Polycyclic Aromatic Hydrocarbons in Foods: Biological Effects, Legislation, Occurrence, Analytical Methods, and Strategies to Reduce Their Formation
Abstract
:1. Introduction
2. Biological Effects of PAHs
Carcinogenicity of PAHs
3. Legislation Concerning PAHs in Food
4. Main Factors Influencing PAHs Contamination in Foods
4.1. Cooking
4.2. Smoking
4.3. Other Processing
4.3.1. Processing of Vegetable Oils
4.3.2. Drying and Roasting in Grains
5. PAHs in Food and Their Impact on Food Quality
5.1. Oils
5.2. Meats and Meat Products
5.3. Cocoa and Chocolates
5.4. Fruits and Vegetables
5.5. Milk, Dairy, and Baby Foods
5.6. Bread and Cereals
5.7. Other Products
6. Analytical Methods for the Quantification of PAHs
7. Risk Assessment of PAHs in Foods
8. Strategies to Reduce Food Contamination with PAHs
8.1. Marinades
8.2. Cooking Methods
8.3. Solvents Used during Extraction Processes
8.4. Washing
8.5. Irradiation
8.6. Reduction of Smoke Contamination Used in the Smoking Process
8.7. Food Packaging
9. Current Knowledge, Future Trends and Recommendations
10. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Compound Name | Abbreviation | Chemical Formula | Molecular Weight (g mol−1) | Melting Point (°C) | Boiling Point (°C) |
---|---|---|---|---|---|
5-Methylchrysene | 5MC | C19H14 | 242.3 | 118 | 458 |
Acenaphthene | ACE | C12H10 | 154.2 | 203 | 279 |
Acenaphthylene | ACY | C12H8 | 152.2 | 92–93 | 265–275 |
Anthracene | ANT | C14H10 | 178.2 | 218 | 340–342 |
Benz[a]anthracene | BaA | C18H12 | 228.3 | 158 | 438 |
Benzo[a]pyrene | BaP | C20H12 | 252.3 | 179 | 495 |
Benzo[b]fluoranthene | BbF | C20H12 | 252.3 | 168 | 481 |
Benzo[c]fluorene | BcF | C17H12 | 216.3 | 125–127 | 398 |
Benzo[e]pyrene | BeP | C20H12 | 252.3 | 177 | 492 |
Benzo[ghi]perylene | BPe | C22H12 | 276.3 | 273 | 550 |
Benzo[j]fluoranthene | BjF | C20H12 | 252.3 | 165–166 | 480 |
Benzo[k]fluoranthene | BkF | C20H12 | 252.3 | 216 | 480 |
Chrysene | Chr | C18H12 | 228.3 | 254 | 448 |
Cyclopenta[cd]pyrene | CPP | C18H10 | 226.3 | 170 | 439 |
Dibenzo[a,e]pyrene | DeP | C24H14 | 302.4 | 233–244 | 592 |
Dibenz[a,h]anthracene | DBA | C22H14 | 278.3 | 262 | 535 |
Dibenzo[a,i]pyrene | DiP | C24H14 | 302.4 | 281–284 | 594 |
Dibenzo[a,l]pyrene | DlP | C24H14 | 302.4 | 162 | 595 |
Flourene | FLR | C13H10 | 166.2 | 116–117 | 295 |
Fluoranthene | FLT | C16H10 | 202.3 | 111 | 375 |
Indeno[1,2,3-cd]pyrene | IcP | C22H12 | 276.3 | 164 | 530 |
Naphthalene | NAP | C10H8 | 128.2 | 80 | 218 |
Phenanthrene | PHN | C14H10 | 178.2 | 100 | 340 |
Pyrene | PYR | C16H10 | 202.3 | 156 | 393–404 |
Group | Compound | Evidence |
---|---|---|
1 | Benzo[a]pyrene | The agent (mixture) is carcinogenic to humans |
2A | Cyclopenta[cd]pyrene | The agent (mixture) is probably carcinogenic to humans |
Dibenzo[a,l]pyrene | ||
Dibenz[a,h]anthracene | ||
2B | Benzo[b]fluoranthene | The agent (mixture) is possibly carcinogenic to humans |
Benzo[k]fluoranthene | ||
Benzo[j]fluoranthene | ||
Benz[a]anthracene | ||
Chrysene | ||
5-Methylchrysene | ||
Dibenzo[a,i]pyrene | ||
Dibenzo[a,h]pyrene | ||
Indeno[1,2,3-cd]pyrene | ||
3 | Benzo[ghi]perylene | The agent (mixture or exposure circumstance) is not classifiable as to its carcinogenicity to humans |
Dibenzo[a,e]pyrene | ||
Benzo[c]fluorene |
Type of Heat | Cooking Procedure | Characteristics |
---|---|---|
Dry | Baking | Indirect heat |
Moist | Baking | Indirect heat, conducted by water |
Moist | Bain-marie | Indirect baking with heat transfer control |
Moist | Deep-frying | Indirect heat, conducted by oil |
Dry | Gas grilling | Direct heat, controlled temperature |
Dry | Charcoal roasting | Direct heat and smoke, partially controlled temperature |
Dry | Smoking | Indirect heat and direct smoke |
Dry | Microwave cooking | Indirect heat, heating by dissipation of water molecules |
Moist | Stewing | Indirect heat, partially conducted by oil |
Product | Processing Method | BaP µg/kg | PAH4 a µg/kg | Total Sum b µg/kg | Reference |
---|---|---|---|---|---|
Milk, Dairy and Baby Foods | |||||
Baby foods (n = 40) | None | 0.19–0.55 | 1.02–3.12 | 11.82–52.25 (14) | [74] |
Milk powder (n = 44) | None | 0.13 | 2.36 | 169.99 (16) | [75] |
Milk powder formula (n = 5) | None | ≤LOD | 0.24 | 1.23 (15) | [76] |
Smoked mozzarella cheese (n = 57) | None | 0.09 | 0.84 | 1.24 (8) | [77] |
Pasteurized milk, UHT milk (n = 29) | None | ≤LOD–0.10 | ≤LOD–0.10 | 5.86–26.60 (16) | [78] |
Milk powder (n = 31) | None | 0.04 | 0.02–10.16 | 11.8–78.40 (15) | [79] |
Raw milk, Pasteurized milk, UHT milk (n = 36) | None | 0.25–0.27 | 1.21–1.59 | 5.43–7.75 (16) | [80] |
Vegetables and Fruits | |||||
Fruits (n = 16) | None | ≤LOD | ≤LOD–0.59 | 0.19–1.08 (8) | [15] |
Vegetables (n = 26) | None | ≤LOD–0.35 | ≤LOD–3.28 | ND–3.81 (8) | [15] |
Vegetables (n = 40) | The samples were prepared according to each type of vegetable | ≤LOD–4.35 | ≤LOD–2.00 | 14.20–413.20 (16) | [81] |
Vegetables (n = 45) | None | ≤LOD–4.40 | 1.40–19.60 | 60.50–312.00 (16) | [82] |
Vegetables (n = 355) | None | 0.01–0.14 | - | 0.20–0.85 (8) | [83] |
Meat and Fish | |||||
Chicken wings (n = 18) | Grilling (temperature) 270 °C | 3.27 | 8.60 | 12.83 (8) | [84] |
240 °C | 2.51 | 7.45 | 11.23 (8) | ||
210 °C | 1.38 | 6.59 | 10.10 (8) | ||
Fish products (n = 18) | Fresh (n = 10) | <LOQ | <0.33 | <0.33(4) | [85] |
Marinated (n = 4) | |||||
Smoked (n = 4) | |||||
Shellfish (n = 63) | Fresh | <LOQ–3.43 | <0.27–7.92 | <0.27–7.92 (4) | |
Meat products (n = 99) | Fermented sausages (n = 21) | <LOQ–5.40 | <0.40–7.10 | <0.40–7.10 (4) | |
Semi-dry sausages (n = 25) | <LOQ–1.05 | <0.40–2.53 | <0.40–2.53 (4) | ||
Pasteurized sausages (n = 5) | <LOQ–0.57 | 0.46–3.31 | 0.46–3.31 (4) | ||
Dry cured meat (n = 13) | <LOQ–1.90 | 0.46–12.66 | 0.46–12.66 (4) | ||
Semi-dry cured meat (n = 24) | <LOQ–2.48 | <0.40–9.44 | <0.40–9.44 (4) | ||
Dry bacon (n = 8) | <LOQ | <0.40–9.45 | <0.40–9.45 (4) | ||
Meat products (n = 35) | None | 0.19–1.73 | 0.59–7.55 | 0.59–11.05 (8) | [15] |
Cocoa and Chocolate | |||||
Cocoa beans (n = 8) | Fermented and sun dried | <LOQ–9.06 | <LOQ–49.96 | <LOQ–63.30 (8) | [86] |
Cocoa beans (n = 4) and crushed cocoa beans (n = 4) | Fermented and dried | ≤LOD | ≤LOD–0.01 | 0.38–0.76 (11) | [87] |
135 °C (40 min) | |||||
135 °C (50 min) | |||||
150 °C (25 min) | |||||
150 °C (35 min) | |||||
135 °C (7 min) | |||||
135 °C (10 min) | |||||
150 °C (5 min) | |||||
150 °C (7 min) | |||||
Milk chocolate (n = 7) | None | ≤LOD | ≤LOD–36.2 | 48.70–147.00 (13) | [88] |
Dark chocolate (n = 7) | ≤LOD–38.5 | 87.80–149.00 (13) | |||
White chocolate (n = 6) | ≤LOD–17.1 | 44.20–122.00 (13) | |||
Raw cocoa beans (n = 12) | Unshelled, fermented, and dried | ≤LOD–9.98 | 0.88–44.28 | 0.88–44.28 (4) | [89] |
Cocoa mass (n = 22) | Finely ground cocoa nibs | ≤LOD–0.76 | 2.59–9.29 | 2.59–9.29 (4) | |
Cocoa butter (n = 67) | Pressed cocoa mass | ≤LOD–7.86 | 2.09–92.53 | 2.09–92.53 (4) | |
Milk chocolate (n = 27) | None | 0.70 | 10.11 | 10.11 (4) | |
Dark chocolate (n = 69) | None | 0.57 | 5.88 | 5.88 (4) | |
Cocoa powder (n = 12) | Finely ground cocoa press cake | 1.07 | 8.86 | 8.86 (4) | |
Cocoa drink powder (n = 9) | Finely ground cocoa press cake | 1.00 | 9.48 | 9.48 (4) | |
Chocolate candy (n = 25) | None | ≤LOD–12.76 | ≤LOD–17.11 | 2.70–235.16 (16) | [90] |
Cocoa beans (n = 8) | Drying and sun drying (65 °C. 70 °C, and 80 °C) | 0.15–0.42 | - | 0.15–0.42 (1) | [91] |
Chocolate (n = 40) | None | 0.07–0.63 | 0.69–4.45 | 1.33–6.85 (14) | [92] |
Bread and Cereal | |||||
Bread samples (n = 10) | Commercial samples | <LOQ–0.20 | 0.11–0.22 | 0.11–0.22 (4) | [93] |
Breakfast cereals (n = 10) | Commercial samples | <LOQ–0.30 | 0.23–0.87 | 0.23–0.87 (4) | |
Baguette (n = 52) | Baked (industrial) | - | 0.48–12.55 | 20.78–228.98 (13) | [94] |
Lavash (n = 62) | Baked for 80 s at 332 °C | - | 0.48–4.94 | 9.46–152.07 (13) | |
Taftoon (n = 55) | Baked for 2.5 min at 315 °C | - | 0.48–20.66 | 18.19–169.26 (13) | |
Pasta | Commercial samples | ≤LOD | ≤LOD–920 | 168–1980 (16) | [95] |
Cereal | ≤LOD–4200 | ≤LOD–7500 | 3500–22,300 (16) | ||
Flour | ≤LOD | ≤LOD | 803–2486 (16) | ||
Rice | ≤LOD | ≤LOD | 180–10,540 (16) | ||
Bread | ≤LOD | ≤LOD–480 | 1290–4800 (16) | ||
Toast | Toasted on an electric home toaster at 600 W for 2 min | ≤LOD–980 | 240–3450 | 13,000–17,820 (16) |
Food Product | Extraction | Clean-Up Step | Quantification | Reference |
---|---|---|---|---|
Smoked fish and meat | Saponification (3.5 M methanolic potassium hydroxide solution at 70 °C for 2 h) and cyclohexane | Silica SPE cartridge | GC–QMS | [63] |
Dry/fermented sausage | Saponification (potassium hydroxide, methanol and water for 3 h under reflux) and extraction with n-hexane | Florisil SPE cartridge | UHPLC-UV/VIS/FLD | [60] |
Beef meat | Saponification (sodium hydroxide and diatomaceous earth) | Extrelut column connected to a PRS SPE column and silica SPE cartridge | HPLC-FLD | [129] |
Beef stripe, pork, and chicken fillet | Saponification (2 M methanolic potassium hydroxide solution) and extraction with n-hexane | SPE in neutral-Si/basic-Si/acidic-Si/neutral-Si frits | GC–FID | [104] |
Dry fermented sausage | Acetonitrile, magnesium sulfate, and sodium chloride | QuEChERS (C18 + PSA) | GC-QMS | [61] |
Olive and refined pomace olive oils | Acetone/acetonitrile in an alumina-N SPE cartridge | Amine SPE cartridge | HPLC-FLD | [130] |
Salmon, shrimps, mussels, cutlet, bacon, curry spice, wheat flour, infant formula, cereal-based baby foods with fruits, and baby foods with vegetables | QuEChERS (Acetonitrile, and salts combinations) | QuEChERS (C18 + PSA), EMR-Lipid | GC- QqQMS | [131] |
Milk and meat/fish-based baby food | Saponification (1 M ethanolic potassium hydroxide solution at 80 °C for 3 h) | Washed the cyclohex-ane phase with meth-anol:water | HPLC-FLD | [74] |
Chicken breast, smoked ham, ham, roasted bacon, crispy bacon, pork sausage, Swedish meatballs, honey roast salmon, and sweet chili salmon | Saponification (sodium hydroxide and diatomaceous earth) | Silica SPE cartridge | HPLC-DAD/FLD | [106] |
Spices and meat | Homogenized with 1 M sodium hydroxide solution and Extrelut and loaded in an Extrelut 20 column, followed by PRS cartridges with dichloromethane containing 5% toluene | Silica SPE cartridge | HPLC-FLD | [106] |
Fruit, vegetables, and meats and their products | Saponification (ethanolic potassium hydroxide solution 80 °C for 3 h) and extraction with n-hexane–ethanol solution | Silica SPE cartridge | GC-QMS | [15] |
Fish and malt | Acetonitrile and ceramic stone | QuEChERS (Zirconium dispersive SPE) | GC-QTOF MS | [132] |
Fish, mollusk, and shrimp | ELL with ethyl acetate and aqueous solution containing magnesium sulfate and sodium chloride | Silica SPE cartridge | GC-MS | [133] |
Dark chocolate | Dichloromethane and n-hexane | Gel permeation chromatography | [134] | |
Animal-based smoked foods | QuEChERS (Acetonitrile, water, and salts combinations) | QuEChERS (C18 + PSA), EMR-Lipid, DLLME | GC-Iontrap MS | [135] |
Extruded wheat flour, smoked fish, dry infant formula, sausage meat, freeze-dried mussels, edible oil, and wheat flour | n-hexane or cyclohexane | SEC and SPE | GC-MS | [136] |
Edible olive oil, fresh mussels, smoked fish, smoked meat products, processed cereal-based foods for young children, infant formula, chocolate, and food supplements (isoflavones) | Dichloromethane | SEC | HPLC-FLD | [137] |
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Sampaio, G.R.; Guizellini, G.M.; da Silva, S.A.; de Almeida, A.P.; Pinaffi-Langley, A.C.C.; Rogero, M.M.; de Camargo, A.C.; Torres, E.A.F.S. Polycyclic Aromatic Hydrocarbons in Foods: Biological Effects, Legislation, Occurrence, Analytical Methods, and Strategies to Reduce Their Formation. Int. J. Mol. Sci. 2021, 22, 6010. https://doi.org/10.3390/ijms22116010
Sampaio GR, Guizellini GM, da Silva SA, de Almeida AP, Pinaffi-Langley ACC, Rogero MM, de Camargo AC, Torres EAFS. Polycyclic Aromatic Hydrocarbons in Foods: Biological Effects, Legislation, Occurrence, Analytical Methods, and Strategies to Reduce Their Formation. International Journal of Molecular Sciences. 2021; 22(11):6010. https://doi.org/10.3390/ijms22116010
Chicago/Turabian StyleSampaio, Geni Rodrigues, Glória Maria Guizellini, Simone Alves da Silva, Adriana Palma de Almeida, Ana Clara C. Pinaffi-Langley, Marcelo Macedo Rogero, Adriano Costa de Camargo, and Elizabeth A. F. S. Torres. 2021. "Polycyclic Aromatic Hydrocarbons in Foods: Biological Effects, Legislation, Occurrence, Analytical Methods, and Strategies to Reduce Their Formation" International Journal of Molecular Sciences 22, no. 11: 6010. https://doi.org/10.3390/ijms22116010