Vitamins

A vitamin is an organic compound and a vital nutrient that an

organism requires in limited amounts.
An organic chemical compound (or related set of compounds) is
called a vitamin when the organism cannot synthesize the compound
in sufficient quantities, and it must be obtained through the diet; thus,
the term "vitamin" is conditional upon the circumstances and the
particular organism.
For example, ascorbic acid (one form of vitamin C) is a vitamin for
humans, but not for most other animal organisms. Supplementation is
important for the treatment of certain health problems, but there is
little evidence of nutritional benefit when used by otherwise healthy
people
Vitamin A
Vitamin B1, B2, B3, B5, B6, B7, B9, B12
Vitamin C Vitamin E
Vitamin D Vitamin K
Vitamin A - Retinol

Retinol (vitamin A)

Sources in diet - Many plants (photoreceptors), also meat, especially liver. Fat
soluble, so you can get too much, or too little if absorption is a problem.

Some uses:

Vision (11-cis-retinol bound to rhodopsin detects light in our eyes).

Regulating gene transcription (retinoic acid receptors on cell nuclei are part of a
system for regulating transcription of mRNAs for a number of genes).
 Vitamin A is essential for:
Normal functioning of the body epithelia and retina.
Bone growth.
Maintenance of spermatogenesis.
Normal growth of young animals.
The synthetic retinoic acids are used as topical or oral
treatments for acne vulgaris.
Deficiency is indicated by night blindness, drying and crushing
of the mucus membrane, and sterility.
Vitamin B1 - Thiamine

Thiamine

Some uses:

Cofactor for several enzymes (a precursor for thiamine pyrophosphate, one

of the cofactors used by the pyruvate decarboxylase complex (PDC).

Also, a cofactor for branched chain a-keto dehydrogenase.

Found in a wide variety of foods, including meat, grains. Deficiency causes

beriberi (muscle atrophy, neurological problems).
Vitamin B2 - riboflavin
Riboflavin is a precursor
for FAD and FMN.

FAD -
flavin adenine dinucleotide. FMN - Flavin
mononucleotide

FAD is a cofactor for pyruvate FMN is an electron carrier in

dehydrogenase complex (PDC), and the electron transport chain.
succinate dehydrogenase in TCA cycle.
Vitamin B3 - nicotinic acid
(a precursor for NAD).
Also known as niacin.

nicotinic acid

NAD+ is needed for glycolysis, NADH gets oxidized in electron transport

chain, etc.
Vitamin B5 - pantothenic acid (needed for making CoA)

pantothenic acid

Coenzyme A

We get pantothenic acid in our diet as CoA, which must be broken down
to pantothenic acid to be absorbed in intestine. We then use the
pantothenic acid in making our own CoA.
Vitamin B6 - pyridoxine

Precursor for pyridoxal phosphate

(PLP).

PLP is a covalently linked cofactor to PLP

transaminases, and some
decarboxylases, and glycogen
phosphorylase; these are called PLP-
dependent enzymes.
Vitamin B7 - Biotin.

Used in fatty acid synthesis,

also other functions.

Biotin deficiency is rare.

Vitamin B9 - Folic acid.
Required for synthesis of glycine,
methionine, nucleotides T & U
(chapter 15). folic acid

Important for rapidly dividing cells

(very important in early pregnancy).

N5,N10 methylene-tetrahydrofolate is a
donor of methylene groups.

Deficiency in pregnancy causes neural tube defects.

Folic acid is now added to many grain products in the US.
Vitamin B12 - cobalamin. adenosyl-
cobalamin
(also hydroxycobalamin, adenosylcobalamin).

We saw cobalamine in fatty acid

oxidation.

Cobalamin is needed in making

adenosylcobalamin, a cofactor for
methyl malonyl mutase, which
breaks down odd-chain fatty acids.

B12 is also used in regenerating

folate

Sources are meat, milk and eggs.

Vegetarians who eat dairy

products are OK, but non-dairy
vegans may not get enough.
Vitamin C - asorbic acid

Required for collagen synthesis, and

as a cofactor for several enzymes.
Also scavenges oxygen radicals.

In almost all organisms, ascorbic acid is synthesized from glucose in 4

steps.

A relatively recent (40 million years ago) mutation in the ancestor of

humans made us unable to make ascorbic acid. So for us, and some
closely related primates, its a vitamin.

Guinea pigs cant make ascorbic acid, either.

Sources of vitamin C are fruit and fresh meat. Vitamin C deficiency

causes scurvy, and in human history vitamin C deficiency may have
been an impediment to spreading northward.
Vitamin D refers to a group of similar lipid-soluble molecules (major
forms are D2 and D3, also D1, D4, D5).

Vitamin D3 (cholecalciferol) Vitamin D2 (ergocalciferol)

Vitamin D3 can be obtained in diet, or derived from cholesterol in a
reaction that requires UV light.

spontaneous

calcitriol
Vitamin D binds to a vitamin D binding protein (VDP) for transport to target
organs.

Vitamin D is not active itself (its a prohormone); it is modified to yield

biologically active forms, such as calcitriol.

Calcitriol (derived from vitamin D) is a transcription factor, influencing

expression of proteins involved in calcium absorption and transport.

Vitamin D is also important for immune system function.

Deficiency causes rickets, bone loss.

Calcitriol, from
vitamin D.
Vitamin D production requires UV light (sunlight).

Sometime after humans migrated north out of Africa about 50,000 years
ago, mutations appeared that reduced melanin (pigment) production in
the skin, permitting vitamin D production with less sunlight.

Disadvantages of less melanin production are skin that is easily

damaged by the sun, skin cancer risk, and loss of folic acid due to UV
damage.

The melanin-reducing mutations helped early humans make vitamin D

in northern europe in winter.
Vitamin E
Collectively refers to 8 related tocopherols, four tocopherols
and four tocotrienols
Both the tocopherols and tocotrienols occur in (alpha),
(beta), (gamma) and (delta) forms
It is essential, but roles are unclear.
Suggestions include neural membrane
component, antioxidant.

Obtained in diet, deficiency is rare.

Antioxidant activity of Vitamin E
The main function of -tocopherol in humans is that of a fat
soluble antioxidant.
Fats, which are an integral part of all cell membranes, are vulnerable
to damage through lipid peroxidation by free radicals.
-Tocopherol is uniquely suited to intercept peroxyl radicals and
thus prevent a chain reaction of lipid oxidation.
When a molecule of -tocopherol neutralizes a free radical, it is
oxidized and its antioxidant capacity is lost. Other antioxidants, such
as vitamin C, are capable of regenerating the antioxidant capacity of
-tocopherol.
Aside from maintaining the integrity of cell membranes throughout
the body, -tocopherol protects the fats in low-density lipoproteins
(LDLs) from oxidation.
LDLs specifically transport cholesterol from the liver to the tissues
of the body. Oxidized LDLs have been implicated in the
development of cardiovascular disease.
 Vitamin K
Vitamin K represents a group of lipophilic and
hydrophobic vitamins.
Three compounds have the biological activity of vitamin
K
Phylloquinone (Vitamin K1), the normal dietary
source, found in green vegetables
Menaquinones (vitamin K2), synthesized by intestinal
bacteria, with differing lengths of side chain;
and Menadione and menadiol diacetate, synthetic
compounds that can be metabolized to phylloquinone.
Vitamin K
 Dietary Sources
Vitamin K is found in green leafy vegetables such
as kale and spinach, and
Appreciable amounts are also present in
margarine and liver.
Vitamin K is present in vegetable oils and is
particularly rich in olive, canola, and soybean oils.
Some amount is contributed by intestinal bacteria
 Role of vitamin K in coagulation
The ability to bind calcium ions (Ca2+) is acquired by the activation of
the vitamin K-dependent clotting factors, or proteins, in the
coagulation cascade.
Factors II (prothrombin), VII, IX, and X make up the core of the
coagulation cascade. These factors are synthesized in the liver in the
inactive form.
They undergo post translational modifications, gamma carboxylation
of glutamic acid residues.
This process of gamma carboxylation of glutamic acid residues
imparts another negative charge, so as to promote the effective
binding of these factors/proteins to calcium ions.
 Vitamin K cycle
Vitamin K is a fat-soluble vitamin, the body
stores very little of it, and its stores are rapidly
depleted without regular dietary intake.
Because of its limited ability to store vitamin
K, the body recycles it through a process called
the vitamin K cycle.
The vitamin K cycle allows a small amount of
vitamin K to function in the gamma-
carboxylation of proteins many times,
decreasing the dietary requirement.
 Vitamin K cycle

Reduced lipoamide is required for the activity of

Epoxide reductase whereas NADPH is needed for
the action of vitamin K reductase.
 Vitamin K cycle
Vitamin K hydroquinone (active form) is
oxidized to the Epoxide form during the
process of enzymatic reaction.
The initial form (hydroquinone form) is
regenerated by two steps process.
Vitamin K Epoxide is reduced to the quinone
by a Epoxide reductase, and the quinone is
reduced to the active hydroquinone by either
the same reductase or by a vitamin K
reductase(quinone reductase).