Vitamins – Chemistry – Flashcards
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Hormone precursors: |
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Vitamin D Vitamin A |
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Redox cofactors &/or antioxidants: |
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Vitamin C Vitamin E (tocopherols) Vitamin K (phylloquinone, not an antioxidant) Vitamin B3 (Niacin) Vitamin B2 (Riboflavin) |
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Group transfer agents: |
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Vitamin B6 Vitamin B12 Biotin Folic acid Pantothenic acid |
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formed in skin from 7-dehydrocholesterol plus sunlight converted in the liver to a hormone that regulates calcium uptake. |
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Vitamin D |
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-family of is fat-soluble compounds -found in fish oils, liver, eggs, whole milk, and butter |
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Vitamin A |
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________ (found in orange & yellow vegetables), can be enzymatically converted to Vitamin __ |
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Beta-carotene; A |
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Deficiency - dryness of the skin, eyes, & mucous membranes, retarded growth, night blindness |
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Vitamin A |
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Deficiency is the leading cause of preventable blindness in children |
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Vitamin A |
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___________, one form of Vitamin A, functions as a hormone and as a pigment in the eye |
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Retinol |
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________ ________ - active drug in Retin-A used in the treatment of severe acne and other skin problems |
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Retonoic Acid |
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___ - ___ - ________ is a cofactor for rhodopsin, playing a role in vision |
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11-cis-retinol |
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What is the technical name for too much Vitamin A and D? |
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hypervitaminosis A/D |
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prevents free radicals (i.e. superoxide anions) from oxidizing compounds (i.e. polyunsaturated fats), thus maintaining integrity of cellular membranes |
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Vitamin E, C |
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found in eggs and vegetable oils |
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Vitamin E |
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Deficiency is very rare in humans; primary symptom is fragile erythrocytes, atherosclerosis, cardiovascular disease |
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Vitamin E |
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phylloquinone |
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Vitamin K |
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blood-clotting cofactor |
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Vitamin K |
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undergoes redox rxn to form prothrombin |
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Vitamin K |
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found in green plant leaves; deficiency is very rare. |
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Vitamin K |
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_______ (coumadin), with a similar structure, is used to prevent excessive blood clotting. |
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Warfarin |
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Isoprenoids = __ linear carbons, __ carbon off to the side |
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4;5 |
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Vitamins __ and __ are isoprenoid derivatives |
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E;K |
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__________ (also called coenzyme Q) is an isoprenoid |
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Ubiquinone |
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Comes in three flavors: reduced, oxidized, ionized |
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Vitamin C |
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regenerates vitamin E from its radical form |
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Vitamin C |
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Most animals make vitamin __, but humans can’t; we obtain it through fruits & vegetables |
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C |
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required for the hydroxylation of proline in collagen (cofactor for prolyl 4-hydroxylase) |
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Vitamin C |
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What is Vitamin C in oxidized form? |
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Dehydroascorbic Acid |
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What is the reduced form of Vitamin C? |
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Ascorbic Acid |
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What is the ionized form of Vitamin C? |
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Ascorbate |
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Scurvy from _________ deficiency |
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ascorbate |
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__-_____________ required in collagen (connective tissue in vertebrates) |
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4 - hydroxyproline |
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Deficiency of vitamin __ causes scurvy, characterized by _______ __________ degradation |
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C; connective tissue degradation |
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Poor healing, bleeding, tooth loss, bone pain, heart failure |
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Vitamin C |
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Milder cases: fatigue, irritability, increased severity of respiratory tract infections |
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Vitamin C |
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Cofactor for pyruvate & alpha-ketoglutarate dehydrogenase; hence, important for metabolism |
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Vitamin B1- thiamine |
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Also does Aldehyde transfers |
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B1- thiamine |
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Deficiency causes Beriberi – characterized by heart failure, peripheral neuropathy, Wernicke-Korsakoff syndrome (alcoholics-ataxia, ophthalmoplegia, confusion) |
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B1- thiamine |
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Activates Vitamin B6 (pyridoxine) |
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B2- Riboflavin |
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Involved in many oxidation-reduction reactions |
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B2- Riboflavin, B3- Niacin |
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Required for metabolism of amino acids, fatty acids, and carbohydrates |
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B2- Riboflavin |
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Found in meats, nuts, cheese, milk, leafy vegetables, fish, legumes, grains |
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B2- Riboflavin |
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Not toxic in high doses (but turns urine dark yellow) |
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B2- Riboflavin |
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Deficiency (not common) causes eye & skin problems, mouth inflammation |
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B2- Riboflavin |
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_______ is synthesized from tryptophan |
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Niacin |
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But humans generally cannot synthesize enough. |
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B3- Niacin |
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Deficiency affects all of the NAD(P)-dependent dehydrogenases, causing pellagra |
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B3- Niacin |
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___________ is characterized by the four D's =diarrhea, dermatitis, dementia, and death, from what deficiency? |
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Pellagra; B3-Niacin |
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100 years ago, when corn was a dietary staple, pellagra was common because corn is low in ______________. |
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tryptophan |
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What is pellagra commonly seen in today? |
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alcoholics who have reduced niacin absorption |
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____-_______ medicine can cause niacin deficiency. |
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Anti-tuberculoid |
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_____ is synthesized from Niacin: no niacin = no ____ |
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NAD+; NAD+ |
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helps maintain healthy nerve and red blood cells |
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B12- cobalamin |
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found in fish, meat, poultry, eggs, milk, milk products |
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B12- cobalamin |
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Vegetarians & vegans are in danger of deficiency |
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B12-cobalamin |
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___ deficiency results in reduced levels of hemoglobin (megaloblastic anemia), as well as nervous system impairment that may be irreversible |
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B12-cobalamin; |
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______ ______ can correct the anemia from B12 deficiency, but not nerve damage. |
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Folic Acid |
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has a weak cobalt-carbon bond |
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B12-Cobalamin |
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organometallic biological molecule |
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B12-Cobalamin |
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Corrin ring structure: tetrapyrrole (4 heterocyclic aromatic rings) ring system |
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B12- Cobalamin |
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With 5'-deoxy-adenosine bound to cobalt, is called coenzyme B12. |
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B12- Cobalamin |
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Needed for more than 100 enzymes that play roles in protein metabolism (aids in group transfers to & from animo acids) |
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B6- Pyridoxine |
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enzyme cofactor _______ ________ is derived from vitamin B6 |
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pyridoxyl phosphate (PLP) |
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Deficiency can result in anemia but is rare |
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B6- Pyridoxine |
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Found in a wide variety of foods |
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B6-Pyridoxine, B7- Biotin |
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Precursor to Coenzyme A, a carrier of carbon fragments such as acetate (i.e. acetyl-CoA); acyl transfers |
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B5- Pantothenic Acid |
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Found in many foods; deficiency not seen |
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B5- Pantothenic Acid |
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Deficiency is rare, but can result from a diet rich in raw eggs, because eggs are rich in avidin, which binds biotin very tightly |
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B7- Biotin |
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Deficiency also can be caused by longterm antibiotic use (synthesized in GI tract) |
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B7-Biotin |
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Carboxylizes pyruvate (to form oxaloacetate), acetyl CoA, and propionyl CoA; hence, necessary for Krebs Cycle |
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B7-Biotin |
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The _______ ________ derivative, tetrahydrofolate, carries 1-carbon units (more reduced form of CO2) |
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Folic Acid |
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Deficiency can stop DNA synthesis, also can cause megaloblastic anemia |
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B9-Folic Acid |
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_______ _______ is found in leafy vegetables, beans and peas. |
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Folic Acid |
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Grains are now (since 1996) enriched with _______ ______. |
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Folic Acid |
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Prevents neural tube defects in the developing fetus, and heart disease |
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Folic Acid |
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phototransduction |
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Retinol; Vitamin A |
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Carbohydrate Metabolism |
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Thiamine B1 |
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redox, respiration |
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Riboflavin B2 |
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redox |
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niacin B3 |
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TCA, FA, and cholesterol |
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Pantothenic Acid B5 |
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aa metabolism, glycogenolysis |
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B6; pyridoxal, pyridoxamine, pyridoxine |
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gluconeogenesis, fa, tca, aa |
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Biotin B7 |
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1 C metabolism |
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B9 Folic Acid |
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hydroxylation |
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ascorbic Acid |
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component of oxidases in oxidative metabolism, neurotransmitter synthesis, collagen synthesis (deficiency = muscle weakness, neurological deficit, abnormal collagen) |
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Copper |
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essential component of thyroid hormone (deficiency =goiter, hypothyroidism) |
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Iodine |
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essential component of hemoglobin, other metallo-enzymes (deficiency = defective hemoglobin, anemia) |
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Iron |
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component of glutathione peroxidase (deficiency = cardiomyopathy) |
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Selenium |
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component of oxidases (deficiency = retarted growth & impaired wound healing) |
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Zinc |