Chemistry and Biology of Food

Filet Mignon and French Onion Soup

Chemistry and Biology of Food

ChiChinese

Chemistry and Biology of Food

Japanesep

Chemistry and Biology of Food

Korean

Chemistry and Biology of Food

Chemistry and Biology of FoodChemistry and Biology of Food

Food

Carbohydrates Fats Proteins OthersCarbohydrates Fats Proteins Others

J. W. Hill and D. K. Kolb, Chemistry for Changing Times, 9th Ed, Chapter 16.

CarbohydratesCarbohydrates

FoodFood

Carbohydrates(Fuels: 4 kcal/g)(Fuels: 4 kcal/g)

Sugars(mono and disaccharides)

Starches/Cellulose( l h id )(mono- and disaccharides) (polysaccharides)

Glucose Sucrose Starch Cellulose

Fructose Lactose

65-80% of our calories should come from complex carbohydrates

Sugars

Starch and Cellulose

- α-1,4 glycosidic bond- Energy storage- can be metabolized

β 1 4 glycosidic bond- β-1,4 glycosidic bond- Structural molecule- cannot be metabolized

(by humans)

- The same sugar linked in a different way can completely change its properties

FatsFats

FoodFood

Fats(Energy Reserves: 9 kcal/g)(Energy Reserves: 9 kcal/g)

Triglycerides Cholesterols

Saturated fats Unsaturated fats

< 30 % of our calories should come from fats (<10% saturated fats)

Triglyceridesg y

- 3 fat molecules linked by a glycerol backbone

- Also can be di- and mono-glycerides

- Deprotonated fatty acids make soap (saponification)

Triglyceridesg y

Condensation reaction

Saturated Fats and Unsaturated Fats

-The “kink” in unsaturated decreases packing (lower van der Waals forces)- Unsaturated fats have a lower melting temperature

Saturated Fats andSaturated Fats and Unsaturated Fats

Cis fats and Trans fats

Cis fats and Trans fatsCis fats and Trans fats

Cis-9-octadecenoic acid Trans-9-octadecenoic acid

Cis fats: unsaturated fats naturally found in vegitable oils etc

(Oleic acid) (Elaidic acid)

Cis fats: unsaturated fats naturally found in vegitable oils, etcbent, does not pack well, liquid, good fat

Trans fats: partially hydrogenation of vegetable oilscorrect the bent to make it linear, pack well, more solid, bad fataccount for more than 80 percent of total (fat) intakeaccount for more than 80 percent of total (fat) intake

Consumption of trans fat: as low as possible (<2 mg/day)http://www.healthierus.gov/dietaryguidelines/

Cis fats and Trans fatsCis fats and Trans fats

Cis-9-octadecenoic acid Trans-9-octadecenoic acid

Trans and Saturated fats can clog arteries by forming plaques

(Oleic acid) (Elaidic acid)

Trans- and Saturated fats can clog arteries by forming plaques- Imagine butter solidifying in your arteries

Current research shows that trans fat can’t be metabolized- Remains in blood stream longer

http://www.healthierus.gov/dietaryguidelines/

Cholesterol

Liver manufactures about 80 percent of cholesterol;Liver manufactures about 80 percent of cholesterol;From eating animal products such as meat, eggs and dairy products

A t i l iArteriosclerosis

Blood clots in artery in heart muscle: Heart attacksBlood clots in artery that supplies the brain: Stroke

Good cholesterol (HDL) and bad cholesterol (LDL)

•“Cholesterol” is different from LDL and HDL

•Often used synonymously•Often used synonymously•LDL and HDL are related to the transport mechanism of Cholesterol in the bodyCholesterol in the body

•High density Lipoprotein (HDL)

•Low Density Lipoprotein y p p

http://www.heartcenteronline.com/myheartdr/articles_about_the_heart/The_Cholesterol_Center.html

Good cholesterol (HDL) and bad cholesterol (LDL)Good cholesterol (HDL) and bad cholesterol (LDL)

From: http://www.heartpoint.com/cholgallery.html

The cholesterol levelsThe National Cholesterol Education Program

Blood Lipid Desirable Borderline High

Total Cholesterol < 200 mg/dL 200-239 mg/dL >= 240 mg/dL

Low-Density Lipoproteins (LDL)

< 130 mg/dL 130-159 mg/dL >= 160 mg/dL

High-Density Lipoproteins (HDL)

> 35 mg/dL(values >60 mg/dL are considered a negative risk

factor)

Triglycerides < 200 mg/dL

http://www.healthchecksystems.com/chol.htm

Consumption: < 300 mg/day of cholesterolhttp://www.healthierus.gov/dietaryguidelines/

Proteins and Essential Amino acidsProteins and Essential Amino acids

Myoglobin Cytochrome oxidase

Protein requirement: 0.8 g of protein/kilogram of body weight

Proteins and Essential Amino acids

20 natural amino acids total20 natural amino acids totalAdult human can synthesize all but 8 of them (8 essential amino acids)

The Balancing Act of Protein Nutrition

Sufficient Deficient

Grain Methionine Tryptophan, LysineGrain Methionine Tryptophan, Lysine

Legume (Beans, peas) Tryptophan, Lysine Methionine

Animals All none

Group FoodMexican Corn tortillas and refried beansJapaneseEnglish working classAmerican Indians

Rice and soybean curds (tofu)Baked beans on toasted breadCorn and bean (succotash)American Indians

Western AfricansCajuns (Louisiana)American kids

Corn and bean (succotash)Rice and peanuts (ground nuts)Red beans and ricePean t b tter bread sand ichesAmerican kids Peanut butter bread sandwiches

• Balancing your diet is CRITICAL to proper nutrition and good health

Other Important Ingredients in FoodOther Important Ingredients in Food

FoodFood

Others

Minerals Vitamins Dietary fiber Water

MineralsGroup 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Period

1 1 H 2

He

2 3 Li

4 Be 5

B 6C

7N

8O

9F

10Ne

3 11 Na

12 Mg 13

Al14Si

15P

16S

17Cl

18Ar

19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 364 19 K

20 Ca 21

Sc22Ti

23V

24Cr

25Mn

26Fe

27Co

28Ni

29 Cu

30 Zn

31Ga

32Ge

33As

34Se

35Br

36Kr

5 37 Rb

38 Sr 39

Y40Zr

41Nb

42Mo

43Tc

44Ru

45Rh

46Pd

47 Ag

48 Cd

49In

50Sn

51Sb

52Te

53I

54Xe

6 55 C

56 B * 71

L72Hf

73T

74W

75R

76O

77I

78Pt

79 A

80 H

81Tl

82Pb

83Bi

84P

85At

86R6 Cs Ba Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn

7 87 Fr

88 Ra ** 103

Lr104Rf

105Db

106Sg

107Bh

108Hs

109Mt

110Uun

111 Uuu

112Uub

113Uut

114Uuq

115Uup

116Uuh

117Uus

118Uuo

57 58 59 60 61 62 63 64 65 66 67 68 69 70*Lanthanides * 57La

58Ce

59Pr

60Nd

61Pm

62Sm

63Eu

64Gd

65 Tb

66 Dy

67Ho

68Er

69Tm

70Yb

**Actinides ** 89Ac

90Th

91Pa

92U

93Np

94Pu

95Am

96Cm

97 Bk

98 Cf

99Es

100Fm

101Md

102No

• Essential (Beneficial) minerals ( 4% of body weight)• Essential (Beneficial) minerals (~ 4% of body weight)• Toxic minerals• Radionuclides

MineralsCalcium Healthy bones and teeth; blood clotting; muscle contraction; nerve

transmission; reduce risk of osteoporosisChromium Glucose metabolism; regulating blood sugarCobalt Red-blood cell productionCopper Red-blood cell formation; connective tissue formation; iron storage and release

to help form hemoglobin; central nervous system functionI di N d d b th th id t t t b liIodine Needed by the thyroid to support metabolismIron Red blood cell formation and function (women of childbearing age need more);

Important for brain functionMagnesium Regulates over 100 enzymes; nerves and muscles functiong g y ;Molybdenum Normal growth and developmentPhosphorous Strong bones and teeth; enhances other nutrients

Potassium Regulates heartbeat; maintains fluid balance; helps muscles contractSelenium Essential component of an antioxidant enzyme; normal growth and developmentSulfur Muscle protein and hairZinc Used in > 200 enzymes; digestion; metabolism; reproduction; wound healing

http://www.traceminerals.com/inorganic.html

Lack of MineralsMineral Result of Defiency Protective Additives

Iodine (I) Goiter (improper functioning or failing of the thyroid gland)

Iodized salt

Iron (Fe) Anemia (general weakening of the body due to poor oxygen

Iron-Fortified foods like cereal or breadbody due to poor oxygen

transport)bread

Calcium Osteoporosis, improper Calcium-Fortified foods like milk p , p pdevelopment of bones or orange juice

MineralsMetal ions Toxic Effects Possible Protection

Aluminum (Al) Stomach, Bones, Brain Possibly magnesium.

Arsenic (As) Cells (cellular metabolism) Selenium; Iodine; Calcium; Zinc; Vitamin C; Sulfur; Amino Acids (Found in garlic hen's eggs and(Found in garlic, hen s eggs, and beans)

Cadmium (Cd) Renal Cortex of the Kidney, Heart, Blood Vessels to the Brain,

S C f

Zinc, Calcium, Vitamin C, Sulfur Amino Acids

Appetite and Smell Center of the Brain; Every Known Process in the Development of Cancer.

Lead (Pb) Bone, Liver, Kidney, Pancreas, Zinc, Iron, Calcium, Vitamin C, ( ) , , y, ,Heart, Brain, Nervous System

, , , ,Vitamin E, Sulfur Amino Acids

Mercury (Hg) Nervous System, Appetite and Pain Centers of the Brain, Immune System Cell Membranes

Selenium, Vitamin C, Pectin, Sulfur Amino Acids

Immune System, Cell Membranes

http://www.traceminerals.com/inorganic.html

VitaminsVitamins

FoodFood

Others

Vitamins

Fat soluble vitamins Water soluble vitaminsFat-soluble vitamins(Vitamin A, S, E, and K

Water-soluble vitaminsVitamin B and C

Fat-soluble vitamins can be stored for future useWater soluble vitamins cannot be stored for a long timeWater-soluble vitamins cannot be stored for a long time

Vitamins

Lack of VitaminsLack of Vitamins

Vitamin Result of Defiency Foods containing

A Night Blindness Fish, liver, eggs, butter, cheese, carrots

D Rickets Cod liver oil, milk supplement (irradiated ergosterol)

E Sterility, muscular dystrophy Meat, egg yolks, green vegetables, wheat germ oil

K Hemorrage Spinach, green leafy vegetables

B complex Pellegra, Dermatitis, Beriberi, A i

See pages 459 - 461Anemia

C Scurvy Citrus fruits

Dietary fibersDietary fibers

FoodFood

Others

Dietary fibers

I l bl fib S l bl fibInsoluble fibers(celluloses)

(source: wheat bran)

Soluble fibers(hemicelluloses)

(source: oat or rice brans)

WaterWater

Food

Others

WaterWater

1.0-1.5 L of Water per dayWater is the “solvent” for lifeWater is the solvent for life

The Food Pyramid

http://www.heartpoint.com/Cholfoodpyramid.html

Where does our food come from?

Food additives: molecular flavorings

Food additives: Artificial sweeteners

NutrasweetEqual

Compound Relative Sweetness

Lactose 16

EqualSweet’N Low

Maltose 33

Glucose 74

Sucrose 100Splenda

Fructose 173

Aspartame 16,000

Acesulfame K 20,000

Saccharin 50 000

p

Saccharin 50,000

Sucralose 60,000

P-4000 400,000

Why are non-calorie sweeteners “non-calorie”?non calorie ?

Catalytic Unit of Hexokinase (Glycolysis)

• Most metabolic enzymes are very specific for their substrateMost metabolic enzymes are very specific for their substrate• The energy stored in the chemical bonds of artificial sweeteners is as high as glucose (sucrose)

• We just can’t process artificial sweeteners

Food additives: Artificial sweeteners

Food additives: Food enhancer

Food additives: Splenda®Food additives: Splenda®

The comet assay with 8 mouse organs: results with 39 currently used food additives. Sasaki YF, Kawaguchi S, Kamaya A, Ohshita M, Kabasawa K, Iwama K, Taniguchi K, Tsuda S., Mutation Research 2002 Aug 26;519(1-2):103-19

Repeated dose study of sucralose tolerance in human subjects. Baird IM, Shephard NW, Merritt RJ, Hildick-Smith G. Food Chem Toxicol. 2000;38 Suppl 2:S123-9.

A carcinogenicity study of sucralose in the CD-1 mouse. Mann SW, Yuschak MM, Amyes SJ, Aughton P, Finn JP. Food Chem Toxicol. 2000;38 Suppl 2:S91 72:S91-7.

Acute and subchronic toxicity of sucralose. Goldsmith LA. Food Chem Toxicol. 2000;38 Suppl 2:S53-69. Sucralose: assessment of teratogenic potential in the rat and the rabbit. Kille JW, Tesh JM, McAnulty PA, Ross FW, Willoughby CR, Bailey GP, Wilby OK,

Tesh SA. Food Chem Toxicol. 2000;38 Suppl 2:S43-52. Sucralose: lack of effects on sperm glycolysis and reproduction in the rat. Kille JW, Ford WC, McAnulty P, Tesh JM, Ross FW, Willoughby CR. Food

Chem Toxicol. 2000;38 Suppl 2:S19-29. The pharmacokinetics and metabolism of sucralose in the mouse. John BA, Wood SG, Hawkins DR. Food Chem Toxicol. 2000;38 Suppl 2:S107-10. p , , ; pp

The pharmacokinetics and metabolism of sucralose in the dog. Wood SG, John BA, Hawkins DR. Food Chem Toxicol. 2000;38 Suppl 2:S99-106. Gas chromatographic method for detection of urinary sucralose: application to the assessment of intestinal permeability. Farhadi A, Keshavarzian A,

Holmes EW, Fields J, Zhang L, Banan A. Neurotoxicity studies on sucralose and its hydrolysis products with special reference to histopathologic and ultrastructural changes. Finn JP, Lord

GH. Food Chem Toxicol. 2000;38 Suppl 2:S7-17.

Food additives: Food coloring

Natural food color from carrots, can be converted to vitamin A

Artificial food colors (banned by US FDA)

Poisons in food

Charcoal-broiled steak contains 3,4-benzpyreneCinnamon contains safroleMoles growing on stored peanuts and grains contains aflatoxins

Food with all natural ingredients ≠ safe or good foodFood with synthetic ingredients ≠ bad food

Fertilizers, Herbicides, Pesticides

Are they Safe?!?!?!?! (depends)

Nitrogen, Phosphorus and Potassium Fertilizers

The Haber Process: 3H2 + N2 2NH3

Made possible both nitrogen fertilizing (no need for fixing) and easy, cheap production of Nazi explosives.

Fertilizers, Herbicides, Pesticides

Pheromone Mimics

• Partition of Fish Pheromones between Water and Aggregates of Humic Acids. Consequences f S l Si lifor Sexual SignalingMesquita, R. M. R. S.; Canario, A. V. M.; Melo, E.Environ. Sci. Technol.; (Article); 2003; 37(4); 742-746.

• Reduction of Carpophilus freemani Dobson (Coleoptera: Nitidulidae) Aggregation(Coleoptera: Nitidulidae) Aggregation Pheromone Response by Synthetic AnaloguesPetroski, R. J.; Weisleder, D.J. Agric. Food Chem.; (Article); 1999; 47(3); 1189-1195.

• Recent Reviews 60• Recent Reviews. 60Cornel, V. M.J. Org. Chem.; 2001; 66(7); 2538-2546.

• Discrimination of Pheromone Enantiomers by Two Pheromone Binding Proteins from the Gypsy Moth Lymantria disparGypsy Moth Lymantria disparPlettner, E.; Lazar, J.; Prestwich, E. G.; Prestwich, G. D.Biochemistry; (Article); 2000; 39(30); 8953-8962.

• Comprehensive Natural Products Chemistry, vol. 8. In the Chem Library Reference Section.y