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METABOLISM OF
AROMATIC AMINO ACIDS
By
N.Santhosh Kumar
Asst.Professor
Department of Biochemistry
SIMS & RH
Benzene group
Indole ring
Phenol group
Neutral, nutritionally essential,
metabolically both glucogenic and
ketogenic amino acid
Neutral, nutritionally non essential,
metabolically glucogenic & ketogenic amino
acid
Neutral, Nutritionally essential,
metabolically both Glucogenic & ketogenic
amino acid
AAM 06c: CATABOLISM OF
TRYPTOPHAN
Neutral, Nutritionally essential, Metabolically
both Glucogenic & ketogenic a.a
TRYPTOPHAN
Alanine Glucose
Acetyl CoA Fat
Synthesis of Niacin (B3)
Formation of Melatonin
Biosynthesis of Serotonin
Formyl group (one“C” pool)
Excretory products
(5 –OH IAA, Indican)
Serotonin pathway
Kynurenine pathway
Tryptophan catabolized by two ways
Kynurenine Alanine
Niacin Acetyl Co-A
Serotonin
Melatonin 5-HIAA
Kynurenine
pathway
Tryptophan
L-Formylkynurenine
3-OH Kynurenine
3-OH Anthranilic acid
L-Kynurenine
Tryptophan dioxygnase /
Pyrrolase (Fe2+)
Kynurenine formylase
Kynurenine hydroxylase
Kynureninase
PLP
O2
O2
H2O
Formyl- group
One Carbon pool
NADPH + H+
Acetyl CoA
Alanine
Glucogenic nature
Ketogenic
Niacin
NAD + & NADP+ Decarboxylation
3%
60mg of try=1mg of
Niacin
NADH & NADPH
Deficiency of Vit-B6
(pyridoxine)
Normal excreted in urine 1-3mg/day
But vitB6 def excreted 3-11mg/day
Greenish blue / yellow urine
Serotonin Pathway
Serotonin (Biological amine) synthesized by brain, mast cells,
GIT mucosa, neurons, pineal gland,
(5-HT)
5-OH tryptamine
NADPH
NADP+
1-3% Tryptophan daily used to synthesis of serotonin
Functions of Serotonin
• Powerful neurotransmitter in brain,
• Potent vasoconstrictor
• Stimulator of smooth muscle contraction
• Induces peristaltic movements
• Anti depressant
• Serotonin is Pain reducer
12
Oxidative deamination of serotonin by MAO
leads to form 5-HIAA- excreted free form
MAO inhibitors used in treatment of
psychiatric disorders (Iproniazid, tricyclic
antidepressants)
(Excreted form)
Degradation of serotonin
Clinical Significance Of Serotonin
• Plays imp role in depression and carcinoid tumors
• Involved in a variety of behavioral patterns like sleep, perception of
pain, social behavior, mental depression
• Decreased serotonin leads to depression
Treatment:
• Anti-depressant drugs (amitriptyline & trazodone),
• Results inhibit the reuptake of serotonin by presynaptic neurons-
• Increased conc. of serotonin at serotonergic synapses
Carcinoid Tumors (Argentaffinoma)
• Characterized by serotonin producing tumor cells in argentaffin
tissues of the abdominal cavity.
• Develop from enterochromaffin cells, distributed throughout the
GIT, biliary tract, gall bladder & pancreatic duct
• Up to 60% of Try is diverted to serotonin formation
Clinical symptoms:
– Pellagra may also seen
– Bronchial constriction,
– Diarrhea,
– Cardiac lesions associated with heart failure
• Increased urinary excretion of 5-OH Indolaceticacid
Diagnostic test:
• Measurement of urinary 5-HIAA conc.
• More than 25mg/day (normal 5-HIAA conc. is 2 to 7mg/day)
• Measurement of 5-HTP (5- OH tryptophan)
17
Blocks MSH & ACTH
Synthesis of Melatonin
(Pineal gland)
Regulated by light dark cycle (mostly at night)
Functions of Melatonin
• It is sleep inducing substance
• Regulated by sleep-wake cycle
• Involved in regulation of circadian rhythm &
reproductive fraction of the body
• It is anti-ageing agent
Disorders
of
Tryptophan
Impaired transport of Try & neutral amino acids in
intestine & renal tubules
Defect limits tryptophan availability for niacin
synthesis & accounts for pellagra like symptoms.
Due to intestine bacteria try is metabolized to indol
acetic acid & indol pyruvic acid, excreted more in urine
Inherited disorder, Severity less in adult life
Hartnup’s disease
Cerebral Ataxia
Muscle Discomfort
Psychological Symptoms
Clinical features
Generalized neutral amino aciduria
Rashes, Diarrhoea
Increased urinary excretion of indican, indol acetic acid
& other indol derivatives
Oral tryptophan load produces an abnormal plasma Try
levels verses time curve.
Diagnosis
Indol derivatives in urine measured by Obermeyer test
Oral niacin supplement will permit adequate
syn of NAD+
This corrects pellagra like symptoms but amino
aciduria remains unaltered
Therapy
Case Based Question-01
A 12 year old boy had sudden onset of rashes, diarrhoea, and his school
performance was also decreased because of lose of memory. Laboratory
tests revealed aldehyde test with urine sample of the patient was
positive
Q A: Identify the inborn error and major defect
B: Mention the confirmatory qualitative test for this disorder
C: Which vitamin supplement required for the above condition
Wilma Delphine silvia et al. OSPE& CBL .Competency Based Practical Biochemistry Text book, 2nd ed.; case-8: p146
CBQ-2
A 3 year old boy was admitted to hospital with the symptoms of
pellagra, accompanied by mental retardation and excessive
excretion of neutral amino acids. He was diagnosed as having
hartnup’s disease.
Q A: What is the cause of this disease?
B: Why does it show mental retardation and pellagra like symptoms
C: How will you treat pellagra like symptoms ?
D. Can aminoaciduria be treated?
Textbook of biochemistry by Pankaja naik; p298
MCQs
Increased urinary indole acetic acid is diagnostic of ?
a. Maple syrup urine disease b. Hartnup disease
c. Phenylketonuria d. Homo cysteinuria
Absorption of which one of the following amino acids is defective in Hartnup disease
a. Lysine b. Leucine
c. Tyrosine d. Tryptophan
Malignant carcinoid is a metabolic disorder of ?
a. Lysine b. Leucine
c. Tryptophan d. Tyrosine
Pellagra is manifested in which conditions ?
a. Niacin deficiency b. Tryptophan deficiency
c. Malignant carcinoid d. Above all
Tryptophan is deficient in which food stuff ----------------
Next Presentation on
AAM-07: Metabolism of Sulphur containing
amino acids & its Disorders
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AAM- 6c Metabolism of aromatic amino acids-3 (Catabolism, metabolic fate & disorders of tryptophan)

  • 1. METABOLISM OF AROMATIC AMINO ACIDS By N.Santhosh Kumar Asst.Professor Department of Biochemistry SIMS & RH
  • 2. Benzene group Indole ring Phenol group Neutral, nutritionally essential, metabolically both glucogenic and ketogenic amino acid Neutral, nutritionally non essential, metabolically glucogenic & ketogenic amino acid Neutral, Nutritionally essential, metabolically both Glucogenic & ketogenic amino acid
  • 3. AAM 06c: CATABOLISM OF TRYPTOPHAN Neutral, Nutritionally essential, Metabolically both Glucogenic & ketogenic a.a
  • 4. TRYPTOPHAN Alanine Glucose Acetyl CoA Fat Synthesis of Niacin (B3) Formation of Melatonin Biosynthesis of Serotonin Formyl group (one“C” pool) Excretory products (5 –OH IAA, Indican)
  • 5. Serotonin pathway Kynurenine pathway Tryptophan catabolized by two ways Kynurenine Alanine Niacin Acetyl Co-A Serotonin Melatonin 5-HIAA
  • 7. Tryptophan L-Formylkynurenine 3-OH Kynurenine 3-OH Anthranilic acid L-Kynurenine Tryptophan dioxygnase / Pyrrolase (Fe2+) Kynurenine formylase Kynurenine hydroxylase Kynureninase PLP O2 O2 H2O Formyl- group One Carbon pool NADPH + H+ Acetyl CoA Alanine Glucogenic nature Ketogenic Niacin NAD + & NADP+ Decarboxylation 3% 60mg of try=1mg of Niacin NADH & NADPH
  • 8. Deficiency of Vit-B6 (pyridoxine) Normal excreted in urine 1-3mg/day But vitB6 def excreted 3-11mg/day Greenish blue / yellow urine
  • 10. Serotonin (Biological amine) synthesized by brain, mast cells, GIT mucosa, neurons, pineal gland, (5-HT) 5-OH tryptamine NADPH NADP+ 1-3% Tryptophan daily used to synthesis of serotonin
  • 11. Functions of Serotonin • Powerful neurotransmitter in brain, • Potent vasoconstrictor • Stimulator of smooth muscle contraction • Induces peristaltic movements • Anti depressant • Serotonin is Pain reducer
  • 12. 12 Oxidative deamination of serotonin by MAO leads to form 5-HIAA- excreted free form MAO inhibitors used in treatment of psychiatric disorders (Iproniazid, tricyclic antidepressants) (Excreted form) Degradation of serotonin
  • 13. Clinical Significance Of Serotonin • Plays imp role in depression and carcinoid tumors • Involved in a variety of behavioral patterns like sleep, perception of pain, social behavior, mental depression • Decreased serotonin leads to depression Treatment: • Anti-depressant drugs (amitriptyline & trazodone), • Results inhibit the reuptake of serotonin by presynaptic neurons- • Increased conc. of serotonin at serotonergic synapses
  • 14. Carcinoid Tumors (Argentaffinoma) • Characterized by serotonin producing tumor cells in argentaffin tissues of the abdominal cavity. • Develop from enterochromaffin cells, distributed throughout the GIT, biliary tract, gall bladder & pancreatic duct • Up to 60% of Try is diverted to serotonin formation
  • 15. Clinical symptoms: – Pellagra may also seen – Bronchial constriction, – Diarrhea, – Cardiac lesions associated with heart failure • Increased urinary excretion of 5-OH Indolaceticacid
  • 16. Diagnostic test: • Measurement of urinary 5-HIAA conc. • More than 25mg/day (normal 5-HIAA conc. is 2 to 7mg/day) • Measurement of 5-HTP (5- OH tryptophan)
  • 17. 17 Blocks MSH & ACTH Synthesis of Melatonin (Pineal gland) Regulated by light dark cycle (mostly at night)
  • 18. Functions of Melatonin • It is sleep inducing substance • Regulated by sleep-wake cycle • Involved in regulation of circadian rhythm & reproductive fraction of the body • It is anti-ageing agent
  • 20. Impaired transport of Try & neutral amino acids in intestine & renal tubules Defect limits tryptophan availability for niacin synthesis & accounts for pellagra like symptoms. Due to intestine bacteria try is metabolized to indol acetic acid & indol pyruvic acid, excreted more in urine Inherited disorder, Severity less in adult life Hartnup’s disease
  • 21. Cerebral Ataxia Muscle Discomfort Psychological Symptoms Clinical features Generalized neutral amino aciduria Rashes, Diarrhoea
  • 22. Increased urinary excretion of indican, indol acetic acid & other indol derivatives Oral tryptophan load produces an abnormal plasma Try levels verses time curve. Diagnosis Indol derivatives in urine measured by Obermeyer test
  • 23. Oral niacin supplement will permit adequate syn of NAD+ This corrects pellagra like symptoms but amino aciduria remains unaltered Therapy
  • 24. Case Based Question-01 A 12 year old boy had sudden onset of rashes, diarrhoea, and his school performance was also decreased because of lose of memory. Laboratory tests revealed aldehyde test with urine sample of the patient was positive Q A: Identify the inborn error and major defect B: Mention the confirmatory qualitative test for this disorder C: Which vitamin supplement required for the above condition Wilma Delphine silvia et al. OSPE& CBL .Competency Based Practical Biochemistry Text book, 2nd ed.; case-8: p146
  • 25. CBQ-2 A 3 year old boy was admitted to hospital with the symptoms of pellagra, accompanied by mental retardation and excessive excretion of neutral amino acids. He was diagnosed as having hartnup’s disease. Q A: What is the cause of this disease? B: Why does it show mental retardation and pellagra like symptoms C: How will you treat pellagra like symptoms ? D. Can aminoaciduria be treated? Textbook of biochemistry by Pankaja naik; p298
  • 26. MCQs Increased urinary indole acetic acid is diagnostic of ? a. Maple syrup urine disease b. Hartnup disease c. Phenylketonuria d. Homo cysteinuria Absorption of which one of the following amino acids is defective in Hartnup disease a. Lysine b. Leucine c. Tyrosine d. Tryptophan Malignant carcinoid is a metabolic disorder of ? a. Lysine b. Leucine c. Tryptophan d. Tyrosine Pellagra is manifested in which conditions ? a. Niacin deficiency b. Tryptophan deficiency c. Malignant carcinoid d. Above all Tryptophan is deficient in which food stuff ----------------
  • 27. Next Presentation on AAM-07: Metabolism of Sulphur containing amino acids & its Disorders Thank You Have A Nice Day To All