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Therapeutic Potential of Anthocyanin Against Diabetes
Published in Hafiz Ansar Rasul Suleria, Megh R. Goyal, Health Benefits of Secondary Phytocompounds from Plant and Marine Sources, 2021
Tawheed Amin, H. R. Naik, Bazila Naseer, Syed Zameer Hussain
Anthocyanins are derived from anthocyanidins; therefore, their structure consists of an aglycone or sugar-free anthocyanidin structure [32]. Anthocyanidins do not contain carbohydrate (glucose) esterified at the 3-position, while as it is present in anthocyanin [32]. Based on the number and position of OH– groups on the flavan nucleus, six distinct anthocyanidins exist commonly in plants, such as pelargonidin (pg), cyanidin (cy), peonidin (pn), delphinidin (dp), petunidin (pt), and malvidin (mv) (Figures 5.2) [79]. The most predominant plant sources of anthocyanins are grapes (11%), berries (20%), red or purple vegetables (8%), yogurt (6%), wine (16%), and 100%-non-citrus juice (6%) [17].
Nutraceuticals and Functional Foods
Published in Robert E.C. Wildman, Richard S. Bruno, Handbook of Nutraceuticals and Functional Foods, 2019
The majority of naturally occurring flavonoids are actually glycosides, meaning a sugar moiety is attached. The attachment of hydroxyl groups and sugars will increase the hydrophilic properties of the flavonoid molecule, while attachment of methyl esters or modified isopentyl units will increase the lipophilic character. Anthocyanins and anthocyanidins (Figure 1.9) are produced by plants and function largely as coloring pigments. Basically, anthocyanins are anthocyanidins with sugar moieties attached at position 3 of the 3-carbon bridge between rings A and B.17 These molecules help attract animals for pollination and seed dispersal. They are responsible for the red, pink, blue, and violet coloring of many fruits and vegetables, including blueberries, apples, red cabbage, cherries, grapes, oranges, peaches, plums, radishes, raspberries, and strawberries. Only about 16 anthocyanidins have been identified in plants and include pelargonidin, cyanidin, delphinidin, peonidin, malvidin, and petunidin.
Chemical and Functional Properties of Amazonian Fruits
Published in Luzia Valentina Modolo, Mary Ann Foglio, Brazilian Medicinal Plants, 2019
Elaine Pessoa, Josilene Lima Serra, Hervé Rogez, Sylvain Darnet
During the fruit maturation, the profile of the anthocyanins C3G and C3R vary. In the beginning, the two anthocyanins are present in similar proportions, but in the latter stages, C3R is more abundant (Rogez et al., 2011). Dias et al. (2012) demonstrated that pelargonidin-3-glucoside (Pg3G), peonidin-3-O-glucoside (Pn3G) and peonidin 3-O-rutinoside (Pn3R) are minor anthocyanins in açaí fruits.
The Role of Polyphenol (Flavonoids) Compounds in the Treatment of Cancer Cells
Published in Nutrition and Cancer, 2020
Abu Hazafa, Khalil-Ur- Rehman, Nazish Jahan, Zara Jabeen
Among of all anthocyanidins, delphinidin have the highest anticancer activity. Delphinidin suppress the NF-kB pathway to induce apoptosis and cell cycle arrest in several types of cancer (57). Kausar et al. (58) indicated that the anthocyanidins might show the better role in the combination with other compound than the single one in the treatment of cancer. A study uncovered that the anthocyanidins (peonidin-3-glucoside, cyaniding-3-glucoside, and cyanidin-3-O-sambubioside) that are expelled from black rice and the fruit acanthopanax sessiliflorus, could induce the cell-proliferation, apoptosis, and tumor growth of HER2 cells, and inhibit the angiogenesis and invasion in the positive breast cancer (59,60). Similarly, cyanidin and delphinidin shows the oxidative stress-based cytotoxicity to colorectal cancer cells (60).
Profiling of anthocyanidins against transcriptional activities of steroid and nuclear receptors
Published in Drug and Chemical Toxicology, 2018
Barbora Pastorková, Petr Illés, Zdeněk Dvořák
In the parallel antagonist experiments (Figure 1), the cell lines were treated for 24h with anthocyanidins (10nM to 50µM) in combination with model agonists P4, E2, DHT and DEX corresponding to each receptor (PR, ER, AR, and GR, respectively). Moderate alterations of luciferase activity ranging from 58.9% (25µM delphinidin) to 117.2% (1µM peonidin) of activity induced by 100nM P4 were observed in the 22Rv1-PR cells after the treatment with anthocyanidins. In the MCF-7-ER cells, the induction of luciferase activity was not markedly changed by any of the examined anthocyanidins. The values ranged from 86.0% (10µM malvidin) to 137% (50µM cyanidin) of maximal luciferase activity obtained by 100nM E2. The induction of luciferase activity in the AIZ-AR cells was slightly reduced by increasing concentrations of anthocyanidins to the lowest value of 68.9% (50µM malvidin), compared to 100nM DHT. The highest value of lucifarese activity was measured at 1µM malvidin (111.8%). Similarly, only the slight changes of luciferase activity representing 78.6% (50µM delphinidin) to 127.6% (malvidin 10µM) of maximal luciferase activity induced by 100nM DEX were observed in AZ-GR cells exposed to examined anthocyanidins.
Chemopreventive Potential of Cereal Polyphenols
Published in Nutrition and Cancer, 2018
Shiwangni Rao, Abishek B. Santhakumar, Kenneth A. Chinkwo, Thiru Vanniasinkam, Jixun Luo, Christopher L. Blanchard
The bioactivity of anthocyanins, a flavonoid subclass, has been associated with antiproliferative and pro-apoptotic effects (20–23). It is the structural configuration of anthocyanins and its derivatives that permit hydroxylation and methoxylation to occur in the B ring which has been correlated to free radical scavenging and consequently inhibition of initiation and progression of tumorigenesis pathways (24). Anthocyanins have been identified in a number of cereals, with high levels reported specifically in pigmented varieties (20). Furthermore, cyanidin 3-glucoside has been reported as the most abundant form of anthocyanin followed by peonidin-3-glucoside (19,25). A derivative of anthocyanin is 3-deoxyanthocyanins (3-DXA), a metabolite unique to sorghum (26,27). The higher stability of 3-DXA compared to anthocyanin is due to its deprotonation constant relative to its hydration constant. This configuration results in its tendency to form pigmented quinoidal bases, compared to anthocyanins that favor colorless carbinol species (28). The high stability of 3-DXA compared to anthocyanin consequently results in its higher bioavailability (5,29). Similarly, another bioactive derivative of anthocyanin is 3,4-dihydroxybenzaldehyde or protocatechualdehyde. Protocatechualdehyde has been isolated from barley extracts and has also demonstrated to have anti-cancer properties (26).