Biogenic Amines:Biogenic Amines:

• Descriptions• Descriptions• Sources• Sources• Control• Control Control Control

Dr Charles G EdwardsDr Charles G EdwardsDr. Charles G. EdwardsDr. Charles G. EdwardsWSU Viticulture/Enology TeamWSU Viticulture/Enology Team

Biogenic AminesBiogenic Amines

A. What are these?A. What are these?

1. Organic N1. Organic N--containing bases of lowcontaining bases of lowmolecular weight produced by life forms.molecular weight produced by life forms.

2. Found in many (if not all) fermented foods.2. Found in many (if not all) fermented foods.

a. Many different types found in nature.a. Many different types found in nature.

2. Found in many (if not all) fermented foods.2. Found in many (if not all) fermented foods.

a. Highly variable concentrations.a. Highly variable concentrations.

b Cheese/fermented meat > wine > yogurt*b Cheese/fermented meat > wine > yogurt*b. Cheese/fermented meat > wine > yogurtb. Cheese/fermented meat > wine > yogurt

c. Most abundant in wine =c. Most abundant in wine =putrescine or spermidine.putrescine or spermidine.

*Ancín*Ancín--Azpilicueta et al. (2008)Azpilicueta et al. (2008)

putrescine or spermidine.putrescine or spermidine.

Tyramine*Tyramine*

Histamine*Histamine* TyrosineTyrosineSpermidine*Spermidine*

AminoAminoHistidineHistidine Spermine*Spermine*

Amino Amino AcidAcidPoolPool

OrnithineOrnithine PutrescinePutrescine**

LysineLysine

Cadaverine*Cadaverine* PhenylalaninePhenylalanine

ArginineArginine Agmatine*Agmatine*

CadaverineCadaverine PhenylalaninePhenylalanine

Ph l th l i *Ph l th l i *Phenylethylamine*Phenylethylamine*Biogenic amine*Biogenic amine*

Biogenic AminesBiogenic Amines

COHH

B. Source 1 (amino acid B. Source 1 (amino acid amine)amine)

CO2 CH2 HNH2

CHCNH

C

CN

CH2 COOHNH2

CHCNH

C

CN

Histidine Histamine

CH

CH

C. Source 2 (polyamine)C. Source 2 (polyamine)SAM

P t i

(CH2)4 NH2

HH2N

S idi

SAM

(CH2)4 NH2N NH2(CH2)3

Putrescine Spermidine

Biogenic AminesBiogenic Amines

D. Microorganisms involved:D. Microorganisms involved:

1.1. PediococcusPediococcus and and LactobacillusLactobacillus. .

2. “Wild” strains of 2. “Wild” strains of OenococcusOenococcus. .

3. 3. BrettanomycesBrettanomyces and and Saccharomyces Saccharomyces (some). (some).

E B fit t i b lE B fit t i b l

1. Growth factors? 1. Growth factors?

E. Benefit to microbe unclear:E. Benefit to microbe unclear:

2. Indirect gain of energy?2. Indirect gain of energy?

3. Lessen osmotic shock?3. Lessen osmotic shock?

Biogenic AminesBiogenic Amines

F. Health considerationsF. Health considerations

1. Cause headaches/other health symptoms.1. Cause headaches/other health symptoms.

2. Histamine is probably largest concern.2. Histamine is probably largest concern.

b Tyramine and phenylethylamine also toxicb Tyramine and phenylethylamine also toxic

a. Foa. Focus of governmental regulation.cus of governmental regulation.

b. Tyramine and phenylethylamine also toxic.b. Tyramine and phenylethylamine also toxic.

c. Putrescine/cadaverine can enhance toxicityc. Putrescine/cadaverine can enhance toxicityalthough not toxic themselvesalthough not toxic themselvesalthough not toxic themselves.although not toxic themselves.

3. Most hazardous amine known to humans…..3. Most hazardous amine known to humans…..

Biogenic AminesBiogenic Amines

G. Quality considerationsG. Quality considerations

1. Impact of low concentrations not understood.1. Impact of low concentrations not understood.

a. Cadeverine/putrescine a. Cadeverine/putrescine

b. Complexity?b. Complexity?

ppodors of putrefying fleshodors of putrefying flesh

2. High concentrations (>100 mg/L) can result in2. High concentrations (>100 mg/L) can result in“metallic ” “meaty ” or “putrid” aromas *“metallic ” “meaty ” or “putrid” aromas *metallic, meaty, or putrid aromas.metallic, meaty, or putrid aromas.

3. Does presence of amines = poor winemaking?3. Does presence of amines = poor winemaking?

*ETS Laboratories (2009)*ETS Laboratories (2009)

Controlling Biogenic AminesControlling Biogenic Amines

A. WIDE range of concentrations in wines.A. WIDE range of concentrations in wines.

1. Several studies have been published (esp. Spain).1. Several studies have been published (esp. Spain).

2 VERY difficult to make conclusions regarding2 VERY difficult to make conclusions regarding2. VERY difficult to make conclusions regarding2. VERY difficult to make conclusions regardingimpact of various parameters.impact of various parameters.

• Precursors • Precursors • Microbe with enzymatic activity • Microbe with enzymatic activity

O ti l i b th ditiO ti l i b th diti• Optimal microbe growth conditions • Optimal microbe growth conditions

Risk of biogenic aminesRisk of biogenic amines

Controlling Biogenic AminesControlling Biogenic Amines

B. Total of 295 wines (CA, OR, and WA)*B. Total of 295 wines (CA, OR, and WA)*

1. Putrescine <1 to 296 mg/L (84 wines ≥10 mg/L).1. Putrescine <1 to 296 mg/L (84 wines ≥10 mg/L).

2. Cadaverine <1 to 4 mg/L2. Cadaverine <1 to 4 mg/L

3. Histamine <1 to 72 mg/L (52 wines ≥10 mg/L).3. Histamine <1 to 72 mg/L (52 wines ≥10 mg/L).

4. Tyramine <1 to 20 mg/L (11 wines ≥11 mg/L).4. Tyramine <1 to 20 mg/L (11 wines ≥11 mg/L).

5. Highest total amine in a wine 5. Highest total amine in a wine 359 mg/L359 mg/L

6. WA wines only6. WA wines only6. WA wines only6. WA wines only

a. Total of 29 samplesa. Total of 29 samples(3 wines >25 mg/L total biogenic amines)(3 wines >25 mg/L total biogenic amines)

*ETS Laboratories (2009)*ETS Laboratories (2009)

(3 wines >25 mg/L total biogenic amines)(3 wines >25 mg/L total biogenic amines)

Controlling Biogenic AminesControlling Biogenic Amines

C. Limit unwanted lactic acid bacteria.C. Limit unwanted lactic acid bacteria.

1. Use of SO1. Use of SO22..

2. Lower pH (SO2. Lower pH (SO22 more effective too).more effective too).

3. Lysozyme.3. Lysozyme.3. Lysozyme.3. Lysozyme.

4. Use of commercial ML cultures.4. Use of commercial ML cultures.

5. Limit lees contact (fewer amino acids)?5. Limit lees contact (fewer amino acids)?

Thank You!Thank You!WA Association of Wine Grape GrowersWA Association of Wine Grape GrowersWSU Students, Staff, FacultyWSU Students, Staff, FacultyETS LaboratoriesETS LaboratoriesWA WineriesWA WineriesETS LaboratoriesETS Laboratories