Lecture 2.

Food organoleptic characteristics

Color
Smell and taste Aroma
Food color and changes induced by storage and processing
❑ Color changes induced by exposure to light, air, heat
❑ Color changes as markers of loss of nutritional value of food
❑ Color changes and loss of commercial value

Lipid oxidation
Food color : green in vegetables
Coordinated
Chlorophylls Magnesium ion
Occurring in chloroplasts

Porphyrin
ring

The phytol side chain

imparts high lipophilicity Pigment class: porphyrins

R= CH3 Chlorophyll a
R=CHO Chlorophyll b

The color of chlorophylls as

markers of vegetable
freshness and maturation
stage
Color changes associated to chlorophylls instability
Chlorophylls are unstable to changes of temperature, pH and enzymes.
At acidic pHs : loss of magnesium and replacement with H atoms
with formation of pheophytin a and b (olive green in color )
e.g. induced by acid cellular fluids during heating processes
used in preparation of canned foods

Chlorophylls Pheophytins
Chlorophyllides

By action of enzymes: chlorophyllase

in vegetable tissues induces hydrolysis of
propionate with loss of phytol chain.
Formation of chorophyllides a and b
(green in color but water soluble)
Alkaline conditions: phytol hydrolysis
Food color: red in meats
Pigment class: porphyrins
Myoglobin is a cytoplasmic
protein found at high
concentrations in muscle
cells.
Is responsible for the color of
red meats
Is soluble in water and saline
solutions

Complex of globin with heme (prosthetic

group) coordinating an iron atom. The iron
in the heme is coordinated to the four
nitrogen atoms of a porphyrin and also to
a nitrogen atom of a histidine amino-acid
residue in the myoglobin (4 in-plane and 2
apical coordination sites)
The sixth coordination site around is free
and may be occupied by different ligands
Myoglobin redox states and meat color

O2

Low O2 O
High O2 H H
O O
O2, H2O N
N N N N N
Fe II Fe llI
+O2 Fe lI
N N N N
N _
O2 N
N N
O2
_ . N
His93
His93 His93

Myoglobin
mioglobina (Mb) Oxymyoglobin
ossimioglobina (MbO2) Metmyoglobin
metamioglobina (MMb)
Meat color changes associated to cooking or processing

Heating (cooking) Myoglobin is denatured by heat. His 93 is moved from the

binding site and Iron II is oxidized to Iron III by oxygen

The pale red color of

Cooked meat displays the the inner part of
color of metmyoglobin roasted meats e.g.
except for the inner parts roast beef is due to a
that are not exposed to heme variant in which
oxygen nitrogens of histidine
residues not
necessarily belonging
Cured meat to myoglobin occupy
both coordination
sites at the apical
positions of heme.

The red colour of cured meat results from reduction of nitrate and
nitrite used as additives (to inhibit bacterial and fungal growth) by
enzymes present in the tissues to nitrogen monoxide (NO). NO
coordinates to iron II in place of oxygen forming nitrosomyoglobin
a red pigment that is responsible for the color of ham and bacon.
The binding costant of NO to heme is higher than that of oxygen
and therefore the red color of cured meat is stable in air.
Food color: yellow to red in fruit and vegetables
In chloroplasts of green plant tissues and in the
chromoplasts of flower and fruits tissues
Found in animal tissues (dietary origin, metabolized)

Beta carotene 60-120

mg kg-1 in carrots
I carotenoidi.1
canarini auciello 003

Pigment class: polyenes

3'
Ranked into: 7 11 15 5'
1'
1

Carotenes 3 5
15' 11' 7'

Beta -carotene max 451 nm

Carotene (max 451 nm)
OH
Derived from carotenes
Xanthophylls oxygenation

HO Zeaxantina
Zeaxanthin
Apocarotenoids CO2 H Derived from oxidative fission of
HO2C
carotenes
Crocetina
Crocetin
Color changes associated to thermal/light instability
Carotenoids are pretty stable in the plant and animal tissues
where they occur. Further to extraction they become unstable to
heating and light that induce trans to cis isomerization with
generation of a number of isomers.
The color looses intensity and becomes dull
Klikk for å se større bilde

 20oC, ·⚫50oC; 
75oC, ◼100oC

Heating processes in
canned fruits are
associated to color
Effect of temperature on the color of  - changes
carotene (40 mg/100ml).
Color changes associated to processing 10by13_Regal-Boiled-Lobster

Astaxanthin is the carotenoid occurring in

the lobster carapace tightly embedded in a
protein matrix that masks the color.
On cooking the protein is denatured, the
carotenoid is freed and its color may be
fully appreciated

Changes associated to air oxidation

Freshly milled flour looks light yellow in color due to the presence of
carotenoids. In the presence of air, oxidation processes take place
associated with a rapid discharging of the color. On storing of the flour
hydroperoxides generated from peroxidation of lipids are able to induce
decoloration by addition to the carotenoids with breaking of conjugation of
the polyene chain.
Lipoxygenase, the enzyme that catalyses the formation of hydroperoxides
from polyunsaturated fatty acids, is used to accelerate the flour whitening
process.
Freshly milled flour
 I colori degli alimenti
Food color : red to blue in fruit and vegetables
900071

Anthocyanins occur in the vacuoles of abb_auberginen_01

plant cells and are separated from direct fiordaliso

contact with cytoplasmic enzymes.

red-cabbage-cross-section-AJHD

Glycosylation sites
1
R
ravanello

3'
OH
1 +
HO 7 O 2-phenylbenzopyrilium (flavylium)
5' R2 cation
3

5 OH Found in vegetables as glucose, rhamnose,

OH arabinose glycosides. Aglycones are termed
antocyanidins

R1 R2 max
Pelargodinin
Pigment class: flavonoids
Pelargonidina -H -H 503
Cyanidin
Cianidina -OH -H 517
Peonidin
Peonidina -OCH3 -H 517
Petunidin
Petunidina -OCH3 -OH 526
Malvidin
Malvidina -OCH3 -OCH3 529
Anthocyanins : pH dependent chromophore
Food color : red in vegetables
Le betalaine. I colori degli alimenti

Mainly in Centrospermae

HO
H
+
HO N COOH Betanidin is a most abundant
betacyanin of beet (Beta vulgaris)
occurring in the form of glucoside
betanin
H
N COOH
HOOC
H

Betanidin
Betanidina
Pigment class: betacyanins
Food aroma
Aroma or flavor is a polysensorial perception
According to the International Organization for Standardization Flavor or
Aroma is a complex combination of the olfactory, gustatory and trigeminal
sensations (touch, heat, pain, kinesthetic) perceived during tasting.
 How do we discriminate a golden delicious from a Fuji apple?

Composition w/w%
Water: 86%
Protein: 0.3 %
Carbohydrates : 13.8 %.
Sugar: 10.4 %.
Fiber: 2.4 %
Color Fat: 0.2 %
Lutein and other carotenoids Anthocyanins
And with eyes closed? The volatiles components responsible for aroma (taste and odor)
The five basic tastes and their role
The five basic tastes: the perception threshold and
reference compounds

Sweet Sour Bitter

OH HO2C-CHOH-CHOH-CO2H
Tartaric acid
O
HO
[0.00094%]
HO
OH N
HO
.H2SO4
HO O Salty H
O
NaCl MeO
OH
Sodium chloride
OH [0.0037%]
OH N
Quinine sulfate
Sucrose
[0.000049%]
[0.086%]
Umami
NaO2C CO2

H3N H
Mono sodium L-
glutamate
[0.012%]
[ ] = perception threshold in water [w/v]
 Sweet Sweet molecules of natural origin

Carbohydrates
Mono and disaccharides are usually sweet but with large difference in the intensity

SUCROSE GLUCOSE GALACTOSUCROSE

(i.e. C-4 epimer of sucrose )
(1x) (0.6x) (lightly sweet )
OH
OH

OH O
OH O
HO
HO
HO H
HO OH

OH
H
-D-mannose (sweet) -D-mannose (bitter)
(determined on glycosides) (n.x) = sweetness with respect to sucrose
 Sweet molecules of natural origin

-AMINOACIDS
L- D- L- D-

Triptophan B S (35x) Isoleucine F (or B) F (or S)

Phenylalanine B S (7x) Lysine F (or B) F (or S)

Tyrosine B S (6x) Proline F F

Hystidine B S (7x) Serine F (or S) F (or S)

Leucine B S (4x) Threonine F (or S) F (or S)

Glycine S (1.5x) Valine F (or B) F (or S)

Glutamic
Alanine S(1.5x) B U F
Acid
S Aspartic U
Arginine F (or B) F
(sligthly) Acid (sligthly)

S= sweet B= bitter F= flat U= umami

 Bitter molecules of natural origin
OH
OH O OH
RO O

OH NARINGIN
(Citrus paradisi)
OH O 1:10 000
H R= rutinose
O OH

HO
HO
ALOINS A or B
OH
(Aloe ferox, Aloe vera)

N
N

CAFFEINE
O N N (Coffea arabica)
Sweet taste structural requirements

SHALLENBERGER–ACREE MODEL(1967)
Two interaction sites

B' RECEPTOR
A H
SWEET
B’ and A’H are the groups on the protein receptor.
MOLECULE
2.5-4.0 Å Their distance should be similar to that of B and AH
B A' If closer AH e B would hydrogen bond to each
H other rather than with the receptor
Glycophore
H
A--H+ = electronegative group ;
H
CH2OH O CH2OH O
HO H HO OH
OH OH H
Hydrogen donor HO
H
OH AH,B HO H
AH,B
H H
B = electronegative group; hydrogen H H

acceptor
(B) -D-glucopyranose
-D-Glucopiranosio -D-fructopyranose
-D-Fruttopiranosio

(AH) O
H R
Cl
+ O
H2N NH2
_ N H
H O
S (AH)
H

- N+ O O
(AH) (B) O O
(B)
(AH)
saccharin
D-−D--Amminoacidi
aminoacids m-Nitroaniline
m-nitroaniline Saccarina
(B)
Sweet taste structural requirements

KIER’S THEORY (1972)

Three interaction sites

X X = third bonding site; hydrophobic

interaction based on dispersion forces

~ 5.5 Å Sodium cyclamate

~ 3.5 Å
~ 3.5 Å
SODIUM CICLAMATE
AH ~ 2.6 Å
B (X) (AH)
H (B)
N
CH3
H3C X O Na
X CH S
CH H2C CH3 O
H3C CH2 H H
C O
C
L-leucin +
L-Leucina -OOC NH3
D-leucin
D-Leucina
-OOC
+
NH3 Bitter
(amara)
Sweet
(dolce)
AH B
AH B

≡
Sweet/bitter taste structural requirements

WIESER and BELITZ THEORY (1975)

Two interaction sites (AH, X)

BELITZ (1979)

Hydrophobic contact zone Hydrophobic L- +y

aminoacids are bitter -z
X' ZONE

X sweetness
H
B
R H2C CO2 +x
-x

NH3 Gruppo AH
AH

+z -y

If X is in aregio where x or z <0→ bitter

Sweet/bitter taste structural requirements

Okai unified sweet/bitter taste receptor model

X’ X’ X’

X X X

AH AH B B
B’ A’H B’ A’H B’ A’H
A’ B’

sweet/bitter
bitter sweet inhibitor
 Gli aromi degli alimenti
Umami
From japanese umai=
delicious
FOOD with UMAMI Taste
Beef, pork, chicken meat, ham, sausages

Fish;

Seafood ;

Cheese (parmisan, emmental);

Mushroom;

Tomato
 Gli aromi degli alimenti

UMAMI compouds
GRUPPO MSG
H CO2 H3N H CO2

H3N H
CO2 Na
O O
H
NH NH
CO2 NH3 a non-proteinogenic amino acid
O found in some
O mushrooms
Monosodium Glutamate (MSG) L-Tricholomic Acid L-Ibotenic Acid
(1x) [ 0.012%] (5x) [ 0.03%] (5x) [ 0.03%]
(n.x) = taste enhancer
[%] = perception threshold of the sodium
salt (w/v) From dried fish
5’-RIBONUCLEOTIDES
O
N
OH

O P OH
NH
N
O
O N
X X=H → 5’-inosine monophosphate (IMP) [0.015%]
HO OH X = NH2 → 5’-guanosine monophosphate (GMP) [0.015%]
Synergistic effect of umami taste compounds

MSG + IMP and/or GMP Contents of umami compounds in food

10 MSG + 1 IMP = 55 MSG IMP GMP MSG
10 MSG + 1 GMP = 209 MSG mg per 100 g
Parmisan cheese 1200
Sardines 193 280
Tuna 188
Tomato 260
S. Yamaguchi, K. NinomiyaThe Shitake mushroom 30 67
Use and Utility of Glutamates as Shrimps 92 43
Flavoring Agents in Food Pork 122 3 23
Umami and Food Palatability Cod 44 9
Salmon 20
Human milk 22
Cow milk 2
Food additive 20-80

Origin of umami compounds

The levels of MSG in muscle fibers greatly
increase in meats during meat maturation. Inosine monophosphate (IMP) is
generated by degradation of AMP
that in turn derives from ATP

-fosfato -fosfato -NH3

ATP ADP AMP IMP
[O]
Salty
It is associated to many inorganic salts.
Alkaline metals halides: if the sum of the radii of the ionic species is less than KBr salty is the
prevailing taste, e.g. NaCl, if higher the main taste is bitter as for MgCl2 .

Sour
Typical of low pH solutions. The taste is typically associated to
the organic acids in the non-ionized forms
H2C COOH Malic acid H3C COOH

HO C COOH Acetic acid

COOH
H2C COOH
H C OH
Up to 5% in vinegar
Citric acid CH2

COOH

Organic acids content in fruit juices

COOH Acid content (mmol dm-3)
Sodium lactate confers a
HC OH Malic Citric Tartaric
salty/ vinegarish taste to Orange 13 51 -
CH3 fries and other snacks. Grapefruit 42 100 -
Lemon 17 220 -
Lactic acid Grape 7 16 80
 THE TASTE CELLS

SALTY/SOUR

Salty and acid tastes are mediated by SWEET

ionic channels, while other tastes (sweet,
bitter, umami) are mediated by binding to
specific receptors coupled to G-proteins.
Transduction of the sweet/bitter taste

sweet or
bitter - Metabotropic glutamate
molecule K+ Na+ Ca++
receptor (mGluR)

- Taste receptors (TnRm)

Receptor Cell n=1→ sweet (and umami)

Membrane receptors
Close K+ Open Na+ Open Ca++ n=2→ bitter receptors
channel channel channel

Gustducin Release
G-protein stored Ca++
transducin

Second
Enzyme Messenger

Adenylyl cyclase → synthesis of cAMP

Phosphodiesterase → breakdown of cAMP or cGMP
Phospholipase C → release of IP3+diacylglicerol
Food odor

Odorant perception occurs primarily

in the olfactory epithelium via the
Olfactory mature olfactory sensory neurons
bulb (OSN).

Olfactory OR
epithelium
Cilia

Air

Turbinates OSN

Osmophores: the unit, group of atoms in a molecule capable of stimulating

olfactory receptors (OR)
Odor code: More than 350 genes encode for human odor receptors. Actually the
odors that can be perceived are much more than 350 as each
volatile is able to interact with different receptors and combination of
receptors. It has been estimated that human beings can perceive
more than 1000 different odors but recent studies hint to a much
larger number .
Odour clusters The 10 fundamental odors

10 basic odour clusters have been

identified .

Smells can be lumped into one of ten

categories which include citrus, mint,
pungent and decaying.

Combination of the 10 fundamental

odors leads to the definition of the
ODOR SPACE

Perspective:
to predict smell looking at chemical
structures of the odor components

Castro JB, Ramanathan A, Chennubhotla CS (2013)

Categorical Dimensions of Human Odor Descriptor
Space Revealed by Non-Negative Matrix
Factorization. PLoS ONE 8(9): e73289.
https://doi.org/10.1371/journal.pone.0073289
 Somatosensorial perceptions

• Tactile sensitivity: perception of hard or smooth on the tongue

• Kinestetic sensitivity: perception of the texture, stiffness, elasticity,
adhesiveness
• Trigeminal sensitivity (chemestesis): perception through stimulation of
receptors other than smell or taste receptors
Astringency
Tactile sensitivity due to the stimulation of mechanoreceptors due to
Metal cation salts (e.g. aluminium salts)
Mineral and organic acids
Dehydrating agents like ethanol or acetone
Tannins (catechins)

Epigallocatechin gallate:
the most abundant catechin of tea

Astrigency is perceived in all mouth not only tongue. It is a

main determinant of wine or tea taste due to the presence
of tannins
Spicy/hot
Compounds giving hot/spicy perception are
typically found in Cruciferae

Red pepper Capsicum Active compounds are capsacinoids,

frutesens. the main is capsaicin

H Featuring a
N vanilloid moiety
O
OH
OMe
Capsaicin

Capsaicin is able to interact with sensorial neurons. Having a vanilloid

moiety can bind to the vanilloid receptor 1 (VR1). This a ionic channel
type receptor that can be stimulated also by heat and mechanical
abrasion allowing the transit of cations though the cellular membrane.
The resulting neuron depolarization starts the signalling to the brain
 Spicy/hot

Cauliflower, Bruxel sprouts, radishes belonging to the Brassicaceae

contain glycosinolates.

When vegetable tissues

are cut (or chewed) the
cytoplasmatic
myrosinase gets into
contact and hydrolyses
the S-glucosides leading
to thiohydroxamic acid
O-sulphate. This latter
decomposes to a variety
of metabolites including
isothiocyanates that are
responsible for the
pungent odor and taste

Chemopreventive action against colon

tumor