Anthocyanins, the pigments responsible for spectacular displays of vermilion in the leaves of deciduous trees, have long been considered an extravagant waste of a plant's resources. Contemporary research, in contrast, has begun to show that the pigments can significantly influence the way a leaf responds to environmental stress. Anthocyanins have been implicated in tolerance to stressors as diverse as drought, UV-B, and heavy metals, as well as resistance to herbivores and pathogens. By absorbing high-energy quanta, anthocyanic cell vacuoles both protect chloroplasts from the photoinhibitory and photooxidative effects of strong light, and prevent the catabolism of photolabile defence compounds. Anthocyanins also mitigate photooxidative injury in leaves by efficiently scavenging free radicals and reactive oxygen species. Far from being a useless by-product of the flavonoid pathway, these red pigments may in some instances be critical for plant survival.

Kevin S. Gould

Nature&#39;s Swiss Army Knife: The Diverse Protective Roles of Anthocyanins in Leaves

Plant cells and tissue cultures hold great promise for controlled production of a myriad of useful secondary metabolites on demand. The current yield and productivity cannot fulfill the commercial goal of a plant cell-based bioprocess for the production of most secondary metabolites. In order to stretch the boundary, recent advances, new directions and opportunities in plant cell-based bioprocessing, have been critically examined for the 10 years from 1992 to 2002. A review of the literature indicated that most of the R&amp;D work was devoted predominantly to studies at an empirical level. A rational approach to molecular plant cell bioprocessing based on the fundamental understanding of metabolic pathways and their regulations is urgently required to stimulate further advances; however, the strategies and technical framework are still being developed. It is the aim of this review to take a step forward in framing workable strategies and technologies for molecular plant cell-based bioprocessing. Using anthocyanin biosynthesis as a case study, an integrated postgenomic approach has been proposed. This combines the functional analysis of metabolic pathways for biosynthesis of a particular metabolite from profiling of gene expression and protein expression to metabolic profiling. A global correlation not only can thus be established at the three molecular levels, but also places emphasis on the interactions between primary metabolism and secondary metabolism; between competing and/or complimentary pathways; and between biosynthetic and post-biosynthetic events.

Wei Zhang

Chris Franco

Chris Curtin

Simon Conn

To Stretch the Boundary of Secondary Metabolite Production in Plant Cell-Based Bioprocessing: Anthocyanin as a Case Study

Anthocyanin pigments and associated flavonoids have demonstrated ability to protect against a myriad of human diseases, yet they have been notoriously difficult to study with regard to human health. Anthocyanins frequently interact with other phytochemicals to potentiate biological effects, thus contributions from individual components are difficult to decipher. The complex, multicomponent structure of compounds in a bioactive mixture and the degradation of flavonoids during harsh extraction procedures obscure the precise assignment of bioactivity to individual pigments. Extensive metabolic breakdown after ingestion complicates tracking of anthocyanins to assess absorption, bioavailability, and accumulation in various organs. Anthocyanin pigments and other flavonoids that are uniformly, predictably produced in rigorously controlled plant cell culture systems can be a great advantage for health and nutrition research because they are quickly, easily isolated, lack interferences found in whole fruits, can be elicited to provoke rapid and prolific accumulation, and are amenable to biolabeling so that metabolic fate can be investigated after ingestion.

Mary Ann Lila

Anthocyanins and Human Health: An In Vitro Investigative Approach

Anthocyanin extracts of two blueberries, Vaccinium myrtillus (bilberry) and Vaccinium ashei (rabbiteye blueberry), and of three other berries, Ribes nigrum (black currant), Aronia melanocarpa (chokeberry), and Sambucus nigra (elderberry), were analyzed by high-performance liquid chromatography coupled with photodiode array detection and electrospray ionization - mass spectrometry (LC/PDA/ESI-MS). Both bilberry and rabbiteye blueberry contained 15 identical anthocyanins with different distribution patterns. Black currant, chokeberry, and elderberry contained 6, 4, and 4 kinds of anthocyanins, respectively. The radical scavenging activities of these berry extracts were analyzed by using 2,2-diphenyl-1-picrylhydrazyl (DPPH). All these extracts showed potent antiradical activities.

Jun-ichiro Nakajima

Ippei Tanaka

Shujiro Seo

Mami Yamazaki

Kazuki Saito

LC/PDA/ESI-MS Profiling and Radical Scavenging Activity of Anthocyanins in Various Berries

Anthocyanins are polyphenolic ring-based flavonoids, and are widespread in fruits and vegetables of red-blue color. Epidemiological investigations and animal experiments have indicated that anthocyanins may contribute to cancer chemoprevention. The studies on the mechanism have been done recently at molecular level. This review summarizes current molecular bases for anthocyanidins on several key steps involved in cancer chemoprevention: (i) inhibition of anthocyanidins in cell transformation through targeting mitogen-activated protein kinase (MAPK) pathway and activator protein 1 (AP-1) factor; (ii) suppression of anthocyanidins in inflammation and carcinogenesis through targeting nuclear factor kappa B (NF-<mml:math alttext="$\kappa$" id="E1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mi>κ</mml:mi></mml:math>B) pathway and cyclooxygenase 2 (COX-2) gene; (iii) apoptotic induction of cancer cells by anthocyanidins through reactive oxygen species (ROS) / c-Jun NH<mml:math alttext="${}_2$" id="E2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:math>-terminal kinase (JNK)-mediated caspase activation. These data provide a first molecular view of anthocyanidins contributing to cancer chemoprevention.

De-Xing Hou

Makoto Fujii

Norihiko Terahara

Makoto Yoshimoto

Molecular Mechanisms Behind the Chemopreventive Effects of Anthocyanidins

Anthocyanins are a group of plant antioxidants known for their therapeutic use. The effects of natural light, red light, and far-red light on individual as well as total anthocyanin content in cranberry fruit (Vaccinium macrocarpon Ait) were examined in an experimental setting designed to mimic water-harvesting conditions. The reversed-phase high performance liquid chromatography (HPLC) method was used to separate and analyze the anthocyanins. In contrast to the case of the control sample that was kept in the dark, natural light increased the total anthocyanin level by <mml:math alttext="$75.3$" id="E1" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>75.3</mml:mn></mml:mrow></mml:math>% and <mml:math alttext="$87.2$" id="E2" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>87.2</mml:mn></mml:mrow></mml:math>% after 24 and 48 hours water immersion, respectively. Red light and far-red light increased the total anthocyanin level by <mml:math alttext="$41.5$" id="E3" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>41.5</mml:mn></mml:mrow></mml:math>% and <mml:math alttext="$34.7$" id="E4" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>34.7</mml:mn></mml:mrow></mml:math>%, respectively. The amount of each individual anthocyanin increased differently under natural light, red light, and far-red light, suggesting that expressions of enzymes that catalyze the anthocyanin biosynthesis are regulated differently by environments.

Yu Zhou

Bal Ram Singh

Effect of Light on Anthocyanin Levels in Submerged, Harvested Cranberry Fruit

The concentration of anthocyanins in fruits of &#8220;Assaria&#8221; pomegranate, a sweet Portuguese cultivar typically grown in Algarve (south Portugal), was monitored during storage under different conditions. The fruits were exposed to cold storage (<mml:math alttext="$5^{\circ}$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msup><mml:mn>5</mml:mn><mml:mo>&#8728;</mml:mo></mml:msup></mml:mrow></mml:math>C) after the following treatments: spraying with wax; spraying with <mml:math alttext="$1.5$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>1.5</mml:mn></mml:mrow></mml:math>% CaCl<mml:math alttext="${}_2$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msub><mml:mi></mml:mi><mml:mn>2</mml:mn></mml:msub></mml:mrow></mml:math>; spraying with wax and <mml:math alttext="$1.5$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>1.5</mml:mn></mml:mrow></mml:math>% CaCl<mml:math alttext="${}_2$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msub><mml:mi></mml:mi><mml:mn>2</mml:mn></mml:msub></mml:mrow></mml:math>; covering boxes with 25 <mml:math alttext="$\mu$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mi>&#956;</mml:mi></mml:math>c thickness low-density polyethylene film. Untreated fruits were used as a control. The anthocyanin levels were quantified by either comparison with an external standard of cyanidin 3-rutinoside (based on the peak area) or individual calculation from the peak areas based on standard curves of each anthocyanin type. The storage time as well as the fruit treatment prior to storage influenced total anthocyanin content. The highest levels were observed at the end of the first month of storage, except for the fruits treated with CaCl<mml:math alttext="${}_2$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msub><mml:mi></mml:mi><mml:mn>2</mml:mn></mml:msub></mml:mrow></mml:math>, where the maximal values were achieved at the end of the second month. The anthocyanin quantification method influenced the final result. When total anthocyanin was calculated as a sum of individual pigments quantified based on standard curves of each anthocyanin type, lower values were obtained.

Gra&#231;a  Miguel

Catarina  Fontes

Dulce  Antunes

Alcinda  Neves

Denise  Martins

Anthocyanin Concentration of &#8220;Assaria&#8221; Pomegranate Fruits During Different Cold Storage Conditions

Accumulation of phenolic compounds has been monitored in a suspension culture of anthocyanin-accumulating sweet potato cell line grown under the conditions of modified Murashige and Skoog high-anthocyanin production medium (APM) over a period of 24 days. Tissue samples extracted with 15% acetic acid were analysed using HPLC at a detection wavelength of 326 nm. Among others, the following derivatives of caffeoylquinic acids were detected: 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, and 3,4,5-tricaffeoylquinic acid. Their total amount reached a maximum of 110 mg/gFW between the 4th and the 15th day of culture growth on APM. The major compound of the phenolic mixture was 3,5-dicaffeoylquinic acid with maximum accumulation level of 80 mg/100 gFW. The potential effects of targeted phenolic compounds on the nutraceutical qualities of in vitro produced anthocyanin-rich extracts are discussed.

Izabela Konczak

Shigenori Okuno

Osamu Yamakawa

Caffeoylquinic Acids Generated In Vitro in a High-Anthocyanin-Accumulating Sweet potato Cell Line

In a pilot study with 6 females and 1 male, the metabolism of various cyanidin glucosides after oral administration of elderberry juice was investigated. The anthocyanin metabolites were detected in urinary excretion. After ingestion of a bolus quantity of <mml:math alttext="$3.57$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>3.57</mml:mn></mml:mrow></mml:math> g total anthocyanins in a <mml:math alttext="$150$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>150</mml:mn></mml:mrow></mml:math> mL elderberry juice concentrate, <mml:math alttext="$0.053$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>0.053</mml:mn></mml:mrow></mml:math>% of the administered dose was excreted in urine as glucosidically bound cyanidins within the first 5 hours. Only <mml:math alttext="$0.003$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>0.003</mml:mn></mml:mrow></mml:math>% of the ingested anthocyanin glucosides was excreted as cyanidin glucuronide, suggesting that this conversion step might be of minor importance in urinary excretion.

Roland  Bitsch

Michael  Netzel

Susanne  Sonntag

Gabriele  Strass

Thomas  Frank

Irmgard  Bitsch

Urinary Excretion of Cyanidin Glucosides and Glucuronides in Healthy Humans After Elderberry Juice Ingestion

This study examined the effects of freezing, storage, and cabinet drying on the anthocyanin content and antioxidant activity of blueberries (Vaccinium corymbosum L). Fresh samples were stored for two weeks at <mml:math alttext="$\5^\circ$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:msup><mml:mn>5</mml:mn><mml:mo>&#8728;</mml:mo></mml:msup></mml:mrow></mml:math>C while frozen samples were kept for up to three months at <mml:math alttext="$-20^\circ$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mo>&#8722;</mml:mo><mml:msup><mml:mrow><mml:mn>20</mml:mn></mml:mrow><mml:mo>&#8728;</mml:mo></mml:msup></mml:mrow></mml:math>C. There were two drying treatments, one including osmotic pretreatment followed by cabinet drying and the other involving only cabinet drying. Total anthocyanins found in fresh blueberries were <mml:math alttext="$7.2 \pm 0.5$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>7.2</mml:mn><mml:mo>&#177;</mml:mo><mml:mn>0.5</mml:mn></mml:mrow></mml:math> mg/g dry matter, expressed as cyanidin 3-rutinoside equivalents. In comparison with fresh samples, total anthocyanins in untreated and pretreated dried blueberries were significantly reduced to <mml:math alttext="$4.3 \pm 0.1$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>4.3</mml:mn><mml:mo>&#177;</mml:mo><mml:mn>0.1</mml:mn></mml:mrow></mml:math> mg/g solid content, 41% loss, and <mml:math alttext="$3.7 \pm 0.2$" xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mrow><mml:mn>3.7</mml:mn><mml:mo>&#177;</mml:mo><mml:mn>0.2</mml:mn></mml:mrow></mml:math> mg/g solid content, 49% loss, respectively. Osmotic treatment followed by a thermal treatment had a greater effect on anthocyanin loss than the thermal treatment alone. In contrast, the frozen samples did not show any significant decrease in anthocyanin level during three months of storage. Measurement of the antioxidant activity of anthocyanin extracts from blueberries showed there was no significant difference between fresh, dried, and frozen blueberries.

Virachnee  Lohachoompol

George  Srzednicki

John  Craske

The Change of Total Anthocyanins in Blueberries and Their Antioxidant Effect After Drying and Freezing

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