Prof.

Milagros Leaño
OS 201: Correlative Human Cell Biology
Exam 1
Lecture # 3 – Structures and Functions

density and low-density lipoproteins = HDL

I. Overview of Lipids
and LDL)
A. Major Characteristics
B. Functions
C. Classification of Lipids 6. essential for normal growth and
1. Simple Lipids function (e.g. DHA, docosahexaenoic acid,
2. Compound (or Complex) Lipids for brain development)
3. Precursor and Derived Lipids
4. Steroid Lipids 7. precursors of hormones, coenzymes
5. Miscellaneous Lipids and chemical mediators like your lipid-
II. Fatty Acid (FA) soluble vitamins (A, D, E, K); the
A. Characteristics and Structure prostaglandins (mediators of inflammatory
B. Functions and anaphylactic reactions), the
C. Classification of FA
thromboxanes (mediators of
1. According to Chain Length
2. According to Bond Type
vasoconstriction) and the prostacyclins
3. According to Source (active in the resolution phase of
D. Nomenclature and Common Notations
inflammation.)
E. Other Matters
8. bioeffectors/bioregulators (e.g.
III. Triacylglycerol (TAG)
phosphatidylinositol can act as a
F. Characteristics, Functions and Types
secondary messenger)
A. Structure
IV. Phospholipid 9. Others: In small quantities, lipids are
G. Characteristics and Functions present as enzyme cofactors in electron
A. Glycerophospholipid carriers, as light absorbing pigments, as fat
B. Sphingolipids soluble vitamins (terpenes), as intracellular
V. Glycolipid
H. Characteristics, Structure, and Functions
messengers, as hydrophobic anchors, etc.
I. Major Glycolipids in the Body
VI. Cholesterol C. Classification of Lipids
A. Characteristics, Structure, and Functions
B. Phase Transition Temperature 1. Simple lipids: Esters of fatty acids with
VII. Summary various alcohols.
VIII. Attachment
a. Fats: Esters of fatty acids with glycerol
I. Overview of LIPIDS = acyl glycerols or glycerides;
depending on the no. of esterified FA:
• One of the four major groups of biomolecules mono-/di-/triacylglycerols. Oils
are fats in the liquid state.
• Unlike proteins, nucleic acids, lipids refer to a
group of heterogeneous (no common structural b. Waxes: Esters of fatty acids with higher
unit) molecules unified by common chemical molecular weight monohydric alcohols.
features.
• Similar to carbohydrates, lipids are non- 2. Compound (or Complex) lipids: Esters of
informational molecules fatty acids containing groups in addition to
an alcohol and a fatty acid.
A. General Characteristics
All lipids are: a. Phospholipids: Lipids containing, in
addition to fatty acids and an alcohol, a
1. insoluble in water; phosphoric acid residue. They frequently
2. soluble in nonpolar solvents like ether, have nitrogen containing bases and other
benzene, chloroform, etc.; and substituents,
3. present in biological systems
eg, in glycerophospholipids the alcohol
B. Functions is glycerol and in sphingophospholipids
the alcohol is sphingosine.
1. storage of excess energy (e.g. FAs in b. Glycolipids (glycosphingolipids):
TAGs) Lipids containing a fatty acid,
2. major source of caloric energy (e.g. FAs sphingosine, and carbohydrate.
in TAGs can be hydrolyzed and mobilized
for catabolism)
3. Derived lipids: These include by-products
of metabolic processes like fatty acids,
3. thermal insulation (e.g. adipose tissues in glycerol, mono- and diacylglycerols,
subcutaneous tissues) and thermal lysophosphatides, fatty aldehydes, ketone
insulation (e.g. nonpolar lipids act as bodies.
electrical insulators, allowing rapid
propagation of depolarization waves along
4. Steroid Lipids: cholesterol, cholesteryl
myelinated nerves) esters, cholesterol derivatives: bile acids,
steroid hormones, vitamin D, phytosterols
4. cell membrane components ** Because they are uncharged, acylglycerols
(e.g. phospholipids, glycolipids, cholesterol) (= glycerides), cholesterol, and cholesteryl
5. lipoproteins (e.g. fat transporters like high esters are termed neutral lipids.

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 Prof. Milagros Leaño
OS 201: Correlative Human Cell Biology
Exam 1
Lecture # 3 – Structures and Functions

double bonds
5. Miscellaneous Lipids: – cis-trans isomerism exists;
aliphatic hydrocarbons, carotenoids, – double bonds along the side chain
squalene, terpenes (composed of isoprene produce “kinks” w/c contribute to
units), vitamin E and K, glycerol ether, fluidity and permeability.
glycosyl glycerols (in plants) – kinks prevent efficient packing
IN FOCUS: Principal classes of STORAGE (weakening hydrophobic interaction;
(triacylglycerols or triglycerides) and thus, an unsat’d FA has a lower
MEMBRANE LIPIDS, phospholipids, melting temperature than its sat’d
glycolipids and cholesterol. (see attachment; counterpart
Fig. 1) – is further classified to:
• Monounsaturated
II. Fatty Acid (monoethenoid, monoenoic)
acids, containing one double
A. Characteristics and Structure bond.
1. A carboxylic acid with long chain hydrocarbon • Polyunsaturated (polyethenoid,
side chain: polyenoic) acids, containing two
or more double bonds.
where R = aliphatic (acyclic)
hydrocarbon 3. According to source
a. Non-essential fatty acids
– can be synthesized by the body (e.g.
s
palmitic acid, and other saturated and
monoenoic FAs)
i
d
e b. Essential fatty acids
– must be obtained from exogenous
sources (a.k.a. diet); humans lack the
c anabolic enzymes (desaturases that
h add a double bond in the ω3 and ω6
a positions) that can synthesize FA with
i a double bond beyond C-9 (>∆9)
n
– include your polyunsaturated fatty
acids (PUFAs): linoleic, linolenic and
2. usually biosynthesized by the concatenation or arachidonic acids.
linking of 2 carbon units (acetyl CoA )
D. Nomenclature and Common Notations
3. rarely found free in nature but occur in
esterified form as the major components of 1. Common and Systematic Names: see
various lipids. attachment; Table 1
B. Functions 2. Delta (Δ) Notation: x:y(Δm,n,…)
1. fuel energy • x = no. C atoms; y = no. of double bonds;
2. maintenance of membrane fluidity the positions of any double bonds are
3. component of food oils (coconut oil, etc.) specified by superscript (m,n,…) numbers
4. growth and dev’t (essential fatty acids) following Δ (delta).
5. precursor of long-chain polyunsaturated fatty • E.g. a 18-carbon FA
acids (PUFAs) like arachidonic acid
w/ one double bond
C. Classification between C-9 and
C-10 (C-1 being the
1. According to chain length (no. of methylene carboxyl carbon, C
groups or no. of carbon atoms) in COOH) &
a. Short chain – 2-5 C atoms another bet. C-12
b. Medium chain – 6-12 C atoms and C-13 is
designated Fig. 2 Linoleic Acid
c. Long Chain – up to 25 C atoms 9,12
18:2(Δ ).
2. According to bond type
a. Saturated FAs 3. Omega (ω) Notation
– alkyl side chain contain only single • Recall: The carbon atoms adjacent to the
bonds; carboxyl carbon (Nos. 2, 3, and 4) are also
– exists in different conformations due to known as the α, β, and γ carbons,
the complete freedom of rotation of respectively, and the terminal methyl
the C-C bond ∴ flexible conformation carbon (farthest from COOH) is known as
– extended conformation is most stable the ω or n-carbon.
• E.g. ω9 indicates a double bond on the
b. Unsaturated FAs
ninth carbon counting from the ω-carbon.
– alkyl side chain contain single and

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OS 201: Correlative Human Cell Biology
Lecture # 3 – Structures and Functions
• In animals, additional double bonds are
introduced only between the existing
double bond (e.g. ω9, ω6, or ω3) and the
carboxyl carbon, leading to three series of
fatty acids known as the ω9, ω6, and ω3
[omega] families, respectively.
• For the essential fatty acids:
Linoleic acid 18:2(Δ9,12) 18ω6
Linolenic acid 18:3(Δ9,12,15) 18ω3
Arachidonic acid 20:4(Δ5,8,11,14) 20ω6
Docosahexaenoic
acid (DHA) 22:6(Δ4,7,10,13,16,19) 22ω6
E. Other Matters
1. Why are essential fatty acids important?
EFAs are directly associated with many life-
sustaining biological functions:
• maintenance of healthy cell membranes
• growth requirement
• for healthy skin (prevents dermatitis, dry
flaky skin) (omega-6)
• precursor of long chain polyunsaturated
fatty acids, PUFAs (fr. omega fatty acids)
• for brain dev’t (omega-3)
• visual acuity/retinal dev’t (omega-3)
• EFAs are precursors of eicosanoids, w/c
are signaling molecules made by
oxygenation of twenty-carbon essential
fatty acids, (EFAs)
e.g. Prostaglandins & Thromboxanes
– regulate inflammatory response
– produce pain
– induce sleep
– reproduction
– regulate blood coagulation
Leukotrienes
– muscle contractant properties
– chemotactic properties
– important in allergic reactions
and inflammation
2. More about DHA (Docosahexaenoic acid)
• Dietary sources: marine animals and
planktons, moss, ferns, seed oils
(rapeseed, soya, walnut)
• accumulates in the 3rd trimester of
pregnancy
• plays an important role in brain dev’t and in
visual acuity or retinal dev’t
• supplemented in infant milk formulation
• DHA & EPA – antiatheromatous effect:
– lower LDL-cholesterol, triglycerides
– competes with AA as cyclooxygenase
substrate, lowers thromboxane
production, dec. platelet aggregation
– associated with lower incidence of
atherosclerosis & CVD (cardiovascular
disease)
Monday Page 3 of 7
July 20, 2009
Prof. Milagros Leaño
Exam 1
3. Trans Unsaturated Fatty Acids: Good or
Bad?
• Present in: margarine, breads, chips, fries,
breast milk, shortening
• Produced by the partial hydrogenation of
unsat’d FAs. by the microorganisms in the
GI tract of cattle
• Hydrogenation is done commercially to
increase the melting point of cis-unsat’d
lipids, w/c makes them attractive for baking
and extends their shelf-life. However, the
process frequently has a side effect that
turns some cis-isomers into trans-
unsaturated fats instead of hydrogenating
them completely.
• Adverse Health Effects:
– essential fatty acid balance and growth
in infants
– high maternal intake inhibits low-chain
PUFA production necessary for fetal
growth and dev’t, visual and CNS dev’t
– The human lipase enzyme is ineffective
with the trans configuration, so trans fat
remains in the blood stream for a much
longer period of time and is more prone
to arterial deposition and subsequent
plaque formation.
– Unlike other dietary fats, trans fats are
not essential; raise levels of "bad" LDL
cholesterol and lowering levels of "good"
HDL cholesterol.
– increases risk for CVD, cardiovascular
diseases.
III. Triacylglycerol (also called Triglyceride)
A. Characteristics, Types and Functions
1. nonpolar, hydrophobic & water-insoluble =
lipid
2. energy reservoir in animals (stored in
reduced and anhydrous form in the
adipocytes); major storage lipid: 3 FAs can
be esterified to the glycerol (= efficient
packing).
3. energy source: FAs can be hydrolyzed,
mobilized and catabolized if needed by the
body.
4. Can be simple: composed only of one kind of
fatty acid; or mixed: composed of more than
one type of FA.
B. Structure
+ R1–COOH + R2–COOH+ R3–COOH
Basic structure of triacylglycerol
(if R1=R2=R3  simple TAG)
Mau, Jean, Alphius, Bryan
20144
 Prof. Milagros Leaño
OS 201: Correlative Human Cell Biology
Exam 1
Lecture # 3 – Structures and Functions

1-Stearoyl, 2-linoleoyl, 3-
palmitoyl glycerol, a mixed
triacylglycerol

IV. Phospholipid
A. Characteristics and Functions
• Amphipathic lipids with nonpolar aliphatic
‘tails’ and polar phosphoryl-X ‘head’.
• Amphiphilic or amphipatic property governs
lipid aggregation into higher order structure:
– spontaneous self assembly and self sealing
– principle behind the formation of amphipathic
lipid aggregates in water: micelles (transport Phosphatidylinositols in cellular regulation.
of bile acids), liposomes (transport of drugs) Phosphatidylinositol 4,5-bisphosphate in the plasma
membrane is hydrolyzed by a specific phospholipase C
and bilayers (membranes) in response to hormonal signals. Both products of
hydrolysis act as intracellular messengers.

– lung surfactant, maintains normal lung

function (e.g. Dipalmitoyl lecithin = dipalmitoyl
phosphatidylcholine)
– detergent properties help solubilize
cholesterol
– donors of arachidonic acid for the synthesis
Micelle Bilayer
of prostaglandins, thromboxanes and
leukotrienes
Aqueous
cavity B. Glycerophospholipid
1. also called phosphoglycerides
2. membrane lipids in which two FAs are
attached in ester linkage to the first and
Liposome second carbons of glycerol, and a highly polar
or charged group is attached through a
• Major types of phospholipids: phosphodiester linkage to the third carbon
glycerophospholipids and sphingolipids ∴ structural backbone: phosphatidic acid
• Functions:
– major components of cell membranes and
found in most tissues (e.g.
phosphatidylethanolamine = cephalin and
phosphatidylserine)
– bioeffectors (phosphatidylinositol, etc.)

3. Phospholipids may be regarded as derivatives

of phosphatidic, in which the phosphate is
esterified with the –OH of a suitable alcohol.

Doodle Space:

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OS 201: Correlative Human Cell Biology
Lecture # 3 – Structures and Functions
B. Major Glycolipids in the Body
C. Sphingolipid (~Sphingomyelins)
• Sphingomyelins are found in large quantities in
brain and nerve tissue. On hydrolysis, the
sphingomyelins yield a fatty acid, phosphoric
acid, choline, and a complex amino alcohol,
sphingosine. No glycerol is present.
• The combination of sphingosine plus fatty acid is
known as ceramide, a structure also found in
the glycosphingolipids (also in glycolipids)
• General Structure:
V. Glycolipid
A. Characteristics, Structure and Functions
1. Glycolipids are widely distributed in every
tissue of the body, particularly in nervous tissue
such as brain. They occur particularly in the
outer leaflet of the plasma membrane, where
they contribute to cell surface carbohydrates:
• cell adhesion and cell recognition;
some are antigens (e.g. ABO blood
group substances); some are
receptors for bacterial toxins
2. Structure:
• Lipids containing a fatty acid (FA) +
sphingosine (= ceramide), and one or
more carbohydrate.
• Their backbone is either sphingosine
or dihydrosphingosine, both are
Monday Page 5 of 7
July 20, 2009
Prof. Milagros Leaño
Exam 1
complex amino alcohols
• Fatty acids attach to the amino group
instead of attaching to the –OH group.
1. Cerebrosides
• the simplest glycosphingolipid in the body
• contains ceramide (FA + sphingosine) and
a single sugar residue (the head group)
• contains either glucose
(glucosylcerebroside or GlcCer) or
galactose (galactosylcerebroside or
GalCer)
• GalCer  major lipid of myelin;
• GlcCer  major glycosphingolipid of
extraneural tissues but also present in
small amounts in the brain; and precursor
of most of the more complex
glycosphingolipids
2. Sulfatides (Sulfogalactosylceramides)
• C3 sulfated cerebroside (specifically, a
galactosylcerebroside) or a cerebroside 3-
sulfate
• It is present in high amounts in myelin
• Present in early stages of Alzheimer’s disease and
associated with Metachromic Leukodystrophy.
3. Globoside
• Cerebroside + 2 or more sugars
• N-acetylgalactosamine as its side chain
• If globosides accumulate, Sandhoff disease may
occur
4. Gangliosides
• complex glycosphingolipids derived from
glucosylceramide that contain in addition
one or more molecules of sialic acid
(ceramides + oligosaccharide + at least
sialic acid)
• most common and principal sialic acid
found in human tissues is n-
acetylneuraminic acid or NeuAc or NANA
• at least 60 gangliosides are known (differ
mainly in the position and number of
NeuAc)
• Main functions include the following:
o complex CHO group; receptor for
certain pituitary glycoprotein
hormones
o bacterial protein toxin receptor
o cell to cell recognition
o associated with Tay-Sachs disease
• Gangliosides with one NeuAc: GM3, GM2,
GM1 (G represents ganglioside, M is a monosialo-
containing species, and subscript is a number
assigned on the basis of chromatographic migration)
• GM3 = [5-acetyl-alpha-neuraminic acid] +
[beta-D-galactopyranose] + [beta-D-
Mau, Jean, Alphius, Bryan
20144

OS 201: Correlative Human Cell Biology
Lecture # 3 – Structures and Functions
glucopyranose] + ceramide
• GM2 = GM3 + [N-acetyl-beta-D-
galactopyranose]
• GM2 accumulation in nerve cells of brain
and other tissues is associate with Tay-
Sachs disease and Sandhoff disease
• GM1 = GM2 + [beta-D-galactopyranose]
• GM1 is an important receptor in human
intestine for cholera toxin; GM2 for C.
botulinum toxin
VI. Cholesterol
A. Characteristics, Structure, and Functions
• the major sterol in the body (sterol =
compound has one or more hydroxyl or –OH
group and no carbonyl or carboxyl group)
• hydrophobic but with –OH group
• widely distributed in all cells of the body but
particularly in nervous tissue
• major constituent of plasma membrane and
of plasma lipoproteins
• precursors of bile acids, steroid hormones
(adrenocortical and sex hormones), & vit. D
• often found as cholesteryl ester (-OH group
on position 3 is esterified with a long-chain
FA)
• occurs in animals but not in plants or bacteria
• with a steroid (cyclic) nucleus (derivative of
cyclopentanoperhydrophenanthrene ring) that
resembles a phenanthrene to which a
cyclopentane ring is attached.
• has a planar confirmation
• It acts as a stabilizer by modifying
Monday Page 6 of 7
July 20, 2009
Prof. Milagros Leaño
Exam 1
membrane fluidity (i.e. phase transition
temperature)
B. Phase transition temperature (Tm)
(Some explanations are obtained from Harper’s Illustrated
Biochemistry, 27e – actually, similar din ng explanation ni Dr.
Leano)
• it is the temperature at which the structure
undergoes the transition from ordered to
disordered (i.e. melting)
• the longer and more saturated fatty acid
chains interact more strongly with each other
via their long hydrocarbon chains, the higher
the value of Tm (i.e. higher temperatures are
required to increase the fluidity of the bilayer)
• on the other hand, unsaturated bonds that
exist in the cis configuration tend to increase
the fluidity of a bilayer by decreasing the
compactness of the side chain packing
without diminishing hydrophobicity.
• below Tm: increased fluidity (cholesterol
interferes with interaction of hydrocarbon tails
of FAs)
• above Tm: limited fluidity (cholesterol limits
disorder); more rigid than the hydrocarbon
tails of the FAs and cannot move in the
membrane to the same extent
• at high cholesterol: phospholipid ratios,
transition temperatures are altogether
indistinguishable
VII. Summary
Lipids have the common property of being
relatively insoluble in water (hydrophobic) but
soluble in nonpolar solvents. Amphipathic lipids also
contain one or more polar groups, making them
suitable as constituents of membranes at lipid:water
interfaces. The lipids of major physiologic
significance are fatty acids and their esters, together
with cholesterol and other steroids.
Special Thanks to our References:
• Lehninger PRINCIPLES OF BIOCHEMISTRY, 4e
• Harper’s ILLUSTRATED BIOCHEMISTRY, 27e
• Campbell’s BIOCHEMISTRY
• Prof. Leaño’s lecture – transcribed by Bryan Mesina, Jean
Mendoza, Mark Mauricio and Marvin Masalunga
• Doc Nic’s Biochemistry Module
Greetings from the Transcribers:
Alphius: Hi Class 2014! :-) I am Ralph Julius Mendoza. I
hope that the reader of this trans will find this
Mau, Jean, Alphius, Bryan
20144

OS 201: Correlative Human Cell Biology
Lecture # 3 – Structures and Functions
historical piece useful and inspiring. Good luck to
everybody and may we get to know each other
more…
Should you have any question regarding our trans,
I’d be glad to be of service. Let’s all love biochem :-)
Para iba naman ang greeting… comics time! ~Mau
~AFTG! (All For The Girls?! hahaha)
Oy Bryan ang haba ng greeting mo! Andaming girls sa greeting
mo ha. Sino ba talaga sa kanila?! Hahahaha.
Bryan: Howdy 2014!! Hope y’all enjoy our trans on
nothin’ but fats!! Get it? Fats?? *insert silence here*
I’d like tah give an effer-y shoutout tah mah iMed
peepz!! I miss y’all so effin much!! We should hang
more often…seriously. Hello tah mah fellow iMed
cheerdancers! Sana hindi niyo pa nakakalimutan
yung mga steps!! We’d perform our routine again
someday!! Haha! Hi tah thuh 8 Ducklings!! Hi too tah
mah fellow Alphamales!! Sa next birthday ng isa
sa’tin ah! Hi tah Block 13 and 14 at sa mga nagfee-
feeling na Block 14!! :P Sa bio25 at bio30
VIII. ATTACHMENT
Fig. 1. Lipids-in-focus. Note the “Common Denominator”: Fatty Acid 
Fig. 1. Lipids-in-focus. Note the “Common Denominator”: Fatty Acid 
Table. 1. Some Naturally Occurring Fatty Acids: Structure, Properties, and Nomenclature
Monday Page 7 of 7
July 20, 2009
Prof. Milagros Leaño
Exam 1
groupmates ko, reunion tayo! Siyempre, I wouldn’t
fo’get, hi tah mah 122 new friends!! I’ve talked or
have at least greeted 120 of ye..2 nalang!! And
swear, I’ve memorized all yer faces and names!! :D
So tah those 2 people, watch out! One of these
days..I’d greet ye!! O eto, personal greetings:
Denden, di ko pa kayang baguhin language ko! AA,
may love interest ka na pala ah! Roland, I still hafta
skin ye alive!! Pero not before yer boards sa
Saturday..good luck!! Karla, sana maintindihan mo
‘to..although I doubt it..haha! Mommy Carla Boz..i
miss yer hugs! Lee-Ann, class picture!! :P Jegar and
his narcoleptic buddies, we support ye!! Sa Saturday
futsal club, laro ulit tayo! Shayne, “hun”, I miss ye!
RR, gah! Lau, Julie (aka Bo-bo) and Dana, secret lang
yun ah and thanx sa net!! Sa mga katokayo ko sa
class, hey! Jesha, ligawan mo na kasi si Dr. Papa P!
Jay, may bayad si…ehem…haha! Dogfish!! Maetrix,
di ko na aalamin..kasi sasabihin mo din naman
eventually sa’kin!! Alex, ano nang nickname ni blood
brain barrier?? Hahaha! Jhing, September 5 ah! Bea,
ye really look like Toni…and Reese too…hahaha! Sa
mga fellow LOs ko na nagpapakahirap, saya no?
Marvie!! Makakalimutan ba naman kita? Kahit na 3
seconds lang ang memory mo fo’ me..haha! I miss
ye!! Lastly, a shoutout tah mah bestfriend Pito! Oi
baller ko!! 4-words and Peace&Bounce man! B-)
Waw..haba na pala nitong greeting ko..haha! 1:26am
na sa clock ko…EFFER!!!
P.S.: Mau, ano? I-highlight ko? Hahaha! :P
Jean: CONG-GRA-TU-LATIONS! NOW NA!
Tulong tayo lahat sa Lady Med! Sept 4 na! Yay.
Yay. Yay.
Seryoso ako.
September 4!!!!!!!!
LADY MED!!!!!
Mau, Jean, Alphius, Bryan
20144
 Prof. Milagros Leaño
OS 201: Correlative Human Cell Biology
Exam 1
Lecture # 3 – Structures and Functions

*All acids are shown in their nonionized form. At pH 7, all free fatty acids have an ionized carboxylate. Note that numbering of carbon atoms
begins at the carboxyl carbon.
†The prefix n- indicates the “normal” unbranched structure. For instance, dodecanoic” simply indicates 12 carbon atoms, which could be
arranged in a variety of branched forms; “n-dodecanoic” specifies the linear, unbranched form. For unsaturated fatty acids, the configuration of
each double bond is indicated; in biological fatty acids the configuration is almost always cis.

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