Natural Pigments Flashcards
Food quality attributes of natural pigments
- Flavor (taste/smell)
- Texture
- Nutritive value
- Microbial load
- Color / appearance
Natural Food Pigments (8)
- Chlorophyll
- Myoglobin & Hemoglobin
- Carotenoids
- Anthocyanins
- Flavonoids
- Tannins
- Quinones & Xanthones
- Melanins & Betalains
Chlorophyll
• Plant pigment (main sources are green vegetables, root vegetables, fruits) o Mg in the center o Fat soluble o Can be destroyed by heat o Sensitive to acids and alkali o Green color o Plant sources, algae
Chlorophyll structure
tetrapyrrole
Major chlorophylls are ____
‘a’ & ‘b’ (3:1)
The proportion of a and b chlorophylls is
3:1
What colour is alpha chlorophyll
green-bluish colour
What colour is beta chlorophyll
dull green colour
Is chlorophyll water soluble or fat soluble?
fat soluble
Heme pigments are ____ and ____
hemoglobin and myoglobin
Heme pigments general features
- Responsible for red color of muscle foods;
- Complex molecule with a protein part (globin), and an essential non-protein part (heme);
- Both Mb and Hb are tetrapyrrole compounds.
Mb and Hb structure
tetrapyrrole compounds.
Is heme fat or water soluble
water soluble
What are the major food sources that contain heme
meats (beef, pork, chicken, fish)
o The pigment in the muscle is due to myoglobin, and the intensity of the color depends on the myoglobin content
Myoglobin structure
• Single polypeptide chain
• 4 N’s in the 4 pyrole molecules , covalently linked
to central Fe atom
• Fe also covalently linked to N in a histidine residue in globin (protein);
• Fe can bind electron pair donors (e.g., O2, CO, CO2, CN, etc).
Oxymyoglobin
- Bright red color of fresh meats
- Fe present as ferrous (Fe2+) form
- Mb + O2 <==> MbO2
- Mb (purple color; Fe2+)
- MbO2 (bright red; Fe2+)
What is the compound that gives the fresh color to meat?
oxymyoglobin
Metmyoglobin (Met-Mb)
- Brownish color (Fe3+)
- MbO2 <==> Mb ==> Met-Mb
- MbO2 (bright red)
- Mb (purple)
- Met-Mb (brown)
What is the compound that gives the brown color to meat?
metmyoglobin
Chlorophyll a vs. Chlorophyll b
One of the pyrroles have a methyl group = chlorophyll A
Formyl group –CHO = Chlorophyll B
What makes chlorophyll fat soluble molecule?
Fat soluble bc of the presence of the C20 carbon molecule that is attached to the chlorophyll molecule. 20C unit known as PHYTOL (300g/mol)
Phytol side chain is a hydrocarbon and highly hydrophobic, and this accounts to its insolubility in H2O, but highly solubility in lipids. – wax
What happens when the phytol group is removed form chlorophyll?
If we remove the phytol group, the molecule left behind is water soluble
How can we obtain chlorophyllide from chlorophyll and how does the color change?
loss of phytol by chlorophyllase
very bright color
How can we obtain pheophytin from chlorophyll and how does the color change?
expose it to acid and heat
loss of Mg atom
blue color
How can we obtain pheophorbide from chlorophyllide how does the color change?
expose it to acid and heat
loss of Mg atom
red color
How can we obtain pheophorbide from pheophytin how does the color change?
loss of phytol
chlorophyllase
What happens when chlorophyll is exposed to acid?
- removal of the Mg atom from the centre
- if the centre is removed then the molecule is not green anymore (brownish)
- molecule is still water soluble
- PHEOPHYTIN
Alkali/Acid conditions (chlorophyll) cause the removal of the phytol group.
Alkali
True/False
When the phytol group is cleaved, the molecule is still fat soluble.
False
When the phytol group is cleaved, it becomes water soluble.
Pheophytin can go under hydrolysis to remove the phytol group that forms a new molecule that is called __________. This molecule is also water soluble, but the magnesium is lost so this molecule has a brownish color as well.
PHEOPHORBIDE
Moist Cooking vs Dry Heat on chlorophyll
Processes such as moist cooking (blanching) can cause destruction of green color. (chlorophyll). Dry heat (microwave) on the other hand, inactivates enzymes but does not remove Mg so green color is retained
What other effects can cause color loss in chlorophyll
o Fermentation produces acids and can lead to color destruction
o Exposure to light and air can also cause oxidation and lead to color loss.
True/False
Chlorophylls are antioxidants
true
It is highly unsaturated, therefore it can function as antioxidant
Other uses of chlorophyll containing foods
food additives
mouthwash
toothpaste
The magnesium of chlorophyll helps boost the blood volume.
How does cooking affect chlorophyll?
Cooking –> pheophytins
How does dehydration affect chlorophyll?
Dehydration –> bleaching by photodegradation (lipoxidases)
How does exposure to light and 02 affect chlorophyll?
Exposure to O2&light –> bleaching
How does blanching affect chlorophyll?
Blanching –> pheophytins & phophobides
How does irradiation affect chlorophyll?
Irradiation –> degradation by peroxidation
Heme pigments are complex molecules with a protein part (______), and an essential non-protein part (______);
globin
heme
Structure of heme pigment
Both Mb and Hb are tetrapyrrole compounds.
Is Hb bigger than Mb?
o Mb < Hb
♣ 17 < 64 KDA
♣ muscle vs blood vessels
What is the central atom of heme pigments?
Both Mb and Hb are tetrapyrrole compounds. 4 pyrrole rings attached to a central atom Fe
What is the difference between a Mg central atom and a Fe central atom?
Fe, unlike Mg, can accept 6 lone pairs of electrons: 4 from N, 1 from histidine, and 1 donor (O2, CO2, CO, CN, OH)
Fe central atom can accept 6 lone pairs. What types of molecules does it accept?
can accept 6 lone pairs of electrons: 4 from N, 1 from histidine, and 1 donor (O2, CO2, CO, CN, OH)
What color is Mb?
(purple color; Fe2+)
What color is MbO2?
(bright red; Fe2+)
What color is Met-Mb
Met-Mb (brown) (Fe3+)
Phytol:
size
solubility
structure
296 kda, water insoluble, attached directly to tetrapyrrole
Globin:
size
solubility
structure
16.4 kda, water soluble, Fe
4Mb = ? Hb
1
1Hb = ? Mb
4
red meat/poultry/finish color intensity is due to the amount of Mb/Hb present
Mb
Storage of heme pigments
Storage => gradual oxidation, forming dark/brown color
Cooking of heme pigments
- denatures protein;
- oxidation of Fe2+ to Fe3+;
- formation of dark color (as in barbecued meats - pigment formed known as hemichrome)
in barbecued meats - pigment formed known as _______
hemichrome
Curing of meats with nitrites => red colored _______;
nitrosomyoglobin
cooking of cured meats denatures the protein, also Fe2+ is oxidized to Fe3+ - & brown product – ______;
nitrosohemichrome
nitrosomyoglobin
Curing of meats with nitrites => red colored
nitrosohemichrome
cooking of cured meats denatures the protein, also Fe2+ is oxidized to Fe3+ - & brown product
Give an example of a reducing agent that can prevent sulfmyoglobin formation
with –SH containing reducing agent
what do you prevent oxidation by adding reducing agents to meat?
o By adding reducing agents, it is possible to reverse the oxidation.
♣ Fe2+ Fe3+ +e- (by using cysteine cystine / glutamine (GSH) GSSG)
♣ This reverses the brownish color of Met-Mb. However, a yellowish/greenish tinge forms along edges of meat which would indicate that reducing agents have been applied to “old meat” to make it look fresh
♣ The yellowish/greenish tinge is dues to a product known as sulfmyoglobin
what color is sulfmyoglobin
The yellowish/greenish tinge is dues to a product
what does yellowish/greenish tinge along edges of meat indicate?
indicate that reducing agents have been applied to “old meat” to make it look fresh
Fe 3+ on cooked meats______
not readily absorbed through the GIT although there is the advantage of extensive denaturation to facilitate the hydrolysis as well as the destruction of harmful pathogens that may be present in the meat.
Fe2+ on rare/medium cooked meats _______
Fe2+ is rare/medium cooked meats is much more readily absorbed through the intestinal membrane into the cytosol to make more RBCs.
Use of nitrates in foods can form nitroso-amines that are considered to be ______
carcinogenic
When meats are cured with nitroso-amines, what else should be added to decrease the carcinogenic effect?
ascorbic acid/vitamin C is added to the curing brine to reduce nitrosoamines formed back to nitrates to remove the potential harm.
EXAM QUESTION
Compare chlorophyll and myoglobin
o Different sources (plant vs animal)
o Both tetrapyrrole compounds but central atoms are different (Mg vs Fe)
o Different colors (green vs red)
o Relative solubility (fat soluble vs water soluble)
o side groups attached to molecule
o both are heat sensitive
Carotenoid pigments are present in
- Present in plants, animals & microorganism
* Responsible for yellow, orange & red-orange colors in plants & animals
Animal sources of carotenoids
♣ egg yolk,
♣ milk/dairy products,
♣ shellfish
♣ salmons
Plant sources of carotenoids
♣ Fruit
♣ Vegetables
♣ Palm oil
Microbial sources of carotenoids
♣ Yeast
♣ Fungi