NMDF121 SN09 Lecture AminoAcids2 · © Endeavour College of Natural Health endeavour.edu.au 5 Methionine Food Levels Eggs 31mg/g protein Cod 30mg/g Chicken 28mg/g Beef and pork 26mg/g

© Endeavour College of Natural Health endeavour.edu.au 1

NMDF121

Session 9

AMINO ACIDS PART 2

Naturopathic Medicine Department



Topic Summary

Amino Acids:

• Methionine

• Cysteine

• Taurine

• Glutamine

• Glycine

And the related

antioxidant:

• Glutathione


Methionine

http://commons.wikimedia.org/w

iki/File:Methionine.png

http://upload.wikimedia.org/wikipedia/commons/a/aa/Methionine.png

http://upload.wikimedia.org/wikipedia/commons/a/aa/Methionine.png


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


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


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)


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)


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)


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)


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

https://www.youtube.com/watch?v=_akIWiUIjoU


Cysteine

http://commons.wikimedia.org/wiki/

File:Cysteine.png

http://upload.wikimedia.org/wikipedia/commons/2/2f/Cysteine.png

http://upload.wikimedia.org/wikipedia/commons/2/2f/Cysteine.png


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


Functions• Energy production—deaminated

carbon skeleton plays role in

TCA cycle and provides

precursors for gluconeogenesis


• Glutathione metabolism

• Taurine synthesis

• Cyanide detoxification

• Supply of sulfur groups



• 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)


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


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)


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)


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?


Taurine

http://commons.wikimedia.org/

wiki/File:Taurine.svg

http://upload.wikimedia.org/wikipedia/commons/3/3c/Taurine.svg

http://upload.wikimedia.org/wikipedia/commons/3/3c/Taurine.svg


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


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)


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)


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)


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

https://www.youtube.com/watch?v=Ms0jj3vCLNY


Glutamine

http://commons.wikimedia.org/wiki/Fi

le:Glutamine_simple.png

http://upload.wikimedia.org/wikipedia/commons/d/de/Glutamine_simple.png

http://upload.wikimedia.org/wikipedia/commons/d/de/Glutamine_simple.png


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


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


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


Functions

• Neurotransmitter recycling

• Precursor for glutamate and

GABA

• pH regulation in blood

• Glutathione synthesis



• 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)


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


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)


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)


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)

http://www.youtube.com/watch?v=m4s7A5LwpXo


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?


Glycine

http://commons.wikimedia.org/wiki/File:

Glycine.png

http://upload.wikimedia.org/wikipedia/commons/6/61/Glycine.png

http://upload.wikimedia.org/wikipedia/commons/6/61/Glycine.png


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


Functions

• Energy production—deaminated carbon skeleton

plays role in TCA cycle and provides precursors for

gluconeogenesis


• Methionine metabolism – component of methylation

cycle and transulfuration pathway

• Glutathione, haemoglobin and creatine synthesis


Functions

• Bile acid conjugation

• Detoxification - conjugation

• Inhibitory NT (Wheeler 1999)

• Reduces inflammatory

reactions (Wheeler 1999)


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)


Related Antioxidant: Glutathione

http://commons.wikimedia.org/wiki/File:

Glutathione-skeletal.png

http://upload.wikimedia.org/wikipedia/commons/7/7e/Glutathione-skeletal.png

http://upload.wikimedia.org/wikipedia/commons/7/7e/Glutathione-skeletal.png


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


Glutathione


Functions

• Extracellular antioxidant


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)



• Alcohol consumption (Lieber, 2005)

• Paracetemol use (Eneli et

al, 2005)

• Cystic fibrosis (Hudson, 2004)


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


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)

http://www.youtube.com/watch?v=Eh2PYQBICWs


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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NMDF121 SN09 Lecture AminoAcids2 · © Endeavour College of Natural Health endeavour.edu.au 5 Methionine Food Levels Eggs 31mg/g protein Cod 30mg/g Chicken 28mg/g Beef and pork 26mg/g