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GUL MUNEER
S/O ABDUL
RAZZAQUE

BIOCHEMISTRY

BS PART II
UNIVERSITY OF
SINDH

2K10/BCH/23
PROUD TO BE
BIOCHEMIST
WE EXPLORE THE
SECRETS OF LIFE
1
VITAMIN B3

BY
GUL MUNEER

2
STUDY OBJECTS
Names of
vitamin
 Discovery
 Properties
 Structure
 Chemistry
 Occurrence
 RDA
 Biochemical


functions
 Digestion &
absorption
 Metabolism
 Assessment
 Deficiency
 Toxicity

3
NAMES 0F VITAMIN B3
Niacin
 Niacinamide 0R Nicotinamide
 Vitamin P OR PP (pellagra
preventive)
 Pellagra preventive factor
 Anti black tongue factor
 Nicotinic acid
 Vitamin G (after Goldberger’s
death, vitamin B3 was some times
called in his honor)


4
5
PROPERTIES
Niacin is a white crystalline
substance. It is soluble in water &
ethyl alcohol but is less soluble in
ether & benzene. It is stable in air &
heat. Nicotinamide, when pure,
occurs as white needle like crystals.
6
STRUCTURE
Niacin (C6H5O2N) is simplest of
all the known vitamins. It is
pyridine derivative.
O
C
N

O
OH

C

NH2

N
7
Nicotinic Acid (Plant
form)

Nicotinamide (animal form)
(reduced form)

8
CHEMISTRY
Precursor : Dietary tryptophan
The coenzymes of Niacin (NAD⁺ & NADP⁺)
can be synthesized by the essential amino
acid tryptophan.
 The term “Niacin” is used for Nicotinic acid.
 The amide form of Niacin is known as
niacinamide or nicotinamide.
 The conversion of Niacin to niacinamide
takes place in the kidney, brain slices and
liver slices.
9
The conversion of tryptophan to nicotinic
acid in the body takes place through a
series of intermediate steps, which are
represented below:
Tryptophan → Kynurenine → 3hydroxykynurenine → 3hydroxyanthranilic acid → …… →
Quinolinic acid → Nicotinic acid

10
Dietary nicotinamide, niacin and tryptophan
contribute to the synthesis of the
coenzymes NAD⁺ and NADP⁺.
Niacin undergoes a series of reactions to
produce NAD⁺ and NADP⁺.
60mgs tryptophan=1mg of niacin for the
synthesis of coenzymes.

11
adenine

If Phosphate here ->
NADP
Nicotinamide Adenine Dinucleotide

12
OCCURRENCE
Yeast (most abundantly)
 Liver
 Salmon
 Red meat
 Poultry
 Vegetables & fruits (poor)
 whole grains
 Pulses & peanuts
 Note: Milk & eggs contain very little
or no Niacin, are good pellagrapreventive foods because of their
high content of Tryptophan.


13
Niacin
Sources

14
RECOMMENDED DAILY
ALLOWANCE (RDA)




Adult (men) 15-20 mg/day
Children 10-15mg/day
Adult (women) 13-15mg/day

NOTE : One Niacin Equivalent (NE) = 1 mg
Niacin or 60 mg of Tryptophan.

15
16
Copyright 2005 Wadsworth Group, a division of Thomson Learning
BIOCHEMICAL FUNCTIONS

The coenzymes NAD⁺ and NADP⁺ are involved
in a variety of “oxidation-reduction reactions”.
 A large number of enzymes belonging to the
class “oxidoreductase” are dependent on NAD⁺ or
NADP⁺.
 NAD⁺ and NADP⁺ participate in almost all the
metabolisms (carbohydrate, lipid, protein etc).
 Involved in electron transport chain to generate
ATP.


17
Pyruvate + CoA + NAD+ ------> CO2 + acetyl-CoA + NADH + H+
18
Functions of Niacin


NAD and NADP participates in 200+ reactions in the
body. 2 NAD+
2NADH + H+

Glucose

Pyruvate

NAD+
Pyruvate

NAD+

NADH + H+
Lactate

NADH + H+

Isocitrate
NAD+
Alpha-ketogluterate
NAD+
NADH + H+
Malate


Electron transport chain

Alpha-ketogluterate
NADH + H+
Succinyl CoA

Citric Acid
Cycle

Oxaloacetate

19
Digestion and Absorption of Dietary
Niacin
Coenzyme form in food
 hydrolysis in small intestine to free
vitamin
 absorbed in duodenum
 nicotinic acid protein bound in corn
 requires alkali treatment (lime) to
release niacin


20
Metabolism of B-3
Conversion of free vitamin to
coenzyme in all cells
 No storage
 Excesses metabolized in liver to
variety of chemicals
 Metabolites excreted in urine


21
Assessment of B3 Status
Urinary excretion of niacin
metabolites



N-methyl nicotinamide
 2-pyridone


22
Deficiency of B3
 Pellagra
 commonly
1.

referred to as 3 Ds
Dermatitis

 Inflammation

2.

Dementia
 confused,

3.

of skin

disoriented

Diarrhea
 irritation/inflammation



of mucous membranes

4th D
− if not treated may lead to Death
23
Dermatitis of Pellagra

24
25
 Dermatitis of skin
 Inflammation
Found in the areas of the skin exposed to sun
light (neck, dorsal part of feet, ankle, face).


 Diarrhea

 Increased frequency and
fluidity of the stools, often with
blood and mucus. (loose stools)

 Dementia
 Degeneration of nervous
tissue (weakness of mind)
 Symptoms include:
Anxiety (fear and worry)
Irritability (respond or
reaction to stimulus)
Poor memory
Insomnia (sleeplessness)

26
Niacin


Toxicity symptoms
Painful flush, hives, and rash (“niacin
flush”)
 Excessive sweating
 Blurred vision
 Liver damage, impaired glucose
tolerance


27
28
29

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Vitamin B3 Niacin

  • 1. GUL MUNEER S/O ABDUL RAZZAQUE BIOCHEMISTRY BS PART II UNIVERSITY OF SINDH 2K10/BCH/23 PROUD TO BE BIOCHEMIST WE EXPLORE THE SECRETS OF LIFE 1
  • 3. STUDY OBJECTS Names of vitamin  Discovery  Properties  Structure  Chemistry  Occurrence  RDA  Biochemical  functions  Digestion & absorption  Metabolism  Assessment  Deficiency  Toxicity 3
  • 4. NAMES 0F VITAMIN B3 Niacin  Niacinamide 0R Nicotinamide  Vitamin P OR PP (pellagra preventive)  Pellagra preventive factor  Anti black tongue factor  Nicotinic acid  Vitamin G (after Goldberger’s death, vitamin B3 was some times called in his honor)  4
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  • 6. PROPERTIES Niacin is a white crystalline substance. It is soluble in water & ethyl alcohol but is less soluble in ether & benzene. It is stable in air & heat. Nicotinamide, when pure, occurs as white needle like crystals. 6
  • 7. STRUCTURE Niacin (C6H5O2N) is simplest of all the known vitamins. It is pyridine derivative. O C N O OH C NH2 N 7
  • 8. Nicotinic Acid (Plant form) Nicotinamide (animal form) (reduced form) 8
  • 9. CHEMISTRY Precursor : Dietary tryptophan The coenzymes of Niacin (NAD⁺ & NADP⁺) can be synthesized by the essential amino acid tryptophan.  The term “Niacin” is used for Nicotinic acid.  The amide form of Niacin is known as niacinamide or nicotinamide.  The conversion of Niacin to niacinamide takes place in the kidney, brain slices and liver slices. 9
  • 10. The conversion of tryptophan to nicotinic acid in the body takes place through a series of intermediate steps, which are represented below: Tryptophan → Kynurenine → 3hydroxykynurenine → 3hydroxyanthranilic acid → …… → Quinolinic acid → Nicotinic acid 10
  • 11. Dietary nicotinamide, niacin and tryptophan contribute to the synthesis of the coenzymes NAD⁺ and NADP⁺. Niacin undergoes a series of reactions to produce NAD⁺ and NADP⁺. 60mgs tryptophan=1mg of niacin for the synthesis of coenzymes. 11
  • 12. adenine If Phosphate here -> NADP Nicotinamide Adenine Dinucleotide 12
  • 13. OCCURRENCE Yeast (most abundantly)  Liver  Salmon  Red meat  Poultry  Vegetables & fruits (poor)  whole grains  Pulses & peanuts  Note: Milk & eggs contain very little or no Niacin, are good pellagrapreventive foods because of their high content of Tryptophan.  13
  • 15. RECOMMENDED DAILY ALLOWANCE (RDA)    Adult (men) 15-20 mg/day Children 10-15mg/day Adult (women) 13-15mg/day NOTE : One Niacin Equivalent (NE) = 1 mg Niacin or 60 mg of Tryptophan. 15
  • 16. 16 Copyright 2005 Wadsworth Group, a division of Thomson Learning
  • 17. BIOCHEMICAL FUNCTIONS The coenzymes NAD⁺ and NADP⁺ are involved in a variety of “oxidation-reduction reactions”.  A large number of enzymes belonging to the class “oxidoreductase” are dependent on NAD⁺ or NADP⁺.  NAD⁺ and NADP⁺ participate in almost all the metabolisms (carbohydrate, lipid, protein etc).  Involved in electron transport chain to generate ATP.  17
  • 18. Pyruvate + CoA + NAD+ ------> CO2 + acetyl-CoA + NADH + H+ 18
  • 19. Functions of Niacin  NAD and NADP participates in 200+ reactions in the body. 2 NAD+ 2NADH + H+ Glucose Pyruvate NAD+ Pyruvate NAD+ NADH + H+ Lactate NADH + H+ Isocitrate NAD+ Alpha-ketogluterate NAD+ NADH + H+ Malate  Electron transport chain Alpha-ketogluterate NADH + H+ Succinyl CoA Citric Acid Cycle Oxaloacetate 19
  • 20. Digestion and Absorption of Dietary Niacin Coenzyme form in food  hydrolysis in small intestine to free vitamin  absorbed in duodenum  nicotinic acid protein bound in corn  requires alkali treatment (lime) to release niacin  20
  • 21. Metabolism of B-3 Conversion of free vitamin to coenzyme in all cells  No storage  Excesses metabolized in liver to variety of chemicals  Metabolites excreted in urine  21
  • 22. Assessment of B3 Status Urinary excretion of niacin metabolites  N-methyl nicotinamide  2-pyridone  22
  • 23. Deficiency of B3  Pellagra  commonly 1. referred to as 3 Ds Dermatitis  Inflammation 2. Dementia  confused, 3. of skin disoriented Diarrhea  irritation/inflammation  of mucous membranes 4th D − if not treated may lead to Death 23
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  • 26.  Dermatitis of skin  Inflammation Found in the areas of the skin exposed to sun light (neck, dorsal part of feet, ankle, face).   Diarrhea  Increased frequency and fluidity of the stools, often with blood and mucus. (loose stools)  Dementia  Degeneration of nervous tissue (weakness of mind)  Symptoms include: Anxiety (fear and worry) Irritability (respond or reaction to stimulus) Poor memory Insomnia (sleeplessness) 26
  • 27. Niacin  Toxicity symptoms Painful flush, hives, and rash (“niacin flush”)  Excessive sweating  Blurred vision  Liver damage, impaired glucose tolerance  27
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