Antimutagenicity of Deacylated Anthocyanins in Purple-fleshed Sweetpotato

The antimutagenicity of the 3-sophoroside-5-glucoside of cyanidin and 3-sophoroside-5-glucoside of peonidin, the anthocyanin derivatives deacylated from the 3-(6,6'-caffeylferulylsophoroside)-5-glucoside of cyanidin (YGM-3) and 3-(6,6'-caffeylferulyl-sophoroside)-5-glucoside of peonidin (YGM-6) which had been purified from the sweetpotato with purple-colored flesh, was investigated by using Salmonella typhimurium TA 98. A comparison of the antimutagenicity between YGM-3 and YGM-6 and the deacylated derivatives showed that the activity of cyanidin was stronger than that of peonidin. Deacylation of the peonidin-type pigment markedly decreased this antimutagenicity. Caffeic acid showed the strongest antimutagenicity of the constituent organic acids of the anthocyanin pigments, caffeic acid, ferulic acid, and p-hydroxybenzoic acid. These results suggest that the cathecol structure plays an important role in the strong antimutagenicity of anthocyanin pigments.     

Antimutagenicity of deacylated anthocyanins in purple-fleshed sweetpotato

The antimutagenicity of the 3-sophoroside-5-glucoside of cyanidin and 3-sophoroside-5-glucoside of peonidin, the anthocyanin derivatives deacylated from the 3-(6,6'-caffeylferulylsophoroside)-5-glucoside of cyanidin (YGM-3) and 3-(6,6'-caffeylferulylsophoroside)-5-glucoside of peonidin (YGM-6) which had been purified from the sweetpotato with purple-colored flesh, was investigated by using Salmonella typhimurium TA 98. A comparison of the antimutagenicity between YGM-3 and YGM-6 and the deacylated derivatives showed that the activity of cyanidin was stronger than that of peonidin. Deacylation of the peonidin-type pigment markedly decreased this antimutagenicity. Caffeic acid showed the strongest antimutagenicity of the constituent organic acids of the anthocyanin pigments, caffeic acid, ferulic acid, and p-hydroxybenzoic acid. These results suggest that the cathecol structure plays an important role in the strong antimutagenicity of anthocyanin pigments.     

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.     

Anthocyanin synthesis in tissue cultures of Callistephus chinensis (China aster)

Callus cultures were derived from stems and leaves of 3 anthocyanin producing and 3 acyanic lines of Callistephus chinensis (Compositae). The tissue cultures of the cyanic lines were shown to produce cyanidin whereas in the calli of the acyanic lines no anthocyanin synthesis occurred Culture conditions were improved in order to enhance both anthocyanin production and growth of the tissue cultures.Abbreviations IAA indoleacetic acid - NAA naphtaleneacetic acid - 2,4-D 2,4-dichlorophenoxyacetic acid - MS-medium Murashige and Skoog medium     

Purification of anthocyanins from species of Banksia and Acacia using high-voltage paper electrophoresis

A new method has been developed for the isolation and rapid identification of anthocyanins from two floricultural crops based on the use of high-voltage paper electrophoresis with bisulphite buffer. Using this method, anthocyanin pigments were successfully purified as their negatively charged bisulphite-addition compounds from crude extracts of plant tissue. In conjunction with liquid chromatography-electrospray mass spectrometry, the method enabled the anthocyanins from the flowers of two Banksia species and the leaves of two Acacia species to be identified. The Banksia flowers contained both cyanidin and peonidin-based pigments, while the Acacia leaves contained cyanidin and delphinidin derivatives.     

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.     

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.     

The structure of the major anthocyanin in Arabidopsis thaliana

The major anthocyanin in the leaves and stems of Arabidopsis thaliana has been isolated and shown to be cyanidin 3-O-[2-O(2-O-(sinapoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-p-coumaroyl-beta-D-glucopyranoside] 5-O-[6-O-(malonyl) beta-D-glucopyranoside]. This anthocyanin is a glucosylated version of one of the anthocyanins found in the flowers of the closely related Matthiola incana.     

Cyanidin glycosides in flowers of genus Corydalis (Fumariaceae)

Nine taxa of Corydalis were surveyed for their floral anthocyanins. Five cyanidin glycosides: cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-rutinoside, cyanidin 3-(2^G-xylosylrutinoside) and cyanidin 3-(2^G-xylosylrutinoside)-7-glucoside were isolated from these taxa and identified by chemical and spectroscopic techniques. A novel anthocyanin was found in the flowers of Corydalis elata and Corydalis flexuosa cultivars, and identified to be cyanidin 3-(2^G-xylosylrutinoside)-7-glucoside. Two anthocyanins, cyanidin 3-sambubioside and cyanidin 3-(2^G-xylosylrutinoside), were also found for the first time in Corydalis flowers. Furthermore, the major anthocyanin constituent of the flowers was cyanidin 3-sambubioside in the outer petals of Corydalis ambigua and Corydalis lineariloba, and cyanidin 3-rutinoside in those of Corydalis decumbens, Corydalis curvicalcarata and Corydalis speciosa. Similarly, Corydalis incisa contained cyanidin 3-(2^G-xylosylrutinoside), and C. flexuosa ‘China Blue’ and ‘Blue Panda’, and C. elata contained the most complex structural pigment, cyanidin 3-(2^G-xylosylrutinoside)-7-glucoside, as their dominant anthocyanin in their outer petals. According to the results of anthocyanin analyses, these nine plants were classified into four groups: groups A (three taxa), B (two taxa), C (one taxa) and D (three taxa). On the other hand, the anthocyanin constituent of their inner petals was composed of cyanidin 3-rutinoside as only one dominant anthocyanin.     

Sinapic acid stimulator of anthocyanin accumulation in carrot cell cultures

In clones of wild carrot (Daucus carota L.) cells which accumulate anthocyanin, exogenously supplied sinapic acid increases their anthocyanin accumulation in the presence or absence of dihydroquercetin which is a known precursor of cyanidin. The exogenously supplied sinapic acid was not converted into malvidin by the cells. The cells accumulate anthocyanin with cyanidin as the only chromophore in the presence or absence of sinapic acid. Sinapic acid feeding did not initiate anthocyanin accumulation in clones which were not anthocyanin accumulating.     

Antimutagenicity of sweetpotato (Ipomoea batatas) roots

Antimutagenicity of the water extracts prepared from the storage roots of four varieties of sweetpotato with different flesh colors was investigated using Salmonella typhimurium TA 98. The extract from the whole roots of the purple-colored Ayamurasaki variety effectively decreased the reverse mutation induced not only by Trp-P-1, Trp-P-2, IQ, B[a]P, and 4-NQO but also by dimethyl sulfoxide extracts of grilled beef. Comparison of the inhibitory activity of the extracts from the normal Ayamurasaki and its anthocyanin-deficient mutant one suggested that the anthocyanin pigment in the flesh decreases the mutagenic activity of the mutagens as heterocyclic amines. Two anthocyanin pigments purified from purple-colored sweet-potato, 3-(6,6'-caffeylferulylsophoroside)-5-glucoside of cyanidin (YGM-3) and peonidin (YGM-6) effectively inhibited the reverse mutation induced by heterocyclic amines, Trp-P-1, Trp-P-2, and IQ in the presence of rat liver microsomal activation systems.     

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.     

Anthocyanins from flowers of the orchids Dracula chimaera and D. cordobae

The main anthocyanins from flowers of the orchids Dracula chimaera and D. cordobae were isolated from a purified methanolic extract by preparative HPLC. Their structures were determined to be cyanidin 3-O-(6"-O-malonyl-beta-glucopyranoside), cyanidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside), cyanidin 3-O-beta-glucopyranoside, peonidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside) and peonidin 3-O-(6"-O-malonyl-beta-glucopyranoside). The structure determinations were mainly based on extensive use of 2D and 1D NMR spectroscopy, UV-vis spectroscopy and MS. The anthocyanin contents of species belonging to the subtribe Pleurothallidinae including genus Dracula Luer (Orchidaceae) have previously not been determined. The high content of anthocyanin rutinosides found in D. chimaera and D. cordobae (78 and 28% of the total anthocyanin content, respectively) differs from previously analysed orchid species, in which glucose is found as the only anthocyanin sugar moiety.     

Cyanidin 3-malonylglucoside in Cichorium intybus

The major anthocyanin of red leaves of Cichorium intybus has been identified as cyanidin 3-O-β-(6-O-malonyl)-d-glucopyranoside by fast atom bombardment mass spectrometry and NMR spectroscopy.     

Cyanidin 3-glucoside accumulation in plane tree (Platanus acerifolia) cell-suspension cultures

The accumulation of only one anthocyanin, cyanidin 3-glucoside, in cell-suspension cultures of plane tree (Platanus aceriflia) is reported for the first time. During a time span of 6 years, no new anthocyanin was detected and cyanidin 3-glucoside was maintained at about 35 mg l^–1 cell culture medium. This stable cell culture system could therefore be used for the biotechnological production of cyanidin 3-glucoside.     

The anthocyanin in blue flowers ofCentaurea cyanus

The anthocyanin in the blue cornflower (Centaurea cyanus) has been known for many years to be cyanidin 3,5-diglucoside, namely cyanin. However, in the course of this study, it became evident that the major anthocyanin in the blue cornflower is not cyanin but cyanidin 3-succinyl glucoside 5-glucoside. This anthocyanin has not been reported in the literature and is tentatively called “centaurocyanin”. Centaurocyanin is chromatographically identical with the anthocyanin contained in crystalline protocyanin, the blue pigment from the cornflower. thus, there seems no doubt that this anthocyanin, but not cyanin, forms the blue complex pigment protocyanin.