Team:Dalhousie Halifax NS/What

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Anthocyanins are a class of water soluble, pigmented compounds derived from the much larger flavonoid class of plant metabolites. Beginning with the amino acid substrate phenylalanine, anthocyanins are produced through a complex biochemical pathway involving the actions of multiple enzymes, as seen in Figure 1. The colour of the compound is determined by the substitution patterns observed on the B ring such that colour intensifies with each additional hydroxyl group. The colour is also dependent on the pH of the medium; in high acidity, anthocyanins are stable flavylium cations that appear red but in neutral/basic solutions the compound is unstable and colourless. There are six common anthocyanins: cyanidin, delphinidin, petunidin, peonidin, pelargonidin, and malvidin. As indicated in Figure 1, delphinidin is the anthocyanin iGEM Dalhousie is studying.

Anthocyanins have tremendous health benefits and can be found in a variety of easily accessible foods such as honey, fruits and vegetables, nuts, cocoa and olive oil. Some of these benefits include:
• Prevention of DNA cleavage (Wallace, 2011, p.3)
• Regulation of inflammation by controlling the production of cytokines (Lila, 2004, p.307)
• Modulation of cognitive and motor functions, enhancing memory formation, and prevention of age related declines in neural function in mice models (Lila, 2004, p. 307)
• Regulation of free radicals due to intrinsic antioxidant ability which is vital for the preservation of important cellular components such as DNA and membranes (Lila, 2004, p.307)
• Minimization of lipid peroxidation, reducing pancreatic swelling and decreasing blood sugar concentration (Lila, 2004, p. 307)
• Anticarcinogenic properties that interfere with cell proliferation and therefore tumor formation studied in both in vitro (human colon cancer cells) and in vivo (mice) models (Kang et al., 2003, p.13-14)
• Enhanced visual acuity in human and animal models (Lila, 2004, p.307)

Why Delphinidin?

Delphinidin was chosen due to its phenotypic benefit because when produced within E.coli, delphinidin should cause the bacteria to turn blue.

Delphinidins are associated with specifics health benefits such as:
• Regulation of epidermal growth factor receptor in in vitro models using human vulva carcinoma cell line A431 (Meiers et al., 2001, p.958-961)
• Reduction of vascular inflammatory situations by modulating the expression of cell adhesion molecules ICAM and VCAM (Watson & Schönlau, 2015 p. 1)
• Reduction of platelet activity which could contribute to thrombosis prevention (Watson & Schönlau, 2015 p. 1)
• Suppression of the differentiation and function of osteoclasts demonstrated in rodent models (Watson & Schönlau, 2015 p. 1)
• Protection from UVB radiation by inhibiting keratinocyte apoptosis in human keratinocyte skin cells and mouse skin (Watson & Schönlau, 2015 p. 4-6)
• Reaction to both reactive oxygen and nitrogen due to large number of hydroxyl groups associated with the B ring making delphinidin especially effective as an antioxidant (Watson & Schönlau, 2015 p. 1)
• Protection of heart from oxidative stress by vasorelaxation as seen in rat aorta (Lila, 2004, p.307)

Anthocyanin Digestion
The exact mechanism by which absorption of anthocyanin takes place in unclear but various research groups have begun to narrow down the possibilities.
• Anthocyanins are absorbed during digestion as there is less anthocyanin excreted than was originally consumed in human models (Kuntz et al., 2015, p. 2)
• Transport membrane carriers such as bilitranslocase are being studied as they are found in the stomach (possible site of absorption) and anthocyanins have been shown to be competitive inhibitors to bilitranslocase activity (Passamonti et al., 2002, p. 631)
• Active rather than passive transport is being considered as experiments performed at pH levels comparable to the stomach (around 1.5-3) indicate that anthocyanins are positively charged hindering their ability to diffuse through the membrane (Fernandes et al., 2012, p. 513)


Fernandes, I., de Freitas, V., Reis, C., & Mateus, N. (2012). A New Approach on the Gastric Absorption of Anthocyanins. Food & Function, 3, 508-515. doi: 10.1039/c2fo10295a
Kang, SY., Seeram NP., Nair MG., & Bourquin LD. (2003). Tart Cherry Anthocyanins Inhibit Tumor Development in APCMin Mice and Reduce Proliferation of Luman Colon Cancer Cells. Cancer Letters, 194, 13-14. doi: 1 0.1016/S0304-3940(02)00583-9
Klein-Marcuschamer, D., Kumaran Ajikumar, P., & Stephanopoulos, G. (2007). Engineering microbial cell factories for the biosynthesis of isoprenoid molecules: Beyond lycopene. Trends in Biotechnology, 25(9). 417-424. doi:10.1016/j.tibtech.2007.07.006
Korzak, I., & Zhang, W. (2004). Anthocyanins, More Than Nature’s Colours. Journal of Biomedicine and Biotechnology, 2004(5), 239-240. doi: 10.1155/S1110724304407013
Kuntz, S,. Rudloff, S., Asseburg, H., Borsh. C., Fröhling,. Unger, F., Dold, S., Spengler, B., Römpp, A., & Kunz, C. (2015). Uptake and Bioavailability of Anthocyanins and Phenolic Acids from Grape/Blueberry Juice and Smoothie in vitro and in vivo. British Journal of Nutrition, 113, 1044-1055. doi: 10.1017/S0007114515000161
Lila, M.A. (2004). Anthocyanins and human health: An in vitro investigative approach. Journal of Biomedicine and Biotechnology, 2004(5), 306-313. doi: 10.1155/S111072430440401X
Meiers, S., Kemény, M., Weyand, U., Gastpar, R., Angerer, E., & Marko, D. (2001). The Anthocyanidins Cyanidin and Delphinidin Are Potent Inhibitors of the Epidermal Growth-Factor Receptor. Journal of Agriculture and Food Chemistry, 49(2), 958-962. doi: 10.1021/jf0009100
Passamonti, S., Vrhovesk, U., & Mattivi, F. (2002). The Interaction of Anthocyanins with Bilitranslocase. Biochemical and Biophysical Research Communications, 296(3), 631-636. Retrieved from http://
Watson, R., & Schönlau, F. (2015). Nutraceutical and Antioxidant Effects of a Delphinidin-Rich Maqui Berry Extract Delphinol ®: A Review. Minerva Cardioangiol, 63, 1-11. Retreived from
Wrolstad, RE. (2003). Anthocyanin pigments-Bioactivity and Colouring Properties. Journal of Food Science, 69(5), 419-421. doi: 10.1111/j.1365-2621.2004.tb10709.x
Wallace, TC. (2011). Anthocyanins in Cardiovascular Disease. Advances in Nutrition, 2, 1-7. doi: 10.3945/ an.110.000042