[LIPIDS] BIOCHEMISTRY LECTURE

LIPIDS i. Fats
ii. Oils
 an organic compound found in living organisms that is 2. Membrane lipids
insoluble (or only sparingly soluble) in water but soluble in a. Phospholipids
nonpolar organic solvents. i. Glycerophospholipids
 are a heterogeneous group of compounds, 1. Lecithins
including fats, oils, steroids, waxes, and related 2. Cephalins
compounds, which are related more by their ii. Sphingophospholipids
physical than by their chemical properties. 1. Sphingomyelins
 Common property of being b. sphingoglycolipids
(1) relatively insoluble in water i. Cerebrosides
(2)soluble in nonpolar or organic solvents ii. Gangliosides
GENERAL FUNCTIONS OF LIPIDS
c. Cholesterol
3. Emulsification lipids
 i. They are efficient energy sources. a. Bile acids
 Body lipids are reservoir of potential i. Cholic acids
chemical energy. Lipids can be stored in ii. Deoxycholic acids
the body in almost unlimited amount in 4. Messenger lipids
contrast to carbohydrates. Furthermore, a. steroid hormones
lipids have a high calorific value (calories i. Sex Hormones
per gram) which is twice as great as 1. Estrogens
carbohydrate. Large amount of energy is 2. Androgens
stored as lipid than as carbohydrates 3. Progestins
 ii. Serve as thermal insulators. ii. Adrenocorticoids
 The subcutaneous lipids serve as 1. Mineralocorticoids
insulating materials against atmospheric 2. Glucocorticoids
heat and cold and protect internal organs. b. Eicosanoids
 Nonpolar lipids act as electrical insulators, i. Prostaglandins
allowing rapid propagation of ii. Thromboxanes
depolarization waves along myelinated iii. Leukotrienes
nerves.
 iii. They are structural components of the cell BASED UPON WHETHER OR NOT SAPONIFICATION
membrane. OCCURS
 Lipids which form the major constituent of
biomembranes are responsible for
membrane integrity and regulation of 1. Saponifiable lipids - is a lipid that undergoes
membrane permeability.
 Lipids present in inner mitochondrial hydrolysis in basic solution to yield two or
membrane actively participate in electron more smaller product molecules.
transport chain. a. Triacylglycerols
 Combinations of lipid and protein b. Glycerophospholipids
(lipoproteins) are important cellular c. sphingophospholipids,
constituents, occurring both in the cell d. sphingoglycolipids
membrane and in the mitochondria, and e. waxes
serving also as the means of transporting 2. Nonsaponifiable lipids - does not undergo
lipids in the blood. hydrolysis in basic solution. Such lipids cannot be
 iv. Serve as precursors for hormones (steroid broken up into smaller component parts using
hormones). hydrolysis.
 Lipids serve as metabolic regulators of a. Cholesterol
steroid hormones and prostaglandins. b. Steroid hormones
 v. They also dissolve the vitamins, which are fat- c. Bile acids
soluble and assist their digestion. d. Eicosanoids
 They serve also as a source of fat soluble
vitamins (Vitamin A, D, E and K) and
essential fatty acids. (Linoleic, Linolenic
and Arachidonic acid).
FATTY ACIDS:
 vii. Polyunsaturated fatty acids help in lowering
blood cholesterol.
 building blocks of lipids
 viii. Squalamine, a steroid, is a potential antibiotic
and antifungal agent.  are naturally occurring monocarboxylic acid.

CHARACTERIZATION OF FATTY ACIDS BASED ON

PHYSICAL PROPERTIES OF LIPIDS
CARBON CHAIN LENGTH
1. long-chain fatty acids (C12 to C26)
1. WATER SOLUBILITY 2. medium-chain fatty acids (C8 and C10)
a. Solubility decreases with increasing 3. short-chain fatty acids (C4 and C6)
carbon chain length
2. MELTING POINT
a. Degree of unsaturation CLASSIFICATION OF FATTY
i. Increase unsaturation =
decrease in melting point ACIDS:
-----------------------------------------------------------------------------------------------------------------------
CLASSIFICATION OF LIPIDS ---------
I. Based on the degree of unsaturation
1. Saturated fatty acid – aka BAD FAT
BASED ON FUNCTIONS  is a fatty acid with a carbon chain in which all
1. Energy-storage lipids carbon–carbon bonds are single bonds.
a. Triacylglycerols
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 Dietary effect is an increase in heart disease Capric acid C9H19COOH 10 Goat and Cow butter;
risk. Coconut fat; Fat of
2. Monounsaturated fatty acids – aka GOOD FAT spice bush
 is a fatty acid with a carbon chain in which Lauric C11H23COOH 12 Spermaceti,
one carbon–carbon double bond is present. cinnamon, palm
 Dietary effect is a decrease in heart disease kernel oil, coconut
risk. oils, laurels, butter
3. Polyunsaturated fatty acids – aka GOOD-BAD FAT Myristic C13H27COOH 14 Nutmeg, palm kernel,
 is a fatty acid with a carbon chain in which two acid coconut oils,
or more carbon–carbon double bonds are myrtles, butter
present. Palmitic C15H31COOH 16 Animal and vegetable
 Dietary effect is “mixed”; acid fats; spermaceti;
 As GOOD FAT- decrease heart disease risk beeswax
 As BAD FAT – increase cancer risk Stearic acid C17H35COOH 18 Animal and vegetable
fats
II. Based on the configuration of Double Bond
 cis –
o Naturally occurring fatty acids generally
contain cis double bonds. (associated
with GOOD FAT)
 trans – FATTY No. of Carbon & OCCURENCE
No. of double
o Hydrogenation converts some cis double ACID bonds
bonds to trans double bonds.
o Trans fatty acids have effects on blood UNSATURATED FATTY ACIDS
chemistry similar to those of saturated Monoenoic acids (one double bond)
fatty acids.(Associated with BAD FAT)
III. Base on Location of Double Bond Palmitoleic 16:1∆9 In nearly all fats
Aka ESSENTIAL FATTY ACIDS ω7
 OMEGA- 3 FATTY ACIDS
o First double bond is three carbons away Oleic acid 18:1∆9 Animal and Vegetal fats and oil
from the CH3 end of the carbon chain. ω9
o LINOLENIC ACID (18:3) is the primary
member of this family and a precursor for Elaidic acid 18:1∆9 Hydrogenated and ruminant fats.
EPA and DHA. ω9
o OTHER MEMBER:
 EPA and DHA - important Dienoic acids (two double bonds)
constituents of the
Linoleic 18:2∆9,12 Linseed oil, Corn, peanut,
communication membranes of cottonseed,
Acid ω6
the brain and are necessary for soybean,
normal brain development and and many plant oils.
are also active in the retina of Trienoic acids (three double bonds)
the eye.
 OMEGA-6 FATTY ACIDS Gamma- 18:3∆6,9,12 Linseed oil, Some plants, eg, oil of
Linolenic ω6 evening primrose,
o First double bond is six carbons away
acid borage oil; minor fatty acid in
from the CH3 end of the carbon chain. animals.
o LINOLEIC ACID (18:2) is the primary Frequently found with linoleic acid
-Linolenic 18:3∆9,12,15
member of this family and a precursor for but particularly
acid ω3
arachidonic acid in linseed oil.
o OTHER MEMBER Tetraenoic acids (four double bonds)
 Arachidonic acid - the major
starting material for eicosanoids Arachidonic 20:4∆5,8,11,14 Lipids of the liver and brain;
Unsaturated Fatty Acids and Double-Bond Position acid ω6 eggyolk.Found in animal fats
SHORT HAND NOTATION and in peanut oil; important
 Delta designation (∆) component of phospholipids
 Omega designation (ω) in animals
Pentaenoic acids (five double bonds)
FATTY FORMULA No. OCCURENCE
ACID of Timnodonic Important component of fish
20:5∆5,8,11,14,17
Carb oils, eg, cod liver, mackerel,
on menhaden, salmon oils.
SATURATED FATTY ACIDS Hexaenoic acids (six double bonds)
Acetic acid CH3COOH 2 Vinegar
Cervonic 22:6∆4,7,10,13,16, Fish oils, phospholipids in brain.
19

Propionic CH3CH2COOH 3 An end product of ω3

acid carbohydrate
fermentation by LIPIDS ARE CLASSIFIED AS SIMPLE
rumen Organisms OR COMPLEX
Butyric acid C3H7COOH 4 Glycerides in butter I. Simple lipids: Esters of fatty acids with various
alcohols.
a. Fats: Esters of fatty acids with glycerol.
Caproic C5H11COOH 6 Goat and Cow butter; Oils are fats in the liquid state.
acid Coconut fat b. Waxes: Esters of fatty acids with higher
molecular weight monohydric alcohols.
Caprylic C7H15COOH 8 Goat and Cow butter; II. Complex or compound lipids: Esters of fatty
acid Coconut fat; Human acids containing groups in addition to an alcohol
Fat and a fatty acid.
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a. Phospholipids: Lipids containing, in Carboxylic acid + alcohol ------- ester + H2O

addition to fatty acids and an alcohol, a
phosphoric acid residue. They frequently Example:
have nitrogen containing bases and other
Glycerol + stearic acid ----------- triacylglerol + H2O
substituents.

2 TYPES OF TRIACYLGLYCEROL
 Simple Triacylglycerol
Complex lipids Nitrogenous base o Is a triester formed from the esterification
Cephalin Ethanolamine Choline of glycerol with three identical fatty acids
Lipositol Inositol molecule.
 Mixed Triacylglycerol
Phosphatidyl serine Serine o A triester formed from the esterification of
Plasmalogen Resembles lecithins and glycerol with more than one kind of fatty
cephalins acid molecules.
Sphingomyelin Sphingosine and choline
EXAMPLES OF TRIACYLGLYCEROL

FEATURES FATS OILS/ FIXED OILS

b. Glycolipids: contain carbohydrate and
nitrogenous base PHYSICAL Solid or semisolid at Liquid at room temp
i. Glycosphingolipids- Lipids STATE room temp
containing a fatty acid,
sphingosine, and carbohydrate. SOURCE Obtained from Obtained from plants
c. Other complex lipids: Lipids such as animal sources
sulfolipids and aminolipids. Lipoproteins
PREDOMINANT Saturated Mono and
may also be placed in this category.
FATTY ACIDS compounds polyunsaturated
predominates compounds
III. Precursor and Derived lipids: Products of
predominates
hydrolysis of I and II but still exhibiting the general
physical characteristics of lipids STRUCTURE “Linearity” of fatty “Bends” chain causing
a. Saturated and unsaturated fatty acids acids causing the the molecule
b. Mono and di-glycerides molecule to be incapable of close
c. Alcohols closely packed packing
i. Straight chain – products of
hydrolysis of waxes MELTING Higher Lower
ii. Alcohols containing b-ionone POINT
ring –Vitamin A and some
carotenols
iii. Sterols FEATURES
d. Miscellaneous SATURATED UNSATURATED FATS
i. Aliphatic hydrocarbons FATS
Type of bonds Consist of Consist of at least 1 DOUBLE
ii. Squalene – hydrocarbons in
SINGLE bond bond
shark liver and human
iii. Carotenoids Recommended Not more than Not more than 30% of total
iv. Vitamins D,E,K consumption 10% of total calories per day
calories per day

CLASSIFICATION OF Health Effects Excessive

consumption is
MUFAs reduces heart disease
risk
LIPIDS: based on not good
because of their PUFAs – reduce heart risk but

FUNCTIONS association with

heart diseases.
promote risk of some types of
cancer

I. ENERGY STORAGE LIPIDS Cholesterol Saturated

increase
fats
Low
Unsaturated fats increase High-
Density Lipoprotein (HDL or
Density good cholesterol) and decrease
Lipoproteins Low Density Lipoproteins (LDL
(LDL or bad or bad cholesterol). Sources of
ADIPOCYTE – specialized cells that function as the storage cholesterol) & HDL include onions and
Very Low Omega-3 fatty acids like flax oil,
site for Triacylglycerl (TAG). Density fish, foods rich in fiber like
Lipoproteins grains.
(VLDL's)
TRIACYGLYCEROL (TAG) OR
TRIACYLGLYCERIDE Commonly Butter, coconut Avocado, soybean oil, canola oil
 Most abundant type of lipids present in the body found in oil, whole milk, and olive oil, sunflower oil, fish
and are the main storage form of fatty acids, and butter, oils walnuts,
they account for greater than 90% of dietary fat margarine,
intake cheese, fried
 More efficient at storing energy than glycogen, foods, & frozen
large quantities can be packed in very small dinners
volume.
Shelf Life long lasting and spoil quickly
 Lipid formed through esterification of 3 fatty acid do not spoil
with glycerol quickly
 FAT – substitute term

ESTERIFICATION REACTION:

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Melting Point High Low SERINE 2 ionic group Phosphatidylserine

Aka Cephalins
Physical state Solid (Trans Fats Liquid (Monounsaturated &
at room & Saturated Polyunsaturated Fats- Omega
temperature Fats) 3's & 9's) PHOSPHATIDYLCHOLINE (lecithins)
 the most abundant phospholipids of the cell
Rancidity Low High membrane
 represents a large proportion of the body’s store
Examples Hydrogenated Olive Oil, linoleic acid, alpha- of choline.
Oils, Butter, linolenic acid  Choline is important in nervous transmission, as
Processed acetylcholine, and as a store of labile methyl
Meats
groups.
 Dipalmitoyl lecithin - is a very effective surface
active agent and a major constituent of the
surfactant preventing adherence, due to surface
tension, of the inner surfaces of the lungs.
TERMINOLOGIES FOR FAT SUBSTITUTE o Its absence from the lungs of premature
infants causes respiratory distress
Terms DEFINITIONS syndrome
PHOSPHATIDYLSERINE (CEPHALINS)
Fat free means less than 0.5g of fat per serving  Lipids associated with blood clotting
Low fat means 3g or less fat per 50g serving 2. Sphingophospholipids
Reduce means at least 25% less fat per serving than COMPOSITION:
fat or less the regular food  one fatty acid
fat  one phosphate group attached to a
sphingosine molecule
Calorie means less than 0.5 kilo calories per serving  an alcohol attached to the phosphate group.
free

II. MEMBRANE LIPIDS

A. PHOSPHOLIPIDS
COMPOSITION
 one or more fatty acids  SPHINGOMYELIN -
Sphingophospholipids in which the
 a phosphate group alcohol esterified to the phosphate group
is choline.
 a platform molecule to o are found in all cell membranes
which the fatty acid(s) and and are important structural
components of the myelin
the phosphate group are sheath, the protective and
insulating coating that surrounds
attached nerves.
 alcohol that is attached to
B. SPHINGOLIPIDS (as SPHINGOGLYCOLIPIDS)
the phosphate group. COMPOSITION:
 contains both a fatty acid and a
 Phosphatidic acid- parent carbohydrate component attached to a
sphingosine molecule.
compound
1. Glycerophospholipids
COMPOSITION:
 two fatty acids
 phosphate group esterified to a
glycerol molecule
 an alcohol esterified to the
phosphate group

Globosides
cytolipins
1. Cerebrosides
o simplest sphingoglycolipids,
o contain a single
AMINO IONIC GROUP GLYCEROPHOSPHOLIPIDs OR
GLYCEROPHOSPHATIDES monosaccharide unit—either
ALCOHOL
glucose or galactose, one fatty
CHOLINE Quaternary Phosphatidylcholine aka acid and sphingosine, but no
ammonium Lecithin phosphoric acid and glycerol.
group o occur primarily in the brain (7%
ETHANOL (+) ion group Phosphatidylethanolamine of dry mass).
AMINE Aka Cephalins

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 [LIPIDS] BIOCHEMISTRY LECTURE

o also present in the myelin Atherosclerosis - a form of cardiovascular

sheath of nerves. disease characterized by the buildup of
2. Gangliosides plaque along the inner walls of arteries.
 More complex o Plaque - is a mound of lipid material
sphingoglycolipids, mixed with smooth muscle cells and
 contain a branched chain of up calcium. Much of the lipid material in
to seven monosaccharide plaque is cholesterol.
 contain sphingosine, long chain CELL MEMBRANE
fatty acids, hexoses (usually  is a lipid-based structure that separates a
galactose or glucose) and cell’s aqueous-based interior from the
neuramic acid aqueous environment surrounding the cell.
 residues.occur in the gray  LIPID BILAYER- is a two-layer-thick
matter of the brain as well as in structure of phospholipids and glycolipids in
the myelin sheath. which the nonpolar tails of the lipids are in the
3. Globosides middle of the structure and the polar heads
C. CHOLESTEROL are on the outside surfaces of the structure.
 C27 steroid molecule that is a component o 6 to 9 nanometers thick.
of cell membranes and a precursor for o 3 distinct parts to the bilayer:
other steroid-based lipids.  the exterior polar “heads,”
 most abundant steroid in the human body  the interior polar “heads,”
 steroid alcohol  and the central nonpolar
 can be isolated from plants, animals, and “tails
human beings
 LIMITED WATER SOLUBILITY: due to
the lack of a large polar head group. The
--OH group on carbon 3 is considered the
head of the molecule.

STEROID - is a lipid whose structure is based on a fused

ring system that involves three 6-membered rings and one
5-membered ring. This steroid fused-ring system, which is
called the steroid nucleus,

2 TYPES OF MEMBRANE PROTEINS

1. Integral membrane protein- is a membrane
protein that penetrates the cell membrane
CHOLESTEROL 2. Peripheral membrane protein- is a
nonpenetrating membrane protein located on the
OTHER SIGNIFICANCE: Within the human body surface of the cell membrane.
 found in cell membranes (up to 25% by mass)
 in nerve tissue, in brain tissue (about 10% by dry
mass)
TRANSPORT MECHANISM ACROSS THE
 Every 100 mL of human blood plasma contains CELL:
about 50 mg of free cholesterol and about 170 mg
of cholesterol esterified with various fatty acids.
SOURCES OF CHOLESTEROL
 Dietary intake
 Biosynthesis in the liver and to a lesser extent in
the intestines
LIPOPROTEIN : Protein carrier system
1. LDL - carry cholesterol from the liver to various
cells or tissues of the body
 a major cholesterol transport protein
which comprises 60% to 70% of total
serum cholesterol
 is considered the “bad” cholesterol, and
has been linked to atherosclerosis
2. HDL - carry excess cholesterol from body tissues
back to the liver for degradation to bile acids
 Are responsible for transport of 20% to  PASSIVE DIFFUSION aka PASSIVE TRANSPORT
30% of serum cholesterol. o 90% drugs are transported across
 It is considered the “good” cholesterol, biologic membranes
and elevated HDL levels are associated o Movement of drug if there is a
with a decreased risk for CHD or Chronic concentration gradient , meaning,
Heart Disease drug concentration on one side of
3. VLDL – transport triacylglycerols from the liver to the membrane is higher than that of
adipose tissue the other side
4. CHYLOMICRONS – transport dietary o No energy expenditure
triavylglycerols from the intestines to the liver and o Drugs must be unionized, nonpolar
adipose tissue and lipophilic
o First order kinetics
DISEASE ASSOCIATED WITH CHOLESTEROL: o Non-saturable process

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o Consistent with Fick’s law of  Parasympathetic stimulation of

diffusion the vagus nerves causing the
o Examples of molecules that crosses liver to contract and synthesize
this manner: bile to be stored in the
 O2, N2, H2O, CO2,urea, and gallbladder to release bile acids
ethanol  Stimulation of the duodenum to
 FACILITATED DIFFUSION secrete secretin, a hormone that
o The drug binds with an intrinsic allows contraction of liver to
factor carrier like vitamin B12 produce bile
o It passes through the membrane but  Stimulation of the duodenum to
no energy expenditure secrete cholecystokinin to
o Transfer is downhill and fast directly contract the gallbladder
o Saturable process. The rate limiting to release bile acids.
step is the number of intrinsic factor  EMULSIFIER - is a substance that can disperse
o Examples of molecules that crosses and stabilize water-insoluble substances as
this manner: colloidal particles in an aqueous solution
 Glucose, chloride ion, and
bicarbonate ion
 ACTIVE TRANSPORT
o Carier mediated
o Permeability is dependent on the
number of carriers
o 5-10% of drugs are transported this
way, usually small MW drugs with
structures similar to food
(peptides,nucleosides,nucleotides)
so permeability is affected by the
presence of food due to carrier
competition of nutrients
o Saturable process. The rate limiting
step is the number of carriers
o Zero order kinetics FUNCTIONS OF BILE ACIDS:
o Can go against concentration 1. EMULSIFIER: it functions to emulsify fats and aids
gradient in the digestion and absorption in the small intestine.
o Expends energy They lower surface tension and thus can emulsify fats.
o Examples of molecules & drugs that 2. Helps neutralize acids in the stomach
crosses this manner: 3. They also activate lipases.
 Sodium, potassium, and
hydronium ions
 Centrally active amino acid-
like drugs,
methyldopa,gabapentin
 Oral B-lactams antibiotics
like amoxicillin and
cephalexin
 ACE inhibitors like enalapril
 Folic acid
Three respects of difference between cholesterol and bile
acids:
1. They are tri- or dihydroxy cholesterol derivatives.
2. The carbon 17 side chain of cholesterol has been
OTHERS: oxidized to a carboxylic acid.
 ENDOCYTOSIS 3. The oxidized acid side chain is bonded to an
o Drug particles are engulfed by the cell amino acid (either glycine or taurine) through an
o Examples: Vitamin A,D,E,K amide linkage.
o 2 TYPES:
 Pinocytosis, in which the fluid
material is engulfed (CELL
DRINKING)
 Phagocytosis, in which large
sized solid material is engulfed.
(CELL EATING)

III. EMULSIFICATION LIPIDS: Bile

Acids

 BILE - a fluid containing emulsifying agents that is

secreted by the liver, stored in the gallbladder, and
released into the small intestine during digestion.
 BILE ACID - a cholesterol derivative that functions
as a lipid-emulsifying agent in the aqueous Average bile acid composition in normal human adult bile:
environment of the digestive tract  38% - cholic acid derivatives,
o Secreted in the duodenal papillae  34% - 7-deoxycholic acid derivatives
o 3 ways Synthesization  28% - 12-deoxycholic acid derivatives

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A. SEX HORMONE: which control reproduction and

secondary sex characteristics
i.ESTROGEN: the female sex hormones
a.Sources:
 WOMEN: ovaries and adrenal cortex
 MEN: testes and adrenal gland
b.Function in WOMEN:
 for the development of female secondary
sex characteristics at the onset of puberty
 for regulation of the menstrual cycle
 stimulate the development of the
mammary glands during pregnancy
 induce estrus (heat) in animals
c.TYPES OF ESTROGEN
1. Estradiol - the most commonly
measured type of estrogen for
nonpregnant women. The amount of
estradiol in a woman's blood varies
throughout her menstrual cycle. After
menopause, estradiol production drops to
 either glycine or taurine attached to the side-chain a very low but constant level.
carboxyl group via an amide linkage 2. Estriol - levels usually are only
 The presence of this amino acid attachment measured during pregnancy. Estriol is
increases both the polarity of the bile acid and its produced in large amounts by the
water solubility. placenta, the tissue that links the fetus to
the mother. It can be detected as early as
the 9th week of pregnancy, and its levels
increase until delivery. Estriol can also be
measured in urine.
3. Estrone- may be measured in women
who have gone through menopause to
determine their estrogen levels. It also
may be measured in men or women who
might have cancer of the ovaries,
testicles,or adrenal glands.

Estrogen & Pregnancy

During the reproductive years, the pituitary gland in the

brain generates hormones that cause a new egg to be
GALLSTONE: Formation
released from its follicle each month. As the follicle
 increased secretion of cholesterol develops, it produces estrogen, which causes the lining of
 decrease in the size of the bile pool the uterus to thicken.
IV. MESSENGER LIPIDS: Progesterone production increases after ovulation in the
middle of a woman's cycle to prepare the lining to receive
 Regulatory lipids that act in the tissue where they and nourish a fertilized egg so it can develop into a fetus. If
are synthesized or at other locations after fertilization does not occur, estrogen and progesterone
transport via the blood stream. levels drop sharply, the lining of the uterus breaks down
 HORMONE and menstruation occurs.
o Aka chemical messenger
o is a biochemical substance, produced by
a ductless gland, that has a messenger If fertilization does occur, estrogen and progesterone work
function. together to prevent additional ovulation during pregnancy.
o It serves as a means of communication Birth control pills (oral contraceptives) take advantage of
between various tissues. this effect by regulating hormone levels. They also result in
o carry information and instructions from
the production of a very thin uterine lining, called the
one group of cells to another.
endometrium, which is unreceptive to a fertilized egg. Plus,
I. STEROID HORMONES they thicken the cervical mucus to prevent sperm from
a. Sex Hormones - which control entering the cervix and fertilizing an egg.
reproduction and secondary sex
characteristics
Other Roles of Estrogen
i. Estrogen
 Bone. Estrogen produced by the ovaries helps
ii. Progestins
prevent bone loss and works together with calcium,
iii. Androgen
vitamin D and other hormones and minerals to
b. Adrenoicorticoids
build bones. Thus preventing osteoporosis.
i. Mineralocorticoids
 Vagina and Urinary Tract. When estrogen levels
ii. Glucocorticoids
are low, as in menopause, the vagina can become
II. EICOCANOIDS
drier and the vaginal walls thinner, making sex
a. Prostaglandins
painful.
b. Thromboxanes
c. Leukotrienes
Other uses of Estrogen
 Estrogen Therapy to treat certain conditions:
I.STEROID HORMONE: is a hormone that is a o For delayed onset of puberty
cholesterol derivative

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 [LIPIDS] BIOCHEMISTRY LECTURE

o menopausal symptoms such as hot  key role to prevent bone loss and
flashes and symptomatic vaginal atrophy. send desire for satisfaction
Vaginal atrophy is a condition in which III.TYPES OF ESTROGEN
low estrogen levels cause a woman's  TESTOSTERONE
vagina to narrow, lose flexibility and take  ANDROSTENEDIONE
longer to lubricate. Other androgens
o Female hypogonadism, a condition in  dihydrotestosterone (DHT),
which the ovaries produce little or no  dehydroepiandrosterone (DHEA)
hormones, as well as premature ovarian  DHEA sulfate (DHEA-S)
failure, can also cause vaginal dryness,
breast atrophy and lower sex drive
o to prevent osteoporosis and to improve
women's overall health.

HIGH ESTROGEN IN WOMEN

 swelling and tenderness in the breasts
 irregular menstrual periods
 headaches
 mood swings
 fibrocystic developments in the breast
 weight gain
 hair loss
 cold hands or feet
 feeling tired or lacking energy
 difficulty with memory
 trouble sleeping
HIGH ESTROGEN IN MEN
 Infertility
 Erectile dysfunction
 Gynecomastia HIGH ANDROGEN:
 VIRILIZING EFFECTS
ii.PROGESTINS - the pregnancy hormones  ACNE
a. Sources:  HIRSUTISM
 synthesized : ovaries and the placenta  SCALP BALDING
b. Function: Additional effects in women:
 Prepare the lining of the uterus for  PCOS – polycystic ovarian syndrome
implantation of the fertilized ovum. o IRREGULAR MENSTRUATION
 They also suppress ovulation. o WEIGHT GAIN
 properly regulate the menstrual cycle and o INFERTILITY
treat unusual stopping of the menstrual o DIABETES – due to problem using
periods (amenorrhea) insulin or insulin resistance
 To prevent estrogen from thickening the
lining of the uterus (endometrial ANABOLIC STEROIDS or ANABOLIC-ANDROGENIC
hyperplasia) in women with HRT STEROIDS
(hormone replacement therapy)  Are used to build up muscle strength and enhance
 To treat pain that is related to endurance
endometriosis  ANDROGENIC EFFECT - masculinizing effect
 To treat loss of appetite and severe  ANABOLIC EFFECT – muscle building
weight or muscle loss in patients with
AIDS or cancer Common Side Effects That May Occur with Anabolic
Steroid Use
 Severe acne, oily skin and hair
ORAL CONTRACEPTIVE PILLS  Hair loss
 May contain estrogen and progesterone  Kidney disease
combination or progestins alone  Heart disease such as heart attack and stroke
 used to suppress ovulation as a method of birth  Altered mood, irritability, increased aggression,
control depression or suicidal tendencies
 relieve menstrual cramps and some  Alterations in cholesterol and other blood lipids
perimenopausal symptoms  High blood pressure
 regulate menstrual cycles in women with polycystic  Gynecomastia (abnormal development of
ovarian syndrome (PCOS) mammary glands in men causing breast
enlargement)
 Shrinking of testicles
iii.ANDROGEN - the male sex hormones  Azoospermia (absence of sperm in semen)
I.Sources:  Menstrual irregularities in women
 MEN: testes and adrenal cortex  Infertility
 WOMEN: androgens are produced in the  Excess facial or body hair deeper voice in women
ovaries, adrenal glands and fat cells  Stunted growth and height in teens
II. Function in Men:  Risk of viral or bacterial infections due to unsterile
 development of male secondary sex injections
characteristics.  Suicidal attitudes
 promote muscle growth
Function in women:
 stimulation of hair growth in pubic II.ADRENOCORTICOID HORMONES:
area and under arm during puberty A. MINERALOCORTICOIDS - control the balance of
 precursor in the synthesis of Na+ and K+ ions in cells and body fluids
estrogen a. ALDOSTERONE

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 [LIPIDS] BIOCHEMISTRY LECTURE

 the main mineralocorticoid, is The physiological effects of eicosanoids include medication

necessary for regulation of salt of:
and water in the body. 1. The inflammatory response, a normal response
 acts on the kidneys to provide to tissue damage
active reabsorption of sodium 2. The production of pain and fever
and an associated passive 3. The regulation of blood pressure
reabsorption of water, as well as, 4. The induction of blood clotting
the active secretion of 5. The control of reproductive functions, such as
potassium in the principle cells induction of labor
of the cortical collecting tubule. 6. The regulation of the sleep/wake cycle
This in turn results in an
increase of blood pressure and
blood volume.

MAJOR TYPE OF EICOSANOIDS:

I. PROSTAGLANDINS - is a messenger lipid that
is a C20-fatty-acid derivative that contains a
B. GLUCOCORTICOIDS - control glucose metabolism cyclopentane ring and oxygen-containing
and counteract inflammation. functional groups.
a. CORTISOL- the major glucocorticoid  Regulatory functions:
hormone and is produced in humans by  including raising body
the zona fasciculata of the adrenal temperature,
cortex within the adrenal gland.  inhibiting the secretion of gastric
 It is released in response to stress and juices,
low blood-glucose concentration.  increasing the secretion of a
 It functions to increase blood protective mucus layer into the
sugar through gluconeogenesis, to stomach,
suppress the immune system, and to aid  relaxing and contracting smooth
in muscle,
themetabolism of fat, protein,and carbohy  directing water and electrolyte
drates. It also decreases bone formation. balance,
 Cortisol and its synthetic ketone  Intensifying pain, and enhancing
derivative cortisone exert powerful anti- inflammation responses.
inflammatory effects in the body. Note: Aspirin reduces inflammation and fever because it
inactivates enzymes needed for prostaglandin synthesis.

II. THOMBOXANES - is a messenger lipid that is a

C20-fatty-acid derivative that contains a cyclic
ether ring and oxygen-containing functional groups.
 are produced by blood platelets
and promote platelet
aggregation.
 FUNCTIONS
 to promote the formation of
blood clots.
III. LEUKOTRIENES - is a messenger lipid that is a
C20-fatty-acid derivative that contains three
conjugated double bonds and hydroxy groups.
 found in leukocytes (white blood
cells).
 FUNCTIONS
 Various inflammatory and
 cortisone and prednisolone, are used as hypersensitivity (allergy)
prescription drugs to control inflammatory responses
diseases such as rheumatoid arthritis. PROTECTIVE COATING LIPIDS: BIOLOGICAL
II.EICOSANOIDS: WAXES
 is an oxygenated C20 fatty acid derivative that
functions as a messenger lipid.
 metabolic precursor for most eicosanoids is
 BIOLOGICAL WAX
arachidonic acid, the 20:4 fatty acid.
o is a lipid that is a monoester of a long-
 are hormonelike molecules rather than true
chain fatty acid and a longchain alcohol
hormones because they are not transported in the
o are monoesters, unlike fats and oils
bloodstream to their site of action as true
which are triesters.
hormones are.

9 SOUTHWESTERN UNIVERSITY-PHINMA EDUCATION/ SCHOOL OF HEALTH & ALLIED HEALTH SCIENCES/

 [LIPIDS] BIOCHEMISTRY LECTURE

o fatty acids found in biological waxes

generally are saturated and contain from
14 to 36 carbon atoms.
 WAX
o is a pliable, water-repelling substance
used particularly in protecting surfaces
and producing polished surfaces
o esters of high molecular weight,
monohydric alcohols and high molecular
weight fatty acids.
 MINERAL WAX
o is a mixture of long-chain alkanes
obtained from the processing of
petroleum.

EXAMPLES OF WAXES:
1. CARNAUBA WAX
 obtained from a species of Brazilian palm
tree
 is a particularly hard wax whose uses
involve high-gloss finishes: automobile
wax, boat wax, floor wax, and shoe wax.
2. LANOLIN
 a mixture of waxes obtained from sheep
wool,
 used as a base for skin creams and
ointments intended to enhance retention
of water (which softens the skin).
3. PARAFFIN
 Mineral waxes
 resist moisture and chemicals and have
no odor or taste.
 They serve as a waterproof coating for
such paper products as milk cartons and
waxed paper.
4. BEESWAX
 a blend of biological and mineral waxes
 sometimes a component of candle wax

10 SOUTHWESTERN UNIVERSITY-PHINMA EDUCATION/ SCHOOL OF HEALTH & ALLIED HEALTH SCIENCES/