BCH 210.1 Lesson Note

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BCH 210.

VITAMINS AND MINERALS

VITAMINS

The vitamins are organic, low-molecular-weight compound the body requires in small amounts for
normal metabolic functions, deficiency of any vitamin can cause serious symptoms.

Vitamins act as coenzymes to regulate metabolism; assist the body to convert the energy in fat,
carbohydrates, and protein into ATP; and promote growth and reproduction. Vitamins do not provide
energy themselves, There Are Criteria for Classifying Vitamins

Thirteen (13) compounds are classified as vitamins. The vitamins are further organized according to
their solubility. There are four fat-soluble (hydrophobic) vitamins: A, D, E, and K, and nine water-
soluble (hydrophilic) vitamins, including the B vitamin complex and vitamin C.

Water-Soluble Vitamins Are Not Stored after Absorption. Water-soluble vitamins are absorbed with
water and enter the bloodstream directly from the small intestine. Most water-soluble vitamins are
absorbed in the duodenum and jejunum, although vitamin B12 is absorbed in the ileum. Water-
soluble vitamins are not stored in the body, and excess amounts are excreted, so it’s important to
consume adequate amounts of them every day. Note that even though most water-soluble vitamins
aren’t stored, dietary excesses can still be harmful.

Water soluble vitamins and their respective coenzymes


VITAMINS COMMON NAME COENZYMES
Vitamin B1 Thiamine Thiamin pyrophosphate
Vitamin B2 Riboflavin Flavin mononucleotide [FMN] and Flavin adenine
dinucleotide [FAD]
Vitamin B3 Niacin, nicotinic Nicotinamide adenine Dinucleotide [NAD] and
acid, Niacinamide Nicotinamide adenine dinucleotide 2´-phosphate
[NADP]
Vitamin B5 Pantothenic Acid Coenzyme A
Vitamin B6 Pyridoxine, Pyridoxal phosphate
pyridoxal,
Vitamin B12 Cobalamin 5´-Deoxyadenosyl cobalamin and methylcobalamin
Biotin Carboxybiotin
Folic acid Folate, folacin Tetrahydrofolate (THF)
Vitamin C (ascorbic acid)
Lipoic acid Lipoamide

Fat-soluble vitamins are absorbed primarily in the duodenum. They are packaged with fatty acids and
bile in micelles that transport them close to the intestinal mucosa. Once there, the fat-soluble
vitamins travel through the cells in the intestinal wall into the bloodstream via the lymph system as
chylomicrons. Fat-soluble vitamins are stored in the body and used as needed when dietary intake
falls short of the body’s needs. The liver, fat and muscle tissues are the main storage depot for fat
soluble vitamins. Because they are stored in the body, large quantities of some of the fat-soluble
vitamins could lead to toxicity, causing harmful symptoms and conditions.

Some preparation and storage methods (exposure to air, ultraviolet (UV) light, water, changes in pH,
or heat) can accelerate vitamin loss.

BIOCHEMICAL FUNCTIONS, DIETARY SOURCES, DEFICIENCY SYMPTOMS OF VITAMINS

Vitamin A The term vitamin A refers to a family of fat-soluble retinoids that include retinol, retinal,
and retinoic acid. These compounds are similar in their chemical structure. They each contain a ring
with a polyunsaturated fatty acid tail. Attached at the end of the fatty acid tail is either an alcohol
group (retinol), an aldehyde group (retinal), or an acid group (retinoic acid). Whereas retinol, retinal,
and retinoic acid all participate in essential functions in the body, retinol, the alcohol form, is the most
usable. In foods, vitamin A is found as retinol or as a retinyl ester, which has an ester group attached
at the fatty acid tail. The body also stores vitamin A as a retinyl ester in the liver.

Chemical structure
VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY
SYMPTOMS
A Plays an important role in vision Beef, liver, lean ham Night blindness, dry,
and reproduction and pork chops, eggs, rough skin, poor bone
• Needed for formation and shrimp, fish, fortified and teeth growth and
maintenance of mucous milk, cheddar cheese, development, a
membrane, skin and bone Swiss cheese, darkly susceptibility to
• Supports the immune system colored orange or infectious diseases
(helps make white blood cells) green vegetables
 act as antioxidants that (carrots, sweet
prevent some cancers and potatoes, pumpkin,
fight heart disease turnip greens and
• Growth and spinach), orange fruits
development (cantaloupe, apricots,
• Red blood cell peaches, mangoes)
formation

VITAMIN D

Vitamin D (calciferol) is called the “sunshine vitamin” because it is derived from the reaction between
ultraviolet (UV) rays and a form of cholesterol found in the skin. Exposure to sunlight can synthesize
up to 100 percent of the vitamin D the body needs.41 For this reason, vitamin D is often considered a
conditionally essential nutrient. However, it still fits the criteria of a vitamin because a deficiency of
this compound can cause symptoms that are cured once adequate intake is restored. Because of its
function, vitamin D is also considered a prohormone, an inactive precursor, that is activated inside the
body. Vitamin D is found in two forms. Cholecalciferol or vitamin D3 is the form produced in the skin
and found in animal foods. Ergocalciferol or vitamin D2 is found in plants and dietary supplements.
Chemical structure:

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
D  Helps maintain normal Fortified milk or Weak, soft bones and
blood levels of calcium margarine, fortified skeletal deformities
which strengthen bones. cereals, fatty fish, liver, Rickets
 Helps form teeth and eggs in children
bones. Osteomalacia in adult
• Plays an important role in insulin
production
 Needed for utilization of
calcium in nerve/muscle
activity
 Vitamin D Helps Regulate
the Growth of Cell
 Vitamin D May Help
Regulate Blood Pressure
 Immune function
Vitamin E There are eight different forms of naturally occurring vitamin E, but one form, alpha-
tocopherol (α-tocopherol), is most active in the body with a side chain of saturated carbons
( Figure 9.18). The synthetic form of vitamin E found in dietary supplements is only half as active as
the natural form.

Chemical structure

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
E  Acts as an antioxidant, Vegetable oils, nuts Though rare, a chronic
neutralizing free radicals and seeds, peanuts and deficiency can cause
that can damage cells. peanut butter, wheat nerve problems,
 Helps the healing of skins germ, whole-grain and muscle weakness, and
and prevents scarring. fortified cereals uncontrolled
 Formation of blood movement of body
vessels parts.
 Immune function As an antioxidant
 Vitamin E as an deficiency can increase
Anticoagulant susceptibility of cell
membranes to damage
by free radicals.

Vitamin K

Vitamin K is found naturally in two forms. Some plants manufacture phylloquinone, or vitamin K1.
Phylloquinone, has a long chain of carbons with methyl groups attached at every fourth carbon. This is
the primary source of vitamin K in the diet. In animals, bacteria that reside naturally in the colon
synthesize menaquinone, also referred to as vitamin K2. A third form of vitamin K, called menadione,
or vitamin K3, is synthetic and formulated for use in animal feed and vitamin supplements.

Chemical structure
VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY
SYMPTOMS
K  Plays an essential role in Cabbage, liver, eggs, A shortage of this
formation and regulation of milk, spinach, broccoli, vitamin may result in
blood clotting proteins sprouts, kale, collards, nosebleeds, internal
• Supports the utilization of and other green hemorrhaging.
calcium in teeth/bone vegetable
formation

WATER SOLUBLE VITAMINS

VITAMIN C

Vitamin C (chemical names: ascorbic acid and ascorbate) is a six-carbon lactone which is synthesized
from glucose by many animals. Vitamin C is synthesized in the liver in some mammals and in the
kidney in birds and reptiles. However, several species—including humans, are unable to synthesize
vitamin C. Vitamin C is an electron donor (reducing agent or antioxidant), hence exhibiting its
potentially protective role as an antioxidant . Humans lack the terminal enzyme in the biosynthetic
pathway of ascorbic acid, l-gulonolactone oxidase, because the gene encoding for the enzyme has
undergone substantial mutation so that no protein is produced.

Chemical structure:

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
C  Needed for formation and Fruits and fruit juices Bleeding and inflamed
maintenance of (especially citrus), gums, loose teeth, poor
neurotransmitters and potatoes, broccoli, bell wound healing, and
hormone peppers, spinach, anemia
 Vitamin C is needed to form strawberries,
collagen, a tissue that helps tomatoes, Brussels
to hold cells together. sprouts
 It's essential for healthy
bones, teeth, gums, and
blood vessels.
 It helps the body absorb
iron,
 aids in wound healing,
contributes to brain
function.
 Vitamin C as an antioxidant
may lower the risk for some
cancers, including those of
the mouth, esophagus,
stomach and breast.

VITAMIN B1 THIAMIN

The term thiamin is the trivial designation of the compound 3-[(4-amino-2-methyl-5-


pyrimidinyl)methyl]5-(2-hydroxyethyl)-4-methylthiazolium, formerly known as vitamin B1, aneurine,
and thiamine. Free thiamin is unstable because of its quaternary nitrogen; in water it is cleaved to the
thiol form.

Chemical structure:

Essential features of the chemical structure:

1. Conjoined pyrimidine and thiazole rings


2. Thiazole ring contains a quaternary nitrogen, an open C-2, and a phosphorylatable alkyl group on C-
5
3. Amino group on C-4 of the pyrimidine ring
VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY
SYMPTOMS
Thiamine Are co-enzymes involved in Lean pork, legumes, Early symptoms of
(B1) energy metabolism bananas, most fish, thiamin deficiency
(carbohydrate, fat, and liver, nuts and seeds, include fatigue, weak
protein) and energy potatoes, peas, muscles, anorexia,
production watermelon, avocado, weight loss and mental
• Needed for functioning poultry, whole-grain changes, such as
and maintenance of the and fortified cereals confusion or irritability,
nervous system and muscle sensitivity of the teeth,
tissue cheeks and gums, as
• Supports growth and well as "cracks" in the
tissue repair lips. More severe
deficiencies can result
in anemia, paralysis,
muscular atrophy

RIBOFLAVIN (B2)

Chemical structure

Essential features of the chemical structure

1. Substituted isoalloxazine nucleus

2. d-Ribityl side chain 3. Reducible nitrogen atoms in nucleus

Riboflavin is the trivial designation of the compound 7,8-dimethyl-10-(1 ′-d-ribityl)isoalloxazine,


formerly known as vitamin B2. The metabolically active forms are commonly called flavin
mononucleotide (FMN) and flavin adenine dinucleotide (FAD). Riboflavin is a yellow tricyclic molecule
that is usually phosphorylated (to FMN and FAD) in biological systems. The catalytic functions of
riboflavin are carried out primarily at positions N-1, N-5, and C-4 of the isoalloxazine nucleus. In
addition, the methyl group at C-8 participates in covalent bonding with enzyme proteins. The flavin
coenzymes are highly versatile redox cofactors because they can participate in either one- or two-
electron redox reactions.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Riboflavin  Coenzyme form Helps Milk, yogurt, cheese, Itching and irritation of
(B2) convert food into energy. eggs, fish and shellfish, lips, eyes, skin and
 Needed for skin, hair fortified cereals, meat, mucous membranes,
formation. poultry, kiwi, avocado, and can cause eyes to
 Helps to prevent sores and broccoli, turnip greens, be light sensitive
swelling of the mouth and asparagus
lips.
 Red blood cell formation
 Needed for functioning and
maintenance of the nervous
system and muscle tissue

NIACIN B3

Chemical structure

Essential features of the chemical structure

1. Pyridine nucleus substituted with a β-carboxylic acid or a corresponding amine

2. Pyridine nitrogen must be able to undergo reversible oxidation/reduction (i.e., quaternary


pyridinium ion to/from tertiary amine)

3. Pyridine carbons adjacent to the nuclear nitrogen atom must be open

Niacin is the generic descriptor for pyridine 3-carboxylic acid and derivatives exhibiting qualitatively
the biological activity of nicotinamide.
Nicotinic acid is slightly soluble in water and ethanol; nicotinamide is very soluble in water and
moderately soluble in ethanol. The coenzyme forms of niacin are the pyridine nucleotides, NAD(H)
and NADP(H). In each of these compounds, the electron-withdrawing effect of the N-1 atom and the
amide group of the oxidized pyridine nucleus enables the pyridine C-4 atom to react with many
nucleophilic agents (e.g., sulfite, cyanide, and hydride ions). It is the reaction with hydride ions (H−)
that is the basis of the enzymatic hydrogen transfer by the pyridine nucleotides; the reaction involves
the transfer of two electrons in a single step.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Riboflavin  Helps to release energy Meat, poultry, fish, Depression, diarrhea,
(B2) from carbohydrates. fortified and whole dizziness, fatigue,
 It is important in the grains, mushrooms, halitosis, headaches,
maintenance of healthy potatoes, mango, indigestion, insomnia,
skin, lentils, peanuts limb pains, loss of
 It is important in nerves appetite, low blood
function sugar, muscular
 It is important in digestive weakness, skin
system eruptions, and
 cholesterol synthesis inflammation

Vitamin B6

Chemical structure

Essential features of the chemical structure

1. Derivative of 3-hydroxy-2-methyl-5 hydroxypyridine

2. Phosphorylatable 5-hydroxymethyl group

3. Substituent at ring carbon para to the pyridine nitrogen must be metabolizable to an aldehyde

The term pyridoxine is the trivial designation of one vitamin B6-active compound (i.e., 3-hydroxy-4,5-
bis(hydroxymethyl)2-methylpyridine), which was formerly called adermin or pyridoxol. The
biologically active analogs of pyridoxine are the aldehyde pyridoxal and the amine pyridoxamine.
Vitamins B6 are colorless crystals at room temperature. Each is very soluble in water. Each is fairly
stable in dry form and in solution. Pyridoxine is oxidized in vivo and under mild oxidizing conditions in
vitro to yield pyridoxal. The prominent feature of the chemical reactivity of pyridoxal is the ability of
its aldehyde group to react with primary amino groups (e.g., of amino acids) to form Schiff bases. The
electron-withdrawing effect of the resulting Schiff base labilizes the other bonds on the bound carbon,
thus serving as the basis of the catalytic roles of pyridoxal and pyridoxamine.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Vitamin B6  May reduce the risk of Bananas, watermelon, Can cause skin
heart disease. Brewer’s yeast, wheat disorders, an abnormal
 Regulates the metabolism bran, walnuts, brown nervous system,
of amino acids and rice, meat, fish, confusion, poor
carbohydrates. poultry, potatoes, soy coordination and
 Aids healthy nervous insomnia.
system function
 aid in the production of red
blood cells.
 Important for normal brain
function.

Biotin

Essential features of the chemical structure:

1. Conjoined ureido and tetrahydrothiophene nuclei

2. Ureido 3′ nitrogen is sterically hindered, preventing substitution

3. Ureido 1′ nitrogen is poorly nucleophilic

Biotin Nomenclature Biotin is the trivial designation of the compound cis-hexahydro-2-oxo-1H-


thieno[3,4-d]imidazole4-pentanoic acid, formerly known as vitamin H or coenzyme R.

Biotin is a white crystalline substance that, in dry form, is fairly stable to air, heat, and light. Its
structure consists of a planar ureido nucleus and a folded tetrahydrothiophene (thiophane) nucleus.
The molecule has eight possible stereoisomers, only the (+)-isomer (called d-biotin) has biological
activity. Biotin is covalently bound to its enzymes by an amide bond to the ε-amino group of a lysine
residue and C-2 of the thiophane nucleus. This bond is flexible, allowing the coenzyme to move
between the active centers of some enzymes. The biotin molecule is activated by polarization of the O
and N-1′ atoms of the ureido nucleus. This leads to increased nucleophilicity at N-1 ′, which promotes
the formation of a covalent bond between the electrophilic carbonyl phosphate formed from
bicarbonate and ATP, and allows biotin to serve as a transport agent for CO 2.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Biotin  Energy storage •Avocados simple deficiencies
Vitamin H  Protein,carbohydrate, and fat •Cauliflower of biotin in animals
metabolism •Eggs or humans are rare
•Fruits(e.g.,raspberries
) •Liver
•Pork
•Salmon
•Wholegrains

Pantothenic Acid

Essential features of the chemical structure:

1. Formal derivative of pantoic acid and alanine


2. Optically active

Pantothenic acid is the trivial designation for the compound dihydroxy-β,β-dimethylbutyryl-β-


alanine, which was formerly known as pantoyl-β-alanine. It has two metabolically active forms:
coenzyme A, in which the vitamin is linked via a phosphodiester group with adenosine-3 ′,5 ′-
diphosphate; and acyl-carrier protein, in which it is linked via a phosphodiester to a serinyl residue of
the protein. Pantothenic acid is composed of β-alanine joined to 2,4-dihydroxy-3,3-dimethylbutyric
acid via an amide linkage. The molecule has an asymmetric center, and only the R-enantiomer,
usually called D-(+)pantothenic acid, is biologically active and occurs naturally.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Pantotheni  Conversion of food into •Beans dietary deficiencies of
c acid energy •Beef pantothenic acid are
 Fat metabolism •Enriched grain rare;
 Hormone production products (e.g.,
 Nervous system bread, cereal, pasta,
function rice)
 Red blood cell •Nuts
formation •Pork
•Poultry
•Seafood
•Whole grain

FOLATE
Chemical structure

Essential features of the chemical structureare


1. Pteridine derivative
2. Variable degree of hydrogenation of pteridine nucleus
3. Single-carbon units can bind nitrogens at position 5 and/or 10
4. One or more glutamyl residues linked via peptide bonds
Folate Nomenclature Folate is the generic descriptor for folic acid (pteroylmonoglutamic acid) and
related compounds exhibiting the biological activity of folic acid. The terms folacin, folic acids,
and folates are used only as general terms for this group of heterocyclic c ompounds. Folates can
consist of a mono- or polyglutamyl conjugate; these are named for the number of glutamyl
residues (n), using such notations as PteGlun. The reduced compound tetrahydropteroylglutamic
acid is called tetrahydrofolic acid; its single-carbon derivatives are named according to the specific
carbon moiety bound.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Vitamin B9 Dark green vegetables Anemia and a
(Folate/Foli  Plays an important role in Dry beans Peas Lentils reduction in growth
c Acid) DNA, RNA synthesis vital Enriched grain rates. Other subtle
for new cell creation products Fortified symptoms may include
 important in red blood cell cereals Liver Orange digestive disorders
synthesis juice Wheat germ such as diarrhea, loss
 Needed for metabolism and Yeast of appetite, and weight
maintenance of loss can occur, as can
homocysteine levels weakness, sore tongue,
 Vital for producing and headaches, heart
maintaining cells especially palpitations,
during periods of rapid cell irritability,
growth and division forgetfulness, and
(babies, children, behavioral disorders
adolescents)
 Essential for women who
are or may become
pregnant. Adequate intake
of folate reduces risk of
neural tube defects.

VITAMIN B12
Chemical structure

Essential features of the chemical structure are


1. Cobalt (Co)-centered corrin nucleus
2. Cobalt α position (below the plane of the corrin ring as shown) may be open or occupied by a
side-chain heterocyclic nitrogen, or solvent
3. Cobalt β position (above the plane of the corrin ring as shown) may be occupied by a hydroxo,
aqua, methyl, 5-deoxyadenosyl, CN−, Cl−, Br−, nitro, sulfito, or sulfato group

Vitamin B12 is the generic descriptor for all corrinoids (i.e., compounds containing the corrin
nucleus) exhibiting the qualitative biological activity of cyanocobalamin. Cyanocobalamin is the
trivial designation of the vitamin B12-active corrinoid (also called cobalamin) with a cyano ligand
(CN−) at the β position of the cobalt atom. The analogs containing methyl-, 5 ′-deoxyadenosyl-,
hydroxo- (OH) groups at that position are called methylcobalamin, adenosylcobalamin, and
hydroxocobalamin.
Vitamin B12 is an octahedral cobalt complex consisting of a porphyrin-like, cobalt-centered
macroring (called a corrin ring or nucleus), a nucleotide, and a second cobalt-bound group (e.g.,
CH3, H2O, CN−). The corrin nucleus consists of four reduced pyrrole nuclei linked by three
methylene bridges and one direct bond. The triply ionized cobalt atom (i.e., Co3+) can form up to
six coordinate bonds, is tightly bound to the four pyrrole nitrogen atoms, and can also bond a
nucleotide and a small ligand below and above, respectively, the plane of the ring system. The
cobalt atom is removed in vitro only with difficulty, resulting in loss of biological activity.

VITAMIN FUNCTIONS DIETARY SOURCE DEFICIENCY


SYMPTOMS
Vitamin  Is a co-enzyme involved in Meat, poultry, fish, Demyelination and
B12 DNA, RNA and myelin milk, cheese, eggs, irreversible nerve cell
synthesis fortified cereals, death. Symptoms
 Needed for development fortified soymilk include numbness or
and maintenance of the tingling of the
red blood cells extremities and an
 Required for amino acid abnormal gait
production (helps converts
homocysteine into
methionine
 Protects nerve cells and
encourages their normal
growth

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