presence of polar polyglycosylated derivatives makes the fruits of A. chilensis an interesting source of anthocyanin extracts for food and pharmaceutical uses.     

A survey of anthocyanins in fruits of some angiosperms,I

The anthocyanin pigments in the fruits of fifty-two species belonging to seventeen families of angiosperms were investigated paper-chromatographicallly. They were identified as cyanidin 3-monoglucoside, pelargonidin 3-monoglucoside, cyanidin 3-rutinoside, pelargonidin 3-rutinoside, cyanidin 3-xylosylglucoside, cyanidin 3-xylosylgalactoside, delphinidin 3-xylosylglucoside and delphinidin 3-sophorosido-5-monoglucoside. Of those anthocyanins detected, the most common was cyanidin 3-monoglucoside. In general, the plants belonging to a certain genus contained the same anthocyanin.     

Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures

Four anthocyanins from Ajuga reptans flowers and its cell cultures were isolated, and a fifth was also characterized by HPLC-mass spectrometry. By means of chemical and spectroscopic analyses, their structures were identified as delphinidin 3-(p-coumaroyl-feruloyl)sophoroside-5-malonylglucoside, delphinidin 3-(diferuloyl)sophoroside-5-malonylglucoside, and cyanidin 3-(di-p-coumaroyl)sophoroside-5-glucoside, respectively. The other two were tentatively identified as delphinidin 3-(diferuloyl)sophoroside-5-glucoside and cyanidin 3-(feruloyl-p-coumaroyl)sophoroside-5-malonylglucoside. In neutral aqueous solution, the crude extract from A. reptans flower cell cultures and the major anthocyanin cyanidin 3-(di-p-coumaroyl)sophoroside-5-malonylglucoside were more stable than cyanidin 3-glucoside, and also prevented more efficiently peroxidation than did the latter. A. reptans flower cell culture anthocyanins may have a potential as natural colorants for food utilities or other purposes.     

响应面设计法优化仙鹤草总多酚的超声提取工艺

在单因素实验的基础上,采用响应面分析法对影响超声辅助提取仙鹤草总多酚得率的主要因素(超声温度、料液比和乙醇浓度)进行优化,建立了影响因素与总多酚之间的函数关系。获得最佳工艺条件为:71%乙醇,料液比1∶24,超声提取温度60℃,提取时间20 min。在此最佳条件下,总多酚得率为3.56%,试验结果与模型预测值相符。     

Delphinidin accumulation is associated with abnormal flower development in petunias

The relative floral anthocyanidin contents of 195 commercial petunias with floral colours other than white and yellow were determined using HPLC, and the presence of five anthocyanidins (cyanidin, peonidin, delphinidin, petunidin, and malvidin) was confirmed. Pelargonidin was not detected, and delphinidin was not a major component. Using a principal component analysis of the relative anthocyanidin contents, the petunias were classified into three phenotype-groups accumulating cyanidin, peonidin, or malvidin, (plus petunidin) as the major anthocyanidin. A fourth phenotype was segregated in the progeny obtained by self-pollinating an F1 hybrid of the malvidin group; this accumulated delphinidin 3-glucoside in a markedly crumpled corolla-limb (delphinidin group). Such inferior floral traits, associated with the accumulation of delphinidin 3-glucoside, are thought to be the driving force that removed the delphinidin group from commercial petunias. A comparison of flowers of the delphinidin group and those of the other groups may provide a useful tool towards a deeper understanding of how anthocyanin biosynthesis relates to normal development of the corolla.     

A rationale for the shift in colour towards blue in transgenic carnation flowers expressing the flavonoid 3',5'-hydroxylase gene

Recently marketed genetically modified violet carnations cv. Moondust and Moonshadow (Dianthus caryophyllus) produce a delphinidin type anthocyanin that native carnations cannot produce and this was achieved by heterologous flavonoid 3',5'-hydroxylase gene expression. Since wild type carnations lack a flavonoid 3',5'-hydroxylase gene, they cannot produce delphinidin, and instead accumulate pelargonidin or cyanidin type anthocyanins, such as pelargonidin or cyanidin 3,5-diglucoside-6"-O-4, 6"'-O-1-cyclic-malyl diester. On the other hand, the anthocyanins in the transgenic flowers were revealed to be delphinidin 3,5-diglucoside-6"-O-4, 6"'-O-1-cyclic-malyl diester (main pigment), delphinidin 3,5-diglucoside-6"-malyl ester, and delphinidin 3,5-diglucoside-6",6"'- dimalyl ester. These are delphinidin derivatives analogous to the natural carnation anthocyanins. This observation indicates that carnation anthocyanin biosynthetic enzymes are versatile enough to modify delphinidin. Additionally, the petals contained flavonol and flavone glycosides. Three of them were identified by spectroscopic methods to be kaempferol 3-(6"'-rhamnosyl-2"'-glucosyl-glucoside), kaempferol 3-(6"'-rhamnosyl-2"'-(6-malyl-glucosyl)-glucoside), and apigenin 6-C-glucosyl-7-O-glucoside-6"'-malyl ester. Among these flavonoids, the apigenin derivative exhibited the strongest co-pigment effect. When two equivalents of the apigenin derivative were added to 1 mM of the main pigment (delphinidin 3,5-diglucoside-6"-O-4,6"'-O-1-cyclic-malyl diester) dissolved in pH 5.0 buffer solution, the lambda(max) shifted to a wavelength 28 nm longer. The vacuolar pH of the Moonshadow flower was estimated to be around 5.5 by measuring the pH of petal. We conclude that the following reasons account for the bluish hue of the transgenic carnation flowers: (1). accumulation of the delphinidin type anthocyanins as a result of flavonoid 3',5'-hydroxylase gene expression, (2). the presence of the flavone derivative strong co-pigment, and (3). an estimated relatively high vacuolar pH of 5.5.     

Anthocyanin composition of the fruit of Coriaria myrtifolia L

The anthocyanin composition of the fruit of Coriaria myrtifolia L. and the changes which occur during ripening were studied using HPLC-PAD and LC-MS. Ten anthocyanins were detected and identified by their absorption and mass spectra as the 3-glucoside and 3-galactoside derivatives of delphinidin, cyanidin, petunidin, peonidin and malvidin. Fruit ripening was accompanied by substantial changes in the anthocyanin profile, with methoxylated anthocyanins, i.e. malvidin and peonidin, predominating in the final stages of ripening, and the trihydroxylated anthocyanin, delphinidin, during the earlier stages. Furthermore, galactoside derivatives were more abundant than glucosides in the ripe fruit. At full maturity, the fruits of C. myrtifolia were very rich in anthocyanins with a content of 10.7% (on a dry weight basis), a level which is higher than that found in most fruits usually considered to be anthocyanin-rich. The ability to grow C. myrtifolia in damaged and nitrogen poor soils, together with the possibility of using this plant for the extraction of anthocyanin, makes it ideal for consolidating soils and repopulating semi-desert or fire-damaged areas.     

无花果果皮中花青素的提取工艺的建立

本研究使用单因素方法考察了无花果(Ficus carica L.)果皮中花青素的最佳提取条件,并考察了7种参数对花青素提取率的影响。参数设置如下:溶剂性质(水,甲醇,乙醇和丙酮)、提取次数(1~3次)、固液比(1/50,1/100,1/150和1/200)、提取时间(60 min,120 min,180 min和240 min)、甲醇浓度(0,20%,40%,60%,80%和100%)、酸类型(盐酸,乙酸,柠檬酸和酒石酸)和酸浓度(0,1%,2%,5%和10%)。使用pH-示差法测量无花果果皮中单体花色素的含量。研究显示,无花果果皮中花青素的最佳提取条件为:溶剂为甲醇溶剂,提取次数为2次,固液比为1/100,提取时间为180 min,甲醇浓度为80%,酸类型为柠檬酸,柠檬酸浓度为5%。该最佳提取条件下的花青素的提取率达到最高(345.62 mg/100g DS)。     

Anthocyanins of grasses

The anthocyanin content of 23 grass species (Poaceae) belonging to five subfamilies has been determined. Altogether 11 anthocyanins were identified; the 3-(6″-malonylglucosides) and 3-glucosides of cyanidin, peonidin and delphinidin, the 3-(3″,6″-dimalonylglucoside), 3-(6″-rhamnosylglucoside) and 3-(6″-glucosylglucoside) of cyanidin, in addition to peonidin 3-(dimalonylglucoside) and delphinidin 3-(6″-rhamnosylglucoside). Anthocyanins acylated with one and/or two malonic acid moieties dominated the anthocyanin profiles of all the species in the subfamilies Pooideae and Panicoideae. On the other hand, the 3-glucoside and 3-rutinoside of cyanidin were the major anthocyanins in Sinarundinaria murielae (subfamily Bambusoideae) and Molinia caerulea (subfamily Arundinoideae), while the 3-glucosides of cyanidin and peonidin were the principal anthocyanins in rice, Oryza sativum (subfamily Oryzoideae). Pelargonidin derivatives and free anthocyanidins have previously been reported to occur in several Poaceae species, however, not identified in any of the species included in this survey.     

Distribution of anthocyanins in aceraceae leaves

The distribution of anthocyanins in spring sprouted and/or autumn coloured leaves of Dipteronia sinensis and Acer (119 taxa) was studied.

Dipteronia contained four cyanidin glycosides: the 3-glucoside, 3-rutinoside, 3-galloylglucoside and 3,5-diglucoside. Acer contained five cyanidin glycosides: 3-glucoside, 3-rutinoside, 3-galloylglucoside, 3-galloylrutinoside and 3,5-diglucoside, two delphinidin glucosides: 3-glucoside and 3-rutinoside and three unidentified anthocyanins. Both Dipteronia and Acer contained the recently reported cyanidin 3-galloylglucoside. The anthocyanin constituents in spring leaves were more complex than those found in autumn coloured leaves: nine in spring and six in autumn. The presence/absence of the major anthocyanins in the spring sprouted leaves of 111 Acer taxa analysed were grouped into 17 distribution patterns. In the autumn the number of anthocyanin distribution patterns was found to be 11. In Acer, cyanidin glycosides were found in 20 sections and delphinidin glycosides in 17 out of the 21 sections analysed. Although the distribution of anthocyanins showed no clear relations among sections, delphinidin glycosides were mainly found in sections Macrantha, Goniocarpa and Saccharina. There were no differences in the pigment constituents in the species native to different countries, such as A. rubrum in North America and A. pycnanthum in Japan, both containing the same pigments: cyanidin 3-glucoside, 3-rutinoside, 3-galloylglucoside, 3-galloylrutinoside and 3,5-diglucoside.     

The extraction process optimization and physicochemical properties of polysaccharides from the roots of Euphorbia fischeriana

Response surface methodology (RSM) was used to determine the optimum extraction conditions for polysaccharides (EFP) from the roots of Euphorbia fischeriana. A Box-Behnken design (BBD) with four independent variables was investigated, such as extraction temperature (°C), water/solid ratio, extraction number (n), and extraction time (h). The results indicated optimum extraction conditions were extraction temperature of 97 °C, water/solid ratio of 9:1, extraction number of 2 and extraction time of 2.4 h, respectively. Under these conditions, the experimental value was 24.6 ± 0.62, which was well in close agreement with value predicted by the model. The preliminary chemical analysis of EFP revealed the EFP contained 25.43% polysaccharides, 20.42% uronic acids, 2.54% sulfate radical and 23.41% proteins. And the neutral polysaccharides were mainly composed of glucose, arabinose, rhamnose, galactose, xylose, mannose in the ratio of 21:8:5:3:1:1.     

Anthocyanins and their distribution in the genusEpimedium

Anthocyanins contained in plants belonging to the genusEpimedium in Japan are discussed in this study. Two kinds of anthocyanin, delphinidin 3-p-coumaroyl-sophoroside-5-glucoside (cayratinin) and cyanidin 3-p-coumaroylsophoroside, were identified, and the latter is new to the literature. Only cayratinin was found in the colored petals of theEpimedium species, but cayratinin and cyanidin glucoside were contained in the stems, young leaves and autumn leaves of all the species surveyed.     

Superoxide radical- and peroxynitrite-scavenging activity of anthocyanins; structure-activity relationship and their synergism

Antioxidant activities of 15 purified bilberry anthocyanins together with pelargonidin 3-O-beta-D-glucopyranoside and 4'-O-methyl delphinidin 3-O-beta-D-glucopyranoside (MDp 3-glc), the major metabolite of delphinidin 3-O-beta-D-glucopyranoside (Dp 3-glc), were evaluated in order to study the structure-antioxidant activity relationship and any synergism among them in the mixture. Both aglycone structure and the attached sugar moiety affected the O*2- and ONOO- -scavenging activities, although the effect of the attached sugar moiety was smaller than that of the aglycone structure. The potency of activity toward the superoxide radical was in the following order: delphinidin > petunidin > malvidin =approximately cyanidin>(+)-catechin > peonidin > pelargonidin. The activity toward ONOO- was: delphinidin > cyanidin =approximately petunidin > malvidin =approximately (+)-catechin > peonidin > pelargonidin. It was confirmed that methylation of 4'-OH markedly reduced the antioxidant activity of anthocyanin. Further, it was revealed that synergism occurred in both - and ONOO- -scavenging activities among the anthocyanins in the mixture.     

Temperature-sensitive anthocyanin production in flowers of Plantago lanceolata

Flower color in the weedy perennial Plantago lanceolata is phenotypically plastic. Darker flowers are produced at cooler ambient temperatures, and circumstantial evidence suggests that this is adaptive. The goal of this project was to investigate the chemical basis for the color plasticity. To test the hypothesis that increased anthocyanin production at low temperatures underlies the plasticity, extracts of P. lanceolata flowers produced at warm and cool temperatures were analyzed using UV/visible spectrophotometry coupled with mass spectrometry. Mass spectrometry allowed us to compare relative abundances of individual anthocyanins. Seventeen anthocyanins, derived from both cyanidin and delphinidin branches of the anthocyanin biosynthetic pathway, were detected. Most of these significantly increased in abundance under cool conditions. Genotypes differed significantly in anthocyanin levels and in their sensitivity to temperature change. Genotypes that showed greater floral color plasticity tended to show also greater temperature sensitivity with respect to anthocyanin production. Data suggest that the temperature regulation of the anthocyanin biosynthetic pathway occurs both upstream and downstream of the divergence of the cyanidin and delphinidin branches. The degree of temperature sensitivity, i.e. phenotypic plasticity, appears to be controlled downstream, whereas the overall temperature effect appears to be controlled upstream.     

Anthocyanins in the epacridaceae

An examination of 73 species of the family Epacridaceae resulted in the identification of the following anthocyanins: cyanidin 3-galactoside, cyanidin 3-glucoside, cyanidin 3-arabinoside, cyanidin 3-rhamnoside, cyanidin 3-rhamnosylgalactoside, cyanidin 3-rhamnosylglucoside, cyanidin 3-xylosylgalactoside, cyanidin 3-xylosylarabinoside, delphinidin 3-galactoside, delphinidin 3-arabinoside, delphinidin 3-rhamnosylgalactoside, delphinidin 3-rhamnosylglucoside and pelargonidin 3-rhamnosylglucoside. No acylated or 5-substituted anthocyanins were detected in any of the species examined. Evidence of methylated anthocyanidin was found only in one species, Woollsia pungens. The occurrence of cyanidin 3-galactoside and cyanidin 3-arabinoside forms a chemical link between this family and the related Ericaceae.     

星点设计-效应面法优化杉木枝叶中双黄酮的提取工艺

采用星点设计-效应面法优化杉木枝叶中穗花杉双黄酮和金松双黄酮的提取工艺.以乙醇体积分数、料液比、提取时间为自变量,穗花杉双黄酮和金松双黄酮转移率的归一化值为因变量,通过对自变量与因变量的二次多项式拟合,采用效应面法选取较优的工艺条件,并进行预测分析.最终确定穗花杉双黄酮和金松双黄酮的最佳提取工艺为:乙醇体积分数为50％,料液比为1∶13,超声提取3次,每次提取60 min,最佳工艺验证结果与模型预测值相差-2.55％.结果表明:星点设计-效应面法优选的穗花杉双黄酮和金松双黄酮的提取工艺,方法简便、可靠.     

铁筷子花瓣中花青素苷成分及含量对其呈色的影响北大核心CSCD

该研究以7个品种铁筷子(Helleborus thibetanus Franch.)为试验材料,借助目视测色、RHSCC比色卡、色差仪进行花色表型的测定,采用高效液相色谱法-光电二极管阵列检测方法(HPLC-DAD)及高效液相色谱-电喷雾离子化-质谱联用技术(HPLC-ESI-MS)测定分析铁筷子花瓣中花青素苷成分及含量,以探究不同品种铁筷子的花色与花青素苷成分及含量之间的关系。结果显示:(1)紫色系品种花瓣的a*值最高b*值最低,黄色系品种花瓣的b*值最高a*值最低,不同品种的铁筷子花色越深L*值越低。(2)从5个有花青素苷积累的铁筷子品种中检测出11种花青素苷成分,分别为6种矢车菊素苷,4种飞燕草素苷,1种矮牵牛素苷;供试的铁筷子材料中红色系2个品种的花青素苷含量最高,紫色系品种次之;矢车菊素苷与飞燕草素苷为影响铁筷子花瓣呈色的主要色素物质。(3)不同种类的花青素和修饰基团的差异,导致铁筷子花瓣呈现不同的色彩,含有多种酰基化修饰的飞燕草素苷使铁筷子花色蓝移进而使花色加深。(4)相关分析表明,铁筷子花瓣的L*值与a*值呈显著负相关关系,与b*值呈显著的正相关关系;L*值与总花青素苷含量呈显著负相关关系,且随着花青素苷含量的累积a*值增加,花色红移。研究表明,花青素苷的成分及含量是导致铁筷子花瓣呈现不同颜色的主要原因,矢车菊素苷和飞燕草素苷的互作以及酰基化的修饰使铁筷子呈现不同程度的紫色,花青素苷的不同累积量影响了花瓣颜色的明暗变化,从而使铁筷子花瓣颜色丰富。     

响应面优化纤维素酶辅助提取木豆叶总黄酮工艺

为探讨纤维素酶辅助提取木豆叶总黄酮最佳工艺条件,在单因素试验基础上,以酶用量、酶解温度、酶解时间和酶解pH为影响因子,总黄酮得率为响应值,采用Box-behnken中心组合设计建立4个影响因子与总黄酮得率关系的数学模型,进行响应面法分析。结果表明,纤维素酶辅助提取木豆叶总黄酮的最佳工艺条件为：酶用量为8.65 mg,酶解温度为33.88℃,酶解时间为2.02 h,酶解pH为5.02。在最优条件下总黄酮理论得率为4.86%,实测值为4.88%,拟合得到的模型与实际吻合良好。本研究建立的提取工艺条件稳定可靠,为以后木豆叶总黄酮的应用开发提供实验依据。     

ANTHOCYANIN SYNTHESIS IN SALPIGLOSSIS SINUATA

Measurements were made of the growth and pigment content of developing flower buds of Salpiglossis sinuata. From the time the buds were approximately 10 mm long they grew in length exponentially until they reached their final length. The logarithm of bud length increased linearly with time and served as a convenient morphological index on which to relate the progress of anthocyanin synthesis. Buds shorter than about 42 mm had no anthocyanin, but when buds reached this length, anthocyanin production was initiated and proceeded rapidly. The maximum relative pigment concentration (pigment/mg fresh weight) was attained by the buds about 17 hr after the initiation of pigment synthesis. In the mahogany-colored variety used in these studies, two anthocyanidins were found and identified as cyanidin and delphinidin. Buds excised from the plants could be cultured in vitro. Buds started in culture at a length of 30–35 mm when they contained no anthocyanins developed pigment during their growth. The amount of pigment formed increased with increasing light intensity, while only small amounts of pigment could be formed in buds cultured in darkness. The anthocyanidins of these cultured buds were the same as those of the intact flowers, but the ratio of delphinidin to cyanidin decreased with decreasing light intensity. Brief daily irradiation of dark-grown buds with red, far-red or blue light did not increase pigment synthesis nor change the anthocyanidin ratio. If buds were placed in culture at 20–25 mm and grown in darkness, they developed a third anthocyanidin, identified as malvidin, which was not present in intact flowers, light-grown buds or 30–35-mm buds cultured in darkness.