Glyconutrient posts

Title: Sugars give energy and structure to life (July 16, 2013)
/This is the first of a few posts about glycocompounds. //second one: Neuraminic acid was known first as sialic acid// third one: To termites, trees are kind of like giant sugar cubes/
Carbohydrates are formed from carbon and water molecules. The name means ‘hydrate of carbon.’ Individual carbohydrate molecules are called simple sugars or monosaccharides. They are commonly found in the diet as disaccharides, pairs of two monosaccharides, and as long chain polysaccharides in the form of the energy rich starches and the indigestible fiber found in cell walls of plants. The individual monosaccharides may be found as a straight chain of linked carbon atoms or as closed rings. The ring form is more stable chemically. A glass of sugar water made with pure glucose would only have ~0.0026% of the glucose molecules in the straight chain formation, the rest would be in some variation of the the ring form.
The juice of the sugar cane gives us sucrose or table sugar, which is made up of two 6 carbon monosaccharides, one molecule of glucose and one of fructose. The disaccharide lactose is better known as milk sugar and is made up of one molecule of galactose and one of glucose.
Mannose and fucose are monosaccharides that are less common in unprocessed foods but are very useful as food additives in mixtures such as ice cream or pudding. Fucose is commonly found in brown seaweeds. About forty percent of the dry weight of brown seaweeds is the commercially useful alginate polysaccharides. Alginates are used as food additives to help stabilize mixtures and act as emulsifiers which help keep the mixture well mixed while standing on the grocery shelf. Mannans are the polysaccharide of mannose. Mannans are found in red algae which is useful for its agar and carrageenan content. They are used as food additives for their gelatinous properties and as thickeners. Carrageenan may be a health risk and has been shown to cause inflammation, impaired glucose tolerance and increased insulin resistance in lab animals at levels that might be found in comparable amounts in an average day’s food for a person.
Mannans are also the main type of energy storage starch in the seeds of the oil palm trees. One variety of the tree species, the ivory nut tree, is also known as ‘vegetable ivory.’ The mannan within the ivory like seeds resembles the overlapping long polysaccharide chains of cellulose, which is the type of fiber more commonly found in plant cell walls.

Other uses of the oil palm:  There are two types of oil produced from the seed of oil palm trees. Palm kernel oil is paler in color than the reddish color, beta-carotene rich, palm oil. Palm kernel oil contains a higher percentage of saturated fat than palm oil. It may increase the risk of high blood cholesterol but is an inexpensive cooking oil. Palm kernel oil is also frequently used in the production of soap because some of the saturated fatty acids produce good lather, even in salty sea water. Fibrous seed pulp that is left after oil production is used as animal feed.

The monosaccharide mannose may be the active factor that gives cranberries a reputation for helping prevent urinary tract infections (UTIs). The monsaccharide is thought to help make the lining of the bladder more resistant to infectious bacteria. More research is needed though to prove health benefits from cranberries or from more concentrated supplemental doses of D-Mannose.
(To be continued later – Glyconutrients are essential for helping protect cell surfaces from infectious agents – so fans of cranberries are probably onto a good thing.)
/Disclaimer: Information presented on this site is not intended as a substitute for medical care and should not be considered as a substitute for medical advice, diagnosis or treatment by your physician./

  1. S.A. Brooks, M. V. Dwek, U. Schumacher, Functional and Molecular Glycobiology, (BIOS Scientific Publishers, Ltd., 2002), Amazon.
  2. “Out of One Many, or How to Use Agar Agar,” (Dec. 17, 2008) by
  3. “Palm Kernel,” Wikipedia (Warning: this Wikipedia entry contains an old war propaganda poster about harvesting palm seeds which may offend some people and for that very reason should never be forgotten.)
  4. “Palm Kernel Oil,” Wikipedia.
  5. “Palm Oil,” Wikipedia.
  6. “D-Mannose Offers Great Protection Against Urinary Tract Infections,”
  7. “Scientific Opinion on the substantiation of a health claim related to a UrovalĀ® and urinary tract infection pursuant to Article 14 of Regulation,” (EC) No 1924/20061, EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA), European Food Safety Authority (EFSA), Parma, Italy
  8. L. Johnston, “Natural Urinary Tract Health: The D-Mannose Solution,”
  9. A Weil, “Is Carrageenan Safe?” (Oct. 1, 2012),

Title: Neuraminic acid was known first as sialic acid (8/21/2013)
Neuraminic acid, or sialic acid as it was first called, is a monosaccharide with nine carbons. It has a negative electric charge which gives compounds containing it a negative charge. This is useful for keeping molecules like red blood cells from getting to near to each other. The negative charge on the surface glycoproteins repels the red blood cell from each other or from the walls of blood vessels which also have compounds containing sialic acid.
Mature red blood cells have an active life for about seven days.  White blood cells remove older red blood cells and de-sialylation of the surface proteins is one way the older cells are identified. Cancer cells with the ability to produce excess surface sialyation may have an increased chance to metastasize and turn up somewhere else in the body. [13]
Our bodies need to be healthy and well enough nourished overall to keep the whole system working. The neuraminic acid is produced within our cells from other chemicals in a series of membranous channels called the endoplasmic reticulum and the golgi apparatus. The channels have embedded enzymes along the way somewhat like an assembly line in a factory.
Therapeutic glycoproteins are being developed and the problem of just the right amount of sialylation is one of the hurdles being studied. [2] In addition to the negative charge sialic acid tends to stabilize and stiffen the protein portion of the compound.  The proteins that line vessels were described to be somewhat like bottle-brushes; the protein being somewhat like the wire handle with the negatively charged sialic acid acting as bristles. [1]
/Disclaimer: Information presented on this site is not intended as a substitute for medical care and should not be considered as a substitute for medical advice, diagnosis or treatment by your physician./

  1. S.A. Brooks, M. V. Dwek, U. Schumacher, Functional and Molecular Glycobiology, (BIOS Scientific Publishers, Ltd., 2002), Amazon.
  2. Bork K, Horstkorte R, Weidemann W., “Increasing the sialylation of therapeutic glycoproteins: the potential of the sialic acid biosynthetic pathway.” J Pharm Sci. 2009 Oct;98(10):3499-508. doi: 10.1002/jps.21684.  []
  3. R. T. Almaraz, et. al., “Metabolic Flux Increases Glycoprotein Sialylation: Implications for Cell Adhesion and Cancer Metastasis.” Mol Cell Proteomics. 2012 July; 11(7): M112.017558. Published online 2012 March 28. doi:  10.1074/mcp.M112.017558 []

Title:  To termites, trees are kind of like giant sugar cubes (8/21/2013)
Sugar cubes contain the disaccharide sucrose which contains the monosaccharide fructose in addition to glucose. The cellulose portion of trees is made of long fairly straight chains of glucose with no fructose, so trees and sugar cubes aren’t really alike. The bonds between table sugar and tree fiber are at slightly different angles but different enzymes are needed to break them down during digestion. The straighter angle between the simple sugars of plant fiber allow the linked chains of glucose to line up with each other. The lined up fibers then can form layers a little like sheets of paper stacked in a book, except it would be a doughnut shaped book. Cellulose or other types of plant fiber is found in the cell walls of the leaves, stems and roots.
Chitin is similar strong chain of the simple sugar N-acetylglucosamine. The simple sugars in chitin and cellulose both have the slightly straighter beta angle than the bonds found in energy storage starches or polysaccharides. Termites [3] and the bacteria found in the stomach of grazing animals are able to digest the stronger beta bonds of cellulose. Humans and most other animals can’t digest them because a specific enzyme is needed.
Energy starches have alpha type bonds between the simple sugars. Alpha bonds connect at an angle that might twist into a spiral chain similar to the double helix spiral of DNA. The angled alpha bonds are also found in branching shapes of storage starches like glycogen or amylose. The sugar molecule at the end of each ‘branch’ is available for rapid digestion. Glycogen is the energy storage polysaccharide of glucose in animals and humans and amylose is the form of glucose storage used in plants. Glycogen is slightly more branched than amylose.
Tree bark and tree sap both contain glucose but the bark contains cellulose and the sap would have amylose or a similar alpha bonded energy storage starch. A shiny insect shell or seashells also are a type of sugar but not glucose. Shells contain N-acetyl-glucosamine in the form of chitin.
Supplements of glucosamine may be helpful for reducing joint pain. Studies have used 1500 mg/day. [2]
/Disclaimer: Information presented on this site is not intended as a substitute for medical care and should not be considered as a substitute for medical advice, diagnosis or treatment by your physician./

  1. S.A. Brooks, M. V. Dwek, U. Schumacher, Functional and Molecular Glycobiology, (BIOS Scientific Publishers, Ltd., 2002), Amazon.
  2. “Questions and Answers: NIH Glucosamine/Chondroitin Arthritis Intervention Trial Primary Study,” National Institutes of Health, National Center for Complementary and Alternative Medicine []
  3. Nakashima K, Watanabe H, Saitoh H, Tokuda G, Azuma JI.,”Dual cellulose-digesting system of the wood-feeding termite, Coptotermes formosanus Shiraki.” Insect Biochem Mol Biol. 2002 Jul;32(7):777-84. []

Title: GPI anchors are cell membrane glycoproteins (8/27/13)
Glycosylphosphatidylinositol (GPI)-anchored proteins have one end that stays embedded firmly within the cell membrane and the other end can attach to a variety of important molecules such as enzymes and antigens. The enzyme or antigen is held above the cell membrane in a position that makes it available to be activated on the cell surface. The phosphatidylinositol end is lipid based and dissolves well in the fatty acid rich environment within the membrane. The glyco- or sugar part of the molecule is able to dissolve in water or form bonds with other proteins or carbohydrates.
GPI anchor proteins are essential for life. Mice that were experimentally made to lack the gene thought to encode for GPI anchor proteins did not survive. Experimental ‘knockout’ mice are usually observed to see what types of function the knocked out gene might have performed. The experiment showed that GPI anchors were necessary for survival. (Ref. 1, Brooks, Dwek, Schumacher, 2002, p 225)
GPI anchors are found in some types of G-protein couple receptors and may have importance within the cannabinoid receptor system.

  1. Brooks SA, Dwek MV, Schumacher U., Functional and Molecular Glycobiology, (Bios, 2002, Oxford, UK)
  2. Landry Y, Niederhoffer N, Sick E, Gies JP., Heptahelical and other G-protein-coupled receptors (GPCRs) signaling., Curr Med Chem. 2006;13(1):51-63. []
  3. Maccarrone M, Bernardi G, […], and Centonze D., Cannabinoid receptor signalling in neurodegenerative diseases: a potential role for membrane fluidity disturbance., Br J Pharmacol. 2011 August; 163(7): 1379-1390 []

Additional note:

GPI anchors

  1. Fujita M, Kinoshita T. “GPI-anchor remodeling: potential functions of GPI-anchors in intracellular trafficking and membrane dynamics.” Biochim Biophys Acta. 2012 Aug;1821(8):1050-8. doi: 10.1016/j.bbalip.2012.01.004. Epub 2012 Jan 11.  Abstract: [] “and discuss how GPI-anchors regulate protein sorting, trafficking, and dynamics.”

/Disclosure: This information is provided for educational purposes within the guidelines of fair use. While I am a Registered Dietitian this information is not intended to provide individual health guidance. Please see a health professional for individual health care purposes./