12.

2 Vitamins

chapter 19
 MICRONUTRIENTS 2

Vitamins are nutritionally important organic

compounds.
Often coenzymes or cofactors for enzyme function.
Vitamins form biochemically through the life
processes of the plants and animals we eat.
Plants and animals synthesize vitamins.
 Originally it was thought these necessary
compounds were all amines. Since they were vital
to our health they became known as
“vital amines”, ie. vitamines.
When it was discovered that some were not
amines, ie. not ' --ines', the name was changed to
vitamins.
The fat - soluble vitamins are much more soluble in
fats, hydrocarbons and similar solvents than in water
Vitamins A, D, K, E

Water- soluble vitamins are much more soluble in

water than in 'organic' solvents.
C, B complex (B1,2,3,6,12), Pantothenic acid(B5),
Biotin(B7), Folate(B9)
 Vitamin Requirements
Name(Letter) RDI
Water-Soluble
Thiamin (B1) 1.5 mg
Riboflavin (B2) 1.7 mg
Niacin (B3) 2 mg
Pantothenic acid (B5) 10 mg
Pyridoxine (B6) 2 mg
Biotin (B7) 0.3 mg
Folic acid (B9) 0.4 mg
Cobalamin (B12) 6 g
Ascorbic acid (C) 60 mg
 Vitamin Requirements
Name(Letter) RDI

Oil-soluble
Retinol (A) 5000 IU
Calciferol (D)
400 IU
*Tocopherol (E)
Phylloquinone (K) 30 IU
70 g
WHAT is An IU??
 Vitamin levels in foods or supplements are
sometimes stated in Retinol Equivalents (RE's) or in
International Units (IU's). (2 sets of Units!!)
Several esters of retinol are equally effective and
thus are retinol equivalents (RE’s).
By definition , 1 RE of retinol = 1 microgram
Also by definition, one International unit (IU) of
Vitamin A =.3 micrograms retinol

Thus 1 RE=3.33 IU’s of Vitamin A

 IU’s
• Can apply to all vitamins and always = 0.3
micrograms or 0.3 x10-6 grams

• RE’s only apply to Vitamin A (retinol)

2 Retinols(A) from 1 beta carotene
 Metabolism of beta carotene
• Oxidative cleavage of C=C and reduction to
alcohol
• Carrots etc. lots of beta carotene and
eventually an excellent source of Vitamin A
Free Radicals - the Metabolic Oxidizers

Free radical = unpaired electron very reactive

. OH
OH
. OH
OH

Oxygen radicals: Hydroxy (HO•) / Peroxy (HOO•)

 Do you smoke??
• Each puff contains ~ 1015 OH radicals
• Also cyanides (bind to hemoglobin)
• PNAH’s
• Try the blow test: exhale through a kleenex
and see the tar!
What’s in cigarette smoke?
 An antioxidant is a chemical so easily
oxidized itself that it protects others from oxidation.

OH

and / or

Double Bond Phenol

eg. Vitamin A Part of Vitamin E molecule
Repel the Enemy !
 Vitamins - Some Generalities
• Fat-soluble vitamins can be accumulated in body
tissue/organs, eg. liver. Often there can be serious
metabolic consequences when ingesting 'mega-
doses', ie.10 - 100X the RDI.
• The water-soluble vitamins are often destroyed by
heat/water in the cooking process; also by
prolonged storage. Since they are excreted there is
usually no danger from 'overdosing' (vit B6!).
• Diet-related deficiencies do occur in vegans, the
elderly and alcoholics
• Chirality! ie. natural (D or L) vs. synthetic (D/L)
 Fat-Soluble Vitamins ( A & D)

H3C C H3 C H3 C H3

CH 2 OH

C H3 Retinol (Vitamin A)
H 3C CH 3

CH3
C H3

CH2

HO
Cholecalciferol (Vitamin D3)
 Fat-Soluble Vitamins ( E & K)

H3C CH3 CH3 CH3

CH3

CH 3
HO O

-Tocopherol (Vitamin E)
H3C CH3

CH3

CH
CH2 C H

O CH3 CH3 3

Phylloquinone (Vitamin K)
 Water-Soluble Vitamins ( B1 & B5)
+ S
H2N N

CH2

N H3C 15
CH2
N OH

H3C
Thiamine (B1)
CH3 O
HOH2C H2 H2
C C
H3C CH N C COOH
H H2
OH

Pantothenic Acid (B5)

 Water-Soluble Vitamins (B2 & B6)

CH 2OH

H C OH CH 2OH
H C OH
HO CH 2 OH
H C OH

H3C N N O
H3C N

NH Pyroxidine
H3C N (Vitamin B6)
O

Riboflavin (Vitamin B2)

 Water-Soluble Vitamins (B3,B7,C &?)
COOH O

HN NH
N
Biotin(B7)
Niacin(B3) H2 H2
C C
S C C COOH
HO H2 H2
O
O
HO

HOCH2CH2N+(CH3)3
HO OH
Ascorbic Acid(C) Choline
Natural = Ascorbic Acid = Synthetic
 Water-Soluble Vitamin (B9)
N

N CH 2 O COOH

H 2N N NH C NH C CH 2 CH 2 COOH

OH
Folic Acid (Vitamin B9)
Water-Soluble Vitamin(B12)

Cobalamin
 A - Retinol
Uses: vision pigment, good anti-oxidant (heart
disease? cancer?)
Deficiency: night blindness, (infant mortality)
Excess: blurred vision, teratogenic for pregnant
women, serious liver disease,skin
yellowing
Sources: highly coloured vegetables, liver, egg
yolks, fish liver oils
 D - Calciferol

Uses: regulates absorption of calcium & phosphorus

Deficiency: rickets (bone deformation)
Excess: damage to kidneys/tissue due to Calcium
'deposits'
Sources: eggs, liver, fish oils, fortified milk, sunshine
 E - Tocopherol
Uses: excellent anti-oxidant (protects cell
membranes); skin care
Deficiency: rare; (anemia, edema in infants)
Excess: 2005 study*** Heart attacks if overused
Source: vegetable oils, green vegetables,
nuts/seeds, wheat germ, meat

Vitamin E is not recommended over and above

what is in a multivitamin as of 2005
E: the vitamin looking for a disease!

• Still no well documented evidence for any

diseases directly due to its deficiency.
• Don’t take supplements!
 K- Phylloquinone
Uses: essential cofactor in blood clotting
Deficiency: (bruising/bleeding in infants-
increased coagulation time)
Excess: dangerous if taking anti-coagulants such
as ASA
Sources: green leafy vegetables (spinach, kale)

Cofactor: a small molecule or atom that is

required for an enzyme to be active
 B1- Thiamin
Uses: necessary for carbohydrate metabolism
Deficiency: nervous system deterioration (beriberi),
esp. in Far East because of milled rice
Excess: not known
Sources: lean meat, legumes, whole grains, in
'fortified' flour since 1940s
 B2 - Riboflavin
Uses: cofactor in much metabolism
Deficiency: poor wound healing, breakdown of
tissue in mouth/nose
Excess: not likely (yellow urine!)
Sources: milk, organ meats, fortified cereals
 B3 - Niacin
Uses: required for all metabolic oxidations (needed
by every cell daily!), lowers cholesterol (in
excess)
Deficiency: deterioration of nervous system & skin
(pellagra)
Excess: not normal (dizziness, liver damage)
Sources: yeasts, meats, legumes, 'enriched' flour
 B5 - Pantothenic Acid
Uses: cofactor in fatty acid metabolism
Deficiency: not observed
Excess: not observed
Sources: organ meats, egg yolks, yoghurt, legumes
 B6 - Pyridoxine
Uses: cofactor in >60 enzymes for a.a.
metabolism (the master vitamin!)
Deficiency: anemia, nervous disorders (est. in
almost 50% of NA women, esp. those
on oral contraceptives)
Excess: disable nervous system (present in body-
building diets)
Sources: green leafy vegetables, meats, fruit
 B7 - Biotin
Uses: cofactor in synthesis of fatty acids
Deficiency: not observed
Excess: not observed
Sources: liver, egg yolks, nuts, legumes, soy
 B9 - Folic Acid
Uses: cofactor for nucleic acid and heme synthesis
Deficiency: some anemias, if during pregnancy the
fetus has high probability of spina bifida
or other birth defects
Excess: possible danger for hormone related
cancers
Sources: green leafy vegetables, asparagus, organ
meats
 B12 - Cobalamin
Uses: controlling factor for pernicious anemia
Deficiency: normally rare, but with inability to
absorb (>50 and vegans)
Excess: not known
Sources: animal protein, organ meats, milk, eggs
Get your Daily ‘B – Complex’ !
 Vegans (ovo-lacto vegetarians)

• Need Vitamin B supplements containing the

cobalamin complex or take Brewers Yeast
 C - Ascorbic Acid
Uses: cofactor for collagen production, enhances
iron absorption, excellent anti-oxidant
Deficiency: scurvy
Excess: probably should avoid >1g/day (Linus
Pauling advocated up to 3g/day but no proven
benefits!)
Sources: citrus fruits, potatoes, cabbage, tomatoes
 Vitamin C - will it cure my cold?
> NO, but….30% decrease in upper respiratory
tract infections
> ~1/3 of all NA ingests Vit.C = tons!
> Loses potency when exposed to air (50% less in
your OJ after 3 weeks in fridge).
> Helps maintain other antioxidants
> Smokers need ~twice the RDI/USRDA
By 1750 it was known that weekly rations of citrus
fruit would prevent scurvy. This fact allowed Britain to
'rule the waves' and for these sailors to be called
"limeys". Not isolated until 1928.
Phytochemicals - non-nutrient compounds,
found in plant-derived foods, that have
biological activity in the body.
2009 OJ: packaging “phytonutrients!”
Antioxidants (anti-aging/cancer/heart disease?) -
catechins (berries, green/black tea), lycopene
(tomatoes,watermelon), bioflavanoids (citrus
fruit, grapes), coenzyme Q (nuts,oils).
 Formation of Vitamin D

Squalene (Cod Liver Oil)

Solar Radiation
HO

7-dehydrocholesterol,
occurs in the skin
CH2

Cholecalciferol
HO (Vitamin D3)
Vitamin A from -Carotene
CH3
CH3 CH3 CH3 CH3

CH3 CH3 CH3 CH3

CH3 -carotene
Chemical reactions
within the body

Vision: Retinals (Rhodopsin)

hv CH3
11/12 cis 11/12 trans
CH3
12

HOH2C
11
CH3 CH3
CH3

Retinol
 Plant Pigments = Potent Antioxidants

Almost 2000 known plant pigments. >800 flavonoids,

~450 carotenoids and ~150 anthocyanins.
Red(lycopene) – tomatoes, pink/red grapefruit,
watermelon, guava, red peppers.
Red/Blue/Purple(anthocyanins) – red/blue grapes,
blue-/straw-/raspberries, beets, cherries,
egg plant, plums, red cabbage.
Orange(carotene) – squash, pumpkin, yams, carrots,
mango, cantaloupe.
Colour your Nutritional World !
 Plant Pigments = Phytochemicals
Orange/Yellow(cryptoxanthin) – peach, orange,
nectarine, papaya.
Yellow/Green(lutein, zeaxanthin =
especially good for health of eyes) –
corn, cucumber skins, yellow/green
peppers, green beans/peas, spinach,
honeydew melon, kiwi, romaine lettuce,
Red, Yellow or Green – It’s all a GO !
 Had your ORAC Foods Today ?
high Oxygen Radical Absorbance Capacity foods –
the top 15(for ~100g/3.5oz)
prunes 5770 kale 1770
raisins 2830 spinach 1260
blueberries 2400 sprouts 980
stawberries 1540 broccoli 890
raspberries 1220 beets 840
plums 949 red pepper 710
oranges 750 corn 400
red grapes 739 eggplant 390
cherries 670 carrot 210
 Too Much Broccoli !
Two women with diseases characterized by
abnormal blood clotting did not improve when they
were given Warfarin. When questioned about their
diets, one woman reported that she ate at least a
pound of broccoli every day, and the other ate
broccoli soup and a broccoli salad every day. When
broccoli was removed from their diets, warfarin
became effective in preventing the abnormal
clotting of their blood. Because broccoli is high in
vitamin K, these patients had been getting enough
dietary vitamin K to compete with the drug, thereby
making the drug ineffective.
Vitamin O - the next miracle supplement!
Recipe: Take 8oz water, add a pinch of salt, bubble
in oxygen/(air?) for 15 seconds then sell
for $20(US) + shipping/handling.
Or maybe you would like to visit an 'oxygen bar'?

Get fined for US$400,000 (for 'fraudulent claims'),

change the wording and keep on selling. To-date an
estimated 1 million bottles have been sold!

Check out the ‘Net’ under ‘vitamin O’

eg. ~first 10 entries on ‘Yahoo’ or ‘Google’
 Beware the Scam!!
• Exotic berry/fruit extracts will cure all!

• Goji Juice (from the Himalayas!)

The Master Molecules in Goji Juice
 CBC “5 th Estate” Aug 31/07
• Goji juice expose!
• Cost is 50$ per liter on sale for 34.95$!
• “Dr” Earl Mindel has fake credentials
• MLM approach (Multi-layer marketing)
 Constituents of Goji Juice
• Vitamin C
• Lycopene, carotene, anthocyanine
• All good, but available from readily
available fruits/vegs at a fraction of the
price!
• Buyer beware!!
 Other exotic berries
• Now the acai berry!

• Has 10x the antioxidant properties of grapes

and 2x those of blueberries
• Used for generations by Brazilian jungle
dwellers!
 21 Chief health Benefits of Acai
• Boosts energy levels, improves digestion, improves mental
clarity, promotes sound sleep, provides all “vital” vitamins,
contains important minerals, powerful free radical fighter,
has high fibre levels, cleans and detoxifies the body,
strengthens immune system, enhances sexual desire and
performance!, fights cancerous cells, slows down aging,
promotes healthier skin, alleviates diabetes!, normalizes
cholesterol levels, maintains healthy heart function,
minimizes inflamation, improves circulation, prevents
atherosclerosis, enhances visual acuity
• WOW!!
 But………….
• Small print “none of these claims have yet
been evaluated by the US FDA”
• “provides disease fighting benefits no
Doctor wants you to know!”
 Acai Berry Products

• 60 tablets for 28.95$

• Labelling!
 Conclusions
Both goji and acai no doubt are both high on
the ORAC scale. But not miracle cures!
 The “magic” of cranberries

• Many people are allergic to antibiotics used

to treat urinary infections
• Recent Harvard Study indicates that
cranberries contain a compound that
prevents E. Coli (Common cause of UI’s)
form binding to the wall of the bladder
 Mechanism of action
• Presently under study
• But looks like Proanthocyanodins present in
cranberry juice are causing expression of
types I and P “Adhesin” , thus preventing
adhesion of E Coli.
• No drug reactions known with cranberry
juice
 A healthy way to start the day
Except……..
 Beware the grapefruit!
• Juice/fruit inhibits the action of 2 enzymes
that are required to break down/metabolize
several drugs and make them effective.

• Including BC pills, cholesterol lowering

statins, several antibiotics, Valium, Zoloft
• And possibly Viagra!
 New Fads in Drinks: 2009
• Vitamin waters $2 for 591mL
• Enough Vit. C (150mg) (RDA~60mg)
• Some of B complex present; but not B1
(thiamine ) and B2 (riboflavin);B3-B6OK
• 120 calories per bottle ( how much sugar??)
• “non-essential ingredients” water, cane
sugar, citric acid, veg juice (for colour),
natural flavor
 Hot Sellers in the Carleton
Unicentre store!
• Many flavours and more on the way!