Vitamins Medical Biochemistry Approach: Lecturer: Chatchawin PETCHLERT, PH.D

Department of Biochemistry
Faculty of Science, Burapha University Vitamins
Vitamins
Medical Biochemistry Approach
Lecturer:
Chatchawin PETCHLERT, Ph.D.
Head, Department of Biochemistry

Deputy Head, Department of Biotechnology
o Chemical structure
o Classification: Fat-soluble & water-soluble vitamins
o General functions
o Synthesis vitamin A, D, E & K
o Specific functions
o A, D, E & K
o B-group & C
o Anti-oxidative action: β-carotene, vitamin E, C
o Requirements
o Cow’s milk & vitamins
o Check your knowledge
Vitamins : organic, essential nutrients required in

small amounts to perform specific functions that
promote growth, reproduction, or the maintenance of
health and life.
VITAMIN
VITA AMINE
(life) (containing nitrogen)
A retinol phototransduction
B1 thiamin carbohydrate metabolism
B2 riboflavin redox, respiration
B3 niacin redox
B5 pantothenic acid TCA, FA and cholesterol
pyridoxine
AA metabolism
B6 pyridoxamine
glycogenolysis
pyridoxal
B7 biotin gluconeogenesis, TCA, FA, AA
B9 folic acid 1C metabolism
B12 cobalamin 1C&H metabolism
C ascorbic acid hydroxylation
D cholecalciferol bone remodeling
E -tocopherol antioxidant
phytylmenaquinone coagulation
K
multiprenylmenaquinone bone remodeling
Vitamin-Like Substances
Choline Acetyl choline, Phospholipids
Carnitine Fatty acyl group transfer
Bioflavonoids Antioxidants
Lipoic acid TCA acyl group transfer
Coenzyme Q Electron transport
Inositol Phospholipids
p-Aminobenzoic acid Folate component

Vitamins : Overview
 First recognized that there were substances in foods that were
“vital to life” in the early 1900s.
 Vit. A deficiency can cause blindness; a lack of the B vitamin –
niacin can cause dementia; and a lack of vit. D can retard bone
growth.
 Vit. C not only prevents the deficiency disease scurvy, but also
seems to protect against certain types of cancer.
 Vit. E seems to help protect against some facets of CVD.
 Vit. B folate helps to prevent birth defects.
Vitamins : Overview
Vitamins differ from CHOs, fats, and proteins in the following
ways:
 Structure. Vitamins are individual units; they are not linked together
(as are molecules of glucose or amino acids).
 Function. Vitamins do not yield usable energy when broken down;
they assist the enzymes that release energy from CHOs, fats, and
proteins.
 Food contents. The amounts of vitamins people ingest daily from
foods and the amounts they require are measured in g or mg, rather
than g.
Vitamins : Functions
 Essential for many processes in the body
 Vitamins play a role in digestion & utilization of
— Protein
— Fat
— Carbohydrates
 Vitamins are components of enzymes (coenzyme particularly water-
soluble vitamins)
Vitamins : Bioavailability
Bioavailability: the rate at and the extent to which a nutrient is absorbed and
used.
Precursors: substances that precede others; with regard to vitamins, compounds
that can be converted into active vitamins; also known as provitamins.
Determining the bioavailability of a vitamin is a more complex task
because it depends on many factors, including:
 efficiency of digestion and transit time through the GI tract.
 previous nutrient intake and nutrition status.
 other foods consumed at the same time that may inhibit or enhance the
absorption of individual vitamins and minerals.
 method of food preparation (raw, cooked, or , processed).
 source of the nutrient (synthetic, fortified, or naturally occurring).
Minimizing vitamin losses

 To slow the degradation of vitamins, refrigerate (most) fruits and vegetables.
 To minimize the oxidation of vitamins, store fruits and vegetables that have been cut
in airtight wrappers and juices that have been opened in closed containers (and
refrigerated them).
 To prevent losses during washing, rinse fruits and vegetables before cutting.
 To minimize losses during cooking, use a microwave oven or steam vegetables in a

small amount of water. Add vegetables after water has come to a boil. Use the cooking
water in mixed dishes such as casseroles and soups. Avoid high temperatures and
long cooking times.
Water-Soluble Vitamins: Fat-Soluble Vitamins:

B Vitamins and Vitamin C Vitamins A, D, E, and K
Absorption Directly into the blood First into the lymph, then the
blood
Transport Travel freely Many require protein carriers
Storage Circulate freely in water-filled Stored in the cells associated
parts of the body with fat
Excretion Kidneys detect and remove Less readily excreted; tend to
excess in urine remain in fat-storage sites
Toxicity Possible to reach toxic levels Likely to reach toxic levels when
when consumed from consumed from supplements
supplements
Requirements Needed in frequent doses Needed in periodic doses
(perhaps 1 - 3 days) (perhaps weeks or even months)
Fat-Soluble
Vitamins
Vitamin A
 Vit. A was the first fat-soluble vitamin
to be recognized.
 Precursors are carotenoids such as
-carotene.
 Different forms of vit. A are active in
the body: retinol, retinal, and retinoic
acid.
 A special transport protein, retinol-
binding protein (RBP), picks up vit. A
from the liver, where it is stored, and
carries it in the blood.
Worldwide data of VAD in 2008

Forms of Vitamin A
Roles of Vitamins A
 Promoting vision
 Participating in protein synthesis and cell
differentiation (and thereby maintaining the
health of epithelial tissues and skin)
 Supporting reproduction and growth
Recommendation
 RDA : 900 g RAE/day (male)
700 g RAE/day (female)
1 g RAE = 1 g retinol
= 2 g -carotene (supplement)
= 12 g -carotene (diet)
= 24 g of other vit. A precursor carotenoids
1 IU retinol = 0.3 g retinol or 0.3 g RAE

1 IU -carotene (suppl.) = 0.5 IU retinol or 0.15 g RAE
1 IU -carotene (diet) = 0.165 IU retinol or 0.05 g RAE
1 IU other vit. A precursor carotenoids = 0.025 g RAE
Retinol activity equivalents (RAE): a measure of vit. A activity; the amount

of retinol that the body will derive from a food containing preformed retinol or
its precursor -carotene.
Deficiency Disease and Symptoms

Hypovitaminosis A
 Night blindness, corneal drying (xerosis), triangular gray spots on
eye (Bitot’s spot), softening of the cornea (keratomalacia), and
corneal degeneration and blindness (xerophthalmia)
 Impaired immunity (infectious diseases)
 plugging of hair follicles with keratin, forming white lumps
(hyperkeratosis)
Bitot’s spot
Conjunctival xerosis
Keratomalacia Corneal xerosis
Corneal scar
Toxicity = Hypervitaminosis A
 Bone defects  osteoporosis (consuming
large amounts), increased activity of osteoclast
 Birth defects  teratogenesis risk (excess vit.
A before the 7th week of pregnancy appear to be
the most damaging)
 Yellow skin but not harmful
 Acne  Accutane is made from vit. A but is
chemically different. It is effective against the deep lesion of
cystic acne. It is highly toxic, however, especially during
growth, and has caused birth defects in infants when women
have taken it during their pregnancies.
Vitamins D (calciferol)
 The body can synthesize vit. D by
sunlight exposure.
 Vit. D comes in many forms, the 2
most important being a plant version
called vit. D2 or ergocalciferol and an
animal version called vit. D3 or

cholecalciferol.
cholecalciferol
 Active form is 1,25-dihydroxy
cholecalciferol (vit. D3).
Roles of Vitamin D
 Mineralization of bones (raises blood Ca2+ and

P by increasing absorption from digestive tract,
withdrawing Ca2+ from bones
 Stimulating retention by kidney
 Vit. D may protect against multiple sclerosis
Recommendation
 Adequate Intake (AI) :
Adults: 5 g/day (19-50 y)
10 g/day (51-70 y)
15 g/day (70 y)
1 IU = 0.025 g cholecalciferol (or vit. D3)


 Rickets
 Osteomalacia
 Osteoporosis
Toxicity = Hypervitaminosis D
 Elevated blood Ca2+
 Calcification of soft tissues (blood vessels, kidney, heart, lung,
tissues around joints)
 frequent urination
Precaution
 prolong exposure to sunlight degrades vit. D precursor in the skin.
 prolong exposure to sunlight increase the risk of skin cancer.
 sunscreens with sun protection factors (SPF) of 8 and higher also
prevent vit. D synthesis.
Vitamin E (Tocopherol)
 Vit. E was discovered in vegetable oils
necessary for reproduction in rats and named
this antisterility factor – tocopherol.
 -Tocopherol is the only one with vit. E
activity in the human body. The other
tocopherols are not readily converted to -
tocopherol in the body, nor do they perform the
same roles.
 RDA : 15 mg/day
 Antioxidant (stabilization of cell membranes,
regulation of oxidation reactions, protection of
PUFA and vit. A)

 diseases of fat malabsorption such as cystic fibrosis
 RBC breakage
 neuromuscular dysfunction involving the spinal cord and retina
 common symptoms include loss of muscle coordination and
reflexes and impaired vision and speech
Toxicity
 rare
 extremely high dose of vit. E may interfere with blood-clotting action
of vit. K and enhance the effects of drugs used to oppose blood clotting
causing hemorrhage.
Vitamin K
 Vit. K can be obtained from a nonfood source.
Bacteria in the GI tract synthesize vit. K that the
body can absorb.
 K stands for the Danish word koagulation
(“coagulation” or “clotting”)
 AI Men : 120 g/day Women : 90 g/day
 Synthesis of blood-clotting proteins and bone
proteins

 Primary deficiency develops in response to an
inadequate dietary intake whereas a secondary
deficiency occurs for other reasons.
 Antibiotics kill the vit. K-producing bacteria in
the intestine, and anticoagulant drugs interfere
with vit. K metabolism and activity.
 Newborn infant s present a unique case of vit.
K nutrition because they are born with a sterile Toxicity
intestinal tract, and vit. K-producing bacteria take  Toxicity is not common, and no
weeks to establish themselves. At the same adverse effects have been reported
time, plasma prothrombin are low (this reduces with high intakes of vit. K.
the fatal blood clotting during the stress of birth).
Water-Soluble
Vitamins
Vitamin B1 (Thiamin)
 Thiamin is the vitamin part of the coenzyme TPP
(Thiamin pyrophosphate), which assists in energy
metabolism.
 reaction removes 1-C from pyruvate to make
acetyl CoA + CO2 and participates in a similar
step in TCA cycle where it helps convert 5-
carbon compound to 4-carbon compound.
 Thiamin occupies a special site on the membrane of
nerve cells.
 RDA : Men: 1.2 mg/day Women: 1.1 mg/day

 Causation: Inadequate intake, malnourished and homeless people, alcoholic person
 Alcohol contributes energy, but provides few nutrients and often displaces food. In addition,
alcohol impairs thiamin absorption and enhances thiamin excretion in urine.
 Beriberi, first observed in Indonesia when the custom of polishing rice became widespread.
 Wet beriberi : with edema
 Dry beriberi : with muscle wasting, but no edema
 Wernicke-Korsakoff syndrome : severe thiamin deficiency in alcohol abusers
 Symptoms: nervous system damage as well as to the heart and other muscles,
disorientation, loss of short-term memory, jerky eye movements, stagging gait, enlarged heart,
cardiac failure, muscular weakness, apathy, confusion, irritability, anorexia, weight loss
Vitamin B2 (Riboflavin)
 Riboflavin serves as a coenzyme in many reactions,
FMN (Flavin mononucleotide) and FAD (Flavin
adenine dinucleotide), which can accept and then
donate 2 hydrogens in TCA cycle and delivers them to
the electron transport chain.
 RDA : Men: 1.3 mg/day Women: 1.1 mg/day
 The greatest sources of riboflavin come from milk
and milk products.

 Riboflavin deficiency most often accompanies other nutrient deficiencies.
 Ariboflavinosis : Inflammation of the membranes of the mouth (cheilosis), skin,
eyes, and GI tract, sensitivity to light, reddening of cornea, sore throat, painful
smooth, purplish red tongue (glossitis)
Vitamin B3 (Niacin)
 The name niacin describes 2 chemical structures:
nicotinic acid and nicotinamide.
 The body can easily convert nicotinic acid to
nicotinamide, which is the major form of niacin in the
blood.
 The 2 coenzyme forms of niacin, NAD (nicotinamide
adenine dinucleotide) and NADP (nicotinamide
adenine dinucleotide phosphate), participate in
numerous metabolic reactions.
 Niacin can be made in the body from its precursor,
tryptophan.
 RDA : Men: 16 mg NE/day Women: 14 mg NE/day 1 niacin equivalent; NE = 1 mg niacin
= 60 mg Trp

 Diarrhea, abdominal pain, vomiting; inflamed, swollen, smooth, bright red tongue,
depression, apathy, fatigue, loss of memory, headache; bilateral symmetrical rash
on areas exposed to sunlight (pellagra)
Pellagra = pellis (skin)

+ agra (rough)
Toxicity
 Painful flush, hives, and rush (“Niacin flush”)

 Excessive sweating
 Blurred vision,
 Liver damage
 Impaired glucose tolerance
Biotin
 Biotin plays an important role in metabolism as a
coenzyme that carries activated CO2. This role is critical in
TCA cycle.
 Biotin delivers one-carbon to pyruvate, thus replenishing
oxaloacetate. The biotin coenzyme also serves crucial roles
in gluconeogenesis, fatty acid synthesis, and the
breakdown of certain fatty acids and amino acids.
 The 2 coenzyme forms of niacin, NAD (nicotinamide
adenine dinucleotide) and NADP (nicotinamide adenine
dinucleotide phosphate), participate in numerous
metabolic reactions.
 Niacin can be made in the body from its precursor,
1 niacin equivalent; NE = 1 mg niacin
tryptophan. = 60 mg Trp
 RDA : Adults : 30 g/day

 Depression, lethargy, hullucinations, numb or tingling sensation in the arms and
legs,
 Red scaly rash around the eyes, nose, and mouth
 hair loss
Vitamin B6 (pyridoxine)
 occur in form pyridoxal and pyridoxamine.
 they can be converted to the coenzyme PLP
(pyridoxal phosphate), which is active in amino
acid metabolism
 The conversion of the amino acid, Trp to niacin
or to the neurotransmitter, serotonin also depend
on PLP as does the synthesis of heme, nucleic
acids and lecithin.
 RDA : Adults (19-50 y): 1.3 mg/day

 Scaly dermatitis, anemia (small-cell type), depression, confusion, abnormal brain
wave pattern, convulsions
Toxicity
 depression, fatigue, irritability, headaches, nerve damage causing
numbness and muscle weakness leading to an inability to walk and
convulsions, skin lesions
Vitamin B9 (folate, folic acid, folacin)

 Pteroylglutamic acid (PGA)
 Its primary coenzyme form, Tetrahydrofolate
(THF), serves as part of enzyme complex that
transfer one-carbon units that arise during
metabolism.
 This action helps convert vit. B12 to one of its
coenzyme forms and helps synthesize the DNA
required for all rapidly growing cells.
 RDA : Adults: 400 g/day

 Anemia (large-cell type)
 smooth, red tongue
Mental confusion, weakness, fatigue, irritability, headache
Toxicity
 mask vit. B12-deficiency symptoms
Vitamin B12 (cobalamin)

 closely related with folate
 vit. B12 removes a methyl group to activate the folate; when
folate gives up its methyl group, the vit. B12 becomes activated.
 The regeneration of the amino acid Met and the synthesis of
DNA and RNA depend on both folate and vit. B12.
 In the stomach, HCl and the pepsin release vit. B12 from the
protein to which it is attached in foods.
 As the vit. Passes to the small intestine, it binds with a
molecule called intrinsic factor. Bound together, intrinsic factor +
vit. B12 travel to the end of the small intestine, where receptors
recognize the complex. Importantly, the receptors do not
recognize Vit. B12 alone without intrinsic factor.
 RDA : Adults: 2.4 g/day

 Anemia (large-cell type)
 degeneration of peripheral nerves progressing to paralysis
Mental confusion, weakness, fatigue, irritability, headache
Vitamin C (ascorbic acid)

 250 years ago, any man who joined the crew of a seagoing
ship knew he had at best a 50-50 chance of returning alive-not
because he might be slain by pirates or die in a storm, but
because he might contract the dread disease scurvy.
 Only men on short voyages, especially around the
Mediterranean Sea, were free of scurvy.
 The antiscurvy in limes and other foods was dubbed the
antiscorbutic factor.
 Nearly 200 years later, the factor was isolated and found to be
a 6-carbon compound similar to glucose; it was names ascorbic
acid.
 RDA : Men: 90 mg/day Women: 75 mg/day
smoker: +35 mg/day

 Scurvy
 Anemia (small-cell type)
 Atherosclerotic plaques
 Pinpoint hemorrhages
 Bone fragility, joint pain
 Frequent infections
 muscle degeneration and pain
Toxicity
 Nausea, abdominal cramps, diarrhea, headache, fatigue, insomnia,
hot flashes, rashes

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Department of Biochemistry

Faculty of Science, Burapha University Vitamins

Head, Department of Biochemistry

Vitamins : organic, essential nutrients required in

Carnitine Fatty acyl group transfer

Lipoic acid TCA acyl group transfer

Coenzyme Q Electron transport

p-Aminobenzoic acid Folate component

Minimizing vitamin losses

 To minimize losses during cooking, use a microwave oven or steam vegetables in a

Water-Soluble Vitamins: Fat-Soluble Vitamins:

Worldwide data of VAD in 2008

1 IU retinol = 0.3 g retinol or 0.3 g RAE

Retinol activity equivalents (RAE): a measure of vit. A activity; the amount

Deficiency Disease and Symptoms

Keratomalacia Corneal xerosis

animal version called vit. D3 or

 Mineralization of bones (raises blood Ca2+ and

1 IU = 0.025 g cholecalciferol (or vit. D3)

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Pellagra = pellis (skin)

 Painful flush, hives, and rush (“Niacin flush”)

Deficiency Disease and Symptoms

Deficiency Disease and Symptoms

Vitamin B9 (folate, folic acid, folacin)

Deficiency Disease and Symptoms

Vitamin B12 (cobalamin)

Deficiency Disease and Symptoms

Vitamin C (ascorbic acid)

Deficiency Disease and Symptoms

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