PHARMACOGNOSY

• Carbohydrates


  The most abundant and widespread organic compound in nature
• Saccharides


  Also known as carbohydrates, because of the sweet taste of the simpler members of the family, the sugars
• Polyhydroxy aldehydes / ketones


  Another name for carbohydrates
• Organic compound

  Consists only of carbon, hydrogen, and oxygen, with a hydrogen-oxygen atom ratio of 2:1
• General properties of carbohydrates

  • Crystalline
  • Sweet taste
  • Water soluble - due to hydroxyl group
  • Reducing property - due to carbonyl group
  • Optically active - due to chiral center, mutarotation
• Levorotatory


  Rotate polarized light to the LEFT
• Dextrorotatory


  Rotate polarized light to the RIGHT
• Biosynthesis


  Not provided
• Classification of carbohydrates


  • Monosaccharide
  • Oligosaccharide
  • Polysaccharide

  
• Monosaccharide


  Simplest carbohydrate unit, cannot be hydrolyzed to simpler sugars
• Aldoses

  Type of monosaccharide
• Ketoses


  Type of monosaccharide
• Xylose / D-xylose / Wood sugar

  Obtained by boiling corn cobs, straw or similar materials with dilute acid to hydrolyze the xylan polymer. Has a sweet taste and is normally absorbed from the small intestines, but IS NOT METABOLIZED to a significant extent by mammalian enzymes. Approved as a diagnostic agent to INTESTINAL ABSORPTION. May accompany conditions such as celiac diseases, sprue, Crohn's disease (regional ileitis), pellagra, radiation enteritis and surgical resection.
• Glucose / Dextrose / a-D (+)-Glucopyranose / D-Glucose

  Occurs in grapes (grape sugar) and other fruits. Obtained through controlled enzymatic hydrolysis of STARCH. Use/s: a nutrient that may be given by mouth, by enema, by SQ inj, or IV
• Dextrose Excipient


  A crystalline dextrose monohydrate that has undergone less rigorous purification
• Fructose


  Also known as D-fructose, levulose, b-D-(-)-fructopyranose, b-D-(-)-fructofuranose, fruit sugar. Fructose is a ketone sugar that occurs naturally in most sweet fruits and in HONEY. Obtained from the inversion of aqueous solutions of sucrose and hydrolysis of INULIN. MANGO - fruit with highest fructose content (sweetest)
• High-fructose sweetener


  Prepared by controlled enzymatic isomerization of glucose to fructose. High-fructose corn syrups containing up to 90% fructose are available commercially.
• Galactose


  Brain sugar, found in milk as lactose and in neuronal fibers as galactosides. C4 epimer of glucose.
• Disaccharides


  Composed of two monosaccharides linked by glycosidic bonds
• Sucrose


  Also known as table sugar. Obtained from sugar cane, sugar beets, and sugar maple. Uses: SYRUP, flavorant
• Sweeteners / Sugar substitutes

  • Saccharin (300x)
  • Cyclamate (30x)
  • Aspartame (160-200x)
  • Acesulfame K (130x)
  • Sucralose (600x)
  • Stevia (30x)
• Maltose


  From germination of barley. Enzymic hydrolysis of starch converts starch to maltose via enzyme - amylase. Glucose + Glucose = Maltose. Linkage: Alpha 1,4 glycosidic bond.
• Lactose


  Found in milk. Divided into: cream/fat globules -> butter -> liquid buttermilk, liquid -> skimmed milk -> coagulum via rennins -> cheese, coagulum -> whey (lactose + inorganic salts). Bos taurus.
• Milk products

  • Butter
  • Buttermilk
  • Skimmed milk
  • Coagulum
  • Cheese
  • Condensed milk
  • Malted milk
  • Kumyss
  • Whey
• Lactulose


  Yields fructose and galactose upon hydrolysis. Is a semisynthetic sugar prepared by alkaline rearrangement of lactose. Poorly absorbed, and most orally ingested lactulose reaches the colon unchanged. Bacteria in the colon metabolize the disaccharide. Type of a stimulant laxative used for myocardial infarction.
• Cellobiose


  Enzymic breakdown of cellulose. Glucose + Glucose = Cellobiose. Linkage: Beta 1,4 glycosidic bonds.
• Trehalose


  Found in Ergot, Rhodophyceae, yeasts. Glucose + Glucose = Trehalose. Linkage: Alpha 1,1 glycosidic bonds.
• Sophorose


  Found in Japanese pagoda tree (Sophora japonica / Styphnolobium japonicum, Leguminosae). Hydrolysis of stevioside. Glucose + Glucose = Sophorose.
• Primeverose

  Found in Meadow wort / meadowsweet (Filipendula ulmaria, Rosaceae). Hydrolysis of spiraein. Glucose + Xylose = Primeverose.
• Trisaccharides

  Contains three monosaccharides linked via glycosidic bonds
• Gentianose


  Found in Gentiana spp. 2 Glucose + Fructose = Gentianose (same with melezitose but differ in connection)
• Melezitose


  Found in Manna from Larix. 2 Glucose + Fructose = Melezitose (same with gentianose but differ in connection)
• Planteose


  Found in seeds of Psyllium spp. Glucose + Fructose + Galactose = Planteose (same with raffinose but differ in connection)
• Raffinose


  Found in cotton seeds (Gossypium hirsutum). Glucose + Fructose + Galactose = Raffinose (same with planteose but differ in connection)
• Manneotriose


  Found in Manna of ash (Fraxinus ornus, Oleaceae). 2 Galactose + Glucose = Manneotriose
• Rhamninose


  Found in Rhamnus infectoria. 2 Rhamnose + Galactose = Rhaminose
• Scillatriose

  Glycoside of squill (Scilla siberica, Asparagaceae). 2 Glucose + Rhamnose = Scillatriose
• Tetrasaccharides


  Contains four monosaccharide units joined by glycosidic bonds
• Stachyose


  Also known as MANNEOTETROSE. Found in tubers of Stachys japonica, Lamiaceae. Glucose + Fructose + 2 Galactose = Stachyose
• Polysaccharides


  Also known as "Glycans". More than 10 monosaccharide units complete, high MW polymers of monosaccharides linked by GLYCOSIDIC BONDS