nmdf121 sn09 lecture aminoacids2 · © endeavour college of natural health endeavour.edu.au 5...
TRANSCRIPT
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NMDF121
Session 9
AMINO ACIDS PART 2
Naturopathic Medicine Department
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Topic Summary
Amino Acids:
• Methionine
• Cysteine
• Taurine
• Glutamine
• Glycine
And the related
antioxidant:
• Glutathione
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Methionine
http://commons.wikimedia.org/w
iki/File:Methionine.png
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MethionineFood Levels
Eggs 31mg/g
protein
Cod 30mg/g
Chicken 28mg/g
Beef and pork 26mg/g
Milk 25mg/g
Corn 21mg/g
Wheat and oats 18mg/g
Rye and beans 15mg/g
Cauliflower 14mg/g
RDI
• Infants 49mg/kg body weight
• Child 22mg/kg body weight
• Adult 10mg/kg body weight
• Suggested Range
• 200-800mg
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Functions
• Protein synthesis
• Energy production—deaminated carbon skeleton plays role in
TCA cycle and provides precursors for gluconeogenesis
• Methyl group transfer
• A large number of reactions rely on methionine metabolites
for methyl group donation.
• Polyamine synthesis—SAMe
• Homocysteine synthesis
• Produced from methionine during methylation reactions
• Cysteine synthesis—Occurs when cysteine intake is low
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Factors Increasing Demand
• Inflammation (Mercier et al, 2006)
• Aging (Mercier et al, 2006)
• Vaccination (Mercier et al, 2006)
• HIV/AIDS (Beytout and Grizard, 1998)
• Alcohol (Lieber, 2000)
• Liver cirrhosis (Martinez-Chantar et al, 2002)
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Deficiency Symptoms &
Contraindications• Deficiency of methionine may present as:
• Hypercholesterolemia and atherosclerosis (Moundras et al,
1995)
• Carcinogenesis (James, Cross and Miller, 1992)
• Contraindications:
• Cancer patients, as tumors may rely on elevated levels of
methionine for growth (Tan et al, 1996)
• Schizophrenic patients, as high doses may exacerbate
hallucinations
• Osteoporosis, via increasing calcium excretion (Zimmerman,
2001)
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Toxicity Symptoms
• Hyperhomocysteinemia
• Diets low in protein and high in methionine can result in
imbalanced methionine metabolism and increased levels
of homocysteine (Rees, 2002)
• Deficiencies of folate and B12 or B6 exacerbate increased
homocysteine production (Kohlmeier, 2003)
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Therapeutic Uses
• Depression – NT synthesis (Williams et al, 2005)
• Liver detoxification – assists in cholestasis (Mato et al,
2002)
• Parkinson’s disease, as L-dopa medication lowers
SAMe levels (Zimmerman, 2001)
• Urinary tract infections – acidifies urine (Zimmerman,
2001)
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Activity
• View the following video on the methylation cycle to
assist in your understanding of this process
Methylation and MTHFR - Simple Explanation
https://www.youtube.com/watch?v=_akIWiUIjoU
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Cysteine
http://commons.wikimedia.org/wiki/
File:Cysteine.png
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Cysteine
Food Levels
Eggs and grains 20mg/g
Corn 10mg/g
Meats and milk 9-13mg/g
• Levels in food reduced by heat
• Manufactured from methionine
• Metabolised to form taurine and cystine
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Functions• Energy production—deaminated
carbon skeleton plays role in
TCA cycle and provides
precursors for gluconeogenesis
• Protein synthesis
• Glutathione metabolism
• Taurine synthesis
• Cyanide detoxification
• Supply of sulfur groups
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Factors Increasing Demand
• Chemotherapy increases
urinary excretion (Lauterburg et al,
1994)
• Heavy metal toxicity (Quig, 1998)
• HIV/AIDS (Naisbitt et al, 2000)
• Low antioxidant intake
increases its oxidation (Moriarty-
Craige et al, 2005)
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Deficiency Signs & Dosage
• Low immunity - cysteine levels associated with NK cell activity
• Cachexia – low levels associated with muscle wasting and
fatigue (Droge and Holm, 1997)
• Homocysteinuria (deficiency of cystathionine synthetase)
• Atherosclerosis
• Light complexion
• Failure to thrive
• Mental retardation
• RDI 500mg/day
• Suggested Range 200-500mg/day with B6 and C
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Therapeutic Uses
• Chronic obstructive pulmonary disease – reduces risk of
hospital readmission (Gerrits et al, 2003)
• Inflammation – decreases TNF-alpha (Droge, 2005)
• Alcoholic Hepatitis – decreased serum liver enzymes
and increased survival rate (Madhotra and Gilmore, 2003)
• HIV/AIDS – assists CD4 T-cell levels (Spada et al, 2002)
• Reducing oxidative stress – glutathione production (Badaloo et al, 2002)
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Therapeutic Uses
• Bronchitis – loosens and thins mucus in bronchi allowing
easier removal via coughing
• Immune support – NK cell activity
• Gastritis and ulcers – enhances function of protective
gastric lining
• Cataracts
• Exercise
(Zimmerman, 2001)
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Review Questions
1. List the main foods which contain methionine and
cysteine?
2. What is the main function of methionine?
3. List the contraindications for excess methionine
supplementation?
4. What are some important amino acids and other
compounds synthesised via cysteine?
5. Which factors may increase the demand for cysteine?
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Taurine
http://commons.wikimedia.org/
wiki/File:Taurine.svg
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TaurineFood Levels
Meat 200-400mg/kg
Fish 300-700mg/kg
Clam 1500-2400mg/kg
Milk 6mg/L
Plant Foods 0mg/kg
Functions:• Bile acid conjugation
• Osmolar buffering, abundant intracellular
free amino acid
• Inhibitory neurotransmitter
• Regulates thyroid and parathyroid function
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Functions
• Antioxidant – hypochlorus acid produced by
macrophages
• Calcium homeostasis – regulates channels (Redmond et al,
1998)
• Growth hormone synthesis (Redmond et al, 1998)
• Immune regulation – modulates apoptosis (Redmond et al,
1998)
• Insulin secretion and action (Brons et al, 2004)
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Deficiency
• Deficiency during gestation –
• Growth retardation in offspring
• Impaired glucose tolerance in offspring
• Vascular dysfunction in offspring
(Aerts and Van Assche, 2002)
• Visual dysfunction – retinal lesions (Militante and
Lombardini, 2002)
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Therapeutic Uses
• Enhances bile production
– Gall stones
– Hypercholesterolaemia
– Detoxification (Zimmerman, 2001)
• Anaemia with iron sulfate supplementation (Sirdah, 2002)
• Myocardial infarctions – protective (Birdsall, 1998)
• Acute hepatitis – protective (Birdsall, 1998)
• Cystic Fibrosis – benefits steatorrhea (Birdsall, 1998)
• Epilepsy – with zinc stablises nerve membranes (Zimmerman 2001)
• Cataracts – antioxidant activity (Zimmerman 2001)
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Activity
• View the following video on ‘What is Taurine and Why’s it
in My Energy Drink?’ to assist in your understanding of this
substance
https://www.youtube.com/watch?v=Ms0jj3vCLNY
(2 mins)
• Considering other ingredients in the popular ‘energy drinks’
what do you think might be some of the long-term issues
with excessive consumption of these beverages?
o Discuss your thoughts initially in small groups then with the class
o Online students should discuss these within this sessions discussion forum
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Glutamine
http://commons.wikimedia.org/wiki/Fi
le:Glutamine_simple.png
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Glutamine
• Suggested Range – 500-3000mg
• Athletes 8-10g
Food Serving Size mg
Ham 100g 2860
Cheddar cheese 30g 1600
Turkey, breast 100g 1330
Chicken, breast 100g 990
Milk 1 large glass 820
Egg 1, average size 800
Taken from Zimmerman, 2001
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Glutamine
o Sources
• All protein foods contain glutamine
o Digestion and Metabolism:
• Non essential
• Synthesised from arginine, ornithine and proline
• Penetrates blood brain barrier (only amino acid
metabolised in brain [Kohlmeier, 2003])
• 50% of intestinal glutamine is extracted by the
splanchnic bed
• High amounts produced in skeletal muscles
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Functions• Protein synthesis
• Nucleotide synthesis
• Energy production—deaminated carbon
skeleton plays role in TCA cycle and
provides precursors for gluconeogenesis
• A major fuel for lymphocytes and
other immune cells
• Utilized by intestinal cells for energy
production
• Hexosamine synthesis – glycoproteins
and glycoaminoglycans
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Functions
• Neurotransmitter recycling
• Precursor for glutamate and
GABA
• pH regulation in blood
• Glutathione synthesis
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Factors Increasing Demand
• Intensive care patients (Coeffier and Dechelotte, 2005)
• Inflammation (Hulsewe et al, 2004)
• GI surgery (Heuschen 2002)
• Exercise (Bowtell and Bruce, 2002)
• Burns suppress endogenous production (Biolo et al, 2000)
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Deficiency & Toxicity Signs and
Symptoms• Deficiency:
• Colonic damage (Evans, Jones and Ziegler, 2003)
• Intestinal permeability (Clark et al, 2003)
• Reduced lymphocyte function (Oehler et al, 2002)
• Toxicity –
• MSG excess (same as Aspartate toxicity)
• treated with B6
• >300mg may cause mania
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Therapeutic Uses
• Intestinal permeability with NSAID usage (Hond et al, 1999)
• Stress situations – increased demands (Zimmerman, 2001)
• Disorders of the gastrointestinal tract –
main fuel for enterocytes (Zimmerman, 2001)
• Immune function – enhances WBC
function (Zimmerman, 2001)
• Antioxidant system – via GTH production (Zimmerman, 2001)
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Therapeutic Uses
• Critically ill and surgical patients (Coeffier and Dechelotte, 2005)
• Insulin resistance (Coeffier and Dechelotte, 2005)
• Colon damage (Evans, Jones and Ziegler, 2003)
• Protects against muscle wasting during
Trauma (Flaring et al, 2003)
Cancer (Yoshida et al, 2001)
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Activity
• View the following video on glutamine to assist in
your understanding of this amino acid and its
supplemental use in physical activity
http://www.youtube.com/watch?v=m4s7A5Lwp
Xo
(9 mins)
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Review Questions
1. List the main foods which contain taurine and
glutamine?
2. How does taurine decrease cholesterol levels and also
facilitate detoxification?
3. How might a taurine deficiency in pregnancy manifest in
the offspring?
4. From which other amino acids can glutamine be
synthesised?
5. How might we recognise a glutamine deficiency?
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Glycine
http://commons.wikimedia.org/wiki/File:
Glycine.png
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Glycine
Food Levels
Beef 55mg/g protein
Pork 57mg/g
Milk 21mg/g
• Endogenous production from serine, threonine,
choline
• Suggested Range – 4-30gm
• Average Daily Intake 3-5 gm
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Functions
• Energy production—deaminated carbon skeleton
plays role in TCA cycle and provides precursors for
gluconeogenesis
• Protein synthesis
• Methionine metabolism – component of methylation
cycle and transulfuration pathway
• Glutathione, haemoglobin and creatine synthesis
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Functions
• Bile acid conjugation
• Detoxification - conjugation
• Inhibitory NT (Wheeler 1999)
• Reduces inflammatory
reactions (Wheeler 1999)
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Therapeutic Uses
• Shock – decreases inflammatory effects (Wheeler 1999)
• Alcohol Poisoning – protects liver (Wheeler 1999)
• Cancer – may improve outcomes (Wheeler 1999)
• Kidney damage – protects against drugs (Wheeler 1999)
• Ischemic cell injury – prevents cell membrane
leakage, hence cell death during hypoxia (Pan 2005)
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Related Antioxidant: Glutathione
http://commons.wikimedia.org/wiki/File:
Glutathione-skeletal.png
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Glutathione
• Principal antioxidant in cells and the blood.
• Exogenous supply of cysteine is a primary
determinant of how much glutathione is synthesised
endogenously.
• Tripeptide – glutamine, glycine, cysteine
• Sources
• Garlic, plant and animal tissue, cysteine
supplementation
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Glutathione
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Functions
• Extracellular antioxidant
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Functions
• Anti-toxin – DDT, epoxides in glue and resins
• Cell membrane synthesis and repair – RBC integrity,
myelin production and fatty acid synthesis (Zimmerman
2001)
• Connective-tissue synthesis (Zimmerman 2001)
• Leukotriene synthesis – modulates inflammation and
immune responses (Zimmerman 2001)
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Factors Increasing Demand
• Alcohol consumption (Lieber, 2005)
• Paracetemol use (Eneli et
al, 2005)
• Cystic fibrosis (Hudson, 2004)
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Deficiency & Dosage
• Deficiency can increase risk of :
• Cancer (Hu et al, 2005)
• Inflammation (Adamy et al, 2005)
• Lung disease (Hudson, 2004)
• Cataracts (Giblin, 2000)
• Dose:
• Suggested Range – 100-500mg
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Activity
• View the following video on glutathione ‘The mother
of all antioxidants’ to assist in your understanding of
this substance
http://www.youtube.com/watch?v=Eh2PYQBICWs
(9 mins)
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Review Questions
1. List the main food sources of glycine and
glutathione.
2. Which amino acids can produce glycine?
3. Which important biochemical pathways is glycine
required?
4. What 3 amino acids make up glutathione?
5. Which other nutrients are essential for its
formation?
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ReferencesAnderson, R. A., Polansky, M. M., & Bryden, N. A. (2004). Stability and absorption of chromium and
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Baslow, M. H. (2002). Evidence supporting a role for N-acetyl-l-aspartate as a molecular water pump
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Cooke, J. P. (1998). Is atherosclerosis an arginine deficiency disease?. Journal of Investigative
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Experimental Biology and Medicine, 227(11), 998-1000. Retrieved from
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de Boer, J., Duyvendak, M., Schuurman, F. E., Pouw, F. M., Zaagsma, J., & Meurs, H. (1999). Role of
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de Jonge, W. J., Kwikkers, K. L., te Velde, A. A., van Deventer, S. H., Nolte, M. A., Mebius, R. E., & ...
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de Koning, T. J., & Klomp, L. J. (2004). Serine-deficiency syndromes. Current Opinion in Neurology,
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ReferencesFell, D., & Steele, R. D. (1982). Enhancement of histidine and one-carbon metabolism in rats fed high
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Fujita, S., & Volpi, E. (2006). Amino acids and muscle loss with aging. The Journal of Nutrition,
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Houdijk, A. P., Teerlink, T., Visser, J. J., van Lambalgen, A. A., & van Leeuwen, P. A. (1997). Arginine
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Jaeken, J. (2002). Genetic disorders of gamma-aminobutyric acid, glycine, and serine as causes of
epilepsy. Journal of Child Neurology, 17(Suppl. 3), 84- 87. Retrieved from
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Kasaoka, S., Tsuboyama-Kasaoka, N., Kawahara, Y., Inoue, S., Tsuji, M., Ezaki, O., ... Nakajima, S.
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ReferencesLaurichesse, H., Tauveron, I., Gourdon, F., Cormerais, L., Champredon, C., Charrier, S., & ... Grizard,
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Luiking, Y. C., Poeze, M., Dejong, C. H., Ramsay, G., & Deutz, N. E. (2004). Sepsis: An arginine
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McLaughlin, J. T., Ai, W., Sinclair, N. F., Colucci, R., Raychowdhury, R., Koh, T. J., & Wang, T. C.
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ReferencesPap, E., Rácz, K., Kovács, J. K., Varga, I., Buzás, E., Madarász, B., ... Falus, A. (2002). Histidine
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Pau, M. Y., & Milner, J. A. (1982). Dietary arginine and sexual maturation of the female rat. The Journal
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Plauth, M., Egberts, E. H., Abele, R., Müller, P. H., & Fürst, P. (1990). Characteristic pattern of free
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Reyes, A. A., Karl, I. E., & Klahr, S. (1994). Role of arginine in health and in renal disease. The
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Rushton, D. H. (2002). Nutritional factors and hair loss. Clinical & Experimental Dermatology, 27(5),
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ReferencesSoeters, P. B., van de Poll, M. G., van Gemert, W. G., & Dejong, C. C. (2004). Amino acid adequacy in
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