Article

The Anthocyanins of Strawberry, Rhubarb, Radish and Onion

Wiley
Journal of Food Science
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  • Independent Researcher
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Abstract

SUMMARY—The presence of a large number of previously unnoticed anthocyanins was demonstrated in strawberry, rhubarb, radish and onion. The number of anthocyanins found in this survey and those reported previously (in brackets) in each plant were: strawberry: 6 (4), rhubarb: 3 (2), radish: 13 (5), onion: 8 (3). Some of the chromatograms indicated that the number of anthocyanins present was even greater than that. A quantitative difference was found between the anthocyanin pattern of the examined varieties. The survey was carried out using paper chromatography on Whatman No. 3 MM paper with two new solvent systems of high resolving power. The solvents were: 1-butanol-benzene-formic acid-water (100: 19: 10: 25) and 1-butanol-formic acid-water (100: 25: 60).

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... The exterior skins were removed, air dried at room temperature and then soaked overnight in methanol at S 0 C. The methanol solution was maintained at or below S°C during concentration. Descending paper chromatography using butanol, formic acid, water (BFW) (100/2S/60, v/v/v) (9) was carried out at S°C in a cold storage room. From the BFW-developed chromatographs, selected bands of both suspected acylated and non-acylated pigments (Du and Francis, personal communication) were eluted, concentrated at S°C and further purified by rechromatography in 10%formic acid/water, v/v, atS 0 C. Seven fractions were obtained in this fashion (fable 1). ...
... Workers have reported that the pigment(s) was 'cyanidin-3-pentosa-glycoside' in Sutton's Blood red variety (15); 'a cyanidin monoside, a cyanidin diglycoside and a third cyanidin derivative' in Sutton's Blood red variety (8); 'peonidin-3-arabinoside' in Southport Red Globe variety (5) and '8 pigments' in Ruby and Southport Red Globe varieties (!},10). Fuleki (9,10) identified two pigments as cyanidin-3-glucoside and peonidin-3glycoside and a third pigment to be a new cyanidin-3diglucoside. This new pigment was subsequently identified by Du and coworkers (6) as cyanidin-3-laminariobioside. ...
... Du and coworkers found cyanidin to be the only anthocyanidin present and glucose to be the only glycosidating element. In unpublished work, Du and Francis used an extracting solvent which was low in mineral acid and recovered some of the previously unidentified bands noted by Fuleki (9,10). It was postulated that many of these pigments were acylated with non-cinnamic acid derivatives. ...
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Chromatographic fractions of the onion pigment profile were examined for acyaltion by alkaline hydrolysis, visible/UV spectral, IR spectral, GLC, and NMR techniques. Results indicative of acylation were shown by alkaline hydrolysis and IR spectral analyses. The suspected acyl portion was shown not to be a cinnamic acid by visible/UV spectral analysis. NMR and GLC methods failed to detect acylation in the onion pigment system. Small amounts of assay material, low sensitivity for detection of some of the possible acyl acids, removal of the acyl by complex formation, loss of the acyl due to high volatility and low acid transfer in partitioning systems are some of the factors identified as interfering with acyl detection.
... The pigments of red radish (Raphanus sativus L.) have been identified by previous workers (Harborne, 1963;Hayashi, 1962, 1963;Fuleki, 1969), the major ones being pelargonidin-3-sophoroside-5-glucoside with p-coumaric, ferulic and caffeic acid esterified to the sugar substituents. Pelargonidin (Pg) has an orange-red hue, and acylation would be expected to shift the hue to a longer wavelength (red hue) and impart improved stability. ...
... Comparison of retention times and spectra with pure standards (Fig. 2b) permitted the identification of acylating acids as p-coumaric (peak 3) and ferulic acids (peak 4). Caffeic acid, previously reported as an acylating acid in radish anthocyanins (Ishikura and Hayashi, 1963;Fuleki, 1969), was not found. Peak 1 corresponded to the saponified anthocyanin. ...
... Acid hydrolysis of the saponified radish anthocyanins resulted in only one anthocyanidin. The retention time and spectrum of the hydrolyzed pigment matched that of pelargonidin from strawberry, confirming previous identification of radish anthocyanins as Pg derivatives (Ishikura and Hayashi, 1962;Harborne, 1963;Fuleki, 1969). ...
Article
Red radish (Raphanus sativus L.) anthocyanins were extracted from liquid nitrogen powdered epidermal tissue using acetone, partitioned with chloroform and isolated using C-18 resin. The monomeric anthocyanin content, determined by pH-differential, was 154 ± 13 mg/100g epidermal tissue (pelargonidin-glucoside basis). Thermal processing of radishes showed that the pigments were stable to heat. Four major pigments were identified by Mass Spectroscopy, HPLC, and spectral analyses as pelargonidin-3-sophoroside-5-glucoside derivatives. The two major pigments were acylated with malonic acid and either ferulic or p-coumaric acid. The two other pigments were acylated with only ferulic or p-coumaric acid. Acylation increased pigment resistance to acid hydrolysis.
... Rhubarb has been touted as top source of antioxidant phenols (Dimitrios, 2006) based on its anthocyanin content of up to 2000 mg kg À1 (Clifford, 2000). Rhubarb contains two major anthocyanins, cyanidin 3-glucoside and cyanidin 3-rutinoside (Gallop, 1965;Wrolstad & Heatherbell, 1968;Fuleki, 1969). Cyanidin 3-glucoside has been shown to inhibit tumour promoter-induced carcinogenesis and tumour metastasis in vivo (Ding et al., 2006). ...
... Numerous minor peaks were observed in our chromatograms (a typical example is shown in Fig. 1), but their identities were unknown, so only proportions of the two major anthocyanins were reported. Wrolstad & Heatherbell (1968) reported that cyanidin 3-glucoside and cyanidin 3-rutinoside comprised 87% and 13% of the total anthocyanins, respectively, in the rhubarb variety, Canada Red. Fuleki (1969) examined four rhubarb varieties and found they contained cyanidin 3-glucoside and cyanidin 3-rutinoside in the following percentages: German Wine (33% and 66%), Sunrise (48% and 51%), Sutton's Seedless (48% and 50%) and Valentine (58% and 41%). A third anthocyanin was present in small quantities (1-2%) in all samples and was identified as a bioside of cyanidin. ...
Article
Antioxidant activity (ABTS assay), total phenolics and total anthocyanins were determined in the petioles of twenty-nine rhubarb (Rheum spp.) varieties. Antioxidant activity ranged from 463 ± 50 (Rheum officinale) to 1242 ± 2 μmol Trolox per g DW (Valentine). The phenolic content varied from 673 ± 41 (Loher Blut) to 4173 ± 23 mg GAE/100 g DW (Plum Hutt) and had a low correlation (r = 0.663) with antioxidant results. Seven of the varieties (Plum Hutt, Valentine, Minnesota No. 8, Cherry Red, Cawood Delight, Coulter McDonald and OR 23) had higher total phenolics than kale, a vegetable rich in phenolics. The concentration of anthocyanins ranged from 19.8 ± 1.5 (Crimson Red) to 341.1 ± 41.6 mg/100 g DW (Valentine). The percentages of two main anthocyanins in rhubarb, cyanidin 3-glucoside and cyanidin 3-rutinoside varied from 66.07:33.93, respectively, in Valentine to 9.36:90.64, respectively, in R. officinale.
... The total anthocyanins (TA) content of four different flower colors was measured according to the protocol within Equation 1 (Fuleki, 1969). The dried petal powder was 0.3 g and crushed to obtain three replicates, and soaked in 1% hydrochloric acid methanol solution for 24 hours at a constant volume of 25 mL. ...
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Introduction Flower color is one of the important ornamental traits in the plants, which plays an active role in attracting pollinators to pollinate plants and reproduce their offspring. The flower color of Impatiens uliginosa is rich, there are four main flower colors in nature: deep red, red, pink, and white. However, it remains unclear whether on four different flower colors mechanism of I. uliginosa. Methods We investigate colorimetric measurement, observation of epidermal cells, cellular pH determination, extraction and determination of total anthocyanins and flavonoid, semi-quantitative determination of pigment components, and gene cloning and qRT-PCR of CHS genes to study four flower colors of I. uliginosa. Results The L* and b* values were the highest in white flower, while the a* values were the highest in pink flower. The same shape of epidermal cells was observed in different flower colors, which was all irregular flat polygons, and there were partial lignification. Their cellular pH values were weakly acidic, while the pH values of the deep red flower was the highest and the white flower was the lowest. The highest pigment content of the four flower colors was total anthocyanin content. And malvidin-3-galactosidechloride (C23H25ClO12), cyanidin-3-O-glucoside (C21H21O11) and delphinidin (C15H11O7) were the main pigment components affecting the color of four different flower colors. The anthocyanin synthesis gene IuCHS was expressed in four flowers, and all three copies of it had the highest expression level in pink flower and the lowest expression level in white flower. Discussion These results revealed the influence of main internal factors on four different flower colors of I. uliginosa, and provided a basis for further understanding of the intracellular and molecular regulatory mechanisms of flower color variation, and laid a foundation for the improvement of flower color breeding of Impatiens.
... Berry total soluble solids (TSS) was measured using temperature compensated refractometer calibrated at Room Temperature of 25 o C. Titratable acidity was measured using titration method where in 10 ml of grape juice was titrated against 0.1 N sodium hydroxide using phenolphthalein as indicator. Peel anthocyanin concentration was estimated as per the procedure reported by Fuleki, (1969) using spectrophotometer and quantity of anthocyanin in the sample was calculated using cyanidin hydrochloride as standard and expressed as mg/100g fresh weight. Total phenol content in grape juice was estimated by spectrophotometric method using Folin Ciocalteu Reagent (FCR) as per the method developed by Singleton and Rossi, (1965 ...
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Crimson Seedless is a coloured seedless grape, gaining popularity in India for its attractive colour, bunch and berry quality with better shelf life. In cultivation of any seedless grape variety, application of GA3 at different stages is very much essential to produce good quality berries and bunches. However, this variety is highly sensitive to excess application of GA3 and practicing GA3 schedule similar to that of Thompson Seedless grapes adversely affects bunch quality. Hence, there was a need to standardize mild dose of GA3 just for rachis elongation which will help to reduce bunch compactness to a greater extent. Hence, an experiment was initiated to standardize concentration of GA3 for rachis elongation of Crimson Seedless grapes. Three different concentrations of GA3 {viz., 5 ppm (T1), 7.5 ppm (T2) and 10 ppm (T3)} were sprayed during pre bloom stage and compared with unsprayed control (T4). Among different treatments, pre-bloom spray of GA3@5 ppm could produce less compact bunches with highest average bunch weight, berry weight, berry length and TSS. However, bunches sprayed with 7.5 ppm and 10 ppm GA3 could also produce good quality bunches average berry weight and TSS was less. Because of severe coiling of rachis at 7.5 ppm and 10 ppm GA3 spraying, bunches were too straggly compared to spraying of 5 ppm GA3. The control bunches without GA3 spray produced very compact clusters with less average bunch weight, berry weight, berry diameter and berry length.
... Red radish anthocyanins were first identified in the 1960's [19,20] with predominantly pelargonidin forms, while purple radishes are composed mainly of cyanidin derivatives [21]. The major anthocyanins in red radish are pelargonidin-3-sophoroside-5-glucoside (P) with malonic acid and either ferulic (PFM) or p-coumaric acid (PCM) moieties, while the two secondary anthocyanins are P with either ferulic or p-coumaric acid [22,23]. ...
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Red radish anthocyanins are relatively stable due to the acylation of anthocyanins with organic and phenolic acid moieties. The objective of this study was to create and identify a novel ethyl-bridged acylated anthocyanin with a stable violet color from red radishes in the presence of acetaldehyde and catechin. After incubation at ambient temperature for one week at 21 °C the reaction mixture with acetaldehyde and catechin turned from bright red to a vivid purple color. The newly formed compounds were tentatively identified with liquid chromatography-electrospray ionization-mass spectrometry. Color stability (CIE L*C*h) was monitored over six months at 21 °C and anthocyanin stability was evaluated by HPLC. Next, radishes were fermented by Zymomonas mobilis, a high acetaldehyde producing bacteria. Natural sources of catechin were used to replace the catechin standard, but the same purple color did not appear with the addition of cocoa powder or fava beans. The ethyliden-bridged radish anthocyanins possess excellent color stability and could serve as a natural food colorant.
... The superiority of the extracts prepared from the roots of the red radish in terms of the TPC over their counterparts prepared from the roots of the white radish could be due to the presence of the red color. It has been reported that the red and blue colors of plants are due to the presence of anthocyanin pigments which are major natural phenolic compounds and are water soluble glycosides and acyl glycosides of anthocyanidins (Fuleki, 1969). Al-Hassan et al (2006) isolated new pigment from aqueous extract of Iraqi red radish peels and according to the obtained spectroscopic and chromatography data, a proposed structure of the anthocyanin of Iraqi red radish peels was suggested to be Raphanusin A (pelargonidin-3p-coumaroyl sophoroside-5-glucoside). ...
... Radish is an easy vegetable to grow and can be harvested within 4-6 weeks (Giusti et al. 1998a), and the yield of roots is very high. The anthocyanins responsible for red and purple radishes have been successfully extracted and characterized by different researchers (Ishikura, Hayashi 1962;Harborne 1963;Fuleki 1969;Otsuki 2002). The use of red radish anthocyanins extract was assessed (Giusti, Wrolstad 1996) and the colour characteristics were found very stable storage at room temperature (Giusti et al. 1998b). ...
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Red anthocyanins from Carmine radish is rich both in root flesh and peel and it is relatively simple and efficient to extract these compounds. The accumulation, distribution and content of anthocyanins in root are related to phenylalanine ammonia lyase (PAL) activity, soluble sugar and chlorophyll contents. The results showed that anthocyanins were synthesized at the first day of seed germination and were most abundant in the top of hypocotyls. The content of anthocyanins was higher in the root peel than in flesh and root apex, and in aboveground parts compared with underground sections. The anthocyanins contents in cotyledon grown under light and dark and hypocotyls grown in the dark increased initially and then reduced, and in roots grown under light was higher than in those grown in the dark. Chlorophyll content in leaves fluctuated but increased overall, whereas it was almost unchanged in the petioles. The correlations between anthocyanins content and PAL activity, soluble sugar and chlorophyll contents in different treatments showed positive by Day 4 then negative. These results are helpful to understand the mechanism of anthocyanins biosynthesis in carmine radish.
... Radish includes raphanin that act as anti-bacterial, fungal, tumors, and reduces the normal p roduction of thyroid hormones. It has been found that anthocyanin (ACN) pigments are responsible for red and purple radishes (Tibor, 2006). It's one of the flavonoid compounds, soluble in water, and the color changes according to pH, they are odorless and may be found in different parts of the plant (Park et al., 2011).Biosynthesis of anthocyanin pigments as all other flavonoids are assembled from two different cascades of chemical raw materials in the cell. ...
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Medicinal plants have the ability to synthesize different compounds that have important biological functions. These compounds in plants mediate their effect on the human body. This enables the plants to have a beneficial pharmaceutical effect, but also with some side effects, one of these plants is the Red Radish, which produces different compounds such as pigment, that is chemically related to anthocyanin. In this study, the effects of this crude pigment at different concentrations (200, 100, 50, 25, 12.5) µg/200µl on several locally isolated pathogenic bacteria (Escherichia coli, Klebsiellia pneumoniae, Pseudomonas aeruginosa, and Staphylococcus aureus) showed, no effect at all. Also, this study aimed to find the counteract proliferation ability of this crude pigment extract on two types of cell lines (RD and L20B). Depending on inhibition rate, the crude pigment exhibited excellent affectivity against cancer cell lines, but with various degrees depending on the usable concentrations. On the other hand, DR cell line was more sensitive than L20B despite the effectiveness of pigment on both cell lines. Whereas, Interleukins (TNF-α, INF-γ, and IL-1β ) analysis of all tested concentrations of pigment in both cell lines showed, significant elevation (P≤ 0.05 ) of these cytokines in comparison with the control group. Thus we can concluded, the cytotoxic effects of red radish pigment depends on the type of cell line used, the concentration of the crude pigment extract, and the duration of the exposed time. And this pigment has an excellent effect on cancerous tissues throughout induction of tumor cells to produce pro-inflammatory cytokines.
... These pigments are formed as the fruit matures and ripens. Examples are for strawberries (Fuleki, 1969), certain varieties of cranberries ( Lees and Francis, 1971;Zapsalis and Francis, 1965), apples (Bishop and Klein, 1975;Proctor and Creasy, 1971), black grapes ( Liao and Luh, 1970) and blueberries (Suomalainen and Keränen, 1961). Anthocyanins are synthesized at an increasing rate during maturation reaching a maximum in a fully ripe fruit ( Rodrigo et al., 2012). ...
... Fuleki (7,8) reported 8 anthocyanin pigments in Ruby and Southport Red Globe onions. Du and Francis (personal communication) found cyanidin to be the anthocyanin and glucose to be the only glycosidating moiety present in the system. ...
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The role of acidifying agent in extracting anthocyanins from red onions was investigated. Cl⁻ of HCl disrupted complex structures present in onion tissue to release anthocyanins and also induced formation of other complexes containing the pigment. Formate did not produce these effects. A schematic was developed to illustrate the interaction and decomposition of anthocyanin fractions during HCl extraction. The implications of the presence of Cl⁻ in the extractant on interpretation of extraction results were discussed. Anthocyanins possibly acylated with non-cinnamic acids were considered to be particularly affected by mineral acids in the extractant.
... Total soluble solid (TSS) of juice was determined with refractometer and results were reported in degree Brix. Estimation of total soluble protein was done by following the method described by Lowry et al. (1951).Total anthocyanin content of the fruit juice was determined by measuring absorbance at 540nm (Fuleki,1969). Total phenol content was estimated by spectrophotometric method described by Malick and Singh, 1980. ...
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Aril browning (AB) is one of the major physiological problems of pomegranate, resulting in diminution of quality and commercial value of the fruits. The present study was taken up to investigate the biochemical changes in pulp and seed of aril browning affected fruit in comparison with healthy fruits. Biochemical studies revealed that AB affected aril had higher total sugars (84.45 mg g-1 fresh weight of tissue), reducing sugar (53.40 mg g-1 fresh weight of tissue), TSS (16.3%) and starch (194.96 mg g-1 of tissue dry weight) as compared to healthy aril. Whereas, protein content was lower in AB affected seeds (6.92 mg g-1 FW of tissue) as compared to healthy seeds (7.832 mg g-1 FW of tissue). There was a gradual decrease in anthocyanin (from 0.53 to 0.33 mg 100-1 g) and total phenol content (from 141.25 to 109.70 mg 100-1 g) with the increase in intensity of browning. AB affected seeds showed reduced activities of enzyme like amylase (7.36 mg maltose liberated h-1 g-1 of protein) and total dehydrogenase (1.44 ΔA485 g-1 fresh weight of tissue), in contrast to this there was increased activity of enzyme polyphenol oxidase (0.0063 ΔA412mg-1 protein min-1) as compared to seed of healthy aril.
... The genus Allium in Alliaceae contains important vegetables, some of which are colored with anthocyanins. Earlier studies (Robinson and Robinson, 1932;Fouassin, 1956;Brandwein, 1965;Fuleki, 1969Fuleki, , 1971Du et al., 1974;Kenmochi and Katayama, 1975) on the anthocyanin content of red onion (Allium cepa L.) showed that the main pigment in the cultivars 'Ruby', 'Southport Red Globe' and the Japanese variety 'Kurenai' was cyanidin 3-glucoside. Cyanidin 3-laminariobioside occurred as the next largest component together with smaller amounts of several uncharacterized cyanidin derivatives. ...
Article
Three red onion (Allium cepa) cultivars, top onion (A. cepa var. vivi-parum), A. altaicum and chive (A. schoenoprasum) contained several or all of the following anthocyanins: 3-(6′-malonyl-3′-glucosylglucoside), 3-(3′,6′-dimalonylglucoside), 3-(6′-malonylglucoside), 3-(3′-malonyl-glucoside), 3-(3′-glucosylglucoside) and 3-glucoside of cyanidin. Trace amounts of two pelargonidin derivatives and the 3,5-diglucosides of cyanidin and peonidin were for the first time reported in red onion. Carbon NMR data showed that the sugars of the 3-(6′-malonyl-3′-glu-cosylglucoside), 3-(6′-malonylglucoside) and 3-glucoside of cyanidin were pyranoses. Substitution either by sugar or acid in the sugar 3-position of an anthocyanin has never been reported outside the genus Allium.
... The different susceptibilities of fruit juice anthocyanins to H 2 O 2 may be due to their varying anthocyanidin composition. The cyanidins were reported as the main anthocyanidins in pomegranate seed coats (Du, Wang, & Francis, 1975) and sour cherries (Dekazos, 1970), whereas the pelargonidins were reported as the major ones in strawberries (Fuleki, 1969). Thus, higher resistance of sour cherry and pomegranate juice anthocyanins to H 2 O 2 may be attributed to the presence of cyanidins in these juices. ...
Article
Degradation kinetics of anthocyanins was studied in sour cherry nectar, pomegranate and strawberry juices at high hydrogen peroxide (H2O2) concentrations (9.31–27.92 mmol l−1) at 10–30 °C and in only sour cherry nectar at low H2O2 concentrations (0.23–2.33 mmol l−1) at 20 °C. Degradation of anthocyanins followed the first-order reaction kinetics. Sour cherry anthocyanins were the most resistant to H2O2, followed by pomegranate and strawberry anthocyanins. Degradation of anthocyanins was also studied in sour cherry nectar and pomegranate juice in the presence of ascorbic acid at 60 and 80 mg l−1 concentrations at 20 °C. At 80 mg level, ascorbic acid significantly accelerated the degradation of anthocyanins in sour cherry nectar at 4.65, 6.98 and 9.31 mmol l−1 H2O2 concentrations. In contrast, ascorbic acid at both 60 and 80 mg levels protected the anthocyanins from degradation by H2O2 in pomegranate juice.
... Recently, red radish (Raphanus sativus L.) root anthocyanins have been widely used as natural food colorant because they are potential alternatives to synthetic dyes (Giusti and Wrolstad, 2003). These anthocyanins have been identified by several research groups (Fuleki, 1969;Harborne, 1964;Ishikura and Hayashi, 1962, 1963, and the presence of pelargonidin and cyanidin derivatives was reported in red and purple roots of red radish cultivars, respectively. Moreover, several groups (Giusti et al., 1998;Mori et al., 2006;Otsuki et al., 2002;Tatsuzawa et al., 2008) characterized the structures of acylated pelargonidin glycosides from the red roots of red radish cultivars; however, a detailed structural study of the purple root anthocyanins of red radish cultivars has not been reported until now. ...
Article
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Four new acylated cyanidin glycosides were isolated from the purple root peers of Raphanus sativus L. ‘Benikanmi’, along with five known anthocyanins. These pigments were based on cyanidin 3-sophoroside-5-glucoside, and acylated diversely with malonic, p-coumaric, caffeic, and ferulic acids. Two pigments of these four new anthocyanins were determined to be cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] and cyanidin 3-[2-(glucosyl)-6-(cis-p-coumaroyl)-glucoside]-5-[6-(malonyl)-glucoside] by chemical and spectroscopic methods. Since two other new pigments were obtained in small quantities, their structures were tentatively assigned to be malonyl cyanidin 3-sophoroside-5-glucoside and malonyl cyanidin 3-[2-(glucosyl)-6-(trans-caffeoyl)-glucoside]-5-glucoside, mainly on the basis of their spectroscopic data. From the results, the potential of these purple root anthocyanins as natural food colorants is discussed. http://www.jstage.jst.go.jp/article/jjshs1/79/1/79_103/_article
... From the chemotaxonomic point of view, there are two typical glycoside patterns in the Cruciferae at OH-3 position of anthocyanins, such as acylated 3sambubioside (Bloor and Abrahams, 2002;Honda et al., 2005;Saito et al., 1995Saito et al., , 1996Takeda et al., 1988;Tatsuzawa et al., 2006Tatsuzawa et al., , 2007Tatsuzawa et al., , 2008a) and 3-sophoroside (Fuleki, 1969;Giusti et al., 1998;Harborne, 1964;Hrazdina et al., 1977;Idaka et al., 1987a, b;Igarashi et al., 1990;Ikeda et al., 1987;Hayashi, 1962, 1963;Mori et al., 2006;Nakatani et al., 1987;Otsuki et al., 2002;Saito et al., 2008;Suzuki et al., 1997;Tanchev and Timberlake, 1969;Tatsuzawa et al., 2008b); therefore, the floral anthocyanins of L. maritima are grouped into the former pattern. HMBC of 1 is indicated by dotted arrows. ...
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Six acylated pelargonidin 3-O-sambubioside-5-O-glucosides were isolated from red-purple flowers of Lobularia maritima (L.) Desv. ‘Easter Bonnet Deep Rose’. These pigments were determined by chemical and spectroscopic methods to be pelargonidin 3-O-[2-O-(2-O-(acyl-II)-β-xylopyranosyl)-6-O-(acyl-I)-β-glucopyranoside]-5-O-β-glucopyranoside, in which the acyl-I group was replaced by 4-O-glucosyl-p-coumaric acid, p-coumaric acid or ferulic acid, and acyl-II by caffeic acid or ferulic acid, respectively. In comparison with the floral anthocyanins of purple-violet flowers in L. maritima cultivar ‘Easter Bonnet Violet’, the molecular composition of organic acids and sugars of ‘Easter Bonnet Deep Rose’ were identical, however, aglycones of both cultivars were different, and pelargonidin is the floral anthocyanin of ‘Easter Bonnet Deep Rose’ and cyanidin is that of ‘Easter Bonnet Violet’. Variations of the flower colors of these cultivars are responsible for the aglycone component in their floral anthocyanins. In this paper, the relation between flower color and anthocyanins in L. maritima cultivars is discussed. http://www.jstage.jst.go.jp/article/jjshs1/79/1/79_84/_article
... The major difference between purple carrot and red radish was the structure of their anthocyanins , although purple carrot also displayed lower anthocyanin concentrations. For purple carrot, the main pigments derived from cyanidin and for red radish from pelargonidin, as reported by Harborne and Grayer (1988) and Fuleki (1969). Cyanidin derivatives, previously described by Hrazdina et al. (1977) and Idaka (1987), were also found in red cabbage. ...
Article
Anthocyanin extracts are increasingly used as food ingredients. A current challenge is to maintain their color properties. The stability of some colorants has been studied in sugar and non-sugar drink models at three pH values (3, 4, and 5) under thermal and light conditions simulating rapid food aging. At a given pH, color stability mainly depends on the structures of anthocyanins and of colorless phenolic compounds. Colorants rich in acylated anthocyanins (purple carrot, red radish, and red cabbage) display great stability due to intramolecular copigmentation. The protection of red chromophore is higher for diacylated anthocyanins in red radish and red cabbage. For colorants without acylated anthocyanins (grape-marc, elderberry, black currant, and chokeberry), intermolecular copigmentation plays a key role in color protection. Colorants rich in flavonols and with the highest copigment/pigment ratio show a remarkable stability. By contrast, catechins appear to have a negative effect on red colorants, quickly turning yellowish in drink models. This effect is more pronounced when the pH is increased. Finally, color does not seem to be greatly influenced by the addition of sugar.
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Guava fruits are a rich source of carotenoids, lycopene, and anthocyanin pigments. Colored guava fruits contain a higher concentration of these pigments in comparison to white pulped varieties. The aim of this study was to evaluate the suitability of color reader values for indirect estimation of pigment content in guava fruits. Using the CIELAB’s color space values (L*, a*, b*, C*, and h°), we quantitatively estimated the variations in pulp color (white, red, and purple) across 35 guava genotypes, including hybrids and germplasm. Using spectrophotometric methods, the contents of total carotenoids, lycopene, and anthocyanins were estimated, revealing significant discrepancies among the genotypes. The color value a* was positively correlated with total carotenoids (rp = 0.81, rg = 0.85 at p < 0.01), total lycopene (rp = 0.86, rg = 0.93 at p < 0.001) and total anthocyanin contents (rp = 0.56, rg = 0.52 at p < 0.001). The phenotypic path analysis revealed that total carotenoids (0.31), lycopene (0.51), and anthocyanin (0.13) contents exerted a positive direct effect on color a* value, while genotypic path analysis demonstrated a direct positive effect by lycopene (1.12) and an indirect positive effect by carotenoids (1.02) and anthocyanins (0.63) mediated through total lycopene. These findings suggest that each pigment contributes uniquely to the color a* values, with lycopene being the primary contributor.
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The quality of radishes depends on the production environment and postharvest management throughout the supply chain. Quality monitoring is therefore important for post-harvest management in the supply chain. Here we estimate the quality of radishes by non-destructive methods based on color and shape using a random forest algorithm in a data-driven predictive model. The explanatory variables (i.e., color and shape) were obtained by capturing images of radish under a controlled photographic environment. Color information was converted from RGB to HSL or HSV to minimize potential effects of light conditions on the radish surface. Model performance was assessed using Pearson’s correlation coefficient (COR), Nash-Sutcliffe efficiency (NSE), and root mean squared error (RMSE). Experimental results indicate high model performance, supporting the applicability of non-destructive weight estimation using only radish color and shape. Among the models using different color components, the HSV model exhibited the best result of all performance measures in this study (i.e., COR, NSE, and RMSE were 0.889, 0.776, and 1.55, respectively). In accordance with the radish variety in this study, the R value was the most important variable among all color components. Partial dependence plots provided more detailed visual relationships between each unique pair of color components and radish weights. This method is promising for application in other photographic environments, specifically where sunlight is present. Further studies on the assessment of internal conditions of fresh radish such as vitamin C and anthocyanin could be useful for consumer-oriented quality assessment in future.
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An attempt was made to analyze the morphological, biochemical and molecular diversity in karonda (Carissa carandas L.) populations maintained at Indian Institute of Horticultural Research in Bangalore, India, using a multivariate analysis approach.Morphological and biochemical traits were recorded andevaluated for variance and mean comparisons.Sequence Related Amplified Polymorphism (SRAP) molecular markers were used for generating information on genetic variation and relationships among the accessions. Significant variation was found in fruit related morphological characters and fruit quality traits. The combined analysis used in this study successfully categorized the different karonda accessions into various clusters based on the genetic diversity and also established relatedness among them. Mantel test was used for comparing the distance matrices derived from morphological, biochemical and molecular markers. High correlation was found between Euclidean distance matrices of biochemical and morphological data. This work will be useful for the breeders working on this future crop for characterization, genotype identification and selection of parents. Keywords Karonda, Morphological variability, SRAP markers, Genetic diversity, Biochemical markers
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The present investigation was carried out to understand the temperature induced dynamics of berry anthocyanin development and berry quality in wine grape (Vitis vinifera L.) cultivars Shiraz and Cabernet Sauvignon. Temperature variations during fruit maturation period were achieved by altering the pruning dates. Vines were pruned at weekly intervals starting from third or fourth week of October to the end of November. The changes in berry quality parameters such as total soluble solids (TSS), titratable acidity, total anthocyanins, total phenols and total flavonoids were recorded at weekly intervals starting from veraison to harvest. All the quality parameters were significantly higher in early pruned vines of both the cultivars indicating that the best time for pruning to get good quality wine grapes is during the third or fourth week of October. The major quality parameter affected by the temperature during the berry maturation stage was total anthocyanin content. Maximum and minimum temperature (weekly average) during different week from veraison to harvest were recorded. Early pruned vines exposed to a mean day/night temperatures of 30.7°C/14.9°C and 29.6°C/14.1°C in cv. Shiraz and late pruned vines exposed to a mean day/night temperatures of 32.0°C/16.2°C and 32.1°C/16.0°C in cv. Cabernet Sauvignon during 2010 and 2011 respectively. The pattern of anthocyanin development during the berry maturation period (veraison to harvest) indicated that the maximum anthocyanin accumulation was in the second and third week of March; the concentration decreased thereafter irrespective of dates of pruning in both the cultivars during the two years of the study. Correlation coefficients between the skin anthocyanin content and mean maximum and minimum temperatures showed a negative relationship in both the cultivars indicating that the increase in both maximum and minimum temperatures caused a reduction in anthocyanin content at harvest in late pruned vines.
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Wine quality is determined by the stage of harvest of grapes. In order to understand the effect of ripening stages on the berry aroma and antioxidant quality, berries were grouped into three categories, namely: (a) full ripe (before skin shriveling); (b) partially shriveled; and (c) 75% shriveled berries. Total terpenoids, alcohols, hydrocarbons, radical scavenging capacity (DPPH), and total anthocyanins were higher in grapes harvested at full ripe stage, when compared to other stages. Therefore, for better aroma and antioxidants in wines, grapes should be harvested at full ripe (no shriveled berries) stage instead of overripe shriveled berry stages.
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Fruits from five accessions of mulberry (Morussp.) representing Morus nigra, Morus lavigeta, and Morus alba were evaluated for ferric reducing antioxidant potential, diphenyl picryl hydrazyl radical scavenging ability, total phenols, flavonoids, anthocyanins, and ascorbic acid contents. In fresh fruits, higher antioxidant capacity was found in M. nigra followed by M. lavigeta and the lowest capacity was observed in M. alba. Higher ferric reducing antioxidant potential and diphenyl picryl hydrazyl scavenging capacities were mainly due to higher anthocyanins. Among the black accessions evaluated, Acc. No. 362 and 497 recorded the highest ferric reducing antioxidant potential (4,515.75 and 4,224.24 mg ascorbic acid equivalent antioxidant capacity 100 g dry wt, respectively), diphenyl picryl hydrazyl (IC50 values of 0.124 and 0.116 mg, respectively), and anthocyanin (4,255.65 and 4,103.93 mg/100 g dry wt, respectively) content when compared to other accessions. Accession number 249 (M. alba) with white colored fruits recorded the lowest antioxidant capacity. A phenolic acid profile of fruits indicated that these accessions are rich in caffeic and gallic acids. Gentisic and protocatechuic acids were also found in fairly good quantities. Dried fruits also recorded very high antioxidant (0.18–2.32 g ascorbic acid equivalent antioxidant capacity 100 g dry weight) and diphenyl picryl hydrazyl radical scavenging abilities (IC50 of 0.3–2.98 mg, quantity needed for removing 50% of diphenyl picryl hydrazyl radicals). Results indicated that black mulberry fruits could be used for preparation of high antioxidant postharvest products.
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Three novel acylated pelargonidin 3-sophoroside-5-glucosides were isolated from the root peels, petioles and flowers of red radish, Raphanus sativus ‘Cherry Mate’, in addition to five known anthocyanins namely, pelargonidin 3-sophoroside-5-glucoside, pelargonidin 3-[2-(glucosyl)-6-(trans-p-coumaroyl)-glucoside]-5-glucoside, pelargonidin 3-[2-(glucosyl)-6-(trans-feruloyl)-glucoside]-5-glucoside, pelargonidin 3-[2-(glucosyl)-6-(trans-p-coumaroyl)-glucoside]-5-(6-malonylglucoside) and pelargonidin 3-[2-(glucosyl)-6-(trans-feruloyl)-glucoside]-5-(6-malonylglucoside). The structures of three new acylated anthocyanins were shown to be pelargonidin 3-O-[2-O-(β-d-glucopyranosyl)-6-O-(trans-caffeoyl)-β-d-glucopyranoside]-5-O-(6-O-malonyl-β-d-glucopyranoside), its demalonyl derivative, and pelargonidin 3-O-[2-O-(β-d-glucopyranosyl)-6-O-(cis-p-coumaroyl)-β-d-glucopyranoside]-5-O-(6-O-malonyl-β-d-glucopyranoside). These pigments were the main components present not only in the root but also in the petioles and flowers of red radish. p-Coumaroyl anthocyanins were the main pigments found in the root, petioles and flowers. Although the trans-p-coumaroyl form was abundant in all three plant organs, its cis form was present in very low amount within the root but in large amount in the flowers and petioles.
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It is possible to select strawberry cultivars that give a satisfactory, naturally coloured canned product as an alternative to the commercially dyed one. Spectrophotometric measurements of the syrup from cans, the canned fruit and fresh fruit were compared with visual scoring. A preliminary screening for colour based on visual assessment of fresh flesh colour is possible.
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The effectiveness of gamma radiation as an enhancer of anthocyanin and flavonol pigment synthesis in cranberries was determined. Three different maturities of cranberries, based on their degree of coloration, and radiation levels of 150 and 300 krad were employed. The changes in the anthocyanin and flavonol pigments were measured quantitatively at regular intervals during storage. Radiation had a beneficial effect on the pigmentation of full-red cranberries and resulted in a significant increase in the anthocyanin and flavonol pigment contents. Effects on the less colored berries were not as great and in some cases flavonoid synthesis was reduced. The radiation induced changes were strictly quantitative in nature and there were no qualitative changes in the anthocyanins and flavonols. The visual effects of radiation on cranberries were minor softening and a stimulation of pigment production in the endocarp area of the fruit, resulting in internal coloration of the fruit. It was concluded that gamma radiation has an effect on the biosynthesis of the pigments involved and that the maturity stage of the cranberries was the controlling factor in determining the degree of response to radiation treatment. A possible mode of action of radiation on flavonoid synthesis was postulated.
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Different one- and two-dimensional NMR techniques were used to elucidate the structural conformation of purified anthocyanins obtained from red radish (Raphanus sativus). Two novel diacylated anthocyanins, pelargonidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside] 5-O-(6-O-malonyl-β-glucopyranoside) and pelargonidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside] 5-O-(6-O-malonyl-β-glucopyranoside), were characterized. Two other monoacylated anthocyanins were determined to be pelargonidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-d-glucopyranoside] 5-O-(β-glucopyranoside) and pelargonidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside] 5-O-(β-glucopyranoside). Three-dimensional conformation of the molecule was investigated using NOESY techniques, which showed proximity between hydrogens from the cinnamic acid acylating group and the C-4 of the pelargonidin. Keywords: Anthocyanins; red radish (Raphanus sativus L.); 1D and 2D NMR; pelargonidin derivatives
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Fresh fruits of tart cherries (Prunus cerasus L. var. Montmorency) were extracted with acidic methanol. The anthocyanin pigments were isolated and purified by conventional paper chromatography. They were identified by spectral and Rf data and by acid hydrolysis. The pigments were cy anidin-3-glucosylrutinoside, cyanidin-3-glucosylsambubioside, cyani-din-3-sophoroside, cyanidin-3-rutinoside, cyanidin-3-glucoside and peoni-din-3-rutinoside. No free cyanidin or peonidin was found. Cyanidin-3-glucosylsambubioside, reported in cherries for the first time, was also found in the varieties of English Morello, Early Richmond and Meteor
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The colour stability of juice and purées made from a mixture of two strawberry varieties, stored at + 20°C or at –20°C under aerobic and anaerobic conditions, was studied. High-performance liquid chromatography and spectrophotometric analysis were used to monitor the changes in colour during storage. Pelargonidin 3-glucoside comprised 80% of the total anthocyanin content. Four other pelargonidin-based peaks were found, being 10.4%, 3.5%, 0.7% and 0.3% of the total and two cyanidin peaks were present, being 3.3% and 0.4% of the total. Clarification before storage caused considerable losses in the initial anthocyanin concentrations. Storage conditions (air versus nitrogen) did not influence the rate of loss of anthocyanins during storage or the formation of polymeric pigments. There were no losses in anthocyanins and no increase in the amount of colour measured at 510 nm due to polymers in samples stored at–20°C. Polymerisation occurred in the samples stored at + 20°C, especially in the clarified samples.
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SUMMARY– Seven cyanidin and one peonidin glycosides were found in the bulbs of the Ruby and Southport Red Globe varieties of red onion. The major anthocyanin and the one present in second largest quantity were identified on the basis of their chromatographic and spectral properties as cyanidin 3-glucoside and cyanidin 3-diglucoside, respectively. The cyanidin 3-diglucoside was not found identical with either the 3-sophoroside or the 3-gentiobioside of cyanidin, therefore, this pigment is not only a “new” compound but it also represents a “new” glycosidic class for antho-cyanins. The peonidin monoside present only in minor quantity was identified as peonidin 3-glucoside.
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Physico-chemical changes, organic acids content and activities of enzymes related to softening, glycolytic, gluconeogenic and organic acids metabolism were studied from 70 to 100 days after anthesis in ripening of berries of Gulabi grape. Uneven ripening was observed in 70 day old clusters. The disorder affected 22.76 and 32.38% of berries in bunches harvested at 90 and 100 days, respectively. Unripe berries had less dry matter, sugars, skin anthocyanins and more seed, fresh weight and acidity compared to ripe berries. Green berries had more malic and less tartaric acid, while brown berries had less malic acid and black berries contained more tartaric acid. Green berries contained more polygalacturonase, cellulase, hexokinase, glucose 6-phosphatase, phosphoenol pyruvate carboxylase, pyruvate decarboxylase and polyphenol oxidase activities than ripe fruit. Brown berries contained the highest phosphofractokinase, malate and glutamate dehydrogenase activities, and black berries had the highest activities of pectinesterase, fructose 1,6-bisphosphatase and malic enzyme. The role of dry matter, malic acid, pectinesterase and certain enzymes of gluconeogenic and organic acids metabolism in uneven ripening is discussed.
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Degradations were studied at different hydrogen peroxide (H2O2) concentrations (9.31 to 27.92 mmol. L1) over a range of 10° to 30 °C. Degradation of anthocyanins by H2O2 was described by first-order function. Comparison of t1/2 values revealed that sour cherry anthocyanins were the most resistant to H2O2, followed by pomegranate and strawberry anthocyanins. Thus, the removal of residual H2O2 from the juice contact surfaces of aseptically packaged strawberry juices should be controlled more carefully to prevent anthocyanin degradation. Respective Ea values were between 9.4 to 11.1, 9.5 to 11.4, and 11.4 to 12.2 kcal.mol1; and Q10 values between 1.59 to 2.22, 1.62 to 2.05, and 1.76 to 2.36 for strawberry, sour cherry, and pomegranate anthocyanins.
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Informations on root flavonoids have been extensively reviewed and their functional diversity critically appraised. Root flavonoids play significant roles in protecting the plants against pests and diseases, regulating root growth and functions, influencing different aspects of nitrogen cycle and exerting allelopathic growth effects. They also constitute an essential source of Pharmaceuticals. An exhaustive list of flavonoids which are of significance in relation to these properties has been compiled. A thorough understanding of the flavonoid composition, level, metabolism and regulation in the roots of various plants may help us in developing several applied topics. Safe and specific chemicals against root pests; chemicals regulating root growth and mineral nutrition; plant varieties resistant to root pests and adverse allelopathic effects; an improved nitrogen economy in agroecosystems; desirable varieties of medicinal plants, in whose roots flavonoids are the active principles; in vitro systems for flavonoid production obtained from root cultures, at a commercial scale.
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The antioxidant and pro-oxidant potential of an extract from red radish, in which the major compounds were acylated pelargonidin derivatives, were assessed with a variety of assays in vitro. The extract appeared to form a complex with Fe(3+) or Cu(2+). It displayed a concentration-dependant reducing power (1.16OD(700 nm) at a concentration of 4mM) and scavenging effect against 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals (with IC(50)=1.74 +/- 0.03 mM). It could promote the cleavage of plasmid DNA with Cu(II)/H(2)O(2) or Cu(II) alone. This DNA damage could be inhibited by horseradish peroxidase, catalase, and EDTA, respectively. The extract also showed growth inhibition of Bel-7402 cells at lower concentration. The results suggested that the formation of reactive oxygen species might be involved in the mechanism of DNA damage. The acylated pelargonidin derivatives extracted from red radish could act as antioxidant and pro-oxidant and their antioxidant and pro-oxidant properties were relative to the reaction conditions. It might provide novel antioxidant and anticarcinogenic agents.
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In der vorliegenden Arbeit wird durch Stufenkontrollen bei der Herstellung von Fruchtsäften geklärt, welchen Einfluss klassische und moderne Verfahrenstechnologien auf die antioxidativ wirksamen Inhaltsstoffe von Apfel- und Beerensäften haben. Ziel ist es, Fruchtsäfte mit hohen, optimierten Gehalten antioxidativ wirksamen Inhaltsstoffe (Polyphenolen, antioxidative Vitamine) bei hoher Stabilität und sensorischer Qualität herzustellen. Dabei müssen in der Fruchtsaftherstellung speziell die Polyphenole auf eine neue Art betrachtet werden. Es wurde hauptsächlich Apfel- und schwarzer Johannisbeersaft untersucht. Weiterhin wurde die Herstellung von Holunder-, Brombeer-, Stachelbeer- und Sauerkirschsaft sowie die Herstellung von Fruchtweinen und die Veränderung von antioxidativ wirksamen Inhaltsstoffen bei der Reifung von Erdbeeren untersucht. Zur Bestimmung der antioxidativen Kapazität in wässrigen Proben wurde der ABTS+.-Radikalkationen-Test (TEAC assay) verwendet und den Anforderungen entsprechend modifiziert. Eine neue Methode zur Analytik der Polyphenole mittels HPLC an einer fluorierten RP-Phase und einer Detektion mittels DAD und ECD wurde entwickelt. Es zeigt sich grundsätzlich, dass Beerensäfte aufgrund der hohen Polyphenolgehalte eine deutlich bessere Quelle für Antioxidantien für die menschliche Ernährung sind, als Apfelsäfte mit vergleichsweise eher geringen Polyphenolgehalten. Als wichtigste Einflussgröße zum Erreichen einer hohen antioxidativen Kapazität im Endprodukt zeigte sich die Wahl der Rohware, da sich verschiedene untersuchten Apfel- bzw. schwarze Johannisbeersorten teilweise erheblich in ihren Gehalten an antioxidativ wirksamen Inhaltsstoffen unterscheiden. Die Wahl der richtigen, polyphenolreichen Rohware stellt die Grundlage für eine hohe antioxidative Kapazität im späteren Produkt dar. Bei der Herstellung von Apfelsaft wurden die Einflüsse auf die antioxidative Kapazität und die Polyphenole von Entsaftung, Maischestandzeit, fruchteigener Polyphenoloxidasen, industriellen Entsaftungssystemen, Separation, thermischer Belastung, Lagerung, Schönung mit Gelatine, Ultrafiltration, der Stabilisierung von ultrafiltriertem Saft mit PVPP oder Adsorberharz und Laccase/O2-Behandlung mit anschließender Ultrafiltration untersucht und bewertet. Bezogen auf den frischen Presssaft wurden bei der Herstellung von naturtrübem Apfelsaft ein Verlust an antioxidativer Kapazität durch Separation und Oxidation von 20 - 40% festgestellt. Oxidationsprozesse konnten durch eine KZE des frischen Presssaftes unterbunden werden. Die drei Verfahren in Verbindung mit der Ultrafiltration zur Herstellung von klarem Apfelsaft zeigte hohe Verluste an antioxidativer Kapazität von 45 - 75% und waren der klassischen Gelatine-Schönung mit Verlusten von 25 - 40% unterlegen. Bei der Herstellung von schwarzem Johannisbeersaft wurden die Einflüsse auf die antioxidative Kapazität von Separation, thermischer Belastung, Schönung mit Gelatine, Behandlung mit PVPP oder Bentonit und Konzentratherstellung untersucht und bewertet. Bei allen untersuchten Verarbeitungsschritten zur Herstellung von schwarzem Johannisbeersaft war die prozentuale Abnahme der antioxidativen Kapazität um 10 - 15% und damit geringer als beim Apfelsaft. Die Maischeerwärmung und -enzymierung erweist sich als günstig, da die Extraktion der Polyphenole verbessert wird und durch die Temperatur fruchteigene Polyphenoloxidasen inaktiviert werden. Holunder-, Brombeer- und Sauerkirschsaft zeigt sich während der Herstellung ähnlich stabil (prozentuale Abnahmen < 20%). Auch bei diesen stark rot gefärbten Säften ist die Schönung mit Gelatine die günstigste Methode zur Klärung des Saftes. Thermische Belastung verändert die antioxidative Kapazität zwar nicht, ist aber wegen der hohen Verluste in den Gehalten an monomeren Polyphenolen möglichst gering zu halten. Generell sollte ein zügiger und logistisch gut durchdachter Herstellungsprozess ohne lange Standzeit angestrebt werden und auf Prozessschritten und Behandlungsmaßnahmen, die eine starke Abnahme der antioxidativen Kapazität und der Polyphenole verursachen, verzichtet werden. Die Lagerung verringert die antioxidative Kapazität von trübem Apfelsaft und trübem Holundersaft vor allem durch das Ausfallen des Trubes, verändert sich bei klarem Apfelsaft aber nicht, obwohl deutlich Veränderungen bei den Polyphenolen festgestellt werden. Die Ergebnisse können der Fruchtsaftindustrie zur Hinterfragung von Herstellungsprozessen im Hinblick auf die antioxidative Kapazität und Polyphenole dienen wie auch als Grundlage zur Entwicklung neuartiger Produkte auf Basis von hochwertigen Fruchtsäften verwendet werden. The objective of the work is the determination of the influence of modern and classic processing techniques on the antioxidant constituents in apple and berry juices by stepwise control during the production process of the fruit juices. Those antioxidant constituents in fruit juices are mainly represented by a group of compounds called polyphenols, which meant to have many positive effect on human health. Further determinations are performed about the influence of the variety, the ripeness and juice storage on the antioxidative capacity of the fruit juices. The most important antioxidative compounds in apple and berry juices are the polyphenols and in some berry juices L-ascorbic acid especially in blackcurrant. Apple and blackcurrant juice were chosen because of their great differences in amount and spectra of polyphenols, the amount of L-ascorbic acid and the production process. Stepwise control in the production of elderberry, blackberry, gooseberry and sour cherry juice are also carried out. The changes in antioxidative capacity and the contents of antioxidative compounds are also determined during fruit wine production and the ripening of strawberry. The antioxidative capacity was performed by the ABTS+.-radicalcation-assay which was modified to meet the present demands. Methodological sources of error could be detected and were eliminated. The used principle of measurement for evaluating the antioxidative capacity is fast and effective. A new method for the analysis of polyphenols by HPLC was developed using a fluorinated RP-phase and Diode-Array-Detection (DAD) and Electrochemical-Detection (ECD). A good separation of the single polyphenols, simultaneous analysis of colourless polyphenols and anthocyanins and a sensitive and informative detection using two detection systems were achieved. Three anthocyanins from blackcurrant juice and two polyphenols from apple juice, all commercially not available, could be isolated. Due to their high polyphenol contents, most berry juices are generally a better source of antioxidants in human nutrition than apple juice, which contains lower amounts of polyphenols. The variety has the greatest influence on the antioxidative capacity of apple and blackcurrant juice. The amounts of antioxidative components differ widely in different apple as well as blackcurrant varieties. Choosing a polyphenol-rich variety appeared to be the basis for a high antioxidative capacity in the juice. The influence of mash treatment, mash extraction, apple polyphenol oxidase, industrial extraction system, separation, thermal treatment, storage, fining with gelatine, ultrafiltration with following stabilisation by PVPP or adsorber resin and laccase/O2 treatment followed by ultrafiltration on apple juice during processing were studied and discussed. The extraction of the mash transfers only 32% of the potential antioxidative capacity and 43% of the polyphenols into the juice and could be considered as the processing step causing the greatest loss during juice production. Mash treatment, e.g. a hold for one hour or heating to 60°C, improves the yield of antioxidants after extraction. Different extraction systems such as horizontal press and decanter yield the same antioxidative capacity but different amounts of individual polyphenols, even though the total polyphenols (measured by the Folin-Ciocalteu method) are similar. Oxidation processes during production and separation decrease the antioxidative capacity and the polyphenols of freshly pressed apple juice 20 to 40%, which could be inhibited by heating of the freshly pressed juice to 55....C. All modern processing techniques for the production of a clear juice using ultrafiltration strongly reduce antioxidative capacity as well as the polyphenols (40 – 75%), while fining with gelatine is more gentle (25 – 40% decrease). Therefore, fining with gelatine is the favoured method for apple juice clarification. Generally, under the here applied criteria cloudy apple juice could considered to be superior to its clear counterpart. The influence of mash extraction, separation, thermal treatment, fining with gelatine, treatment with PVPP and bentonite and concentration process on blackcurrant juice during processing were studied and discussed. Decrease of antioxidative capacity and polyphenols during blackcurrant juice processing (extraction, separation, pasteurisation) is 10 to 15%, which is reasonably lower than observed decrease in apple juice processing. Mash heating and depectinisation is recommended due to a better extraction of polyphenols from the mash (59% antioxidative capacity, 64% polyphenols) and inhibition of polyphenoloxidase activity via temperature induced protein denaturation. Thermal treatment during the concentration process hardly reduces the antioxidative capacity and total polyphenols (Folin-Ciocalteu) but causes a massive decrease in the amounts of individual polyphenols, especially the anthocyanins. Therefore, the concentration process could not be recommended when refering to recent data on the bioavailability of anthocyanins. Elderberry, blackberry and sour cherry show comparable stability during processing (decrease < 20%). As the generally recommended method for the clarification of berry juices occurs the fining with gelatine. The higher amounts of antioxidants and a lower activity of polyphenol oxidases are most likely responsible for the difference in stability during processing of high coloured berry juice and apple juice. Storage of clear juices, apple and elderberry juice, reduces the total polphenols as well as the indiviual polyphenols while the antioxidative capacity remains constant. Formation of new antioxidative compounds, polymeric phenols, maillard product etc., during storage is suggested as a possible reason for the constant antioxidative capacity. Fermentation during fruit wine processing hardly effects the antioxidative capacity while the amounts of individual polyphenols are drastically reduced. Taking this observation into account condensation and polymerisation products formed during fermentation should posses a similar antioxidative capacity as their basic molecules. Based on the results, clear recommendations for fruit juice production can be confirmed in order to achieve the highest possible antioxidative capacity and an optimised amount of polyphenols: 1.The choice of polyphenol-rich fruits is the basis for high antioxidative capacity in the juice. 2.Heating of mash or freshly pressed juice to inactivate polyphenol oxidases. 3.A minimisation of processing steps during fruit juice production to avoid unnecessary reductionsof antioxidative capacity and polyphenols. 4.Fast and effective processing lines to avoid unnecessary hold time. 5.Avoiding all processing steps and juice treatments causing a high reduction of antioxidative capacity and individual polyphenols. The possibility of the development of an antioxidant-rich beverage based on various berry juices could be demonstrated. Polyphenols as fruit juice ingredients were considered from a new point of view and their changes during fruit juice processing were newly valued. The results represent a useful tool for the fruit juice industry to evaluate fruit juice processing with the focus on antioxidative capacity and individual polyphenols and provide information for the development of new products with a high antioxidative capacity.
Article
Alliums have been grown for many centuries for their characteristic, pungent flavor and medicinal properties. The present review, which includes references published up to the middle of 1984, is primarily concerned with the chemical composition, flavor, and physiological properties of these crops, their extracts, and processed products. Special emphasis is placed upon the relationship between the organoleptically and biologically active components of onion and garlic. Following a brief historical introduction, current production of commercially important alliums is described and their botanical origins and interrelationships are explained. Following consideration of the major economic diseases and pests of alliums, the agronomic, husbandry, and practices associated with their cultivation are described, particular emphasis being placed upon the storage and processing of onion and garlic. The detailed, overall chemical composition and nutritional value of members of the genus Allium are presented in Section 7; after an outline of the origin and nature of flavor components and precursors, the flavor volatiles of individual members are presented. The effects of agronomic, environmental, and processing practices on chemical and flavor content and quality are considered in Section 9. The following section deals critically with the human and animal studies which have been conducted into the medical and therapeutic properties of alliums, emphasis being placed upon the studies into the antiatherosclerotic effect of onion and garlic and their essential oils. After a study of antimicrobial properties of alliums and their effects on insects and animals, an overview is presented which highlights unexplored or inadequately studied areas and suggests rewarding areas for future research.
Article
Twelve acylated anthocyanins were isolated from the red radish (Raphanus sativus L.) and their structures were determined by spectroscopic analyses. Six of these were identified as pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-beta-D-glucopyranosyl]-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-caffeoyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), and pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(2-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside).
Article
The official, first action paper chromatographic method for detecting adulteration in Concord grape juice has been applied to several dark colored fruit juices, including cherry, raspberry, blackberry, and strawberry. In contrast to the complicated anthocyanin patterns on the paper chromatograms of grape juices, these juices show simple patterns of one or two major red bands. Since most advUterants have more complicated anthocyanin patterns, they can be readily detected by this method, even at low concentrations. If adulteration cannot be detected by the anthocyanin patterns, it can usually be shown by the anthocyanidin patterns. In this paper chromatographic test, three separate anthocyanidin spots are formed. The dark colored juices tested here showed most of the anthocyanidin color in the central spot, whereas the possible adulterants showed other patterns. Therefore, mixtures will have abnormal anthocyanidin patterns in this test. Examples of both laboratory-prepared adulterated juices and some adulterated commercial juices are given.
Article
Paper chromatography of the anthocyanidins, the phenolic components of the anthocyanins, is the most satisfactory means of detecting adulteration of Concord grape juice with other red grape juice and colored Italian grape skin extract. The 5 aniliocyanidins found in grape colors can be readily separated into 3 spots by paper chromatography. In the proposed method, anthocyanins are separated by lead precipitation, dissolved in water, and acid-hydrolyzed to obtain the anthocyanidins. Thirty Concord samples, 7 red grape juice samples, and 5 Italian grape skin extracts were examined and results were good. Four unknown samples were analyzed by 5 collaborators; all collaborators correctly detected the adulterated sample and the pure Concord sample. This method was recommended for adoption as official, first action
Article
Gradient elution, paper, and thin layer chromatography were used to detect adulteration in black raspberry juice concentrates. Results show that a combination of gradient elution chromatography plus thin layer chromatography of the anthocyanin isolates provide definite indications of the purity of concentrated fruit juices.
Article
A method is proposed for the detection of the adulteration of Concord grape juice with other anthocyanin-containing products. This method is.based on the aqueous separation of the monoglucosides followed by a densitometer tracing. An increase in the malvidin inonoglucoside content of the juice indicates the possibility of adulteration with the vinifera or hybrid varieties. To more specifically determine adulteration with hybrids, an evaluation of an increase in the diglucosidc content would be used as the criterion, primarily the large increase in the malvidin 3,5-diglucoside
Article
THE major pigment of the cultivated strawberry is pelargonidin-3-glucoside1,2. Studies reported in 1951 to the National Preservers Association showed that commercial varieties Marshall, Brightmore, Sovereign and Shasta contained a second anthocyanin in low concentration. We now present evidence that the pigment is cyanidin-3-glucoside.
Article
The anthocyanin from the red root of a radish (Iwakuni-aka, one of the horticultural varieties of Raphanus sativus L.) was separated into five pigment components in sufficient purity by means of column chromatography (mixture of cellulose powder and silicic acid) and paper electrophoresis.These anthocyanins are the acylated derivatives of a common basic glycoside called raphanusin (3-diglucosido-5-monoglucoside of pelargonidin). According to the paper chromatographic analyses, the following aromatic acids have been detected: p-coumaric acid in raphanusin A, ferulic acid in raphanusin B-1, caffeic acid in raphanusin B-2, p-coumaric and ferulic acids in raphanusin C-1, and p-coumaric, ferulic and caffeic acids in raphanusin C-2.From the spectrographic studies on these acylated anthocyanins, it is suggested that the cinnamic acid residues are linked to some of the sugar hydroxyl groups of raphanusin.
Article
Bright red pigment was prepared from the root of a radish (Iwakuni-aka, one of the horticultural varieties of Raphanus sativus L.), and was shown to be a mixture of two complex anthocyanins; namely, raphanusin A being acylated with p-coumaric acid, and raphanusin B having both caffeic and ferulic acids. Here, it must be noted that the name 'raphanin' improperly called by Harborne and Sherratt is replaced by “raphanusin” in this paper.After liberation of organic acid residues by mild treatment with alkali, both anthocyanins are converted into one and the same ground substance called raphanusin, which was obtained in a crystalline state and proved to be a triglucoside of pelargonidin by chemical analysis. The positions of sugar attachment were determined paperchromatographically by persuing intermediary products of lesser glycosidation during the course of acid hydrolysis.In consequence, the structure of raphanusin was established on a material basis as 3-diglucosido-5-monoglucoside of pelargonidin. Further experiments on crystallization of raphanusins A and B are in progress.
Article
A new, crystalline, deep blue pigment has been isolated from cornflowers (Centaurea cyanus L.). The pigment is an iron complex of 4 molecules of cyanidin 3,5-diglucoside and 3 molecules of a “bisflavone” glucoside. The “bisflavone” glucoside is liberated on acid decomposition of the blue pigment, and chromatographic examination indicates that it is a single substance. On acid hydrolysis, however, it yields 7-O-methylapigenin and a second flavone which appears to be new and has not yet been positively identified. It is spectrally identical with 7-O-methylapigenin, and on the basis of its Rf values it may be the 7-O-methyl derivative of vitexin. The reported properties of commelinin, the blue pigment of Commelina communis L., are strikingly similar to those of the cornflower pigment and suggest that these two pigments have an essentially identical type of structure.
Article
The color changes produced by treating anthocyanins on filter paper chromatograms with neutral and basic lead acetate are described. An ethanolic solution of neutral lead acetate is proposed as a chromogenic reagent to detect anthocyanins which contain a catechol group. The reaction with lead acetate is faster and the color change is more definite than that produced by AlCl3.
Article
THE pigment of the copper beech was identified in 19321 as cyanidin 3-galactoside; two years later, the colouring matter of wild strawberries was stated to be pelargonidin 3-galactoside2.
Article
Der cyaninhaltige blaue Farbstoff der Kornblume wurde isoliert und als Aluminium-Eisen-Komplex des Cyanins erkannt. De nicht dialysierbare Komplex ist in saurem pH-Bereich stabil. Die Variation der Blütenfarben wird allgemein auf Aluminium- und Eisenkomplexe zurückgeführt, da nur diese Verbindungen zwischen pH 3.8 – 5.5, dem pH der Blütenblätter, stabil sind. Die synthetisch zugänglichen Aluminium- und Eisenkomplexe des Cyanins stimmen in ihrer Farbintensität und pH-Stabilität mit dem natürlichen Farbstoff überein und sind somit die künstlichen Modelle für den Farbstoff der Blüte.
Article
The red pigments from Early Black cranberries were extracted with methanol, purified by lead acetate precipitation and polyamide columns, separated on silicic acid columns, and crystallized. The four pigments were identified as cyanidin-3-monogalactoside, peonidin-3-monogalactoside, cyanidin-3-monoar-abinoside, and peonidin-3-monoarabinoside based on the following evidence: Rt data in three solvents, fluorescence, sugar-aglycone ratios, formic acid and hydrogen peroxide hydrolysis, and spectral data. The absorption coefficients in ethanol-0.1/N hydrochloric acid (85:15) were also determined.
Article
The effect of ingoing sirup concentration, various headspace atmospheres, and time and temperature of storage on the retention of the anthocyanin pigments in canned red and black raspberries was determined. The four anthoeyanins of red raspberries and the three anthocyanins of black raspberries were separated by column chromatography and analyzed spectrophotometrically. The anthocyanins appeared to be similar in the two species as determined by paper chromatography. The absorption maximum of the pigments shifted during storage. Prolonged times and higher temperatures of storage both significantly reduced the recoverable anthocyanins. Increased concentration of ingoing sirup and the presence of oxygen resulted in greater pigment destruction.
Article
The flavonoid and anthocyanin pigments were isolated and identified in three onion cultivars: Southport Yellow Globe, Southport White Globe, and Southport Red Globe. All three varieties contain quercetin-4′-glucoside, quercetin-3,4′-diglucoside, quercetin-4′,7-diglucoside, and quercetin-3-glucoside. In addition, Southport Yellow Globe contains quercetin, and Southport Red Globe contains quercetin and peonidin-3-arabinoside.
Article
Cyanidin 3-glucoside and peonidin 3-glucoside were identified as minor (< 1 %) pigments in cranberries. Their isolation was possible with a new developing solvent of high resolving power.
Article
The anthocyanins present in colour varieties of Lathyrus odoratus and Streptocarpus have been identified; the sugars of some forty other anthocyanins have also been examined. In all, twenty-two new anthocyanins have been found; they include the first representatives of the following glycosidic classes: 3-rhamnosides, 3-(xylosylgalactosides), 5-glucoside-3-rhamnosides, 5-glucosides-3-sophoroside, 3-sophoroside-7-glucosides and 5-glucoside-3-sambubiosides. Each of the two unusual disaccharides sophorose and sambubiose occurs combined in the anthocyanins of several plant genera. Structures previously proposed for pigments of Matthiola incana flowers and of red cabbage have been revised. This work brings the number of known classes of anthocyanins to seventeen.
Article
Fifty-five species, representing ten of the eleven genera of the family Plumbaginaceae have been surveyed for flavonoids and other phenolic constituents in root, leaf and flower. The results reveal a close correlation between chemistry, pollen morphology and taxonomy. The most useful chemical “marker” is 5-hydroxy-2-methyl-naphthoquinone (plumbagin) which occurs in roots of all ten taxa examined of the tribe Plumbagineae (plants with monomorphic pollen) and which is uniformly absent (0 out of 44 species) from plants of the tribe Staticeae (with dimorphic pollen). There are also characteristic differences between the tribes in their flavonoid pigments. Thus, all but two of the Plumbago and Ceratostigma species studied contain one or other of five rare O-methylated flavonoids, namely azaleatin, 5-O-methylmyricetin, capensinidin, pulchellidin and europinidin. The two latter pigments are new anthocyanidins, provisionally identified as 5-O-monomethyl and 5,3′-di-O-methyldelphinidin. In addition, Plumbago europea leaf contains a new flavonol 7-O-methylmyricetin (europetin), a substance which forms a link between the Plumbaginaceae and a neighbouring family, the Primulaceae. Of the seven Plumbago species examined, P. rosea is the most distinctive, for besides lacking 5-O-methylated flavonols, it contains in its flowers a mono- and a digalloylglucose. The anthocyanidins in the Plumbagineae occur as 3-rhamnosides, 3-galactosides or 3-glucosides. By contrast, in the tribe Staticeae, the main anthocyanins are malvidin 3,5-diglucoside (Armeria spp.) and petunidin 3-rhamnoside-5-glucoside (most Limonium spp.). Members of the Staticeae characteristically have large amounts of myricetin glycosides in the leaves. Examination of the most primitive member of the Staticeae, Aegialitis annulata, which is anomalous in having monomorphic (instead of dimorphic) pollen, showed it to be unusual chemically. The main leaf flavonoids were 3-O-methyl ethers of quercetin and myricetin; the latter is a new pigment, annulatin. The absence of plumbagin and 5-O-methylated flavonols from this plant indicates that it has been correctly placed, in spite of its pollen morphology, in the Staticeae.
Article
ALTHOUGH it has been definitely established that cultivated strawberries contain pelargonidin-3-monoglucoside as the major anthocyanin1,2 and cyanidin-3-monoglucoside as a minor component3, there is still some question about the identity of the pigments of Fragaria vesca. As a result of qualitative tests, Robinson4 suggested in 1934 that the anthocyanin of F. vesca is pelargonidin-3-monogalactoside. In a more recent paper, Robinson and Smith2 described a chromatographic procedure for distinguishing pelargonidin-3-monoglucoside and the galactoside, but left the identity of the anthocyanins of wild strawberries as an open question.
Article
A new developing solvent for paper chromatography is described, which is capable of separating the 3-arabinosides and 3-galactosides of cyanidin and peonidin. It is the upper phase of 1-butanol-benzene-formic acid-water (100:19:10:25). The solvent is also applicable to many other classes of compounds and gives excellent separations of sugars in particular. RF or RG values are given for a number of anthocyanins, anthoxanthines, simple phenols, sugars, phenolic and amino acids.
Article
Neun Glykoside des Pelargonidins wurden durch papierchromatographische Methoden gekennzeichnet. Es war notwendig, die Methode der Zuckeridentifizierung abzuändern, um die Bildung des Kunstprodukts Arabinose zu vermeiden. Einige der neun Glykoside gehören zu neuen Sorten von Anthocyanidinglykosiden, die bisher noch nicht in der Natur entdeckt waren. Die dadurch erklärte Variation im Glykosidformelbild der Anthocyane wird in bezug auf ihre Biosynthese diskutiert.
Variety, composition and colour in canned fruits, particularly rhubarb
  • R A Gallop
The pigments of red fruits. Research Report Fruit and Vegetable Preservation Research Association Chipping
  • H A W Blundstone
Recherches sur les anthocyannes des végétaux
  • P Ribéreau-Gayon
  • Yazaki Y.
Utilization of strawberries. III. Detection of strawberry components by paper chromatography
  • Akuta S.
Identification par chromatographie des pigments anthocyaniques des fruits et des légumes
  • Fouassin A.
Paper chromatography of cinnamic acid derivatives
  • Williams A. H.
Fruit and Vegetable Canning and Quick Freezing Research Association Chipping
  • R A Gallop
Chromatographie, spectres d'adsorption et degradation d'anthocyanines de fruits
  • Lamort C.