18 - Lecture #13 - Vitamins Part 2 - 02

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6.

Vitamin B6
• Other Names:
• Pyridoxine
• Pyridoxic acid
• Pyridoxal
• Pyridoxol
• Pyridoxamine
Chemistry of Vitamin B6
• Forms found in foods are pyridoxine, pyridoxal and
pyridixamine
• Can be converted to the coenzyme pyridoxal phosphate
(PLP)
• The body can be degraded to pyridoxic acid that is excreted in
the urine.
• In body tissues, it occurs primarily in the phosporylated forms
of PLP and pyridoxamine phosphate.
• Not destroyed by heat and acids.
• Destroyed in alkaline solutions, by oxidation and ultraviolet
light
• Antagonists are deoxypyridoxine, methoxypyridoxine,
toxopyrimidine and isonicotinic acid hydrazide (INH)
Absorption, Transport & Utilization
• Absorbed mainly in the jejunum in its free form by passive
diffusion.
• Dephosphorylated in the intestinal lumen by the enzyme
alkaline phosphatase
• Bound to albumin and transported to the liver, where
pyridoxine and pyridoxamine are phosporylated by kinase
and converted to PLP by a flavin-dependent oxidase
• Aldehyde oxidase in the liver and kidneys can convert
pyridoxal to pyridoxic acid. This occurs when too much of the
vitamin is absorbed.
• Stores about 250mg of vitamin B6
• In muscles, 80-90% of PLP is bound to the enzyme glycogen
phosphorylase.
Function of Vitamin B6
• In the form of PLP, the vitamin functions as a coenzyme of more than
60 enzymes in the following biochemical reactions.
•  
• Amino acid metabolism
• Transamination reaction where amino group (NH2) is transferred from
one compound to another.
• Decarboxylation reactions where a carboxyl group (COOH or COO) is
moved from a compound.
• Desulfurative deamination of cysteine
• Dehydrative deamination of serine and threonine
• May be beneficial against carpal tunnel syndrome; a pinched nerve
in the wrist that causes pain or numbness in the hand
• May alleviate premenstrual syndrome
• Formation and degradation of cystathionine
Function of Vitamin B6
• Synthesis of neurotransmitters serotonin and norepinephrine
• Synthesis of sphingolipids needed for myelin formation
• Synthesis of delta-amino levulinic acid a precursor of heme
• Part of glycogen phosphorylase
• Transformation of tryptophan
• Biosynthesis of CoA in the liver
• Production of ethanolamine and taurine
• A coenzyme in lysine oxidase that is active in the
biosynthesis of elastin and collagen
• Metabolism of unsaturated fatty acids
• Has an important role in glucocorticoid action
Interactions with Other Nutrients
• Vitamin B6 is closely related with riboflavin and niacin.
The two vitamins are needed for the activity of enzymes
important for the normal metabolism of some forms of B6.
Deficiency of Vitamin B6
• Anemia (microcytic type); smooth tongue; cracked
corners of the mouth; abnormal brain wave pattern,
irritability, muscle twitching convulsions; irritation of sweat
glands, dermatitis, kidney stones.
Toxicity of Vitamin B6
• Bloating, depression, fatigue, irritability, headaches,
numbness, nerve damage leading to loss of reflexes and
sensation, difficulty in walking.
Recommended Intake of Vitamin B6
• For the recommended intake, please refer to the PDRI
• Drugs that increase the body’s need for vitamin B6 include oral
contraceptives, INH and penicillamine.
• Groups considered particularly at-risk for a deficient intake of the vitamin
include:
• Breastfed infants with low vitamin B6 plasma level
• Elderly with poor intakes
• Alcoholics
• Renal patients on maintenance dialysis causing abnormal losses of the
vitamins
• Persons taking certain drugs
• Drugs that increase the body’s need for vitamin B6 include oral
contraceptives, isoniazid (INH) and penicillamine. INH is a vitamin B6
antagonist used to treat tuberculosis, while penicillamine is used to treat
Wilson’s disease, cysteinuria and rheumatoid arthritis.
Food Sources of Vitamin B6
• Vegetable oils (corn, cotton
seed, olive, peanut), rice
and wheat germ, whole
grain cereals, legumes, nuts
and seeds, especially
soybeans
7. Vitamin B9
• Other Names:
• Folic Acid
• Folate
• Folacin
• Citrovorum factor
• Pteroylglutamic acid
• Lactobacillus casei factor
• Vitamin M
• Vitamin Bc
• Factor U
Chemistry of Vitamin B9
• Bright Yellow crystalline compound
• Slightly soluble in water
• Easily oxidized by acids
• Sensitive to light
• Made up of three distinct parts; pteridine, para-amino
benzoic acid and glutamic acid
• Simplest form is pteroylmonoglutamic acid (PGA), but
folic acid usually occurs as polyglutamate derivatives having
2-7 glutamic acid residues.
• In the presence of ascorbic acid and niacin, PGA becomes
THF
• Antagonists are amethopterin, aminopterin
tetrahydroaminophen and pteroylaspartic acid
Absorption, Transport & Utilization
• Glutamic acid residues must be first removed to absorb
the polyglutamate form of folate in foods,
• Hydrolysis of glutamic acid residues in the intestinal
mucosal cells by conjugase (or folate hydrogenase), a
lysosomal enzyme.
• Reduction of free folic acid to THF by the enzyme
dihydrofolate reductase and transported in the blood
mainly as free N5-methyl-THF for distribution to the
different body cells.
• Stored as THF are mainly in the polyglutamate form in the
liver.
Absorption, Transport & Utilization
• For utilization, it is hydrolyzed back to its monoglutamate
form
• Polyglutamates are more active than the monoglutamates
as coenzymes due their greater binding ability with
enzyme.
• For the folate coenzyme to function, the methyl group
must be released from methyl-THF by an enzyme
methionine synthetase that needs vitamin B12 for its
activity
• Folate is excreted in the urine and bile.
Functions of Vitamin B9
• Folate acts as a coenzyme( in the THF form) in reactions,
which transfer one-carbon units (such as the methyl group
CH3) from one compound to another. THF derives serve
as donors of one-C units in the following biologic
reactions.
• Synthesis of amino acid methionine, histidine and serine.
• Conversion of phenylalanine to tyrosine
• Formation of the heme group of hemoglobin
Functions of Vitamin B9
• Synthesis of the purine and pyrimidine bases needed for
the formation of deoxyribonucleic acid (DNA) and
ribonucleic acid (RNA)
• Formation of the vitamin-like compound choline from
ethanolamine
• Conversion of niacin to N-methyl nicotinamide, the form in
which it is excreted
• Folate may play a role against cancer of the breast and
pancreas
• It may also protect the heart from the damage of
homocysteine, which promotes blood clot.
Interactions with Other Nutrients
• Vitamin C protects the folate coenzyme from oxidative
destruction.
• There must be sufficient vitamin B12 for the activity of
methionine synthetase, the enzyme that reduces the
methyl group from N5-methyl-THF to form methionine
from homocysteine.
• Supplement of folate decreases zinc absorption.
Deficiency of Vitamin B9
• Megaloblastic or macrocytic anemia
• Glossitis
• Gastrointestinal upsets
• Neural tube defects- malformations of the brain and
spinal cord that results in disability or death; examples are
spina bifida or anencephaly
• Impairment of histidine metabolism
Toxicity of vitamin B9
• Masking of Vitamin B12 symptoms
Recommended Intake of Vitamin B9
• For the Recommended intake, please refer to the PDRI.
The requirement estimates are based on the amount of
folate that will maintain adequate folate stores based on
erythrocyte folate and plasma homocysteine levels.
• To meet the new higher recommendations (Appendix A),
higher intakes of vegetables and fruits, which are among
the best sources of folate are suggested.
Food Sources of Vitamin B9
• Green leafy vegetables
(alugbati, gabi, malunggay,
saluyot, sitao, talinum) wheat
germ, legumes, seeds and
organ meats like liver.
8. Vitamin B12
• Other Names:
• Cobalamin
• Cyanocobalamin
• Anti-pernicious anemia factor
• Hydroxycobalamin
• Erythrocyte maturation factor
• Animal protein factor
Chemistry of Vitamin B12
• Called corrinoids (cobalamin) because of their corrin nucleus
with an atom of cobalt at the center; group attached to the
cobalt may vary in the formation of different cobalamus.
• Only two cobalamins are coenzymatically active- methyl
cobalamin and 5’-deoxyadenosylcobalamin.
• The body can convert all the other cobalamins into the
coenzyme forms
• Cyanocobalamin is the pharmaceutical form of the vitamin
used in supplements
• Stable in heat
• Converted to the active form by removing the cyano group.
• Animals derive their cobalamin from microorganisms.
Absorption, Transport & Utilization
• Bound protein must be released before it can be utilized
• Released from this protein complex by acid hydrolysis in
the stomach and the proteases in pancreatic juice
• Binds to a salivary polypeptide called R-binder
• Digested by the enzyme trypsin
• Vitamin B12 then combines with the intrinsic factor (IF),
a glycoprotein secreted in the stomach
• Cobalamin-if the complex tavels to the ileum, catalyzed by
calcium ions.
Absorption, Transport & Utilization
• Absorption rate decrease as one’s intake increases; needs
IF for absorption; declines with age due to lack or
inadequate secretion of gastric acid; decreases among
individuals with B6 deficiency (the condition decreases the
release of IF), iron deficiency, hyperthyroidism and gastritis
and those taking anticonvulsants and antibiotics.
• B12 goes to the blood and combines with three transport
called transcobalamins I, II and III, particularly to the liver
and bone marrow.
• With sufficient transport proteins, little of the vitamins are lost
in the urine, as blood is filtered through the kidney.
• Stored in great amounts in liver and kidney as B12-protein
complex; sufficient to supply body for 6-10 years.
Functions of Vitamin B12
• Important in DNA synthesis, and needed for cell growth
and division.
• Needed in the synthesis of myelin, the lipoprotein
substance that surrounds nerve fibers.
• Involved in the conversion of malonyl coenzyme A(CoA)
to succinyl CoA that functions in the degradation of
propionate from odd-chain fatty acids
• Generation of methionine from homocysteine using 5-
methyltertrahydrofolate as a methyl group donor
• Helps folate coenzymes to participate in DNA synthesis by
converting folate to its active form.
Deficiency of Vitamin B12
• Sore tongue, gastrointestinal tract (GIT) discomfort,
coldness of the extremities and neurologic changes due to
the demyelination
• Pernicious anemia is mainly induced by IF deficiency
• With increased risk of vitamin B12 deficiency; the elderly,
alcoholics and gastrectomy patients, vegans
Recommended Intake of Vitamin B12
• For the recommended intake, please refer to the PDRI
• Recommendation > 10 years of age is 2.4mg/day that is
based on the amount needed to maintain adequate
hematological status
Food Sources of Vitamin B12
• Food of animal origin, in particular meat, fish, shellfish,
poultry and milk
9. Biotin
• Other Names:
• Anti-egg white injury factor
• Bios I
• Vitamin H
• Coenzyme R
• Vitamin B7
Chemistry of Biotin
• Sulfur-containing vitamin
• Crystalline in its free form
• Stable to heat, light and acids
• Unstable in alkali and to oxidation
• Produced by intestinal bacteria is in the form of biocytin,
a biologically active derivative; combined with the amino
acid lysine.
• Inactivated by avidin, protein in raw egg whites
Absorption, Transport & Utilization
• Most absorption of biotin takes place in the upper portion
of the small intestine requiring a sodium-activated system.
• Absorption rate and uptake by tissues are related to the
need of a cell.
• Distributed corresponding to localization of the
carboxylases, the enzymes that require biotin as a
coenzyme.
Functions of Biotin
• It functions as a coenzyme for a number of carboxylases
that transfer CO2 between compounds.
• Pyruvate carboxylases that converts pyruvate to
oxaloacetate:gluconeogenesis
• Acetyl CoA carboxylasethat forms malonyl CoA from acetate: fatty acid
synthesis
• Propionyl CoA carboxylase that converts propionate to succinate: amino
acid metabolism
• Beta-methylcrotonyl CoA (MCC) that converts beta-MCC to beta-
methylglutaconyl CoA: amino acid metabolism
• Participates in the deamination of aspartic acid, threonine
and serine
• Synthesis of pancreatic amylase and nicotinic acid
• Plays role in antibody formation
Deficiency of Biotin
• Rare; results from a rare deficiency in biotinidase, an enzyme of
the gut mucosa that can occur in about 1 in 40,000 infants.
• Can also occur in individuals who consume raw eggs (six per day)
over many months because egg white contains protein called
avidin that binds the biotin making it unavailable for utilization.
• Manifested as;
• Abnormal heart action
• Loss of appetite
• Nausea
• Depression
• Muscle pain
• Weaknesses
• Fatigue and
• Drying, scaly dermatitis, hair loss (alopecia)
Recommended Intake of Biotin
• No recommendations in PDRI
• Increased requirements in the following conditions and
populations: achlordyria, alcoholism, excessive egg white
intake, sulfonamide therapy, pregnancy and lactation,
epileptics and elderly.
Food Sources of Biotin
• Eggyolk, kidney, liver, milk, molasses, yeast, peanuts,
dried soya beans
VITAMIN-LIKE
SUBSTANCES
Vitamin-Like Substances
• Substances that, on the basis of current information, fail
to meet all the criteria necessary to be classified as
vitamins but still have some properties of vitamins

• In some cases, they are present in larger amounts than


vitamins; in others, the body can synthesize sufficient
amounts to meet its needs if precursors are present
1. Lipoic acid
• Lipoic acid is a sulfur-containing fat-soluble substance
that participates in carbohydrate metabolism converting
pyruvic acid to acetyl CoA.
• It has not yet been established that the substance is a
dietary essential for humans.
2. Choline
• Choline is a part of the neurotransmitter acetylcholine. It is
required for the synthesis of phospholipids
(phosphatidylcholine, lysophosphatidylcholine, choline
plasmogen and sphingomyelin) that are important
components of all cell membranes
• The compound is distributed widely in foods and can be
synthesized in the body from serine and methionine
• Its deficiency includes liver damage; toxic effects may
cause body odor, sweating, reduced growth and low BP.
3. Myoinositol
• Myoinositol is needed for the integrity of cellular and
intracellular membranes
• It is widely distributed in both plant foods and animal
products
• The compound is synthesized in many body tissues from
glucose. Inositol phospholipids are components of cellular
and intracellular membranes. In particular, myoinositol
seems to regulate certain aspects of membrane-related
metabolism.
4. Carnitine
• Carnitine is not a dietary essential since it can be
synthesized in the liver and kidneys from lysine and
menthionine
• It is an essential substance needed to transport long-
chain fatty acids the cell’s mitochondria where they are
oxidized to provide energy. This function makes carnitine
vital to the survival of premature infants.
• Human and cow’s milk provide adequate amounts of
carnitine.
5. Coenzyme Q10 (ubiquinone)
• Coenzyme Q10 is a generic name for lipid-like substances
found in all cells
• It is concentrated in the mitochondria, where energy
synthesis takes place. It plays an important role in the
respiratory chain where energy from nutrients is trapped
within ATP.
6. Taurine
• Taurine is a sulfur-containing amino acid derived from
cysteine, which has an essential role in regulating the
activity of the nervous system, particularly the retina of the
eye.
• It is also involved in the absorption of fat. Its different
chemical strucyure does not enable the compound to
incorporate into proteins; it is unable to become a part of a
peptide or protein molecule.
• Infants are able to form conjugates between bile salts, and
taurine and glycine, which aid in fat absorption. In the case
of small, preterm infants, the addition of supplementary
taurine results in a more efficient absorption of fat.
THANK YOU!

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