chapter 9 the fat soluble vitamins. “if a little is good, then more must be better” →Χ *$17...
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Chapter 9
The Fat Soluble Vitamins
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“If a little is good, then more must be better” →Χ
*$17 billion/yr in mineral & vit. Supplements in the USA
*↑↑↑Vit. → Extra energy, protection from DZ., & prolonged youth?
*Plants syn. all the vit. they need.
*Animals vary in their ability to syn. vit.
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I. Vitamins: Vital Dietary Components*Definition: Essential organic substances
needed in small amounts in the diet for normal function, growth & maintenance of body tissues.
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*Vitamins→ no energy, but some can facilitate energy-yielding chemical reactions.
*Fat-soluble vit.: A, D, E, K
*Water-soluble vit.: B vitamins & C
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*Indispensable in human diets, Exception: Vit. D, Niacin, Vit. K & biotin.
*Substance to be classified as a Vitamin:
1. The body is unable to synthesize enough of the compound to maintain health.
2. absence →deficient signs & symptoms, quickly cured when the substance is re-supplied.
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*As pharmacological agents- (1) Megadose of niacin → ↓blood Chol. (selected individuals) (2) Vitamin D analogs→ psoriasis*Isolated from food or synthetic → vitamins same chemical compounds & work equally well in the body. Exceptions: 1.Vit. E, Folate. 2. Some vit. exist in several related forms that differ in chemical or physical properties.
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A. Historical perspective on the vitamin 1. Treated night blindness with topical applications of liver extracts. 2. Scurvy was common among sailors 3. Identification of various vitamins →
related deficiencies were dramatically cured
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4. Vitamins were named alphabetically: A,
B, C, D………..
5. It took some time to uncover the true
nature of the various vitamins.
6. We can be relatively confident that
the vitamins needed by humans have
been discovered. Ex.TPN (iv)
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B. Storage of Vitamins in the Body
1. The fat-soluble vitamins are not
readily excreted from the body.
(Exception: Vit. K)
2. The water-soluble vitamins are
generally lost from the body quite
rapidly. (Exceptions: Vit. B6 &12)
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C. Vitamin Toxicity
1. Some fat-soluble vitamins can easily accumulate in the body and cause toxic effects. (Ex. Toxicities of vitamin A & D are the most frequently observed.)
2. Megadose of water-soluble vitamins
are also toxic
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D. Malabsorption of Vitamins - If absorption of a vitamin is defective, a
person must consume larger amounts of it or likely to develop def.
- Fat malabsorption is associated with malabsorption of the fat- soluble
vitamins - Alcohol abuse & GI diseases/B vitamins
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E. Preservation of Vitamins in Foods
*Improper storage and excessive cooking →↓Vit. B-1, Vit. C
*Heat, light, exposure to the air, cooking in water, and alkalinity are all factors that can destroy vitamins.
*If the food is not eaten within a few days, freezing is the best way to retain nutrients
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II. Fat-Soluble Vitamins
A. Absorption of the Fat-soluble Vitamins
1. Fat-soluble vitamins → lipid like mol. ∴absorbed along with dietary fat, and depends on fat digestion (bile salts & lipase) ~ 40-90 % vitamin ingested (in a typical amounts) are absorbed. (Fig 9-1)
2. Absorption efficiency ↓with intake ↑
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B. Distribution of the Fat-soluble Vitamins Fat abs.→chylomicron →TG ↘remnant. fat-sol. Vitamins → liver→→ →→ →→ →→cells & tissues blood lipoprot.
- DZs. or medications (Ex. orlistat ) ↓fat absorption → ↓fat-soluble vitamin absorption
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III. Vitamin A1. Vitamin A def. constitutes one of the major
public health problems in developing countries.
2. Vitamin A def. is the leading cause of non-accidental blindness. (worldwide)
*Children in Africa, Asia and South America
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3. Vit. A structure: Ring + F.A. tail (p.301) 4. Preformed Vit. A: Retinoids: retinal (CHO),
retinol (- CH2OH) and retinoic acid (- COOH), cis or trans form (p.300)
5. Provitamin A: Carotinoids –, Ex.: β- carotene, α-carotene, lutein, lycopene, zeaxanthin, β-cryptoxanthin (converted to retinol or retinal)
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A. Absorption, transport and metabolism 1. Absorption of preformed vit. A or
provitamin A varies from 90% - 3%. depending on the amount of fat.
Vitamin A in foods(1) Animal foods - retinol or retinyl ester
(retinol + F.A.)(2) Plant foods – carotenoids
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Fig 9-1 Digestion and absorption of vitamins
- retinyl ester (thru bile and lipase) → retinol + F.A., 90% retinol then absorbed. Form new retinyl ester in the intestinal cells.
- Carotenoids are absorbed intact → enzymatically split to retinal in intestinal cell → retinol → retinyl ester
- or, absorbed intact carotenoids→ blood stream.
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2. Storage and Transport of Vitamin A
(1) Storage:
a. Retinoids: Liver
Cartenoids: Liver & adipose tissue
liver contains >90 % Vit. A of body
b. Adequate for several months
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(2) Transport: liver to target cells
a. Retinoids: Retinol-binding protein
b. Provitamin (carotenoids): VLDL
(3) Excretion: only some is lost in the urine.
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B. Cellular Retinoid-Binding Proteins (CRBP)
- CRBP take up retinoids and hold retinoids and direct them to functional sites within the cell. (transport)
- CRBP protect the vitamin from oxidation and enzymatic reactions
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C. Retinoid Receptors in the Nucleus
- within cell nucleus: RAR and RXR
- retinoid/RAR or RXR complex bind to DNA to regulate the activity of retinoid-responsive genes on DNA
regulate gene expression → formation mRNA → protein synthesis (Fig. 9-3)
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C. Functions of Vitamin A 1. Vision
a. Fig. 9-4 vision cycle
Retina:
(1) Cones – bright light, color images
(2) Rods – dim light, black-white images
b. Various cell types in the retina, cornea, and epithelium of the eye depend on the presence of retinoic acid for maintaining structural integrity.
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2. Growth and Differentiation of Cells
- all-trans retinoic acid and 9-cis-retionic acid → activate RAR and RXR →code for a variety of structural proteins (Fig. 9-2)
- Retinoic acid is also necessary for the production, the structure, and the normal function of epithelial cells. R.A. is also essential in the formation and maintenance of mucus-forming cells.
- Retinoic Acid – used for wrinkle
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3. Immunity - Vit. A def. →vulnerable to infections - Specific immunity: cell-mediated and
antibody-mediated response, such as macrophage and natural killer cell activity and growth and differentiation of B-lymphocytes
- Non-Specific immunity: insufficient mucus production in the eyes, intestinal tract, and lungs, deterioration of many types of cells.
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D. Vitamin A Analogs for Acne
*Tretinoin (Retin-A): Analog form of vitamin A, acne medication, topical treatment, ↓sebum secretion.
*Accutane (13-cis retinoic acid)- acne medication, oral
*Acintretin – treat severe psosiasis*** fetal malformations (use during
Prg.
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E. Possible Carotenoid functions
1. Heart Disease Prevention *Carotenoids: antioxidants
*Recommendation: at least 5 servings fruits and veg./day
2. Cancer Prevention
- ↓ various cancers in animal studies, but not shown in human study.
- Retinoids influence cell differentiation, inhibition cell proliferation & ↑apoptosis
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3. Lycopene protects against prostate cancer (antioxidant )
4. Age-related macular degeneration (Fig. 9-5): macular contains lutein and zeaxanthin (carotenoids) (↑er carotenoids in the diets ↓ er incidence of macular degeneration)
*Megadose vitamin A supplements to ↓cancer risk is currently not advised (∵toxicity)
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F. Vitamin A in Foods (p.305)
- Preformed vit. A: liver, fish oils, fortified milk, and eggs
- Provitamin A: carotenoids in dark green & yellow-orange vegetables & some fruit
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1. *Retinol Activity Equivalent (RAE)
1 RAE
= 1μg all-trans retinol
= 12μg all-trans β-carotene
= 24μg other carotenoids
Table 9-1 (p.306)
2. Calculating Retinol activity equivalents
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G. Vitamin A Needs
• *RDA for Vitamin A• Adult: ♂: 900 RAE• ♀: 700 RAE• - Actual intake: meet RDAs• - Liver reserves of vitamin A are• 3 – 5X >needed for good health
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H. Vitamin A Deficiency Diseases
- Preschool children who do not eat
enough veg.
- Urban poor, the elderly, people w/ alcoholism or liver disease, children and adult w/ severe fat malabsorption syndromes, cystic fibrosis, AIDS etc.
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*Night Blindness
*Conjunctival xerosis
*Bitot’s spot
*Xerophthalmia
*Follicular hyperkeratosis
Fig 9-6
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I. Upper Level for Vitamin A
* Vitamin A Toxicity
“ Hypervitaminosis A”: long-term supplement 2 – 4X RDA
Fig 9-7
UL: 3000 μg
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- 3 kinds of Vitamin A toxicity:
a. Acute – GI upset, headache,
blurred vision, muscular
in-coordination, death
b. Chronic – wide range of signs
and symptoms
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• c. Teratogenic – birth defect
• * animal study: Accutane causes
spontaneous abortion and birth
defects
• * Pregnant women taking Accutane:
offspring show congenital
malformations of the head.
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*Consuming huge amount of
carotenoids – relatively non-toxic, ∵conversion and absorption
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*Hypercarotenemia: yellow orange color skin (appears to have jaundice, but sclerae are white and liver is not enlarged)
*Lycopenodermia: excessive intake of foods rich in lycopene, A deep orange discoloration.
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*Expert Opinion
Carotinoids and Human Health: Beyond Conversion to Vitamin A
a. Antioxidants:
In vitro: trap free radicals
In vivo: unknow
b. Carotenoids may decrease the risk of cataracts and macular degeneration in the eye, some cancers, some CVD. Clinical trials?
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*Hundreds of studies show that diets rich in fruits and vegetables are ass. w/↓ risk of cancer and other chronic diseases.
*Supplement β-carotene→ X↓lung cancer or heart DZ.
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*Many researchers are now convinced that β- carotene supplement offer no protection against cancer
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c. Eyesight
- Age-related macular degeneration is the leading cause of blindness in American over 65.
- Study of 876 subjects: ↑carotenoids (β- carotene, lutein and zeaxanthine) intake, ↓macular degeneration
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d. Pharmacological use of Vitamin A
*Tretinoin (Retin-A):
acne medication, topical treatment, ↓sebum secretion.
*Accutane (13-cis retinoic acid)- acne medication, oral
*Acintretin – treat severe psosiasis
*** fetal malformations (use during Prg.)
*All trans retinoic acid for leukemia → side effects
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VI. Vitamin D
• *Prohormone – converted to active form by enzymes in the liver & kidney
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• *Amount of sun exposure needed to produce vit. D depends on – skin color, age, time of day, season, and location
• *Def. – rickets in children
- osteomalacia in adults
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A. Vitamin D Formation in the Skin (p.309)
Cholesterol → 7-dehydrocholesterol
(skin) (Provitamin D)
UV ↘(290-315 nm)
→→→→→→→→→ →→ cholecalciferol
lumisterol↗
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B. Absorption and Formation of Vitamin D from Food
• - 80% of Vit. D - micelles
• - Absorbed vit. D w/ chylomicron →liver
• - Def. occurred in persons with fat mal-absorption syndromes.
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c. Metabolism, Transport, storage, and Excretion of Vitamin D
Fig. 9-8
• - Stored : liver & adipose tissue
(25(OH)cholecalciferol)
Shortage of Ca →↑PTH →↑
1, 25(OH)2cholecalciferol
• - Activated in liver & kidney
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Conversion of Provit. to Active Vitamin D
liver
cholecalciferol→→25(OH)cholecalciferol
→→1,25(OH)2 cholecalciferol (Calcitriol)
kidney
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• Animal foods – cholecalciferol (D3)
• Plant foods –
liver
ergosterol (D2)→→25(OH) ergocalciferol
→→→1,25(OH)2 ergocalciferol
kidney
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d. Functions of Vitamin D
* Regulation of Blood Calcium (Fig 9-9)
Blood Ca↓or Vit. D ↓→↑PTH →Sti. Kidney to syn. active Vit. D →
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1. Vitamin D → Intestine→↑abs. Ca
2. PTH & Vit. D →↑ Bone resorption
3. PTH & Vit. D →↑kidney reabsorption ↓, Ca loss
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*Intestinal Calcitriol→Intestinal→
(1)↑Syn. Ca-transport proteins (Ca-
carrier)
(2) Alters the memb. permeability of
intestinal cells
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1,25(OH)2D
• *Stem cell monocytes →→→→→mature
• osteoclasts
• *Human epidermal cells (nuclear receptors) for 1,25(OH)2D → effects proliferation and
differentiation of skin cells
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*Influence differentiation and function in cells of the intestine, skin, immune system, and bones, also cancer cells (skin, bone and breast cancer cells)
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*Rickets and Osteomalacia (Fig 9-10)
Children – rickets, associated with fat malabsorption (Ex. Cystic fibrosis)
Adults – osteomalacia (soft bone), occur in people w/ kidney, stomach, gallbladder, or intestinal disease or liver cirrhosis
*Treatment – combination of sun exposure and vit. D supplement
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e. Vitamin D in Foods
- Fatty fish (Sardine, salmon), fortified milk and some fortified breakfast cereals
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f. Vitamin D Needs
• Adequate Intake (AI) for vitamin D
• <51 years old – 5 μg/day (200 IU/day)
• 51-70 years old – 10 μg/day
• > 70 years old - 15μg/day
• Infant born w/ a sufficient supply of vit. D– last about 9 months
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g. Vitamin D deficiency
• a. Elderly people
• b. Anyone stays indoors most of the
day and ingests little or no vit. D.
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* Vitamin D Resistance
a. Lack of calcitriol synthesis in the
kidney
b. an inability of calcitriol to bind to
nuclear receptors (VDR) thru body
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*Vitamin D supplements
a. Pt’s w/ age-related osteoporosis
treated w/ vit. D & Ca (close medical
supervision is needed)
b. 10μg/day from a multivitamin/ mineral supplement
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h. Pharmacologic Use of Vit. D Analags
Topically treat Psoriasis (a skin
disorder – a failure in differentiation
of keratinocytes) with Vit. D analogs: safe and effective
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I. Upper level for Vit. D- UL: 50 μg/day*Vitamin Toxicity- Intake of 5X AI can be toxic (infant) Adult: 10X AI for 6 months (only from excess supplement, not from sun
exposure or milk consumption)- Symptoms: over absorption of Ca, ↑Ca
deposits in the kidneys, heart, and blood vessels etc. → cell death
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V. VITAMIN E • Many benefits of vit. E have been claimed,
only some have been supported by scientific invest.
*Vitamin E supplements >$300 million /year in the U.S.A.
*Lab. Animal – Vit. E deficiency – muscular dystrophy, inability to produce viable offspring, and impotence.
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a. Natural and Synthetic Vitamin E
*Chemical name: tocopherol (p:317)
*Vitamin E: 1. tocopherols (α, β,γ,δ)
2. tocotrienols (α, β,γ,δ)
Most active form: d-α-tocopherol
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b. Absorption, Transport storage, and Excretion of Vitamin E
*Absorption 1. Depends on the total abs. Of dietary fat
2. Precise degree of absorption is unknown
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* Transport: Chylomicron & other
lipoprotein
*Most conc. in body structures containing an abundance of F.A. (liver, adipose tissues and skeletal muscle. cell membrane (PL))
*Excretion: urine and bile
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c. Function of Vitamin E (T. 9-3)
“ Protecting cell membranes from oxidative destruction”(Fig. 9-11)
1. Stopping Free Radical Chain
Reactions
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ROO . + Vit. E-OH → ROOH + Vit. E-O .
* Free Radicals: Highly reactive molecules containing an unpaired electron, seeking electrons by attacking other compounds (cell membrane, DNA etc.)
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*Cell metabolism and immune-system
function→ Free radical (Ex. White
blood cells generate free radicals as
part of their action to stop infection)
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*Oxidizing agents: singlet oxygen,
hydrogen peroxide, hydroxyl radical, superoxide, ozone, nitro-oxide etc.
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** Free Radicals set off a chain reaction → generate thousands of free radicals→ destruction of cell membranes
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*Vitamin E interrupting free radical chain reactions→ becomes free radical itself (not very active one) → excreted or recycled
*Smoker: low vitamin E conc. in the lung
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• Numerous enzymes convert reactive oxidizing agents to less reactive compounds:
1. Glutathione peroxidase (GPX): A Se-containing enzyme that can destroy peroxides
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2. Superoxide dismutase (SOD): Enzymes containing Mn, Cu or Zn that destroy superoxides.
3. Catalase: destroy superoxides.
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4. Uric acid and bilirubin: interfere w/
oxidizing processes
5. Certain protein bind metals (Fe, Cu)
preventing the metals from
catalyzing free radical production
(Fig. 9-11)
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*Other Roles for Vitamin E
1. Protect the C=C double bonds in
dietary UFA
2. Protect other lipid-soluble nutrients
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3. Needed for Fe metabolism in the
cells
4. Maintenance of nervous tissues and immune function
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“ Anti-aging vitamin”: No clear evidence that supplementation w/ vitamin E and other antioxidants slows the aging process, but an inadequate intake likely promotes this oxidative damage
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d. Vitamin E in Food
*Plant oils (Corn, soybean, safflower, and wheat germ oils), wheat germ, asparagus, peanuts, and margarine. (p.320)
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*Get from Foods: Balance
*Actual vitamin E content of food depends on harvesting, processing, storage, and cooking (highly susceptible to destruction by oxygen, metals, light, and deep-fat frying)
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e. Vitamin E Needs
• RDA for Vitamin E
• Women: 15 mg/day
• Men: 15 mg/day
(22 IU of natural form, 33 IU of synthetic form)
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• *The Need for vitamin E varies w/ the amount of PUFA in the diet.
• Plant oils: high in PUFA, often high in vitamin E, exception: fish oil
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f. Vitamin E Deficiency Diseases
*PUFA in the RBC membrane are
very sensitive to attack by free
radicals→ Vit. E helps prevent
oxidative damage to RBC membrane
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1. Preterm infants are particularly
susceptible to hemolysis:
(1) born w/ limited tissue stores of
vitamin E and inefficiently absorb
vitamin E from the intestinal tract
(2) The rapid growth of preterm
infants exhausts what little vit. E
supplies exist.
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2. Fat malabsorption ass. W/ cystic
fibrosis or GI dz.
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g. Upper Level for Vitamin E
>19 yr. old, UL: 1,000 mg/day of any form of supplementary α-tocopherol
• Large dose of Vitamin E → inhibiting vitamin K metabolism, Hemorrhaging.
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*Large-scale studies are needed to study
1. Vit. E requirement
2. Vit. E reduce the risk or prevent a whole range of chronic diseases.
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VI. VITAMIN K• *Essential for blood clotting
• Phylloquinone (K1): Plants
• Menaquinones (K2): Fish oils , meats and bacteria in the human intestine.
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• Absorption and Transport of Vitamin K
1. Absorption: 40% - 80% of dietary
vitamin K in the small intestine
2. Transport: Chylomicron→ liver
→other lipoproteins→ various
tissues
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• *Functions of Vitamin K
(1) Blood clotting (Fig 9-13)
Intrinsic extrinsic
Preprothrombin ↘ Vit. K ↙
Ca ↘ Vit. K*** ↘ ↙Vit. K
Prothrombin →→→→ Thrombin
↙
Fibrinogen →→→ Fibrin
↙
Clotting
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CO2↘
A. A.-Glutamic acid-A.A.→→→→ Ca, Vit. K
A. A.-γCarboxyl Glutamic acid-A.A
(2) Adding to glutamic acid found in proteins present in bone, muscle, and kidneys.
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• *Dietary Sources of Vitamin
- Liver, green leafy vegetables,
broccoli, peas, and green beans
- Vit. K is quite resistant to cooking
losses
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• Vitamin k Needs
(1) AI: ♀ 90 μg/day
♂120 μg/day
(2) ↑Vitamin A & E→↓Vitamin K
absorption and ↑bleeding time
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• *Deficiency : Antibiotics user and fat malabsorption.
• *Deficiency can occur in newborns: • ∵1. GI tract is relative sterile. 2. Vit.
K in human milk is low. ∴Inject
Vitamin K to newborn at birth
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• *Toxicity: unlikely, ∵readily excreted.
• *Symptoms: jaundice and hemolytic
anemia in infants
• (Table 9-4)