Secoisolariciresinol diglucoside

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Secoisolariciresinol diglucoside
Secoisolarisiresinol diglucoside.svg
Names
IUPAC name
(2R,3R)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diyl di-β-D-glucopyranoside
Preferred IUPAC name
(2R,2′R,3R,3′R,4S,4′S,5S,5′S,6R,6′R)-2,2′-[{(2R,3R)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diyl}bis(oxy)]bis[6-(hydroxymethyl)oxane-3,4,5-triol]
Other names
SDG
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1 Yes check.svgY
    Key: SBVBJPHMDABKJV-PGCJWIIOSA-N Yes check.svgY
  • InChI=1/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1
    Key: SBVBJPHMDABKJV-PGCJWIIOBK
  • OC1=C(OC)C=C(C[C@H]([C@H](CO[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC3=CC(OC)=C(O)C=C3)CO[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)C=C1
Properties
C32H46O16
Molar mass 686.704 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Secoisolariciresinol diglucoside (SDG) is an antioxidant [1] phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. [2] It is a precursor of mammal lignans [3] which are produced in the colon from chemicals in foods.

Contents

Extraction

Secoisolariciresinol diglucoside can be isolated from de-fatted (hexane extraction) flaxseed by extraction of the lignan polymer precursor with a water/acetone mixture, followed by acetone removal and alkaline hydrolysis. [4]

Studies on biological effects

Secoisolariciresinol diglucoside slows the growth of human breast cancer in mice. [5]

Secoisolariciresinol diglucoside may different roles in people. For example, due to 400-500Da size limit for Blood–Brain Barrier permeability, in one assessment of a Grade IV histology group of adult patients diagnosed with malignant glioma, high intake of secoisolariciresinol (for highest tertile compared to lowest tertile, in all cases) was associated with poorer survival. [6]

In rabbits, SDG reduced hypercholesterolemic atherosclerosis and this effect was associated with a decrease in serum cholesterol, LDL-C, and lipid peroxidation product and an increase in HDL-C and antioxidant reserve. [7]

SDG has been shown to counter oxidative stress in human colonic epithelial tissue and protect against mtDNA damage in vitro , by H2O2 exposure, in a dose-dependent manner[ citation needed ], and counters (in-vitro) oxidative stress on heart cells caused by Iron overload. [8]

Related Research Articles

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals and chain reactions that may damage the cells of organisms. Antioxidants such as thiols or ascorbic acid may act to inhibit these reactions. To balance oxidative stress, organisms contain and produce antioxidants, such as glutathione, mycothiol or bacillithiol.

High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are typically composed of 80–100 proteins per particle and transporting up to hundreds of fat molecules per particle.

Flax Flowering plant in the family Linaceae

Flax, also known as common flax or linseed, is a flowering plant, Linum usitatissimum, in the family Linaceae. It is cultivated as a food and fiber crop in regions of the world with temperate climates. Textiles made from flax are known in Western countries as linen and are traditionally used for bed sheets, underclothes, and table linen. Its oil is known as linseed oil. In addition to referring to the plant, the word "flax" may refer to the unspun fibers of the flax plant. The plant species is known only as a cultivated plant and appears to have been domesticated just once from the wild species Linum bienne, called pale flax. The plants "flax" in New Zealand are, by contrast, members of the genus Phormium.

Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vitamin E, can cause nerve problems. Vitamin E is a fat-soluble antioxidant which may help protect cell membranes from reactive oxygen species.

Atherosclerosis Form of arteriosclerosis

Atherosclerosis is a pattern of the disease arteriosclerosis in which the wall of the artery develops abnormalities, called lesions. These lesions may lead to narrowing due to the buildup of atheromatous plaque. At onset there are usually no symptoms, but if they develop, symptoms generally begin around middle age. When severe, it can result in coronary artery disease, stroke, peripheral artery disease, or kidney problems, depending on which arteries are affected.

<i>alpha</i>-Linolenic acid Chemical compound

alpha-Linolenic acid (ALA), also known as α-Linolenic acid, is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

Stanol ester

Stanol esters is a heterogeneous group of chemical compounds known to reduce the level of low-density lipoprotein (LDL) cholesterol in blood when ingested, though to a much lesser degree than prescription drugs such as statins. The starting material is phytosterols from plants. These are first hydrogenated to give a plant stanol which is then esterified with a mixture of fatty acids also derived from plants. Plant stanol esters are found naturally occurring in small quantities in fruits, vegetables, nuts, seeds, cereals, legumes, and vegetable oils.

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.

Phytosterol Class of steroids derived from plants

Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanols. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.

Secoisolariciresinol Chemical compound

Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, e.g. rye, and together with matairesinol, has attracted much attention for its beneficial nutritional effects.

Campesterol Chemical compound

Campesterol is a phytosterol whose chemical structure is similar to that of cholesterol, and is one of the ingredients for E number E499.

Myricetin Chemical compound

Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. Common dietary sources include vegetables, fruits, nuts, berries, tea, and red wine. Myricetin is structurally similar to fisetin, luteolin, and quercetin and is reported to have many of the same functions as these other members of the flavonol class of flavonoids. Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.

β-Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the fruit of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum.

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Fibre supplements are considered to be a form of a subgroup of functional dietary fibre, and in the United States are defined by the Institute of Medicine (IOM). According to the IOM, functional fibre "consists of isolated, non-digestible carbohydrates that have beneficial physiological effects in humans".

Lariciresinol Chemical compound

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.

Herbacetin Chemical compound

Herbacetin is a flavonol, a type of flavonoid.

Enterolactone Chemical compound

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.

There are many types of food trends and fads, not only including weight loss or diets. Recent interest in health foods such as quinoa and soy beans have cause prices to skyrocket and production to vastly increase. This affects the communities in which these foods are grown or produced, and also has environmental impacts. Each food that suddenly has a popularity spike affects those who produce it and the area it comes from.

Senior dog diet

Senior dog food diets are pet foods that are catered toward the senior or mature pet population. The senior dog population consists of dogs that are over the age of seven for most dog breeds, though in general large and giant breed dogs tend to reach this life stage earlier when compared to smaller breed dogs. Senior dog foods contain nutrients and characteristics that are used to improve the health of the aging dog. Aging in dogs causes many changes to occur physiologically that will require a change in nutrient composition of their diet. A major change that occurs is the decrease in energy requirements which is addressed by lowered caloric content of senior pet foods. Although energy requirements decrease, protein requirements increase as the dog ages. Senior dog foods include a higher protein content as well as highly digestible protein sources to deal with this. Nutrients included for joint and bone health include glucosamine, chondroitin, omega-3 fatty acids as well as two main minerals; calcium and phosphorus. Sources of fiber included in senior dog foods include beet pulp and flax seed as well as fructooligosaccharides (FOS) and mannanoligosaccharides (MOS). These act to increase gastrointestinal health. Brain and cognitive health decline as the dog ages which leads to the inclusion of vitamin E and L-carnitine in senior dog diets to combat this decline. Skin and coat health can also decline in older dogs due to various reasons. The inclusion of linoleic acid as well as vitamin A into senior dog diets helps to improve or maintain the skin and coat of senior dogs. Immune system health is important to maintain in older dogs to prevent the development of various diseases. By including omega-3 and omega-6 fatty acids, vitamin E, β-carotene as well as pre- and pro-biotics, the immune system can be boosted and maintained to help improve overall health.

References

  1. Adolphe, J. L., Whiting, S. J., Juurlink, B. H. J., Thorpe, L. U., & Alcorn, J. (2010). "Health effects with consumption of the flax lignan secoisolariciresinol diglucoside". The British Journal of Nutrition. 103 (7): 929–38. doi: 10.1017/S0007114509992753 . PMID   20003621.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman (2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry. 110 (4): 997–999. doi:10.1016/j.foodchem.2008.02.088. PMID   26047292.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Thompson, LU; Robb, P; Serraino, M; Cheung, F (1991). "Mammalian lignan production from various foods". Nutrition and Cancer. 16 (1): 43–52. doi:10.1080/01635589109514139. PMID   1656395.
  4. US 6806356,"Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed"
  5. Chen; et al. (2009). "Flaxseed and Pure Secoisolariciresinol Diglucoside, but Not Flaxseed Hull, Reduce Human Breast Tumor Growth (MCF-7) in Athymic Mice". The Journal of Nutrition. 139 (11): 2061–6. doi: 10.3945/jn.109.112508 . PMID   19776177.
  6. Delorenze, Gerald N; McCoy, Lucie; Tsai, Ai-Lin; Quesenberry Jr, Charles P; Rice, Terri; Il'Yasova, Dora; Wrensch, Margaret (2010). "Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma". BMC Cancer. 10: 215. doi:10.1186/1471-2407-10-215. PMC   2880992 . PMID   20482871.
  7. Prasad, K (1999). "Reduction of Serum Cholesterol and Hypercholesterolemic Atherosclerosis in Rabbits by Secoisolariciresinol Diglucoside Isolated from Flaxseed". Circulation. 99 (10): 1355–1362. doi: 10.1161/01.CIR.99.10.1355 . PMID   10077521.
  8. Puukila, S.; Bryan, S.; Laakso, A.; Abdel-Malak, J.; Gurney, C.; Agostino, A.; Belló-Klein, A.; Prasad, K.; Khaper, N. (2015). "Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition". PLOS ONE. 10 (3): e0122852. Bibcode:2015PLoSO..1022852P. doi: 10.1371/journal.pone.0122852 . PMC   4379144 . PMID   25822525.