Anthocyanidin glycosides from the flowers of Alstroemeria

Three anthocyanins were isolated from the red flowers of four cultivars of Alstroemeria. Two compounds were novel anthocyanidin glycosides; the 3-rutinoside and 3-monoglucoside of 6-hydroxycyanidin. Cyanidin 3-rutinoside was also present in the petals.     

Self-association of some anthocyanins in neutral aqueous solution

A good contrast in optical properties caused by self-association was found between malvin and cyanin quinonoidal bases. Circular dichroism measurements of the pigments in neutral aqueous solutions show that molecules of the malvin quinonoidal base self-associate quickly and the conformational orientation of the aggregates is opposite to those formed by cyanin quinonoidal bases. Hypsochromism and hypochromism in the visible absorption also occurred on the formation of malvin aggregates. CD comparisons of malvin, hirsutin and 4′-O-methylmalvin suggest that a methoxyl group in the B-ring of the anthocyanidin strongly suppresses self-association. It is proposed that the driving forces for self-association are mainly hydrophobic interactions among the aromatic nuclei stacked parallel to each other which are surrounded by the hydrophilic glucose moieties in a suitable spatial arrangement. Furthermore, the glucose moiety at the 5-position rather than that at the 3-position plays an important role in the self-association of these anthocyanidin 3,5-diglucosides. Addition of sodium chloride promotes self-association and the greater stability of the anthocyanins in solution.     

Floral anthocyanins of some malesian Hibiscus species

In 14 Malesian species of Hibiscus (sensu lato) the most common floral anthocyanin was cyanidin 3-sambubioside. Cyanidin 3-glucoside was found     

Axillary shoot proliferation of blue honeysuckle

Callus cultures of Ajuga reptans flowers produced a complex mixture of cyanidin- and delphinidin-based pigments, of which more than 90% were acylated. The anthocyanin composition varied little during one growth period. During a time span of 5 years no new anthocyanin classes appeared. Quantitative differences in anthocyanin composition between the callus lines and during a 5 year time span were more pronounced. In general, the accumulation of delphinidin-based anthocyanins decreased. The percentage of acylated anthocyanins was stable in time. The accumulation of metabolically evolved anthocyanins (5′-substituted and acylated) decreased during passage from solid culture to liquid culture. The accumulation of acylated anthocyanins was influenced by the type of aeration in liquid cultures. This revised version was published online in June 2006 with corrections to the Cover Date.     

Acylated anthocyanins in flowers of Matthiola tricuspidata (L.) R. Br. and Matthiola fruticulosa (L.) Maire (Brassicaceae)

1. Download : Download full-size image

     

Pseudobase of malvidin 3-rhamnosido-5-glucoside in am mutants of Pisum sativum

am Mutants of Pisum sativum with white petals have been shown to contain the pigment malvidin 3-rhamnosido-5-glucoside in colourless pseudobase     

Further Characterization of Ureido Ring Synthetase from Pseudomonas graveolens

Detailed enzymatic properties of the ureido ring synthetase purified from Pseudomonas graveolens were investigated. Nucleotide specificity studies indicated that CTP, UTP, GTP, and ITP were each tenth to one-fifth as active as ATP. The effect of substrate concentration was examined. The Km values for 7,8-diaminopelargonic acid, biotin diaminocarboxylic acid, NaHCO₃, ATP, and MgCl₂ were 1 × 10^?4 M, 4 × 10^?5 M, 1 × 10^?2 m, 5 × 10^?5 M, and 3 × 10^?3 M, respectively. It was elucidated that only ADP was produced from ATP in both the reaction of desthiobiotin synthesis from 7,8-diaminopelargonic acid and biotin synthesis from biotin diaminocarboxylic acid. The reaction was remarkably inhibited by Ni²⁺, Cd²⁺, Cu²⁺, Ag⁺, and As³⁺, while Mn²⁺ remarkably enhanced the enzyme reaction. The reaction was remarkably inhibited by metal-chelating reagents. It was elucidated that ADP had a competitively inhibiting effect on this enzyme reaction. 7,8-DiaminopeIargonic acid, which is the substrate for the desthiobiotin synthesis, competitively inhibited the biotin synthesis from biotin diaminocarboxylic acid. The stoichiometry of the desthiobiotin synthesis indicated that the formation ratio of desthiobiotin to ADP was 1 to 1.     

Tetrahydroisoquinoline-monoterpene glycosides from Cephaelis acuminata.

From the dried roots of Cephaelis acuminata, five tetrahydroisoquinoline-monoterpene glycosides, 2-O-beta-D-glucopyranosyldemethylalangiside, demethylisoalangiside, 6"-O-beta-D-glucopyranosylipecoside, 6"-O-alpha-D-glucopyranosylipecoside and (4R)-4-hydroxyipecoside, were isolated. The structures of these glycosides were determined by spectroscopic and chemical means.     

Anthocyanins of some Malaysian members of the gesneriaceae

The occurrence of 'normal' 3-hydroxylated anthocyanins in 8 Malaysian species of the Gesneriaceae supports the important chemotaxonomic results for this family. New compounds found in Chirita, Didissandra and Didymocarpus are the 3-arabinosylglucoside-5-glucosides of cyanidin and malidin, pigments which may have some systematic value.     

Flavonoids from Erythroxylon argentinum

Quercetin 3-rutinoside, quercetin 3-α-l-rhamnoside, 7,4′-dimethylquercetin 3-rutinoside and the novel glycoside 7,4′-dimethylquercetin 3-rutinoside-5-glucoside have been identified from aerial parts of Erythroxylon argentinum.     

Iridoid glycosides from Galium verum

From the aerial parts of Galium verum in flower, asperuloside and V₁ iridoid were isolated. From the mother liquor obtained on recrystallizatio     

A Unique pattern of anthocyanins in Daucus carota and other umbelliferae

Three cyanidin glycosides have been identified in the black carrot: the known 3-lathyroside and two new pigments, a 3-xylosylglucosylgalactoside and its ferulyl derivative. The same pigments, together with the sinapyl derivative of the triglycoside, occur variously in other tissues of Daucus carota. Ferulyl and sinapyl derivatives of cyanidin 3-glucosylgalactoside occur exceptionally in stem of one subspecies, maritimus. One or other of the same pigments have been found to occur variously in 20 of 22 other umbellifer species surveyed. Both ferulyl and sinapyl derivatives occur in stem of Conium maculatum and Foeniculum vulgare. A further novel acylated pigment based on p-coumaric acid was found in wild celery, Apiurn graveolens. The systematic significance of these various findings is discussed.     

Acylated cyanidin 3-sambubioside-5-glucosides from the purple-violet flowers of Matthiola longipetala subsp. bicornis (Sm) P. W. Ball. (Brassicaceae)

A novel acylated cyanidin 3-sambubioside-5-glucoside was isolated from the purple-violet flowers of Matthiola longipetala subsp. bicornis (Sm) P. W. Ball. (family: Brassicaceae), and determined to be cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] by chemical and spectroscopic methods. In addition, two known acylated cyanidin 3-sambubioside-5-glucosides, cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-β-xylopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] and cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(trans-feruloyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] were identified in the flowers.     

Anthocyanin and pH in the color of ‘Heavenly Blue’ morning glory

The major anthocyanin in blue morning glory flowers, peonidin 3-(dicaffeylsophoroside)- 5-glucoside, is stable in a neutral aqueous solution and is solely responsible for the color of the flowers. Co-ocurring flavonols based on quercetin at the pH's of epidermal cells have no effect on the color of the anthocyanin. Deep or strong reddish-purple buds change to moderate or light blue open flowers within a 4 hr period, and during this time the pH of epidermal tissue increases from ca 6.5 to 7.5.     

Anthocyanin inheritance in petals of flax, Linum usitatissimum

Twelve anthocyanins have been isolated from flax: the 3-glucosylrutinosides of pelargonidin, cyanidin and delphinidin; the 3-triglucosides of delphinid     

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.     

Effects of carbohydrates and nitrogen on the development of anthocyanins of a red leaf peach (Prunus persica (L.) Batsch) in vitro

Heterozygous red leaf peach (Prunus persica (L.) Batsch) shoots were implanted on media with varying nitrogen and carbohydrate regimes to identify a combination which elicited maximum anthocyanin production in explants. A medium with relatively low nitrogen (5 mM NH₄₊ and 10 mM NO_3-) and high sucrose (234 mM) was most effective in stimulating anthocyanin production. Sucrose was more effective as a carbon source than glucose, fructose, or starch under given nitrogen levels. The major anthocyanin in red leaf peach was tentatively identified as cyanidin 3-glucoside based on PC and HPLC analysis.     

Methyl jasmonate promotes anthocyanins’ production in Prunus salicina × Prunus persica in vitro shoot cultures

In vitro shoot cultures of Prunus salicina × Prunus persica, “Citation®” rootstock, were treated with 50-μM methyl jasmonate (MJ) or 100-μM abscisic acid (ABA); in MJ-treated shoots, total anthocyanins increased significantly (1.88 mg/g fresh weight) relative to controls (0.43 mg/g fresh weight). Cyanidin 3-glucoside was the most abundant anthocyanin in both MJ-treated and control explants. The addition of ABA to the culture medium did not elicit anthocyanins’ accumulation.     

Phase change modifies anthocyanin synthesis in Acer palmatum Thunb. (Japanese maple) cultivars

The potential markers of juvenility (cyanidin 3-glucoside and cyanidin 3-rutinoside) in autumn leaves of seven Acer palmatum Thunb. cultivars were investigated. Three shoot positions were marked on each cultivar—crown shoot, middle shoot, and basal shoot—and the anthocyanins were analyzed using HPLC-MS. The results showed great differences in cyanidin 3-glucoside and cyanidin 3-rutinoside concentrations among seven cultivars; moreover, significant differences in cyanidin 3-glucoside content levels were also observed among three shoot positions regardless of the cultivar analyzed. The concentration decreased basipetally and reached levels up to 52 times higher in leaves obtained from crown shoots in comparison to basal shoot leaves. Therefore, the content level of cyanidin 3-glucoside can be defined as a quantitative marker of positional effect in all the Acer palmatum Thunb. cultivars analyzed. The content level of cyanidin 3-rutinoside did not express the same positional dependence.