Names | |
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IUPAC name (8β,8′α)-4,4′-Dihydroxy-3,3′-dimethoxylignano-9,9′-lactone | |
Systematic IUPAC name (3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one | |
Other names (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone | |
Identifiers | |
3D model (JSmol) | |
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ChEMBL | |
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PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C20H22O6 | |
Molar mass | 358.390 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with secoisolariciresinol has attracted much attention for its beneficial nutritional effects. [2]
The plant lignans are precursors of the enterolignans (mammalian lignans). [3] A number of plant lignans are metabolized to the enterolignans (enterodiol and enterolactone) that can potentially reduce the risk of certain cancers and cardiovascular diseases. [4]
Although some studies attribute disease preventative (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are inconclusive. [5] Matairesinol has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1). [6]
Hot flashes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from two to 30 minutes for each occurrence.
Adiponectin is a protein hormone and adipokine, which is involved in regulating glucose levels and fatty acid breakdown. In humans, it is encoded by the ADIPOQ gene and is produced primarily in adipose tissue, but also in muscle and even in the brain.
A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity to estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots.
Secoisolariciresinol diglucoside (SDG) is an antioxidant phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. It is a precursor of mammal lignans which are produced in the colon from chemicals in foods.
The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.
Gramine is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.
Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with matairesinol has attracted much attention for its beneficial nutritional effects.
Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew, after which it is named, and in the closely related tansy. It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.
Adiponectin receptor 1 (AdipoR1) is a protein which in humans is encoded by the ADIPOR1 gene. It is a member of the progestin and adipoQ receptor (PAQR) family, and is also known as PAQR1.
Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock and Saussurea heteromalla. It has shown antiviral and anticancer effects in vitro. It is the aglycone of arctiin.
Arctiin is a lignan found in many plants of the family Asteraceae, particularly the greater burdock and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla, and Forsythia viridissima. It is the glucoside of arctigenin.
Free fatty acid receptor 1 (FFAR1), also known as G-protein coupled receptor 40 (GPR40), is a rhodopsin-like G-protein coupled receptor that is coded by the FFAR1 gene. This gene is located on the short arm of chromosome 19 at position 13.12. G protein-coupled receptors reside on their parent cells' surface membranes, bind any one of the specific set of ligands that they recognize, and thereby are activated to trigger certain responses in their parent cells. FFAR1 is a member of a small family of structurally and functionally related GPRs termed free fatty acid receptors (FFARs). This family includes at least three other FFARs viz., FFAR2, FFAR3, and FFAR4. FFARs bind and thereby are activated by certain fatty acids.
Free fatty acid receptor 2 (FFAR2), also termed G-protein coupled receptor 43 (GPR43), is a rhodopsin-like G-protein coupled receptor. It is coded by the FFAR2 gene. In humans, the FFAR2 gene is located on the long arm of chromosome 19 at position 13.12. Like other GPCRs, FFAR2s reside on the surface membrane of cells and when bond to one of their activating ligands regulate the function of their parent cells. FFAR2 is a member of a small family of structurally and functionally related GPRs termed free fatty acid receptors (FFARs). This family includes three other receptors which, like FFAR2, are activated by certain fatty acids: FFAR1, FFAR3 (GPR41), and FFAR4 (GPR120). FFAR2 and FFAR3 are activated by short-chain fatty acids whereas FFAR1 and FFAR4 are activated by long-chain fatty acids.
Free Fatty acid receptor 4 (FFAR4), also termed G-protein coupled receptor 120 (GPR120), is a protein that in humans is encoded by the FFAR4 gene. This gene is located on the long arm of chromosome 10 at position 23.33. G protein-coupled receptors reside on their parent cells' surface membranes, bind any one of the specific set of ligands that they recognize, and thereby are activated to trigger certain responses in their parent cells. FFAR4 is a rhodopsin-like GPR in the broad family of GPRs which in humans are encoded by more than 800 different genes. It is also a member of a small family of structurally and functionally related GPRs that include at least three other free fatty acid receptors (FFARs) viz., FFAR1, FFAR2, and FFAR3. These four FFARs bind and thereby are activated by certain fatty acids.
Adiponectin receptor 2 (AdipoR2) is a protein which in humans is encoded by the ADIPOR2 gene. It is a member of the progestin and adipoQ receptor (PAQR) family, and is also known as PAQR2.
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated to exhibit beneficial medicinal properties.
Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.
Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.
Christos Socrates Mantzoros is a Greek American physician-scientist, practicing internist-endocrinologist, teacher and researcher. He is a professor of medicine at Harvard Medical School and an adjunct professor at Boston University School of Medicine. He currently serves as the chief of endocrinology, diabetes and metabolism at the VA Boston Healthcare System, where he created de novo a leading academic division true to its tripartite mission and as the founding director of human nutrition at Beth Israel Deaconess Medical Center (BIDMC), Harvard Medical School. Finally, he holds the editor-in-chief position of the journal Metabolism: Clinical and Experimental.