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property of being soluble in non-polar solvents. They are grouped together not by the presence of a
distinguishing functional group or structural feature, but rather on the basis of common solubility properties:
*
they are insoluble in water but highly soluble in one or more organic solvents.
*
- although certain lipids contain ionized groups (e.g., phosphate or choline), the bulk of any lipid
molecule is nonpolar
- widely distributed in biological world and play a wide variety of roles in both plant and animal tissues:
o as an energy source, lipids provide 9 kcal of energy per gram
o triglycerides provide energy storage in adipocytes
o phosphoglycerides, sphingolipids, and steroids are structural components of cell membranes
o steroid hormones are critical intercellular messengers
o lipid-soluble vitamins (A, E, D, K)
o dietary fat acts as a carrier of lipid-soluble vitamins into cells of small intestine
o provide shock absorption and insulation
- the primary form of energy storage; stored fat allows certain animals to hibernate during winter
- has a very high energy value, twice as much as an equal weight of carbohydrates
- the amount of fat in the body is very much related to the carbohydrate level in the body: when
carbohydrate levels become low, fats are degraded to provide energy; when high, fats are stored
in cells of adipose tissues (under the skin, around the kidneys, etc.)
- structurally, the lipids are quite diverse; there is no common subunit in their structure.
- the primary building blocks in human lipids are fatty acids, glycerol, sphingosine, and sterols.
CLASSIFICATION OF LIPIDS
3.1 Fatty Acids 3.4 Complex lipids
3.2 Glycerides 3.4.1 Phospholipids
3.2.1 Neutral glycerides (TAG) 3.4.2 Glycolipids
3.2.2 Phosphoglycerides (lecithins, cephalins) 3.4.3 Lipoproteins
3.3 Nonglycerides 3.5 Miscellaneous Lipids
3.3.1 Waxes 3.5.1 Terpenes (carotenes)
3.3.2 Sphingolipids 3.5.2 Fat-soluble vitamins
a. sphingomyelin
b. glycolipid (cerebrosides)
c. ganglioside
3.3.3 Steroids
a. sterols c. sex hormones
b. bile acids/bile salts d. adrenocortical hormones
Classification of lipids on the basis of polarity and type of structural subunits present
A. Nonpolar, fatty-acid containing lipids (TAG: fats, oils)
B. Polar, fatty-acid containing lipids
a) Phosphoacylglycerols (lecithins, cephalins)
b) Sphingolipids (sphingomyelins, cerebrosides)
C. Non-fatty-acid containing lipids
Steroids: cholesterol, bile salts, steroid hormones (sex hormones, adrenocortical hormones)
unsaturated fatty acids : (up to six double bonds are found in biochemically important fatty acids)
∆9
16:1 palmitoleic cis-9-hexadecenoic acid C15H29COOH
∆9
18:1 oleic cis-9-octadecenoic C17H33COOH olive, corn
∆9,12
18:2 linoleic cis,cis-9,12-octadecadienoic C17H31COOH soybean,
safflower, sunflower
∆9,12,15
18:3 linolenic all cis-9,12,15-octadecatrienoic C17H29COOH herring, linseed
∆5,8,11,14
20:4 arachidonic all cis-5,8,11,14-eicosatetraenoic C19H31COOH
∆5,8,11,14,17
20:5 EPA
∆4,7,10,13,16,19
22:6 DHA
essential fatty acid is a PUFA that is needed by the human body and that must be obtained from dietary
sources because it cannot be synthesized within the body from other substances. Linoleic and linolenic acids
are called essential fatty acids that must be supplied in the diet.
2
- Linolenic acid is the primary member of the ω3 family of fatty acids. From dietary linolenic acid, the body can
make the 20- and 22- carbon members of the ω3 fatty acid series. Omega-3 fatty acids are important for
the structure and function of cell membranes, particularly in the retina of the eye and the CNS. Because
fish are a good ω3 fatty acid source, nutritionists recommend adding more fish to the diet; cold-water fish
tend to have higher ω3fatty acid concentrations than do warm-water fish.
- Linoleic acid is the primary member of the ω6 family of fatty acids. Given dietary linoleic acid, the body can
make necessary longer carbon-chain members of the ω6 fatty acid series such as arachidonic acid (20:4).
Normally, vegetable oils and meats supply enough linoleic acid to meet the body’s needs for it. Omega-6
fatty acids are important for growth, skin integrity, fertility, and maintaining red blood cell structure. Lack
of linoleic acid causes the skin to redden and become irritated. Infants have especial need for linoleic acid
for their growth. Human breast milk has a much higher percentage of it then cow’s milk.
- Arachidonic acid, a 20:4 fatty acid, is an ω6 fatty acid synthesized from linoleic acid. In the body, it serves as the
precursor for a family of molecules called eicosanoids, which are oxygenated derivatives of this acid.
Eicosanoids are present in all cells except the red blood cells. Eicosanoids regulate a wide range of body
functions including blood pressure, blood clotting, blood lipid levels, the sleep/wake cycle, and the
inflammation response to injury and infection
- Eicosanoids are hormone-like molecules; they are not transported in the bloodstream to their site of action but
rather exert their effects in the tissues where they are synthesized. The name eikosanoid is derived from
the Greek word eikos, meaning twenty, because they are all derivatives of 20 carbon fatty acids. The
eicosanoids include three groups of structurally related compounds: the prostaglandins, the leukotrienes,
and the thromboxanes
3
Biological processes regulated by eicosanoids
1. Blood clotting - Thromboxane A2 stimulates constriction of blood vessels and platelet aggregation;
Prostacyclin dilates blood vessels and inhibits platelet aggregation
2. Inflammatory response - Prostaglandins mediate aspects of inflammatory response
3. Reproductive system - Stimulation of smooth muscle by PGE2
4. Gastrointestinal tract - Prostaglandins inhibit gastric secretion; Prostaglandins increase
secretion of protective mucus; Inhibition of hormone-sensitive lipases
5. Kidneys - Prostaglandins dilate renal blood vessels; Results in increased water and electrolyte
excretion
6. Respiratory tract - Leukotrienes promote the constriction of bronchi; Prostaglandins promote
bronchodilation
b) mixed triglyceride
- contain 2 or 3 different fatty acid components; most fats and oils are mixed TAG
e.g., CH2-O-COC17H33
CH–O-COC11H23
CH2-O-COC15H31
Glyceryloleolauropalmitate
Fats vs. Oils
- fats contain a greater proportion of saturated fatty acids than unsaturated fatty acids; so solid or semi-
solid at room temperature; beef tallow and pork lard are fats
- oils contain a greater proportion of unsaturated fatty acids than saturated fatty acids; so liquid at same
temperature; soybean oil, canola oil, peanut oil
4
- coconut oil, which is highly saturated, is an exception: this oil is a liquid not because it contains more
double bonds within the fatty acids but because it is rich in shorter-chain fatty acids, particularly lauric
acid (12:0)
- lipids obtained from animal sources are usually solids whereas oils are generally of plant origin. Hence,
we commonly speak of animal fats and vegetable oils .
5
4) Rancidity
- the development of disagreeable odor
- a fat or oil becomes rancid when its double bonds are oxidized by oxygen and lipases furnished by
microorganisms in the air forming short-chain fatty acids and aldehydes as products which have
disagreeable odor; also responsible for the odors associated with workouts and heavy perspiration
- oxidation also occurs in the oils that accumulate on the surface of the skin during heavy exercise. The
relatively high body temperature and the presence of microorganisms on the skin promote rapid
oxidation of these oils as they are exposed to oxygen and water
a) hydrolytic rancidity
* under moist and warm conditions, microorganisms in the air furnish the lipases that catalyze the
process; hydrolysis of ester linkages occurs, liberating the volatile, low mol. wt. acids (e.g., butyricacid
from rancidity of butter)
* prevented by storing butter covered in a refrigerator
b) oxidative rancidity
* occurs in triglycerides containing unsaturated fatty acids
* highly unsaturated oils react with oxygen forming aldehydes and acids
* antioxidants may be used like Vit. E, ascorbic acid, BHA, BHT
[O] O | [O] | |
-CH=CH- -C-H + H-C=O HO-C=O + HO-C=O
Fat Substitute
Olestra (also known by its brand name Olean) is a fat substitute that adds no fat, calories, or
cholesterol to products. It has a sucrose base instead of the alcohol base of fat. Compared with conventional
fats, which have up to three fatty acids attached to the base, olestra has between six and eight fatty acids
attached to alcohol groups. These groups hang from a ring of sucrose molecules. The ring is completely
impenetrable to fat-removing enzymes and therefore remains indigestible, contributing zero calories. It has
been used in the preparation of traditionally high-fat foods such as potato chips, thereby lowering or
eliminating their fat content. In the late 1990s, Olestra lost its popularity due to side effects (cramping,
flatulence, loose bowels, diarrhea), but products containing the ingredient can still be purchased at grocery
stores.
6
Soaps and Detergents
Soaps are sodium or potassium salt of long-chain fatty acids; potassium soaps are more expensive but
produce a softer lather and are more soluble, used in liquid soaps and shaving creams.
- +
Soap molecule structure, CH3(CH2)16COO Na , is composed of a large nonpolar hydrocarbon portion
(hydrophobic) and a carboxylate salt end (hydrophilic)
The cleansing action of soap: (emulsification and lowering of the surface tension of water)
When soap is added to water, the hydrophilic ends of the molecules are dissolved, but the
hydrophobic ends are not and consequently form a thin film (suds) on the surface of water. When this soap
solution is brought into contact with grease or oil (most of the dirt is held to clothes by a thin film of grease or
oil), soap molecules become reoriented. The hydrophobic portions dissolve in the grease or oil and the
hydrophilic ends remain dissolved in water. Mechanical action, such as scrubbing, causes the oil or grease to
disperse into tiny droplets, and soap molecules arrange themselves around the surface of the globules forming
micelles which don’t coalesce because of repulsions between their surrounding carboxylate groups. The entire
micelle becomes water-soluble which may be washed away by a stream of water.
7
3.2 2 Phosphoglycerides (glycerophospholipids, or phosphatides)
phospholipid is a more general term
- a group of lipids containing a phosphate group; found in all living organisms; abundant in the liver,
brain, & spinal tissue and are found in the outer membranes of most cells
- contain acyl groups derived from long-chain fatty acids esterified at C1 and C2 of glycerol-3-P
- the simplest phosphoglyceride contains a free phosphoryl group and is known as phosphatidate
- when the phosphoryl group is attached to another hydrophilic group, a more complex phospho-
glyceride is formed.
e.g. phosphatidylcholine (lecithin) & phosphatidylethanolamine (cephalin)
- two of the common PL found in membranes; primary function is to act as emulsifying agent at cell
membrane surfaces since it contain both a polar and nonpolar component
- their bipolar nature is central to the structure and function of cell membranes
a) lecithin (phosphatidylcholine)
o +
- contains choline, a 4 ammonium salt, HOCH2CH2 N(CH3)3, joined to a H3PO4 residue by means of an
ester linkage
- the N in choline carries a formal positive charge and the phosphate a negative charge so that in
solution, at most pH values, lecithin exists as an internal salt or ZWITTERION
- pure lecithin is especially abundant in eggyolk and soybeans, wheat germ and yeast; also found in
brain and nervous tissue
- excellent emulsifiers and for this reason eggyolk is an excellent emulsifier to hold olive oil and water
together as mayonnaise; emulsifying agent (aids in the suspension of fats in water) in ice cream
- claims arise that lecithins should be taken as a nutritive supplement; some claims indicate it will
improve memory. There is no evidence that these supplement s are useful. The enzyme lecithinase in
the intestine hydrolyzes most of the phosphatidylcholine taken orally before it passes into body fluids,
so it does not reach body tissues. The phosphatidylcholine present in membranes is made by the liver;
thus phophatidylcholines are not essential nutrients.
8
b) cephalin (phosphatidylethanolamine or phosphatidylserine)
- the term is derived from its chief occurrence in the body, namely the head, & spinal tissue (Greek,
Kephalikos, head); found in heart and liver tissue and in high concentrations in the brain.
- in cephalins, the choline is replaced by ethanolamine, H2N-CH2CH2OH, (phophatidyl ethanolamine) or
by the amino acid serine, H2N-CH(CH2OH)-COOH, (phosphatidyl serine)
- play an important role in the process of blood clotting
- paraffin wax is different because it is merely a mixture of hydrocarbons and is not an ester.
3.3.2 sphingolipids
- derived from sphingosine, an 18-carbon unsaturated amino dialcohol
- can be regarded as derivatives of ceramide (core of each type of sphingolipid), a compound consisting
of sphingosine and a fatty acid
CH3(CH2)12CH = CH – CH – OH
|
H2N – CH
|
Sphingosine CH2OH
a) sphingomyelin
- the white matter of the myelin sheath, a coating surrounding the nerve cells that increases the speed
of nerve impulses and insulates & protects the nerve cells
- located throughout the body but function principally in brain and nerve tissue; found in all cell
membranes and are important structural components of the myelin sheath that surrounds and
insulates cells of the central nervous system. Their role is essential to proper cerebral function and
nerve transmission.
- may also be classified as phospholipids since they contain phosphate group
9
b) glycolipids (cerebrosides)
- occur primarily in the brain (7% of the solid matter) and in the myelin sheath of nerves
- composed of sphingosine, a fatty acid, and a sugar moiety; galactocerebrosides are almost entirely
found in the cell membranes of brain; various members of the class differ only with respect to their
constituent fatty acid
c) gangliosides
- similar to cerebrosides but contain oligosaccharide groups with one or more sialic acid residues.
- important in cell membranes as receptors for hormones, viruses, and several drugs
a) sterols
- steroids containing one, two, or three double bonds and one or more hydroxyl groups
- differ from other lipids in that they do not undergo saponification
e.g., cholesterol
- best known and most abundant (about 240 kg) steroid in the body; high occurrence in the brain and
nervous tissue; the principal constituent of gallstones from which it can be isolated as a white
crystalline solid. Its name is derived from this source (Greek, chole – bile; steros – solid)
- found in the membrane of most animal cells; readily soluble in the hydrophobic region of membranes
and is the principal membrane lipid involved in regulation of the fluidity of the membrane.
- Cholesterol plays a vital biochemical role in chemical synthesis within the human body; it is the
starting material for the synthesis of numerous steroid hormones, vit. D, and bile salts; its presence in
the body is essential to life
- Cholesterol is not necessary in the diet. The human body, mainly within the liver, synthesizes about 1
gram of cholesterol each day, an amount sufficient to meet the body’s biosynthetic needs.; when it is
ingested, the amount synthesized by the body is reduced; however, the reduction is less than the
amount ingested so that the body cholesterol level increases with dietary cholesterol level.
- Medical science now considers high blood cholesterol, along with high blood pressure and smoking, as
the major risk factors for cardiovascular disease (CVD). High blood cholesterol contributes to
atherosclerosis, which is characterized by the buildup of plaque along the inner walls of the arteries.
Plaque is a mound of lipid material mixed with smooth muscle cells and calcium; much of the lipid
material in plaque is cholesterol. Cholesterol, in combination with other substances, appears to coat
the arteries, resulting in a narrowing. As this narrowing increases, more and more pressure is
necessary to ensure adequate blood flow. The pressure in the blood vessels increases, and high blood
pressure (hypertension) develops. Hypertension is also linked to heart disease.
11
b) bile acids/ bile salts
- salts of bile acids are the most important constituents of human bile; bile is produced by the liver,
stored in the gall bladder, and secreted into the intestine
- a bile salt is an emulsifying agent that makes dietary lipids soluble in the aqueous environment of the
digestive tract; main function is to facilitate the absorption of fats through the wall of the intestine
- cholic acid is the most abundant bile acid
- bile salts are cholesterol oxidation products where cholesterol is oxidized to carboxylic acid which is
then bonded to an amino acid by amide linkage; the two principal bile salts are sodium glyocholate
(glycine is the amino acid) and sodium taurocholate (taurine is the amino acid).
c) steroid hormones
- a hormone is a chemical messenger secreted by specific glands and carried by the blood to a target
tissue, where it triggers a particular response. Hormones serve as a means of communication between
various tissues; hormones, together with the central nervous system(CNS), are the regulators of body
reactions like metabolism, growth and development, etc.
adrenocortical hormones
- produced by the outer part, or cortex, of the adrenal glands, small organs on top of each kidney
- regulate numerous biochemical processes in the body; effect the metabolism of foodstuffs and control
+ +
inflammation and allergies (glucocorticoids); maintain the proper balance of electrolytes Na and K
ions in cells (mineralocorticoids)
- adrenal hormones are widely used in the treatment of rheumatic fever and rheumatoid arthritis.
sex hormones
a. androgens - the male sex hormones, the most important is testosterone; synthesized in the testes and
o o
adrenal cortex; regulate the development of 1 and 2 male sex characteristics
b. estrogens - the female sex hormones; synthesized in the ovaries and adrenal cortex; regulate the
o o
development of 1 and 2 female sex characteristics and for regulation of the menstrual cycle; also
stimulate the development of the mammary glands during pregnancy and induce estrus (heat) in animals.
c. progestins - the pregnancy hormones; for normal pregnancy; produced in the ovaries and in the placenta,
it is responsible for both the successful initiation and completion of pregnancy;
it prepares the lining of the uterus (endometrium) for implantation of the ovum. Once the egg is attached,
progesterone is involved in the development of the fetus and also plays a role in the suppression of further
ovulation during pregnancy
Estradiol Testosterone
(the principal estrogen; (the principal androgen; (the principal progestin;
for female sex characteristics) for male sex characteristics) for normal pregnancy)
12
- increased knowledge of the structures and functions of sex hormones has led to the development of a
number of synthetic steroids; among the best known are oral contraceptives and anabolic agents.
- anabolic steroid abuse can result in a wide range of harmful side effects including some that are
physically unattractive such as acne and breast development in men; the side effects can also be life-
threatening, such as liver cancer and heart attacks.
3.4 COMPLEX LIPIDS (lipids that are bonded to other types of molecules)
3.4.1 phospholipids
- see phosphoglycerides, & sphingomyelin;
- fatty acids, glycerol, H3PO4 and a nitrogenous base on hydrolysis
3.4.2 glycolipids
- see cerebrosides, & gangliosides; fatty acids, sphingosine, and a carbohydrate on hydrolysis
3.4.3 lipoproteins
- responsible for the transport of other lipids in the body; lipids are only sparingly soluble in water, and
the movement of lipids from one organ to another through the blood stream requires a transport
system that operates via plasma lipoproteins
- lipoprotein particles consist of a core of hydrophobic molecules such as triglycerides or cholesterol
esters (cholesterol esterified to fa’s). The shell around the core consists of polar lipids and proteins
14
Small carbohydrate molecules are also components of cell membranes. They are found on the outer
membrane surface covalently bonded to protein molecules (a glycoprotein) or lipid molecules (a glycolipid).
They function as markers, substances that play key roles in the process by which different cells recognize each
other.
15
Saponifiable and Nonsaponifiable Lipids
- saponifiable lipids produce fatty acids upon treatment with NaOH
- include fats/oils, waxes, phospholipids (glycerophospholipid, sphingolipid), and glycolipids
- nonsaponifiable lipids include steroids and terpenes, can’t be hydrolyzed by NaOH
a) Vitamin A (retinol)
- a primary alcohol of molecular formula C20H30O; occur only in the animal world, where the best
sources are cod-liver oil and other fish-liver oils, animal liver and dairy products
- provitamin A is found in the plant world in the form of carotenes. Provitamins have no vitamin
activity; however, after ingestion in the diet, β-carotene is cleaved at the central carbon-carbon double
bond to give 2 molecules of Vit. A.
- the major action of Vit. A is probably on epithelial cells, particularly those of the mucous membranes
of the eye, oral cavity, digestive, respiratory, reproductive and genitourinary tracts. Without adequate
supplies of vitamin A these membranes become hard and dry (keratinized)
16
- though harmless, excessive β-carotene ingestion makes the skin yellow or orange. In distinction to
observation in cases of jaundice, the sclera remains white
- Vit. A (retinol) is oxidized to retinal, or vitamin A-aldehyde, which combines with opsin, a protein, to
form rhodopsin, the light-seeing pigment in the retina.
- most obvious effects of vit. A deficiency is on the eye. The cells of the tear glands become keratinized
and stop secreting tears, & the external surface of the eye becomes dry, dull, and often scaly. Without
tears to remove bacteria, the eye is susceptible to serious infection, which if not treated on time,
blindness results xerophthalmia
- a less serious condition is night blindness, the inability to see dim light or to adapt to subdued light
- pigment in the skin, 7-dehydrocholesterol, is a provitamin D; when irradiated by the sunlight becomes
converted to Vit. D3
- humans exposed to sunlight year-round do not require dietary Vit. D
c) Vitamin E
- a group of about seven compounds of similar structure; of these, α-tocopherol has the greatest
potency; tocopherol Greek, promoter of childbirth; the antisterility vitamin
- functions in the body as an antioxidant in that it inhibits the oxidation of unsat’d fatty acids by O2
17
- occurs in fish oil, cottonseed and peanut oil, green leafy vegetables; the richest source is wheat germ
oil
α-tocopherol
d) Vitamin K
- essential for the synthesis of prothrombin in the liver; the antihemorrhagic vitamin
Vitamin K2
(n may be 5, 6, or 8)
18
19
20
Lipids
CHEM2N LAB CLASS BSN1
Presented by
• Delta Nomenclature
/ C – SYSTEM
Fatty Acid Notation
• Omega
Nomenclature/ n-
system
Table 20.1, p.496
Fatty Acids
Melting COOH
Carbon Atoms/ Common Point COOH
Double Bonds* Name (°C)
Saturated Fatty Acids
COOH
12:0 Lauric acid 44
14:0 Myristic acid 58
16:0 Palmitic acid 63
18:0 Stearic acid 70
20:0 Arachidic acid 77
Unsaturated Fatty Acids
16:1 Palmitoleic acid 1
18:1 Oleic acid 16
18:2 Linoleic acid -5
18:3 Linolenic acid -11
20:4 Arachidonic acid -49
Packing of Saturated vs Unsaturated Fatty Acids
• Phospholipids
• Glycolipids
• Lipoproteins
• Phospholipids
– contain an alcohol, two fatty acids, and a phosphate
Complex Lipids ester
– in glycerophospholipids, the alcohol is glycerol
– in sphingolipids, the alcohol is sphingosine
Membrane bilayer
• Hydrophilic head outside
• Hydrophobic tails inside
Simple lipids Complex lipids found in membranes
O CH -
oleic acid O
-
O CH2 -O-P-O
O
– Fatty acid attached to C-2 is always unsaturated
– Can also add small alcohol to the phosphate to
make a glycerophospholipid
Glycerophospholipids
Name of
Name and Formula Glycerophospholipid
ethanolamine cephalin
HOCH2CH2 NH2
choline lecithin
+
HOCH2CH2 N(CH 3)3
serine cephalin
-
HOCH2CHCOO
+
NH3
inositol OH phosphatidylinositol
OH
HO OH
HO OH
Sphingolipids
• Found in the myelin sheath of
nerve axons
– Sphingomyelin deterioration found in
MS
• Contain sphingosine, a long-chain
aminoalcohol
(CH 2 ) 12 CH 3 (CH 2 ) 12 CH 3 (CH 2 ) 12 CH 3
HO HO O HO O
N H2 N HCR N HCR
O- +
OH OH OPOCH 2 CH 2 N(CH 3 ) 3
Sphingosine A ceramide
O
(an N-acylsphingosine)
A sphingomyelin
Glycolipids
• Glycolipid: complex lipid that contains a sugar
– Sugar is glucose or galactose
– Cerebrosides found in brain and nerve synapses
(CH2 ) 12CH 3
a ceramide
a unit of
b-D-glucopyranose HO O
H OH NHCR
HO
HO O
HO a b-glycosidic bond
H
OH
H H
Transport of Lipids
• Lipoproteins
– Classified by their density and function
Lipoproteins
• Cholesterol, along with fats, are transported
by lipoproteins
Composition (% dry weight)
Cholesterol Phospho- Tri-
Lipoprotein Proteins and esters lipids glycerides
High-density 33 30 29 8
lipoprotein (HDL)
Low-density 25 50 21 4
lipoprotein (LDL)
Very-low density 10 22 18 50
lipoprotein (VLDL)
Chylomicrons 1-2 8 7 84
• Cholesterol forms plaque
deposits on inside of blood
vessels (atherosclerosis)
• Narrows blood vessel
diameter
• Lowers blood flow
• Can lead to heart attack,
stroke, kidney disfunction or
other problems
Derived Lipids
• Steroids
• Terpenes
• Eicosanoids
• fat soluble vitamins
Steroids
• Steroids: a group of plant and animal lipids that have a
steroid ring structure
C D
A B
Cholesterol
• Cholesterol is the most abundant steroid in
the human body, and also the most
important
– Component in animal plasma membranes
– Precursor of all steroid hormones and bile acids
HO
Steroid Hormones
• Androgens: male sex hormones
– synthesized in the testes
– responsible for the development of male secondary sex
characteristics
H3 C OH H3 C O
H3 C H3 C
O HO
Testosterone Androsterone
Steroid Hormones
• Among the synthetic anabolic steroids are
H 3C CH3 H3 C OH H3C O
OH
H3 C
H3 C CH 3 H3 C
O O O
Methandienone Methenolone 4-Androstene-3,17-dione
Steroid Hormones
• Estrogens: female sex hormones
– synthesized in the ovaries
– responsible for the development of female
secondary sex characteristics and control of
the menstrual cycle
CH 3
H3C C=O H3C OH
H 3C
O HO
Progesterone Estradiol
Steroid Hormones
• Progesterone-like analogs are used in oral contraceptives
CH3
N
H3 C OH
H3C C CCH3
"Nor" refers to
the absence of a
methyl group here H C OH
3 C CH
O
Mifepristone
(RU486)
O
Norethindrone
Steroid Hormones
• Glucorticoid hormones
– synthesized in the adrenal cortex
– regulate metabolism of carbohydrates
– involved in the reaction to stress
CH 2 OH
– decrease inflammation OH
O C=O
CH
H3 C H
H H
O
Aldosterone
Bile Salts
• Bile salts, the oxidation products of cholesterol
– synthesized in the liver, stored in the gallbladder,
and secreted into the intestine where they emulsify
dietary fats and aid in their absorption and digestion
O O
HO NH HO NH
COO-
2-
SO3
HO OH HO OH
Glycocholate Taurocholate
(from glycine) (from taurine)
Prostaglandins
• Prostaglandins are synthesized in response to
specific physiological triggers
• Made from membrane-bound 20-carbon
polyunsaturated fatty acids such as arachidonic
acid
9 8 6 5
COOH
11 12 14 15
Arachidonic acid
Eicosanoids 9
COOH
• are signaling 11 15
Aspirin and other
NSAIDs inhibit
Arachidonic acid
molecules which this enzyme
atoms). O
9
HO
9
COOH COOH
15 15
11 11
HO HO
OH OH
PGE2 PGF2 a
Prostaglandins
• Prostaglandins:
• play a key role in the generation of the inflammatory
response. Their biosynthesis is significantly increased in
inflamed tissue and they contribute to the development of
the cardinal signs of acute inflammation.
• acts as vasodilators - they widen blood vessels. They also
inhibit platelet aggregation. 7 5 3
1
9
6 2
COOH
8 4
10
12 14 16 18 20
11
13 15 17 19
Thromboxanes
• Thromboxanes are also derived from
arachidonic acid
• acts as vasoconstrictors – they can make the
blood vessels narrower.
9
8 1
10
O COOH
11 15 20
O 12
OH
Thromboxane A
TERPENES
• are aromatic lipids found in many
plants that are multiple of
isoprene units. Terpenes are non
– saponifiable meaning there are
no acid functional group in the
chain.
Fat soluble
vitamins
• Vitamins A, D, E and K
• Vitamin A is best known for its vital role in maintaining
vision. It’s also essential for body growth, immune
function, and reproductive health.
• vitamin D is the maintenance of calcium and phosphorus
levels in blood. It benefits bone health by promoting the
absorption of these minerals.
• Vitamin E’s key role is to serve as an antioxidant,
protecting cells against free radicals and oxidative
damage.
• Vitamin K is vital for blood clotting and supports bone
health.
Tay-Sachs
disease
• is an inherited metabolic
disease caused by the harmful
buildup of lipids in various cells
and tissues in the body. It is
part of a group of genetic
disorders called the
GM2 gangliosidoses.
• Tay-Sachs and its variant form
are caused by a deficiency in
the enzyme hexosaminidase A.
Affected children appear to
develop normally until about
age 6 months and then begin to
show symptoms
Fabry’s disease
• (also called alpha-galactosidase-A
deficiency) is caused by the lack of or faulty
enzyme needed to metabolize lipids, fat-like
substances that include oils, waxes, and fatty
acids.
• The mutated gene allows lipids to build up to
harmful levels in the autonomic nervous
system (which controls involuntary functions
such as breathing and digestion),
cardiovascular system, eyes, and kidneys.
Gaucher disease
Activity 4
Bicarbonate-Carbonic Buffer System
A buffer is a solution that can resist pH change upon the addition of an acidic or basic
components. It is able to neutralize small amounts of added acid or base, thus maintaining the
pH of the solution relatively stable.
Buffering in blood is crucial to our survival. The pH of blood must be kept constant for
normal body functions to work. If blood becomes too acidic, or too basic, then enzymes and
proteins are unable to function. Normal blood pH is 7.4. If it drops below 6.8, or rises above 7.8,
respiratory and cardiac function are compromised, the blood-clotting process changes, and death
may occur.
Red blood cells play an important role in the removal of excess hydrogen ions in the body.
This is achieved by a carbonic acid/Bicarbonate buffering system. This buffer system can be
represented as an equation:
This buffer works well because concentrations of the buffer components HCO3 - and CO2
(formed from H2CO3) are much greater than concentration of H+ ions. This means that changes
in the concentration of H+ ions have little effect on the pH of blood.
Other body organs play important roles in this buffer system. The lungs get rid of most of
the H+ ions produced by metabolism by removing carbon dioxide and driving the reaction
forward. The kidneys also remove H+ ions that are excreted in urine. The kidneys are also
involved in regulation of pH of body fluids through a complex interaction of H+, HCO3 - , H2O, CO2
and ions such as Na+.
OBJECTIVES
Materials :
1. Explain any differences you saw between how quickly each solution changed color.
2. How does this relate to what we’ve discussed about buffers?
3. Why would buffers be helpful in the body? Your answer should refer to the term
homeostasis
4. Create a flow chart of boxes illustrating each step of this activity and the color reaction of
each beaker. Labels should help a reader understand what is happening. It should be
colored.
5. What is alkalosis?
6. What could lead to alkalosis in the body?
7. What is acidosis?
8. What could lead to acidosis?
9. What is the conjugate base and the acid in the buffer solution?
References
https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textboo
k_Maps/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Acids_and_Bas
es/Buffers/Introduction_to_Buffers
https://www.uwa.edu.au/study/-/media/Faculties/Science/Docs/Buffering-systems-in-
the-human-body.pdf
ACTIVITY NO. 3
Write your observations in steps 2-8 of the procedure attach pictures of the color change
record each color change of the solution
the number of drops to change the color of the control and the buffer
CONCLUSION:
Activity 5
Protein denaturation
Proteins are essential for all living things to function. They are large molecules made up
of long chains of amino acids. Depending on the types of amino acids they have, proteins fold in
very specific ways. The way they fold controls what the proteins are able to do. Proteins help
move other molecules, respond to signals, make reactions happen more quickly, and replicate
DNA, among other things. However, if proteins lose their specific folded shape, they are not able
to work properly.
Proteins require specific conditions to keep their shape. For example, most proteins in
our bodies rely on us to keep a warm (but not hot) body temperature, stay hydrated, and take in
enough of specific nutrients like salt. If our bodies aren’t able to maintain these conditions, some
of our proteins may not function as well, or at all. Most organisms actually produce special
proteins called “molecular chaperones” that help other proteins and molecules continue to work
even if conditions are becoming difficult to tolerate.
When a protein is exposed to conditions too far outside of a range it can tolerate, that
protein’s shape will come undone. This is called “denaturing” (basically, breaking) a protein.
Source: Karla Moeller. (2018, May 29). Breaking Proteins. ASU - Ask A Biologist. Retrieved
March 11, 2022 from https://askabiologist.asu.edu/activities/breaking-proteins
OBJECTIVES
Materials :
Water Tissue
Glass containers/ plastic Cups (5)
Procedure:
Note: use 1 syringe only for egg white alone the other syringe wash it with water before drawing
alcohol and vinegar
Preparation of Egg Albumin Solution
Effect of Heat
Effect of Alcohol
Effect of Acid
1. What other things change color when their proteins are denatured?
2. Why might a living organism want to keep their proteins from denaturing?
3. In this activity, why was it important to have egg whites that we did not cook or add
alcohol to?
9. Is denaturation pH reversible?
ACTIVITY NO. 5
CONCLUSION: