Food Labeling

FDA Nutrition FactsFDA Nutrition FactsOriginalOriginal ProposedProposed

Food Labeling

FreeFree LowLow ReducedReduced Light/LiteLight/Lite

All-NaturalAll-Natural Whole grainWhole grain OrganicOrganic

Minerals

Inorganic substancesInorganic substances CofactorsCofactors MacromineralsMacrominerals

Na, K, ClNa, K, Cl--, Mg, P, Mg, P CaCa

MicromineralsMicrominerals CrCr MnMn Cu, Zn, I, FeCu, Zn, I, Fe

Acrodermatitis enteropathicaAcrodermatitis enteropathica GoiterGoiter

FF

Vitamins

Organic compoundsOrganic compounds Necessary for Necessary for

metabolic processesmetabolic processes Insufficient synthesis Insufficient synthesis

in the bodyin the body Recommended Daily Recommended Daily

ValuesValues

Fat-solubleFat-soluble Water-solubleWater-soluble

Figure from Lippincott’s Biochemistry, 2nd ed., 1994

Vitamins

Water-solubleWater-soluble ThiamineThiamine RiboflavinRiboflavin NiacinNiacin PyridoxinePyridoxine BiotinBiotin Folic acidFolic acid CobalaminCobalamin Ascorbic acidAscorbic acid Pantothenic acidPantothenic acid

Fat-solubleFat-soluble Vitamin AVitamin A Vitamin DVitamin D Vitamin KVitamin K Vitamin EVitamin E

Thiamine Vitamin BVitamin B11 Biologically active formBiologically active form

thiamine pyrophosphate (TPP)thiamine pyrophosphate (TPP) Also can have TTPAlso can have TTP

FunctionFunction cofactor in oxidative decarboxylation of cofactor in oxidative decarboxylation of

-keto acids (TCA, AA degradation)-keto acids (TCA, AA degradation) RC(O)COOH to RC(O)OH + CORC(O)COOH to RC(O)OH + CO22 Other coenzymes also involved in Other coenzymes also involved in

processprocess Role of BRole of B11: H between S and N is very : H between S and N is very

acidic; when removed makes an ylideacidic; when removed makes an ylide SourcesSources

pork, whole grains, legumes, tuna, soy pork, whole grains, legumes, tuna, soy milkmilk

RDVRDV 1.5 mg/day1.5 mg/day req. increase with high carb diet or req. increase with high carb diet or

elevated metabolic needselevated metabolic needs DeficiencyDeficiency

decreased ATP productiondecreased ATP production impaired cellular functionimpaired cellular function Beri-BeriBeri-Beri Wernicke-Korsakoff Syndrome, aka Wernicke-Korsakoff Syndrome, aka

“cerebral Beri-Beri”“cerebral Beri-Beri”

HOH2N

N+

S

N

N

H2N

N+

S

N

N

PO

O

O

O

O

P

O

O

ATP

AMP

H

Riboflavin Vitamin BVitamin B22; vit G (formerly); vit G (formerly) Biologically active formsBiologically active forms

Flavin mononucleotide (FMN)Flavin mononucleotide (FMN) Flavin adenine dinucleotide (FAD)Flavin adenine dinucleotide (FAD)

FunctionFunction Electron transferElectron transfer FMNHFMNH22, FADH, FADH22

Redox reactions (TCA, glycolysis, etc.)Redox reactions (TCA, glycolysis, etc.) Needed for good vision and healthy Needed for good vision and healthy

skinskin SourcesSources

Milk, mushrooms, tomatoes, liver, Milk, mushrooms, tomatoes, liver, green leafy vegetablesgreen leafy vegetables

RDvRDv 1.7 mg/day1.7 mg/day

DeficiencyDeficiency Growth retardationGrowth retardation AriboflavinosisAriboflavinosis

CheilosisCheilosis Glossitis Glossitis StomatitisStomatitis

N

NH

O

N

OH

OH

OH

OH

N O

Niacin Nicotinic acid, Vitamin BNicotinic acid, Vitamin B33 Biologically active formsBiologically active forms

NADNAD++, Nicotinamide adenine dinucleotide , Nicotinamide adenine dinucleotide NADPNADP++

Nicotinamide (readily deaminated, also in Nicotinamide (readily deaminated, also in diet)diet)

FunctionFunction Coenzymes in redox reactions (TCA, FA Coenzymes in redox reactions (TCA, FA

synthesis, gluconeogenesis, etc.)synthesis, gluconeogenesis, etc.) DNA repairDNA repair

SourcesSources Unrefined grains, fortified cereal, meat, Unrefined grains, fortified cereal, meat,

fish, tomatoes, mushrooms, milk, liver, ricefish, tomatoes, mushrooms, milk, liver, rice Metabolism of tryptophan when AA is Metabolism of tryptophan when AA is

abundant (needs riboflavin and Babundant (needs riboflavin and B66)) RDVRDV

20 NE/day (NE = niacin equivalents = 1 mg 20 NE/day (NE = niacin equivalents = 1 mg niacin or 60 mg tryptophan)niacin or 60 mg tryptophan)

DeficiencyDeficiency Pellagra = “rough skin” in ItalianPellagra = “rough skin” in Italian

ToxicityToxicity Skin inflammation, heartburn, nausea, liver Skin inflammation, heartburn, nausea, liver

damagedamage

HN O

O

HN O

NH2

Pyridoxine Vitamin BVitamin B66, pyridoxal, , pyridoxal,

pyridoxaminepyridoxamine Biologically active formBiologically active form

pyridoxal phosphate (PLP)pyridoxal phosphate (PLP) FunctionFunction

Coenzyme for transamination Coenzyme for transamination reactions, esp. AAs reactions, esp. AAs (neurotransmitters)(neurotransmitters)

Decarboxylation of carboxylic acidsDecarboxylation of carboxylic acids SourcesSources

Wheat, corn, egg yolk, liver, potato, Wheat, corn, egg yolk, liver, potato, banana, fish, chickpeasbanana, fish, chickpeas

RDVRDV 2 mg2 mg

DeficiencyDeficiency Induced by TB drug isoniazid Induced by TB drug isoniazid

(supplement given)(supplement given) Dermatitis, fatigueDermatitis, fatigue Depression, confusionDepression, confusion Convulsions, seizuresConvulsions, seizures Microcytic hypochromic anemiaMicrocytic hypochromic anemia Epidemic in 1950sEpidemic in 1950s

ToxicityToxicity Neurological disorders at > 2 g /dayNeurological disorders at > 2 g /day

Biotin BB77 Biologically active formBiologically active form

Binds to lysine residue of enzymeBinds to lysine residue of enzyme FunctionFunction

Cofactor in carboxylation reactions, Cofactor in carboxylation reactions, carrier of COcarrier of CO2 2 (acetyl-CoA to malonyl-(acetyl-CoA to malonyl-CoA, synthesis of fatty acids)CoA, synthesis of fatty acids)

Regulation of gene expressionRegulation of gene expression SourcesSources

Almost all food, esp. milk, egg yolk, Almost all food, esp. milk, egg yolk, tomato, almond, peanuts, avocado, tomato, almond, peanuts, avocado, mushroommushroom

Also synthesized by intestinal Also synthesized by intestinal bacteriabacteria

RDVRDV 300 300 g/dayg/day

DeficiencyDeficiency Deficiency does not occur naturally Deficiency does not occur naturally

unless eat 20 raw egg whites per day unless eat 20 raw egg whites per day (protein avidin binds biotin (protein avidin binds biotin irreversibly and excreted)irreversibly and excreted)

Why raw? Why raw?

OH

NO H

N

H

S

O

H

H

Folic acid Biologically active formBiologically active form

Tetrahydrofolate (THF)Tetrahydrofolate (THF) FunctionFunction

Stimulates digestive acids; appetiteStimulates digestive acids; appetite Receive one carbon fragments from Receive one carbon fragments from

donors and transfer them in AA donors and transfer them in AA synthesis and nucleotide synthesissynthesis and nucleotide synthesis

SourcesSources Green leafy veggies (“foliage”), organ Green leafy veggies (“foliage”), organ

meats, legumes, okra, whole grain meats, legumes, okra, whole grain cerealscereals

RDVRDV 400 400 g/day, more during pregnancy and g/day, more during pregnancy and

lactationlactation DeficiencyDeficiency

Megaloblastic/macrocytic anemia and Megaloblastic/macrocytic anemia and growth failuregrowth failure

Once, most common vitamin deficiency Once, most common vitamin deficiency in US; now fortified cerealsin US; now fortified cereals

Absorption inhibited by many medicines, Absorption inhibited by many medicines, so a problem with the elderlyso a problem with the elderly

Cobalamin Vitamin BVitamin B1212

Corrin ring system with Co in centerCorrin ring system with Co in center FunctionFunction

Synthesis of MetSynthesis of Met Methylmalonyl-CoA to succinyl-CoAMethylmalonyl-CoA to succinyl-CoA

Degradation of odd-chain FA, enter Degradation of odd-chain FA, enter TCATCA

Transfer of methyl groupsTransfer of methyl groups Produce red blood cellsProduce red blood cells

SourcesSources Liver, whole milk, cottage cheese, Liver, whole milk, cottage cheese,

oysters, salmon, clams, eggs, oysters, salmon, clams, eggs, shrimp, pork, chicken (animal shrimp, pork, chicken (animal sources)sources)

Semi-synthetic food additive: Semi-synthetic food additive: cyanocobalamincyanocobalamin

RDVRDV 6 6 g/dayg/day

DeficiencyDeficiency Caused by pernicious anemiaCaused by pernicious anemia Methylmalonic acidemia (MMA) Methylmalonic acidemia (MMA)

Ascorbic Acid Vitamin CVitamin C FunctionFunction

Reducing agent, readily oxidized by OReducing agent, readily oxidized by O22 React with free radicals that can damage React with free radicals that can damage

DNA, proteins, lipids, etc.DNA, proteins, lipids, etc. Reduces Fe(III) to Fe(II) for absorptionReduces Fe(III) to Fe(II) for absorption Hydroxylation processes (synthesis of Hydroxylation processes (synthesis of

collagen)collagen) SourcesSources

Citrus, potato skins, tomatoes, green veggies, Citrus, potato skins, tomatoes, green veggies, blueberries, peppers, papaya, strawberriesblueberries, peppers, papaya, strawberries

RDVRDV 10 mg/day to prevent scurvy10 mg/day to prevent scurvy 60 mg/day recommended; more if you smoke 60 mg/day recommended; more if you smoke

b/c of free radicals in smokeb/c of free radicals in smoke DeficiencyDeficiency

Scurvy = swollen and bleeding gums, loose Scurvy = swollen and bleeding gums, loose teeth, red spots on skin from internal teeth, red spots on skin from internal bleedingbleeding

Weakened connective tissue, slow-healing Weakened connective tissue, slow-healing wounds, anemiawounds, anemia

ToxicToxic Metabolize to oxalateMetabolize to oxalate GI problems, so cap dosage at 2 g/dayGI problems, so cap dosage at 2 g/day

OH

OH

HO

OO

HO

Pantothenic acid Vitamin BVitamin B55 FunctionFunction

Component of CoA (transfer of Component of CoA (transfer of acyl groups, most commonly acyl groups, most commonly acetyl)acetyl)

Component of fatty acid Component of fatty acid synthase complexsynthase complex

SourcesSources Eggs, liver, yeast, yogurt, Eggs, liver, yeast, yogurt,

salmon, turkey, sunflower salmon, turkey, sunflower seeds, mushroomsseeds, mushrooms

RDVRDV 10 mg/day10 mg/day

DeficiencyDeficiency Rare due to abundance in Rare due to abundance in

foodsfoods Not well characterizedNot well characterized Burning feet syndromeBurning feet syndrome

HNHO

HO O

O

OH

Vitamin A Collective term for retinol, retinal, retinoic acidCollective term for retinol, retinal, retinoic acid Formed from oxidative cleavage of Formed from oxidative cleavage of -carotene (in liver)-carotene (in liver) FunctionFunction

Alcohol, carboxylic acid: growth, reproductionAlcohol, carboxylic acid: growth, reproduction Aldehyde: visual cycle/processAldehyde: visual cycle/process

SourcesSources Liver, kidney, cream, butter, egg yolk (animal sources)Liver, kidney, cream, butter, egg yolk (animal sources) Pumpkin, sweet potato, carrots: carotene precursors Pumpkin, sweet potato, carrots: carotene precursors

RDVRDV 1500 RE 1500 RE RE = retinol equivalent =RE = retinol equivalent =

1 1 g retinol or 6 g retinol or 6 g g -carotene-carotene DeficiencyDeficiency

HyperkeratosisHyperkeratosis Night blindnessNight blindness XerophthalmiaXerophthalmia

ToxicityToxicity Levels over 7500 RELevels over 7500 RE

Vitamin D Group of compounds, steroids with open B Group of compounds, steroids with open B

ringsrings Most prevalent = DMost prevalent = D33 DD33 active form = 1,25- active form = 1,25-

dihydroxycholecalciferoldihydroxycholecalciferol FunctionFunction

Regulate Ca and P absorption during bone Regulate Ca and P absorption during bone growthgrowth

SourcesSources Diet: DDiet: D22 (milk additive, plant sources) and D (milk additive, plant sources) and D33

(animal sources)(animal sources) Precursor: intermediate in cholesterol Precursor: intermediate in cholesterol

synthesissynthesis Formed in skin non-enzymatically from Formed in skin non-enzymatically from

steroid 7-dehydrocholesterolsteroid 7-dehydrocholesterol RDVRDV

10 10 g Dg D33

DeficiencyDeficiency Soft bones, impaired growth and skeletal Soft bones, impaired growth and skeletal

deformities in children (Rickets)deformities in children (Rickets) Also caused by antiepileptic drugsAlso caused by antiepileptic drugs

ToxicityToxicity Most toxic (stored, slowly metabolized)Most toxic (stored, slowly metabolized)

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Vitamin E -Tocopherol-Tocopherol FunctionFunction

Antioxidant, prevent oxidation of Antioxidant, prevent oxidation of polyunsaturated FAs in polyunsaturated FAs in membranes by Omembranes by O22 and free and free radicalsradicals

SourcesSources Vegetable oils, liver, eggs, nuts, Vegetable oils, liver, eggs, nuts,

seeds, spinach, tomatoesseeds, spinach, tomatoes RDVRDV

20 mg20 mg DeficiencyDeficiency

Associated with defective lipid Associated with defective lipid transport/absorptiontransport/absorption

Hemolytic anemiaHemolytic anemia ToxicityToxicity

Least toxic of fat-soluble vitaminsLeast toxic of fat-soluble vitamins

O

CH3

HO

H3C

CH3

CH3

CH3

CH3 CH3 CH3

Vitamin K Phylloquinone or menaquinonePhylloquinone or menaquinone FunctionFunction

Synthesis of blood-clotting Synthesis of blood-clotting proteinsproteins

SourcesSources KK11 = plants = plants

KK22 = animals, bacteria in intestine = animals, bacteria in intestine Cabbage, cauliflower, spinach, egg Cabbage, cauliflower, spinach, egg

yolk, liveryolk, liver RDVRDV

80 80 g/dayg/day DeficiencyDeficiency

Unlikely due to synthesis and wide Unlikely due to synthesis and wide distribution in fooddistribution in food

Injection for infantsInjection for infants ToxicityToxicity

JaundiceJaundice

O

O

3

O

O

n

Vitamin K1 (phylloquinone)

Vitamin K2 (menaquinone)

Olestra (Olean®)

Artificial, noncaloric fat substitute (indigestible)Artificial, noncaloric fat substitute (indigestible)

FDA warningFDA warning

OH

O

H

H

OH

O

CH2

H

CH2

HCH2

O H

H O

O

O

OC

O

R

O

C

R

O

C

R

O

C

R

O

O

C

R

O

C

R

O

C

R

O

O

R

R = (CH2)7CH=CH(CH2)7CH3