Interesting facts from the world of organic chemistry
Derivatives - ethers:
Matairesinol
Matairesinol is an organic compound that belongs to the class of lignans. Closely related to coniferol, which was briefly discussed in a previous article, is a substance called matairesinol. Due to the presence of two OH groups, Matairesinol could be considered more of an alcohol, which is not the only possibility to classify it. It contains one ether group in its structure, and since it is an interesting molecule, I decided to classify matairesinol as an ether.
Matairesinol is a lignan in plants. Lignans are natural compounds found in plants. Matairesinol is found in some grains, such as rye, and in some seeds and nuts, such as flaxseed, sesame seeds, and walnuts. Together with secoisolariciresinol, they form aglycons in lignans (aglycon is a non-sugar component of glycosides). These substances are created during the formation of lignins. We find them in wood and resins, as well as fruits, where, for example, flax seeds are a rich source of these two aglycones.
Picture above: Structure of matairesinol molecule.
In the gastrointestinal tract, matairesinol and secoisolariciresinol are converted to the metabolites enterodiol and enterolactone. Their typical property is their affinity for estrogen receptors, which makes their behavior similar to hormones. The biological activity of both compounds can touch the areas of antiviral, bacteriostatic or even antitumor.
If we look briefly at the possibilities for the synthesis of matairesinol, we will find that it can be prepared from coniferol by a series of few reactions, as shown in the following figure. The synthesis of coniferol was also discussed in the previous article.
Picture above: Outline of the production of matairesinol from coniferol as the starting substance of the synthesis.
Effects of matairesinol
Matairesinol has a number of potential health effects, including:
• Prevention of heart diseases
• Cancer prevention
• Improving brain function
• Reduction of inflammation
• Improving blood sugar levels
Prevention of heart disease
Matairesinol can help lower cholesterol and triglycerides, two factors that contribute to heart disease. It can also help improve blood vessel function.
Cancer prevention
Matairesinol has antioxidant and anti-inflammatory effects that can help protect cells from damage. Some studies suggest that matairesinol may help reduce the risk of breast cancer, prostate cancer, and colon cancer.
Improving brain function
Matairesinol may help improve brain function by improving blood flow to the brain and reducing inflammation. Some studies suggest that matairesinol may help improve memory and cognitive function.
Reducing inflammation
Matairesinol has anti-inflammatory effects that can help reduce inflammation in the body. Inflammation is linked to a number of chronic diseases, such as cancer, heart disease and type 2 diabetes.
Improving blood sugar levels
Matairesinol can help improve blood sugar levels by improving insulin sensitivity. Insulin is a hormone that helps the body use glucose from food as a source of energy.
Sources of matairesinol
Matairesinol is found in the following foods:
• Rye
• Flaxseed
• Sesame seeds
• Walnuts
• Almonds
• Hazelnuts
• Peanuts
• Cashew nuts
• Chia seeds
• Other whole grain products
Dosage
There is no recommended dosage for matairesinol. Most human studies used a dose of 100-200 mg per day.
Safety
Matairesinol is generally considered safe. Side effects that have been reported include:
• Nausea
• Vomiting
• Constipation
• Headache
Conclusion
Matairesinol is a potentially beneficial compound that has a number of health effects. It is important to note that matairesinol is not a drug and should only be used as part of a healthy diet.
Sources:
[1] J. Ralph a Y. Zhang, „Agricultural Research Service,“ 1998. [Online]. Available: http://www.dfrc.ars.usda.gov/DFRCWebPDFs/1998-Ralph-Tet-54-1349.pdf. [Přístup získán 7 6 2013].
[2] M. Bolognini, F. Cavani, L. D. Pozzo, L. Maselli, F. Zaccarelli, B. Bonelli, M. Armandi a E. Garrone, „ScienceDirect,“ 21 5 2004. [Online]. Available: http://www.sciencedirect.com/science/article/pii/S0926860X04004703. [Přístup získán 7 6 2013].
[3] J. Moravcová, v Biologicky aktivní přírodní látky, Praha, VŠCHT Praha, 2006, pp. 33-34.
[4] OSHA, „United States Department of Labor,“ 30 3 2007. [Online]. Available: http://www.osha.gov/dts/chemicalsampling/data/CH_238925.html. [Přístup získán 7 6 2013].