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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
• In animals, additional double bonds are 3. Trans Unsaturated Fatty Acids: Good or
introduced only between the existing Bad?
double bond (e.g. ω9, ω6, or ω3) and the
carboxyl carbon, leading to three series of • Present in: margarine, breads, chips, fries,
fatty acids known as the ω9, ω6, and ω3 breast milk, shortening
[omega] families, respectively. • Produced by the partial hydrogenation of
• For the essential fatty acids: unsat’d FAs. by the microorganisms in the
Linoleic acid 18:2(Δ9,12) 18ω6 GI tract of cattle
• Hydrogenation is done commercially to
Linolenic acid 18:3(Δ9,12,15) 18ω3 increase the melting point of cis-unsat’d
Arachidonic acid 20:4(Δ5,8,11,14) 20ω6 lipids, w/c makes them attractive for baking
Docosahexaenoic and extends their shelf-life. However, the
acid (DHA) 22:6(Δ4,7,10,13,16,19) 22ω6 process frequently has a side effect that
turns some cis-isomers into trans-
E. Other Matters unsaturated fats instead of hydrogenating
them completely.
1. Why are essential fatty acids important?
• Adverse Health Effects:
EFAs are directly associated with many life- – essential fatty acid balance and growth
sustaining biological functions: in infants
– high maternal intake inhibits low-chain
• maintenance of healthy cell membranes PUFA production necessary for fetal
• growth requirement growth and dev’t, visual and CNS dev’t
• for healthy skin (prevents dermatitis, dry – The human lipase enzyme is ineffective
flaky skin) (omega-6) with the trans configuration, so trans fat
• precursor of long chain polyunsaturated remains in the blood stream for a much
fatty acids, PUFAs (fr. omega fatty acids) longer period of time and is more prone
• for brain dev’t (omega-3) to arterial deposition and subsequent
plaque formation.
• visual acuity/retinal dev’t (omega-3)
– Unlike other dietary fats, trans fats are
not essential; raise levels of "bad" LDL
• EFAs are precursors of eicosanoids, w/c cholesterol and lowering levels of "good"
are signaling molecules made by HDL cholesterol.
oxygenation of twenty-carbon essential – increases risk for CVD, cardiovascular
fatty acids, (EFAs) diseases.
e.g. Prostaglandins & Thromboxanes
– regulate inflammatory response III. Triacylglycerol (also called Triglyceride)
– produce pain A. Characteristics, Types and Functions
– induce sleep 1. nonpolar, hydrophobic & water-insoluble =
– reproduction lipid
– regulate blood coagulation 2. energy reservoir in animals (stored in
Leukotrienes reduced and anhydrous form in the
– muscle contractant properties adipocytes); major storage lipid: 3 FAs can
– chemotactic properties be esterified to the glycerol (= efficient
– important in allergic reactions packing).
and inflammation
3. energy source: FAs can be hydrolyzed,
2. More about DHA (Docosahexaenoic acid) mobilized and catabolized if needed by the
body.
• Dietary sources: marine animals and 4. Can be simple: composed only of one kind of
planktons, moss, ferns, seed oils fatty acid; or mixed: composed of more than
(rapeseed, soya, walnut) one type of FA.
• accumulates in the 3rd trimester of
pregnancy B. Structure
• plays an important role in brain dev’t and in
visual acuity or retinal dev’t
+ R1–COOH + R2–COOH+ R3–COOH
• 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 Basic structure of triacylglycerol
atherosclerosis & CVD (cardiovascular (if R1=R2=R3 simple TAG)
disease)
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.
Doodle Space:
3. Globoside
• Cerebroside + 2 or more sugars
• N-acetylgalactosamine as its side chain
• If globosides accumulate, Sandhoff disease may
V. Glycolipid occur
A. Characteristics, Structure and Functions
4. Gangliosides
1. Glycolipids are widely distributed in every • complex glycosphingolipids derived from
tissue of the body, particularly in nervous tissue glucosylceramide that contain in addition
such as brain. They occur particularly in the one or more molecules of sialic acid
outer leaflet of the plasma membrane, where (ceramides + oligosaccharide + at least
they contribute to cell surface carbohydrates: sialic acid)
• cell adhesion and cell recognition; • most common and principal sialic acid
some are antigens (e.g. ABO blood found in human tissues is n-
group substances); some are acetylneuraminic acid or NeuAc or NANA
receptors for bacterial toxins • 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
2. Structure: o associated with Tay-Sachs disease
• Lipids containing a fatty acid (FA) + • Gangliosides with one NeuAc: GM3, GM2,
sphingosine (= ceramide), and one or GM1 (G represents ganglioside, M is a monosialo-
containing species, and subscript is a number
more carbohydrate.
assigned on the basis of chromatographic migration)
• Their backbone is either sphingosine • GM3 = [5-acetyl-alpha-neuraminic acid] +
or dihydrosphingosine, both are [beta-D-galactopyranose] + [beta-D-
VII. Summary
Lipids have the common property of being
relatively insoluble in water (hydrophobic) but
soluble in nonpolar solvents. Amphipathic lipids also
• hydrophobic but with –OH group
contain one or more polar groups, making them
• widely distributed in all cells of the body but suitable as constituents of membranes at lipid:water
particularly in nervous tissue interfaces. The lipids of major physiologic
• major constituent of plasma membrane and significance are fatty acids and their esters, together
of plasma lipoproteins with cholesterol and other steroids.
• precursors of bile acids, steroid hormones
(adrenocortical and sex hormones), & vit. D
Special Thanks to our References:
• often found as cholesteryl ester (-OH group
on position 3 is esterified with a long-chain • Lehninger PRINCIPLES OF BIOCHEMISTRY, 4e
FA) • Harper’s ILLUSTRATED BIOCHEMISTRY, 27e
• occurs in animals but not in plants or bacteria • Campbell’s BIOCHEMISTRY
• with a steroid (cyclic) nucleus (derivative of • Prof. Leaño’s lecture – transcribed by Bryan Mesina, Jean
cyclopentanoperhydrophenanthrene ring) that Mendoza, Mark Mauricio and Marvin Masalunga
• Doc Nic’s Biochemistry Module
resembles a phenanthrene to which a
cyclopentane ring is attached. Greetings from the Transcribers:
• has a planar confirmation
Alphius: Hi Class 2014! :-) I am Ralph Julius Mendoza. I
• It acts as a stabilizer by modifying hope that the reader of this trans will find this
Oy Bryan ang haba ng greeting mo! Andaming girls sa greeting Jean: CONG-GRA-TU-LATIONS! NOW NA!
mo ha. Sino ba talaga sa kanila?! Hahahaha. Tulong tayo lahat sa Lady Med! Sept 4 na! Yay.
Yay. Yay.
Seryoso ako.
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 September 4!!!!!!!!
peepz!! I miss y’all so effin much!! We should hang
more often…seriously. Hello tah mah fellow iMed LADY MED!!!!!
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
Table. 1. Some Naturally Occurring Fatty Acids: Structure, Properties, and Nomenclature
*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.