UNIT 2.

Lecture 2.9. Lipids

Study material
ADI document:
Lipids: fatty acids and TAG

Reading
Lehninger’s PoB Chapter 10:
10.1. Storage lipids
10.3. Biologically active lipids
 UNIT 2.
Lecture 2.9. Lipids

Learning goals:
• Biological roles of lipids
• Classification of lipids
• Structure and properties of fatty acids
• Structure and properties of storage lipids
• Structure and properties of regulatory lipids
• In Unit 3, Lec 3.1. you will study the structure and
properties of membrane lipids
 Lipids

Lipids are a chemically diverse group

of compounds with one characteristic
in common:

Low solubility in water

Watch this video: Hydrophilic vs Hydrophobic

https://www.youtube.com/watch?v=H3OpcVJb_2E
 Biological functions of lipids
• Storage function
– high energy nutrients
– good packing properties
• Structural function
– main structure of cell membranes
• Cofactors for enzymes
– vitamin K: blood clot formation
– coenzyme Q: ATP synthesis in mitochondria
• Signaling molecules
– paracrine hormones (act locally)
– steroid hormones (act body-wide)
– growth factors
– vitamins A and D (hormone precursors)
• Antioxidants
– vitamin E
 Classification of lipids

• Lipids that contain fatty acids:

• can be further separated into:
• storage lipids
• membrane lipids
• Biologically active lipids that do not contain
fatty acids:
• cholesterol, vitamins, pigments, etc.
 Classification of lipids
Lipids that contain fatty acids
 Fatty acids
H3C OH

• Carboxylic acids with hydrocarbon chains containing between

4 to 36 carbons
– Almost all natural fatty acids have an even number of carbons
– Most natural fatty acids are unbranched
• Saturated: no double bonds between carbons in the chain
• Monounsaturated: one double bond between carbons in the
alkyl chain
• Polyunsaturated (PUFA): two or more double bonds in the
alkyl chain
Fatty acids

Double bonds in natural

monosaturated fatty acids are
commonly in cis configuration
 Fatty acid nomenclature

– systematic name: cis-9-octadecenoic acid

– common name: oleic acid
– delta numbering of carbon skeleton: 18:1Δ9
• describes location of the first carbon of the alkene in
relationship to the carbonyl carbon
– omega numbering of carbon skeleton: 18:1ω9
• describes location of the first carbon of the alkene in
relationship to the terminal methyl
 Unsaturated fatty acids
TABLE 10-1 Some Naturally Occurring Fatty Acids: Structure, Properties, and Nomenclature
Solubility at 30 ˚C
(mg/g solvent)

Melting point
Carbon skeleton Structurea Systematic nameb Common name (derivation) Water Benzene
(˚C)

Lauric acid (Latin laurus,

12:0 CH3(CH2)10COOH n-Dodecanoic acid 44.2 0.063 2,600
“laurel plant”)

Myristic acid (Latin

14:0 CH3(CH2)12COOH n-Tetradecanoic acid 53.9 0.024 874
Myristica, nutmeg genus)

Palmitic acid (Latin palma

16:0 CH3(CH2)14COOH n-Hexadecanoic acid 63.1 0.0083 348
“palm tree”)

Stearic acid (Greek stear,

18:0 CH3(CH2)16COOH n-Octadecanoic acid 69.6 0.0034 124
“hard fat”)

Arachidic acid (Latin

20:0 CH3(CH2)18COOH n-Eicosanoic acid 76.5
Arachis, legume genus)

Lignoceric acid (Latin

24:0 CH3(CH2)22COOH n-Tetracosanoic acid lignum, “wood” + cera, 86.0
“wax”)
aAll 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.
bThe 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-dodecanic” 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.
 Saturated fatty acids
Some Naturally Occurring Fatty Acids: Structure, Properties, and
TABLE 10-1
Nomenclature
Solubility at 30 ˚C
(mg/g solvent)

Common name Melting point

Carbon skeleton Structurea Systematic nameb Water Benzene
(derivation) (˚C)

CH3(CH2)5CH= cis-9-Hexadecenoic
16:1(Δ9) Palmitoleic acid 1 to –0.5
CH(CH2)7COOH acid
CH3(CH2)7CH= cis-9-Octadecenoic Oleic acid (Latin
18:1(Δ9) 13.4
CH(CH2)7COOH acid oleum, “oil”)
CH3(CH2)4CH=
cis-,cis-9,12- Linoleic acid (Greek
18:2(Δ9,12) CHCH2CH= 1–5
Octadecadienoic acid linon, “flax”)
CH(CH2)7COOH
CH3CH2CH=
CHCH2CH= cis-,cis-,cis-9,12,15-
18:3(Δ9,12,15) α-Linolenic acid 211
CHCH2CH= Octadecatrienoic acid
CH(CH2)7COOH
CH3(CH2)4CH=
CHCH2CH= cis-,cis-,cis-, cis-
20:4(Δ5,8,11,14) CHCH2CH= 5,8,11,14- Arachidonic acid –49.5
CHCH2CH= Icosatetraenoic acid
CH(CH2)3COOH
aAll 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.
bThe 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-dodecanic” 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.
 Essential fatty acids

• Two fatty acids are essential (we need them but

our metabolism cannot synthesize them):
– Linoleic acid: 18:2Δ9,12
– α-linolenic acid (ALA): 18:3Δ9,12,15

• ALA is an ω-3 polyunsaturated fatty acid:

– ω-3 PUFAs have been linked to protection against
heart disease
– Other ω-3 PUFAs can be synthesized from ALA: EPA,
DHA
 Solubility and melting point
of fatty acids
• Solubility
– decreases as the chain length increases

• Melting Point
– decreases as the chain length decreases
– decreases as the number of double bonds
increases
Hydrogenation of fatty acids

Watch this video about the molecular structure of margarine

https://www.youtube.com/watch?v=6J26Wmvltzs&feature=youtu.be
 Trans fatty acids
• Trans fatty acids form by partial hydrogenation of
unsaturated fatty acids
– done to increase stability at high temperature of oils used
in cooking and to give foods a desirable taste and texture
• A trans double bond allows a given fatty acid to
adopt an extended conformation
• Trans fatty acids can pack more regularly and show
higher melting points than cis forms
• Intake of trans fats is associated with an increased
risk of cardiovascular disease
 Triacylglycerols

• The majority of fatty acids in biological systems are

found in the form of triacylglycerols
– Solid ones are called fats
– Liquid ones are called oils
• They are the primary storage form of lipids (body fat)
• More hydrophobic (less soluble in water) than fatty
acids due to the esterification of the carboxylate
group
 Triacylglycerols
OH

OH

OH
Glycerol
 Fats provide efficient fuel storage
• The advantage of fats over polysaccharides:
– Fatty acids carry more energy per carbon because
they are more reduced
– Fatty acids carry less water per gram because they
are nonpolar
• Glucose and glycogen are for short-term energy needs:
quick delivery
• Fats are for long-term energy
needs: slow delivery
 Biologically active lipids

• Are present in much smaller amounts than

storage or structural lipids:
– Steroid hormones
– Signaling molecules =Moléculas de señalización Hormonas, neurotransmisores,etc...

– Lipid-soluble vitamins
 Steroid hormones
• Steroids are derivatives of sterols
• Steroid hormones are synthesized from cholesterol
in gonads and adrenal glands
• Many of the steroid hormones are male and female
sex hormones
 Arachidonic acid derivatives

• Enzymatic oxidation of arachidonic acid yields:

• prostaglandins (inflammation and fever)
• thromboxanes (formation of blood clots)
• leukotrienes (smooth muscle contraction in lungs)
Músculo liso
Vitamin D regulates calcium metabolism

El déficit de vitamina D se asocia con

raquitismo en niños y
osteomalacia en adultos. Aunque los
estudios no son concluyentes sí que
sugieren una
relación entre niveles bajos de la vitamina
y mayor riesgo de ciertos tipos de cáncer y
enfermedades crónicas.

Rickets

https://www.boldsky.com/health/
 Vitamin E is an antioxidant
En el cuerpo, actúa como antioxidante, al ayudar a proteger las células contra los daños causados por los
radicales libres. Los radicales libres son compuestos que se forman cuando el cuerpo convierte los alimentos
que consumimos en energía.

Los radicales libres podrían influir en las enfermedades cardíacas, el cáncer y otras enfermedades.

Isoprene

Terpene

Terpenoid (isoprenoid)
 Vitamin A (retinol)
Tu cuerpo transforma los betacarotenos en vitamina

• Derived from β-carotene

A.

• Involved in the visual cycle

• Precursor for other hormones
involved in cell signaling
 La vitamina K es un cofactor de la coagulación

Vitamin K is a clotting cofactor

su función como cofactor en la formación y activación de proteínas de la coagulación sanguínea como la protrombina (factor II) y de los
factores de coagulación (VII, IX y X) en el hígado.

El proceso de coagulación se inicia con la activación del factor X, que transforma a protrombina en trombina. La trombina
finalmentecataliza la formación de monómeros de fibrina a partir de fribrinógeno. Los monóme-ros de fibrina se polimerizan en una
malla de hilos de fibrina en la que se agrupan las células sanguíneas dando lugar a la formación de un trombo, que bloquea el vaso
sanguíneo dañado y detiene el sangrado. Al contario de lo que se ha creído durante muchos años, una ingesta excesiva de vitamina K
no aumenta la propensión a una mayor coagulación de la sangre: las proteínas dependientes de la vitamina K tienen una cantidad
limitada de residuos de ácido glutámico que pueden ser carboxilados y, aunque las concentraciones de vitamina K sean muy elevadas,
no se da una mayor carboxilación o un exceso de coagulación (1).
And many other isoprenoids …