Cyanidin 3-Glucoside -- What is It and Why Should I Supplement with It?

If you want to know what cyanidin 3-glucoside (C3G) is, and how it could help you lose fat and improve body composition, you want to read this article.

 

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You don’t have to go too far these days, or spend much time watching TV before you’re bombarded by a host of commercials and advertisements touting the benefits of fruits and fruit juices. We’ve always known that fruits are good for us to eat. They’re high in water, fiber, vitamins, and minerals. They’re also absolutely delicious when eaten at the point of perfect ripeness.

 

Recently, there’s been a significant uptick in the research into why fruit is good for us, and what is it about fruit in particular that seems to improve our health and help us ward off disease.

 

Today, we’re going to look at the phytochemical primarily responsible for those dark colors in your favorite fruits in Cyanidin-3-Glucoside (C3G).

 

We’ll discuss what it is, what its benefits are, why you should care, and where you can find it.

 

So...

What is Cyanidin 3-Glucoside?

 

Cyanidins are a subgroup of anthocyanins -- a special class of flavonoids responsible for giving fruits, flowers, and leaves, their red, blue, and purple color. Interestingly enough, these compounds are also responsible for the changing color of leaves.

 

In plants, cyanidin is bound to a molecule of glucose, forming the compound cyanidin 3-O-beta-Glucoside, or cyanidin 3-glucoside for short, or C3G for even shorter.

 

What determines if the cyanidin is red, blue, or purple?

 

The color of cyanidin 3-glucoside depends on the pH of the solution it is present in. When the pH is below 3, cyanidin is red. When the pH is neutral, cyanidin is violet. And, when pH is greater than 11, the color is blue.

 

Where Does Cyanidin 3-Glucoside Come From?

 

Cyanidins are most commonly found in fruits, with about 80% of the total cyanidin content coming from Cyanidin-3-Glucoside. The other 20% of cyanidin content is found in the form of  Cyanidin-3-Rutinoside, which is cyanidin bonded to rutinose, a disaccharide).[1] You will also likely encounter skant amounts of other cyanidins including 3,5-diglucoside, 3-galactose.

 

Cyanidin 3-Glucoside, in particular, is naturally occurring in a number of dark-colored foods including, but not limited to,[1,2,3]:

 

  • Black elderberry

  • Blackberry

  • Black bean

  • Black currant

  • Red Raspberry

  • Sweet Cherry

  • Aestivalis Grape

 

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What Does C3G Do?

As a member of the anthocyanin family, cyanidin-3-glucoside serves as a powerful antioxidant. It also helps reduce inflammation. Due to these effects, C3G is currently being investigated for its potential to help in the battle against type II diabetes and cancer.

 

When ingested, cyanidins are absorbed intact into the gastrointestinal wall. There it undergoes “extensive first-pass metabolism”[4], and enters into circulation in one of its numerous metabolites.

 

Here’s a picture of the various metabolites resulting from the breakdown of C3G[4]:

 

 

Research indicates that the half-life of C3G is between 1.5-2.5 hours.[6,7,8]

 

While researchers are still uncovering the exact mechanism by which cyanidin-3-glucoside does what it does, they have discovered a number of interesting effects and benefits of using the color-changing anthocyanin.

 

Benefits of Cyanidin 3-Glucoside

May Be Useful for Type 2 Diabetics

 

Out of control blood sugar levels are an epidemic these days as sugar-laden food is abundantly available for extremely low prices. As a result, we’re seeing stark increases in obesity, metabolic syndrome, and type 2 diabetes.

 

If you’re one of those people who is easily seduced by sweet treats, cyanidin 3-glucoside is something you may want to look into using.

 

Animal studies have shown that C3G  can:

 

  • Reduce fasting blood glucose levels in rats with diabetes[11]

  • Reduce organ complications (liver, kidneys, pancreas) associated with diabetes[11]

  • Decrease insulin resistance[12]

  • Enhance insulin secretion[12]

  • Lower postprandial (after meal) blood sugar levels[12]

  • Reduced fat accumulation in diabetic mice[13]

 

Additionally, cell cultures have noted that c3g prevented early-onset symptoms of diabetes by improving fat cell insulin sensitivity as well as upregulating muscular energy burning[13].

 

And, C3G also reduced pancreatic cell death in mice in an environment simulating the oxidative stress in diabetes.[14]

 

Based on these early findings, researchers are exploring the use of C3G in humans to further understand the potential benefits it may post for those combating chronic blood sugar issues and obesity.

 

Cardiovascular Support

Animal studies using berry extracts containing cyanidin 3-glucoside decreased cholesterol levels in mice fed a high-cholesterol diet. Researchers also noted that C3g increased HDL (“good” )cholesterol, which may be beneficial.[15] Due to this, it’s possible that C3G could aid in the prevention of atherosclerosis, a disease highly associated with high cholesterol levels.

 

Additional research, using human platelets, has shown that C3G can inhibit processes that lead to artery clogging, such as thrombus formation or platelet grouping, which promotes more free flowing blood, and a healthy cardiovascular system.[16]

 

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Antioxidant

Anthocyanin are well-known to serve as powerful antioxidants. Various studies have shown that cyanidin-3-glucoside acts as a potent antioxidant, combatting oxidative stress and protecting cells from radical oxygen species (ROS).[10,17,18]

 

As such, researchers suggest that C3G may be beneficial for preventing cardiovascular complications by reducing oxidative damage, decreasing inflammation, alleviating metabolic dysfunctions and apoptosis pathways in type 2 diabetes.[6]

 

Reduces Inflammation

Inflammation is a dual-edged sword. Acute inflammation, in the case of recovering from exercise or injury is good. Chronic inflammation, the kind that leads to arthritis and numerous other health complications, is bad.

 

As such, it stands to reason that reducing chronic inflammation could be beneficial to treating many of the diseases commonly associated with it.

 

Not only is C3G a powerful antioxidant, it also has been shown to exert some anti-inflammatory benefits as well. Cell studies have noted that cyanidin-3-glucoside decreases inflammation in both human and animal intestinal cells, which may improve symptoms for those battling inflammatory bowel syndrome.[17,19,20]

 

In smooth muscle tissue of organs, C3G has been shown to inhibit TNF-ɑ cell proliferation and prevent downstream cell damage and oxidation.[21] In case you weren’t aware, TNF-ɑ (tumor necrosis factor alpha) is heavily involved in systemic inflammation.

 

May Enhance Fat Burning

Anthocyanin extracts have been shown to increase the activity of certain proteins, such as Uncoupling Protein 2 (UCP-2) in fat cells that are heavily involved in fat burning.[22] Additionally, cyanidin-3-glucoside enhances adiponectin levels and suppresses IL-6 (interleukin-6) and plasminogen activator inhibitor-1 activity, which further supports C3G’s anti-inflammatory effect in the body.[23]

 

May Enhance Glucose Uptake

 

Interestingly enough, C3G also appears to mimic the effects of insulin too.

 

Human cell studies have noted that administration of C3G upregulated PPARy (peroxisome proliferator-activated receptors) activity, and as a result, GLUT4 translocation increased as did glucose uptake in the cells treated with C3G.[24] Additionally, elevated GLUT4 activity helps the body reduce blood sugar levels after a meal. This gene is typically less efficient in individuals with diabetes[32].

 

In other words, C3G may help improve glucose uptake due to its ability to mimic the actions of insulin.

 

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Additional Benefits of Cyanidin-3-Glucoside

May Help Night Vision

Research using eye cells from frogs noted that treatment with cyanidin 3-glucoside stimulates regeneration of a protein called rhodopsin, which is responsible for night vision.[25]

 

May Improve Bone Health

Studies using human bone cells documented that cyanidin 3-glucoside stimulated cells responsible for growth and healing. It also limited the actions of cells responsible for bone destruction, leading researchers to study further if C3G could be beneficial for osteoporosis and other bone degenerative diseases.[26]

 

Potential Neuroprotector

A study using mice brain cells noted that cyanidin 3-glucoside increased survival of the cells when exposed deprived of oxygen and glucose deprivation, symptoms typically associated with stroke. Due to this, researchers theorize that C3g could potentially protect the brain when faced with similar conditions.[27]

 

Possible Cancer Fighter

Cyanidin-3-Glucoside as well as a number of other anthocyanins and phytochemicals are being studied for their cancer-combatting effects.

Various cell studies have noted that administration with cyanidin-3-glucoside can:

 

  • Reduce human colon cancer cell growth[28]

  • Decrease DNA damage in human skin cell due to carcinogenic exposure[29]

  • Killed 40% of aggressive brain tumor cells[30]

  • Reduced proliferation of human lung cancer cells[31]



Best Cyanidin 3-Glucoside Supplements

Pyretic

 

Pyretic is the headlining stimulant-free fat burner from Primeval Labs, helping you reduce cravings, burn fat, and eliminate the dreaded “brain fog” that always accompanies dieting. Each serving of Pyretic provides 125mg of Cyanidin-3-Glucoside to support healthy blood sugar levels, glucose disposal, and fat burning.

 

Click here to try Pyretic for yourself and see how a fat burner doesn’t need stimulants to be effective.

 

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Primalog

 

Due to the intriguing blood sugar-regulating effects of C3G, we’ve included 250mg worth in every serving of our glucose disposal agent Primalog.

 

When taken prior to a high carbohydrate containing meal, Primalog supports healthy insulin levels and helps protect against spillover and the dreaded “carb coma” we all feel after indulging a bit too much.

 

Use it pre workout, to help shuttle those tasty carbs into your muscles where they can be put to immediate use, or take it with your post workout meal, so as to hasten glycogen replenishment and recovery.

 

Click here to learn more about Primalog and the importance of glucose disposal agents.

 

References

  1. Cho, M.J., Howard L.R., Prior R.L., Clark J.R. (2004) Flavonoid glycosides and antioxidant capacity of various blackberry, blueberry and red grape genotypes determined by high-performance liquid chromatography/mass spectrometry. Journal of the Science of Food and Agriculture 84:1771-1782

  2. Hassimotto, N. M. A., Genovese, M. I., & Lajolo, F. M. (2008). Absorption and metabolism of cyanidin-3-glucoside and cyanidin-3-rutinoside extracted from wild mulberry (Morus nigra L.) in rats. Nutrition Research (New York, N.Y.), 28(3), 198–207. https://doi.org/10.1016/j.nutres.2007.12.012

  3. http://phenol-explorer.eu/contents/polyphenol/9

  4. Jim Fang (2014) Bioavailability of anthocyanins, Drug Metabolism Reviews, 46:4, 508-520, DOI: 10.3109/03602532.2014.978080

  5. Ding, M., Feng, R., Wang, S. Y., Bowman, L., Lu, Y., Qian, Y., … Shi, X. (2006). Cyanidin-3-glucoside, a natural product derived from blackberry, exhibits chemopreventive and chemotherapeutic activity. The Journal of Biological Chemistry, 281(25), 17359–17368. https://www.ncbi.nlm.nih.gov/pubmed/16618699

  6. Li, W., Chen, S., Zhou, G., Li, H., Zhong, L., & Liu, S. (2018). Potential role of cyanidin 3-glucoside (C3G) in diabetic cardiomyopathy in diabetic rats: An in vivo approach. Saudi Journal of Biological Sciences, 25(3), 500–506. https://doi.org/https://doi.org/10.1016/j.sjbs.2016.11.007

  7. Jeon S, Han S, Lee J, Hong T, Yim D-S. The Safety and Pharmacokinetics of Cyanidin-3-Glucoside after 2-Week Administration of Black Bean Seed Coat Extract in Healthy Subjects. The Korean Journal of Physiology & Pharmacology : Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology. 2012;16(4):249-253. doi:10.4196/kjpp.2012.16.4.249.

  8. Mertens-talcott SU, Rios J, Jilma-stohlawetz P, Pacheco-palencia LA, Meibohm B, Talcott ST, Derendorf H. Pharmacokinetics of anthocyanins and antioxidant effects after the consumption of anthocyanin-rich acai juice and pulp (Euterpe oleracea Mart.) in human healthy volunteers. J Agric Food Chem. 2008;56:7796–7802

  9. Stoner GD, Sardo C, Apseloff G, Mullet D, Wargo W, Pound V, Singh A, Sanders J, Aziz R, Casto B, Sun X. Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days. J Clin Pharmacol. 2005;45:1153–1164.

  10. Perveen S, Yang JS, Ha TJ, Yoon SH. Cyanidin-3-glucoside Inhibits ATP-induced Intracellular Free Ca2+ Concentration, ROS Formation and Mitochondrial Depolarization in PC12 Cells. The Korean Journal of Physiology & Pharmacology : Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology. 2014;18(4):297-305. doi:10.4196/kjpp.2014.18.4.297.

  11. Chen, Z., Wang, C., Pan, Y., Gao, X., & Chen, H. (2018). Hypoglycemic and hypolipidemic effects of anthocyanins extract from black soybean seed coat in high fat diet and streptozotocin-induced diabetic mice. Food & Function, 9(1), 426–439. https://doi.org/10.1039/c7fo00983f

  12. Rozanska, D., & Regulska-Ilow, B. (2018). The significance of anthocyanins in the prevention and treatment of type 2 diabetes. Advances in Clinical and Experimental Medicine : Official Organ Wroclaw Medical University, 27(1), 135–142.

  13. Matsukawa, T., Inaguma, T., Han, J., Villareal, M. O., & Isoda, H. (2015). Cyanidin-3-glucoside derived from black soybeans ameliorate type 2 diabetes through the induction of differentiation of preadipocytes into smaller and insulin-sensitive adipocytes. The Journal of Nutritional Biochemistry, 26(8), 860–867. https://doi.org/10.1016/j.jnutbio.2015.03.006

  14. Lee, J. S., Kim, Y. R., Song, I. G., Ha, S.-J., Kim, Y. E., Baek, N.-I., & Hong, E. K. (2015). Cyanidin-3-glucoside isolated from mulberry fruit protects pancreatic beta-cells  against oxidative stress-induced apoptosis. International Journal of Molecular Medicine, 35(2), 405–412. https://doi.org/10.3892/ijmm.2014.2013

  15. Liu, S., You, L., Zhao, Y., & Chang, X. (2018). Wild Lonicera caerulea berry polyphenol extract reduces cholesterol accumulation  and enhances antioxidant capacity in vitro and in vivo. Food Research International (Ottawa, Ont.), 107, 73–83. https://doi.org/10.1016/j.foodres.2018.02.016

  16. Yao, Y., Chen, Y., Adili, R., McKeown, T., Chen, P., Zhu, G., … Yang, Y. (2017). Plant-based Food Cyanidin-3-Glucoside Modulates Human Platelet Glycoprotein VI Signaling and Inhibits Platelet Activation and Thrombus Formation. The Journal of Nutrition, 147(10), 1917–1925. https://doi.org/10.3945/jn.116.245944

  17. Jung, H., Kwak, H.-K., & Hwang, K. T. (2014). Antioxidant and anti-inflammatory activities of cyanidin-3-glucoside and cyanidin-3-rutinoside in hydrogen peroxide and lipopolysaccharide treated RAW264.7 cells (830.23). The FASEB Journal, 28(1_supplement), 830.23. https://doi.org/10.1096/fasebj.28.1_supplement.830.23

  18. Abdel-Aal, E.-S. M., Hucl, P., & Rabalski, I. (2018). Compositional and antioxidant properties of anthocyanin-rich products prepared from purple wheat. Food Chemistry, 254, 13–19. https://doi.org/10.1016/j.foodchem.2018.01.170

  19. Serra D, Paixão J, Nunes C, Dinis TCP, Almeida LM. Cyanidin-3-Glucoside Suppresses Cytokine-Induced Inflammatory Response in Human Intestinal Cells: Comparison with 5-Aminosalicylic Acid. Foligne B, ed. PLoS ONE. 2013;8(9):e73001. doi:10.1371/journal.pone.0073001.

  20. Jo, Y.-H., Park, H.-C., Choi, S., Kim, S., Bao, C., Kim, H. W., … Auh, J.-H. (2015). Metabolomic Analysis Reveals Cyanidins in Black Raspberry as Candidates for Suppression of Lipopolysaccharide-Induced Inflammation in Murine Macrophages. Journal of Agricultural and Food Chemistry, 63(22), 5449–5458. https://doi.org/10.1021/acs.jafc.5b00560

  21. Luo X, et al. Cyanidin-3-glucoside suppresses TNF-α-induced cell proliferation through the repression of Nox activator 1 in mouse vascular smooth muscle cells: involvement of the STAT3 signaling. Mol Cell Biochem. (2012)

  22. Tsuda, T., Ueno, Y., Yoshikawa, T., Kojo, H., & Osawa, T. (2006). Microarray profiling of gene expression in human adipocytes in response to anthocyanins. Biochemical Pharmacology, 71(8), 1184–1197. https://doi.org/https://doi.org/10.1016/j.bcp.2005.12.042

  23. Tsuda T, et al. Anthocyanin enhances adipocytokine secretion and adipocyte-specific gene expression in isolated rat adipocytes. Biochem Biophys Res Commun. (2004)

  24. Scazzocchio B, Varì R, Filesi C, et al. Cyanidin-3-O-β-Glucoside and Protocatechuic Acid Exert Insulin-Like Effects by Upregulating PPARγ Activity in Human Omental Adipocytes. Diabetes. 2011;60(9):2234-2244. doi:10.2337/db10-1461.

  25. Matsumoto, H., Nakamura, Y., Tachibanaki, S., Kawamura, S., & Hirayama, M. (2003). Stimulatory effect of cyanidin 3-glycosides on the regeneration of rhodopsin. Journal of Agricultural and Food Chemistry, 51(12), 3560–3563. https://doi.org/10.1021/jf034132y

  26. Park, K. H., Gu, D. R., So, H. S., Kim, K. J., & Lee, S. H. (2015). Dual Role of Cyanidin-3-glucoside on the Differentiation of Bone Cells. Journal of Dental Research, 94(12), 1676–1683. https://doi.org/10.1177/0022034515604620

  27. Bhuiyan MIH, Kim H-B, Kim SY, Cho K-O. The Neuroprotective Potential of Cyanidin-3-glucoside Fraction Extracted from Mulberry Following Oxygen-glucose Deprivation. The Korean Journal of Physiology & Pharmacology : Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology. 2011;15(6):353-361. doi:10.4196/kjpp.2011.15.6.353.

  28. Mazewski, C., Liang, K., & Gonzalez de Mejia, E. (2018). Comparison of the effect of chemical composition of anthocyanin-rich plant extracts on colon cancer cell proliferation and their potential mechanism of action using in vitro, in silico, and biochemical assays. Food Chemistry, 242, 378–388. https://doi.org/10.1016/j.foodchem.2017.09.086

  29. Woo, H., Lee, J., Park, D., & Jung, E. (2017). Protective Effect of Mulberry (Morus alba L.) Extract against Benzo[a]pyrene Induced Skin Damage through Inhibition of Aryl Hydrocarbon Receptor Signaling. Journal of Agricultural and Food Chemistry, 65(50), 10925–10932. https://doi.org/10.1021/acs.jafc.7b04044

  30. Hosseini, M. M., Karimi, A., Behroozaghdam, M., Javidi, M. A., Ghiasvand, S., Bereimipour, A., … Jangholi, E. (2017). Cytotoxic and Apoptogenic Effects of Cyanidin-3-Glucoside on the Glioblastoma Cell Line. World Neurosurgery, 108, 94–100. https://doi.org/10.1016/j.wneu.2017.08.133

  31. Chen, P.-N., Chu, S.-C., Chiou, H.-L., Kuo, W.-H., Chiang, C.-L., & Hsieh, Y.-S. (2006). Mulberry anthocyanins, cyanidin 3-rutinoside and cyanidin 3-glucoside, exhibited  an inhibitory effect on the migration and invasion of a human lung cancer cell line. Cancer Letters, 235(2), 248–259. https://doi.org/10.1016/j.canlet.2005.04.033

  32. Yamashita Y, Wang L, Nanba F, Ito C, Toda T, Ashida H. Procyanidin Promotes Translocation of Glucose Transporter 4 in Muscle of Mice through Activation of Insulin and AMPK Signaling Pathways. Kanzaki M, ed. PLoS ONE. 2016;11(9):e0161704. doi:10.1371/journal.pone.0161704.