Anthocyanins from Natural Sources: Exploiting Targeted Delivery for Improved Health: Volume 12 (Food Chemistry, Function and Analysis) - Hardcover

Hardcover

ISBN 10: 1788012151 ISBN 13: 9781788012157

Verlag: Royal Society of Chemistry, 2019

Inhaltsangabe

Interest in anthocyanins has increased in the past few years, due to their potential health-promoting properties as dietary antioxidants. Previously they were known as an important class of natural colorant, orange-red to blue-violet, found in fruits such as berries and in vegetables. This book discusses ways of targeting the delivery of these compounds, through manipulation of exploitation mechanisms. It addresses all aspects from extraction of anthocyanins from natural sources, their health benefits and metabolism to specialized controlled release applications. It will serve as a unique reference for those specializing in the fate of anthocyanins in the body (pharmacokinetics) and the research related to controlled release systems. It will provide an insight for pharmaceutical scientists, food engineers, food scientists and those interested in human health and nutrition.

Über diesen Titel

Von der hinteren Coverseite

Interest in anthocyanins has increased in the past few years, due to their potential health-promoting properties as dietary antioxidants. Previously they were known as an important class of natural colorant, orange-red to blue-violet, found in fruits such as berries and in vegetables. This book discusses ways of targeting the delivery of these compounds, through manipulation of exploitation mechanisms. It addresses all aspects from extraction of anthocyanins from natural sources, their health benefits and metabolism to specialized controlled release applications. It will serve as a unique reference for those specializing in the fate of anthocyanins in the body (pharmacokinetics) and the research related to controlled release systems. It will provide an insight for pharmaceutical scientists, food engineers, food scientists and those interested in human health and nutrition.

Auszug. © Genehmigter Nachdruck. Alle Rechte vorbehalten.

Anthocyanins from Natural Sources

Exploiting Targeted Delivery for Improved Health

By Marianne Su-Ling Brooks, Giovana B. Celli

The Royal Society of Chemistry

Copyright © 2019 The Royal Society of Chemistry
All rights reserved.

ISBN: 978-1-78801-215-7

Contents

Part I Chemistry and Extraction of Anthocyanins, 
Chapter 1 Natural Sources of Anthocyanins J. Zhang, G. B. Celli and M. S. Brooks, 
Chapter 2 Chemistry of Anthocyanins F. Pina, A. J. Parola, M. J. Melo, J. C. Lima and V. de Freitas, 
Chapter 3 Extraction of Anthocyanins from Natural Sources – Methods and Commercial Considerations J. Zhang, R. Singh and S. Y. Quek, 
Chapter 4 Extraction of Anthocyanins from Food Processing Waste – Potential and Issues N. P. Brunton, 
Part II Health Benefits and Metabolism, 
Chapter 5 Health Benefits of Anthocyanins H. P. Vasantha Rupasinghe and Niroshaathevi Arumuggam, 
Chapter 6 Pharmacokinetics Colin D. Kay and Alan Crozier, 
Chapter 7 The Stability and Absorption of Anthocyanins in the Mouth G. T. Sigurdson and M. M. Giusti, 
Chapter 8 Role of the Stomach in Anthocyanin Absorption S. Passamonti, 
Part III Controlled Release Systems for Anthocyanins, 
Chapter 9 Encapsulation Techniques for Anthocyanins F. P. Flores and F. Kong, 
Chapter 10 Routes of Anthocyanin Delivery and Suitable Systems for Targeted Release G. B. Celli and M. S. Brooks, 
Part IV Conclusions, 
Chapter 11 Closing Remarks and Future Prospects S. Brooks and G. B. Celli, 
Subject Index, 

CHAPTER 1

Natural Sources of Anthocyanins

J. ZHANG, G. B. CELLI AND M. S. BROOKS

1.1 Introduction

Anthocyanins are ubiquitous water-soluble pigments that have important roles in the propagation, protection, and physiology of higher plants. Evidence shows that these compounds can act by repelling herbivores and parasites, attracting pollinators and seed dispersers, and protecting plants against biotic and abiotic stresses. In human health, anthocyanins have been associated with various benefits due to their antioxidant, anti-inflammatory, neuroprotective, and anti-diabetic properties. Chemically, anthocyanins are polyphenols and belong to a large class of secondary metabolites known as flavonoids, with a core structure in the form of 2-phenylbenzopyrylium or flavylium cation (Figure 1.1). They are polyhydroxy and polymethoxy derivatives of this flavylium cation and can have sugar groups or acylated moieties attached at different positions. Although more than 700 compounds have been described in the literature, they are mainly derived of six anthocyanidins (aglycone form): cyanidin, delphinidin, pelargonidin, peonidin, petunidin, and malvidin.

An interesting feature of anthocyanins is that they can display a great diversity of colors depending on their chemical structure and the environment in which they are found, ranging from orange to blue. Several factors likely contribute to the variations in anthocyanin content and profile in plants. Anthocyanin biosynthesis and structural skeleton diversity are controlled by a number of genes. As illustrated in a colored potato study, the red cultivars contained predominantly pelargonidin derivatives, while the purple/blue varieties had peonidin, petunidin, and malvidin as the main aglycones. A color change is usually seen in fruit over the growing and harvest seasons. For example, the intra-seasonal monitoring of total anthocyanins and specific components in blueberries showed that during the harvest season between June and August, the content had a generally increasing trend, but the percentages of delphinidin and malvidin glycosides were inversely mirrored. The environment also has an effect on anthocyanin production in plants. Although the specific role that these plant metabolites have in protecting against biotic and abiotic stresses is not well understood, studies have revealed interesting connections between anthocyanin profiles and various stress conditions. For example, Kovinich et al. reported a clear pattern of difference in model plant Arabidopsis thaliana under abiotic stresses, where low pH and phosphate deficiency induced anthocyanin accumulation, while osmotic stress with mannitol and high pH reduced the total anthocyanins level. Furthermore, some structural differences, mainly in the modification of glycoside chains, were observed under these stress conditions. In field crops, the anthocyanin content and profile are most likely affected by both genetic and environmental variations. A multi-year grape study by Ortega-Regules et al. showed that the total anthocyanins and fingerprint profiles varied considerably over 3 years with different weather conditions during the growing seasons for the same crop varieties, while the differences were relatively smaller for Monastrell variety grapes grown at two different locations.

Aside from their recognized health benefits, these colorful molecules from natural sources are very appealing to the food industry as colorants. The increasing interest in their use in food products has been driven by consumer and regulatory pressure to replace synthetic colorants. However, this substitution is not straightforward as anthocyanins can degrade under normal processing and storage conditions, such as during heat treatment, which would negatively impact the sensory properties of the product. Different strategies to improve the stability of these colorants have been investigated, some of which will be discussed in later chapters.

In this chapter, natural sources of anthocyanins, such as fruits, vegetables, and grains, are highlighted and discussed based largely on the literature of the past 20 years. Examples of anthocyanin-containing plants used in traditional Chinese and Indian medicine, as well as exotic plants found worldwide, are included. Mazza and Miniatihave extensively reviewed the occurrence of anthocyanins in foods, and their work serves as the foundation for this updated account in the area.

1.2 Anthocyanins in Foods

Color is an important attribute of fresh or processed food products that is very appealing to consumers. As one of the largest groups of water-soluble pigments, anthocyanins are present in virtually all types of foods, contributing to the wide range of characteristic colors. The following sections list various types of foods available in North America (in alphabetical order by common name) and describe the main types of anthocyanins reported in the literature. Later sections include examples of anthocyanin sources used in traditional medicine and found in other parts of the world.

1.2.1 Fruits

1.2.1.1 Apple: Malus pumila L.

The red peel of certain cultivars of apples is very attractive and retains most of the pigment. Cyanidin-3-galactoside is the major anthocyanin in the red peel, while cyanidin-3-glucoside and cyanidin-3-arabinoside are minor ones. Apple flesh can also contain anthocyanins, as reported in red-fleshed apple varieties. A recent study of 22 apple cultivars in Poland revealed that the average total anthocyanin content of the whole fruit was 30 mg/100 g dry tissue, ranging from 5 to 133 mg/100 g depending on the cultivar. From this content, 85–100% was found to be cyanidin-3-galactoside.

1.2.1.2 Apricot: Prunus armeniaca L.

Dried apricots were reported to have a total anthocyanin content of 3 mg cyanidin-3-glucoside equivalents/100 g.The major anthocyanin compound found in apricots is cyanidin-3-rutinoside.

1.2.1.3 Bilberry: Vaccinium myrtillus L.

This small berry contains highly diverse anthocyanin compounds with various anthocyanidins and glycosylation patterns. The major anthocyanins are malvidin-3-glucoside (22%), delphinidin-3-galactoside (19%), cyanidin-3-galactoside (15%), petunidin-3-galactoside (14%), cyanidin-3-glucoside (9%), and delphinidin-3-glucoside (9%). Using high-performance liquid chromatography with electrospray ionization mass spectrometry (HPLC-ESI-MS), Dugo and co-workers identified 14 anthocyanins from a black bilberry extract, including 3-arabinosides, 3-glucosides, and 3-galactosides of five anthocyanidins: cyanidin, delphinidin, peonidin, petunidin, and malvidin.

1.2.1.4 Blackberry: Rubus allegheniensis Porter and Other Rubus Species

The predominant anthocyanins identified in blackberries were cyanidin-3-glucoside and cyanidin-3-rutinoside. Additional anthocyanins, such as cyanidin-3-xyloside and cyanidin-3-malonylglucoside, were also found in a study examining 51 blackberry samples using liquid chromatography with ultraviolet detection coupled with mass spectrometry (LCUV/MS). In a Norwegian wild blackberry species, 3-O-β-(6"-(3-hydroxy-3-methylglutaroyl)-glucopyranoside) was also confirmed by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR).

1.2.1.5 Blueberry: V. corymbosum L. (Highbush Blueberry) and V. angustifolium Ait. (Lowbush Blueberry)

Major anthocyanins in highbush blueberries were 3-galactosides and 3-arabinosides of delphinidin, malvidin, and petunidin, in addition to 3-glucosides of these anthocyanidins, as well as cyanidin and peonidin at lower levels. In lowbush blueberry, the 3-galactosides of various anthocyanidins were more predominant. Acylated anthocyanins in the form of 3-acetylglucoside and 3-acetylgalactoside of malvidin were also found in lowbush blueberry, accounting for over 32% of its anthocyanin content. In a Chinese lowbush blueberry species (V. uliginosum L.), the predominant anthocyanin was malvidin-3-glucoside (31.9% of total anthocyanins).

1.2.1.6 Cherry: Prunus avium L. and Other Prunus Species

Cyanidin-3-glucoside and cyanidin-3-rutinoside were the main anthocyanins found in cherries.

1.2.1.7 Cranberry: V. oxycoccus L. (European Cranberry) and V. macrocarpon Ait. (American Cranberry)

Glucosides of peonidin and cyanidin were found to be the main anthocyanins in small European cranberry species (V. oxycoccus L.), while the 3-galactosides and 3-arabinosides of these anthocyanidins were more abundant in American cranberries (V. macrocarpon Ait.). A study of 78 American cranberries revealed that the proportion of the two major anthocyanidins, peonidin and cyanidin, varied between 1 : 0.5 and 1 : 3.6. It also showed variation of glycosylation profiles, with galactosides ranging between 64 and 75%, arabinosides between 20 and 33%, and glucosides between 3 and 9%.

1.2.1.8 Currant: Ribes rubrum L. (Redcurrant) and R. nigrum L. (Blackcurrant)

Cyanidin glycosides, such as 3-xylosylrutinoside, 3-glucosylrutinoside, 3-sambubioside, 3-rutinoside, and 3-glucoside, were the major anthocyanins found in redcurrants, while the 3-rutinoside and 3-glucoside of cyanidin and delphinidin were found in higher concentrations in blackcurrants.

1.2.1.9 Grape: Vitis vinifera L. and Other Vitis Species

The distribution of anthocyanins in grapes is complex and, similar to other fruits, highly dependent on cultivar, climate, and plant maturity, among other factors. The anthocyanidins identified include cyanidin, delphinidin, petunidin, peonidin, and malvidin, mostly monoand di-glucosylated, usually at C-3 and C-3,5 positions. Grapes are also known to have acylated anthocyanins, especially with p-coumaric acid substitutes attached to the glucose moiety. Anthocyanin dimers as minor components were also detected in grapes using HPLC with a diode array detector and tandem MS (HPLC-DAD-MS/MS).

1.2.1.10 Haskap Berry: Lonicera caerulea L.

This fruit is native to Siberia and northeastern Asia, and fairly new in the North America market (Figure 1.2A). Commonly known as blue honeysuckle, these berries contain cyanidin-3-glucoside as the predominant anthocyanin. Minor anthocyanins including cyaniding-3,5-di-glucoside, cyaniding-3-rutinoside, peonidin-3-glucoside, and pelargonidin-3-glucoside were also present.

1.2.1.11Mulberry: Morus alba L.

This fruit mainly contains cyanidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3-galactoside, delphinidin-3-rutinoside, and cyanidin-3-(6"-rhaminosyl) glucoside. A photograph of a mulberry plant is shown in Figure 1.2B.

1.2.1.12 Orange: Citrus sinensis L.

Red oranges and blood oranges contain cyanidin-3-glucoside as the major anthocyanin, along with delphinidin glycosides. In orange juice from the Italian Moro cultivar, cyanidin-3-(6"-malonyl) glucoside was also found to be a predominant anthocyanin.

1.2.1.13 Peach: Prunus persica L.

In a survey of 68 peach cultivars from China, Zhao et al. reported that the most common anthocyanin present was cyanidin-3-glucoside, while its 3-rutinoside was only found in certain cultivars.

1.2.1.14 Pear: Pyrus spp.

Anthocyanins were only found in red skinned pear cultivars among 19 European and Tunisian varieties studied, at levels of 134 mg kg-1 for cyanidin-3-O-hexoside and 38 mg kg-1 for peonidin-3-O-hexoside (on a fresh weight basis). Similar findings were also reported for 37 pear cultivars grown in China, where cyanidin-3-galactoside was revealed as the major anthocyanin in red skinned cultivars.

1.2.1.15 Plum: Prunus domestica L. and Other Prunus Species

Studies from a large number of plum cultivars revealed that cyanidin-3-rutinoside was the predominant anthocyanin, along with its 3-glucoside. In addition, the glycoside of peonidin was also reported for some European plum varieties. In South African plum cultivars, cyanidin-3-glucoside was detected as the predominant anthocyanin.

1.2.1.16 Pomegranate: Punica granatum L.

Cyanidin-3,5-diglucoside, cyanidin-3-glucoside, delphinidin-3,5-diglucoside, delphinidin-3-glucoside, and pelargonidin-3-glucoside were identified as the major anthocyanins in pomegranate juice.

1.2.1.17 Rosehip: Rosa canina L. and Other Rosa Species

Cyanidin-3-rutinoside and 3-diglucoside are anthocyanins that have been identified in rosehip, shown in Figure 1.2C.

1.2.1.18 Saskatoon Berry: Amelanchier alnifolia Nutt.

This plant is native to Canada and the northern US. An example is shown in Figure 1.2D. The major anthocyanins that were found in saskatoon berries were 3-galactoside, 3-glucoside, 3-arabinoside of cyanidin, with its xyloside also present as a minor constituent. However, delphinidin-3-glucoside was reported as the dominant anthocyanin in another study.

1.2.1.19 Strawberry: Fragaria x ananassa Duch.

Pelargonidin-3-glucoside and cyanidin-3-glucoside have been identified as the major anthocyanins in cultivated strawberries. Using LC-MS, the presence of the 3-rutinoside and 3-acetylglucoside of pelargonidin and cyanidin-3-rutinoside was confirmed from the variety Carmarosa. This variety was also shown to contain 5-carboxypyranopelargonidin-3-glucoside. In 14 oriental strawberry cultivars, pelargonidin-3-glucoside, cyanidin-3-glucoside, and pelargonidin-3-rutinoside were the major anthocyanins.

1.2.2 Legumes and Vegetables

1.2.2.1 Asparagus: Asparagus officinalis L.

Cyanidin-3-(3"-glucosyl-6"-rhamnosyl)-glucoside and cyanidin-3-rutinoside were the major anthocyanins found in purple asparagus (A. officinalis cv. Purple Passion).

1.2.2.2 Bean: Phaseolus spp.

In black beans (P. vulgaris L.), delphinidin-3-glucoside, petunidin-3-glucoside, and malvidin-3-glucoside were isolated and identified to be the major anthocyanins, and the total content was determined to be around 213 mg/100 g. Other anthocyanins found in black and kidney beans included delphinidin-3,5-diglucoside, petunidin-3,5-diglucoside, delphinidin-3-galactoside, malvidin-3,5-diglucoside, petunidin-3-galactoside, pelargonidin-3-glucoside, and malvidin-3-galactoside. In addition, some C–C linked flavanol anthocyanin derivatives, such as gallocatechin–delphinidin, catechin–cyanidin-3-glucoside, catechin–cyanidin, catechin–petunidin, catechin–peonidin, and afzelechin–poinidin, were identified in Guatemala kidney beans and scarlet red runner beans (P. coccineus L.).

1.2.2.3 Cabbage: Brassica oleracea L. var. capitata f. rubra

Red cabbage contains a large number of acylated cyanidin glycosides, with cyanidin-3-diglucoside-5-glucoside, cyanidin-3-(p-coumaroyl) diglucoside-5-glucoside, and cyanidin-3-(sinapoyl)-diglucoside-5-glucoside as the predominant compounds. In the Chinese purple cabbage (B. rapa L. ssp. pekinensis), the major anthocyanins were found to be cyanidin-3-(p-coumaroylsophoroside)-5-maolonylglucoside, cyanidin-3-ferulylsophoroside-5-malonylglucoside, cyanidin-3(sinapyl-p-coumaroyl)-sophoroside-5-malonylglucoside, and cyanidin-3-(sinapylferulyl)sophoroside-5-malonylglucoside. It is reported that the level of anthocyanins in red cabbage can reach up to 1780 mg/100 g (dry weight basis). 1.2.2.4Carrot: Daucus carota L.

Several cyanidin glycosides have been reported in purple carrot varieties, including 3-(xylosyl)-glucosyl-galactoside, 3-(xylosyl)(sinapoyl)-glucosyl-galactoside, 3-(xylosyl)(feruloyl)-glycosyl-galactoside, and 3-(xylosyl)(coumaroyl)-glucosylgalactoside. In addition to these cyanidin glycosides, pelargonidin-3-xylosyl(feruloylglucosyl)galactoside, peonidin-3-xylosylgalactoside, and peonidin-3-xylosyl(feryloylglucosyl)galactoside were found as minor constituents in a black carrot cultivar (D. carota ssp. Sativus var. atrorubens Alef).

(Continues...)

Excerpted from Anthocyanins from Natural Sources by Marianne Su-Ling Brooks, Giovana B. Celli. Copyright © 2019 The Royal Society of Chemistry. Excerpted by permission of The Royal Society of Chemistry.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Details zur Ausgabe

• Verlag: Royal Society of Chemistry
• Erscheinungsdatum: 2019
• Sprache: Englisch
• ISBN 10: 1788012151
• ISBN 13: 9781788012157
• Einband: Tapa dura
• Anzahl der Seiten: 336
• Herausgeber: Brooks Marianne Su-Ling, Celli Giovana B
• Kontakt zum Hersteller: Nicht verfügbar
• Verantwortliche Person: Nicht verfügbar