Pelargonidin-based Anthocyanins Research Articles

Flower colour and cytochromes P450

Flavonoids are major constituents of flower colour. Plants accumulate specific flavonoids and thus every species often exhibits a limited flower colour range. Three cytochromes P450 play critical roles in the flavonoid biosynthetic pathway. Flavonoid 3′-hydroxylase (F3′H, CYP75B) and flavonoid 3′,5′-hydroxylase (F3′5′H, CYP75A) catalyze the hydroxylation of the B-ring of flavonoids and are necessary to biosynthesize cyanidin-(red to magenta) and delphinidin-(violet to blue) based anthocyanins, respectively. Pelargonidin-based anthocyanins (orange to red) are synthesized in their absence. Some species such as roses, carnations and chrysanthemums do not have violet/blue flower colour due to deficiency of F3′5′H. Successful expression of heterologous F3′5′H genes in roses and carnations results in delphinidin production, causing a novel blue/violet flower colour. Down-regulation of F3′H and F3′5′H genes has yielded orange petunia and pink torenia colour that accumulate pelargonidin-based anthocyanins. Flavone synthase II (CYP93B) catalyzes the synthesis of flavones that contribute to the bluing of flower colour, and modulation of FNSII gene expression in petunia and tobacco changes their flower colour. Extensive engineering of the anthocyanin pathway is therefore now possible, and can be expected to enhance the range of flower colours.

HIGH PLANT GROWTH TEMPERATURES INCREASE ANTIOXIDANT CAPACITIES IN STRAWBERRY FRUIT

The influence of four day/night growing temperature combinations (18/12, 25/12, 25/22, 30/22 °C) on phenolic acid, flavonol, and anthocyanin content and their antioxidant activities against peroxyl radicals (ROO . ), superoxide radicals (O 2 .- ), hydrogen peroxide (H 2 O 2 ), hydroxyl radicals (OH . ), and singlet oxygen ( 1 O 2 ,) in fruit juice of 'Earliglow' and 'Kent' strawberry (Fragaria x ananassa Duch.) were studied. The content of cyanidin- based anthocyanins, were much lower than pelargonidin-based anthocyanins. High day/night temperature conditions significantly enhanced p-coumaroylglucose, dihydroflavonol, quercetin 3-glucoside, quercetin 3-glucuronide, kaempferol 3-glucoside, kaempferol 3-glucuronide, cyanidin 3-glucoside, pelargonidin 3-glucoside, pelargonidin 3-rutinoside, cyanidin 3-glucoside-succinate and pelargonidin 3-glucoside-succinate content in strawberry juice. Plants grown at low day and night temperatures (18/12 °C) generally had the lowest anthocyanin contents. Plants grown at the highest day/night temperatures (30/22 °C) produced fruit with the most phenolic content as well as antioxidant capacity. Fruit of 'Kent' strawberry had higher contents of phenolic acid, flavonols, anthocyanins and antioxidant capacities compared to fruit of 'Earliglow' strawberry under all temperature regimes.

Cultural system affects fruit quality and antioxidant capacity in strawberries.

Cultural system [hill plasticulture (HC) versus matted row (MR)] and genotype interactions affected strawberry fruit quality. In general, fruit soluble solids content, total sugar, fructose, glucose, ascorbic acid, titratable acid, and citric acid contents were increased in the HC system. Fruit from HC also had higher flavonoid contents and antioxidant capacities. Strawberry fruit contains flavonols as well as other phenolic compounds such as anthocyanins and phenolic acids. Pelargonidin-based anthocyanins such as pelargonidin 3-glucoside, pelargonidin 3-rutinoside, and pelargonidin 3-glucoside-succinate were the predominant anthocyanins in strawberry fruit. The content of cyanidin-based anthocyanins, cyanidin 3-glucoside and cyanidin 3-glucoside-succinate, was much lower than that of pelargonidin-based anthocyanins in either system. Strawberry fruit from the HC system had significantly higher amounts of p-coumaroylglucose, dihydroflavonol, quercetin 3-glucoside, quercetin 3-glucuronide, kaempferol 3-glucoside, kaempferol 3-glucuronide, cyanidin 3-glucoside, pelargonidin 3-glucoside, pelargonidin 3-rutinoside, cyanidin 3-glucoside-succinate, and pelargonidin 3-glucoside-succinate. Fruits from plants grown in the MR system generally had the lowest contents of phenolic acids, flavonols, and anthocyanins. Strawberry fruit grown under HC conditions had significantly higher peroxyl radicals (ROO*) absorbance capacity (ORAC).

Comparison of the Stability of Pelargonidin‐based Anthocyanins in Strawberry Juice and Concentrate

ABSTRACTStrawberries were processed into juice (8° Brix) and concentrate (65° Brix) and different lots were fortified with pelargonidin 3‐glucoside, pelargonidin 3‐sophoroside, and acylated pelargonidin 3‐sophoroside 5‐glucoside. Changes in pigment concentration, color (CIE L*a*b*) and ascorbic acid content were monitored during storage at 25 °C. Anthocyanin and ascorbic acid degradations followed 1st order reaction kinetics. Fortification increased the half‐life of the pigments from 3.5 to 5 d in concentrate and from 5 to 12 d in juice. The half‐life of ascorbic acid was 2 d in juice samples and ranged from 3 to 10 d in concentrate samples. Both systems showed changes in chroma and hue angle, but maintained L* values.

The stability of pelargonidin-based anthocyanins at varying water activity

The stability of pelargonidin 3-glucoside, pelargonidin 3-sophoroside and pelargonidin 3-sophoroside 5-glucoside acylated with malonic and cinnamic acids was determined at varying water activities. Model systems, containing purified anthocyanin in pH 3.4 citrate buffer and glycerol, were stored at 25°C in the dark for 242 days. Changes in pigment, degradation index, and anthocyanin profile, as monitored by high-performance liquid chromatography (HPLC), were studied. In general, anthocyanin degradation followed first order kinetics and the degree of anthocyanin degradation increased with water activity. Half lives of the anthocyanins ranged from 56 to 934 days. Changes in the chromatographic profile showed hydrolysis of pelargonidin 3-sophoroside to pelargonidin 3-glucoside and production of malonic acid from the acylated anthocyanin.

Effect of plant growth temperature on antioxidant capacity in strawberry.

The influence of four day/night growing temperature combinations (18/12, 25/12, 25/22, and 30/22 degrees C) on phenolic acid, flavonol, and anthocyanin content and their antioxidant activities against peroxyl radicals (ROO(*)), superoxide radicals (O(2)(*)(-)), hydrogen peroxide (H(2)O(2)), hydroxyl radicals (OH(*)), and singlet oxygen ((1)O(2)) in fruit juice of Earliglow and Kent strawberry (Fragaria x ananassa Duch.) cultivars was studied. Pelargonidin-based anthocyanins such as pelargonidin 3-glucoside (291.3-945.1 microg/g fresh wt.), pelargonidin 3-rutinoside (24.7-50.9 microg/g fresh wt.), and pelargonidin 3-glucoside-succinate (62.2-244.0 microg/g fresh wt.) were the predominant anthocyanins in strawberry fruit juice. The content of cyanidin-based anthocyanins, cyanidin 3-glucoside and cyanidin 3-glucoside-succinate, was much lower than that of pelargonidin-based anthocyanins. Strawberry growth in high temperature conditions significantly enhanced the content of p-coumaroylglucose, dihydroflavonol, quercetin 3-glucoside, quercetin 3-glucuronide, kaempferol 3-glucoside, kaempferol 3-glucuronide, cyanidin 3-glucoside, pelargonidin 3-glucoside, pelargonidin 3-rutinoside, cyanidin 3-glucoside-succinate, and pelargonidin 3-glucoside-succinate in strawberry juice. Plants grown in the cool day and cool night temperature (18/12 degrees C) generally had the lowest phenolic acid, flavonols, and anthocyanins. An increase in night temperature from 12 to 22 degrees C, with the day temperature kept constant at 25 degrees C, resulted in a significant increase in phenolic acid, flavonols, and anthocyanins. These conditions also resulted in a significant increase in antioxidant capacity. The highest day/night temperature (30/22 degrees C) yielded fruit with the most phenolic content as well as ROO(*), O(2)(*)(-), H(2)O(2), OH(*), and (1)O(2) radical absorbance capacity. Fruit of Kent cv. strawberry had higher values of phenolic acid, flavonols, anthocyanins, and antioxidant capacities than fruit of Earliglow cv. strawberry under all temperature regimes.

Molar absorptivity and color characteristics of acylated and non-acylated pelargonidin-based anthocyanins.

The effects of glycosylation and acylation on the spectral characteristics, molar absorptivity, and color attributes of purified acylated and non-acylated pelargonidin derivatives were compared. Pigments were obtained from strawberries, radishes, red-fleshed potatoes, and partially hydrolyzed radish pigments. Individual pigments were isolated by using semipreparative HPLC. Spectral and color (CIELch) attributes of purified pigments were measured. Molar absorptivity ranged from 15 600 to 39 590 for pelargonidin-3-glucoside (pg-3-glu) and pg-3-rutinoside-5-glucoside acylated with p-coumaric acid, respectively. The presence of cinnamic acid acylation had a considerable impact on spectral and color characteristics, causing a bathochromic shift of lambda(max). Sugar substitution also played an important role, with a hypsochromic shift caused by the presence of glycosylation. Pg-3, 5-diglu and pg-3,5-triglu possessed a higher hue angle (>40 degrees ) than the other pg derivatives at pH 1.0, corresponding to the yellow-orange region of the color solid. Acylation with malonic acid did not affect lambda(max) and showed little effect on color characteristics. The solvent system had an effect not only on the molar absorptivity, but also on the visual color characteristic of the pigments.