Fatty acids

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Prostaglandins and leukotrienes

-Eicosanoids.

-Potent paracrine effects

-Cannot travel long distances

FATTY ACIDS

-Long hydrocarbon chains with a terminal carboxylate (COO-) group.

-Highly reduced – energy dense.

-MUFA: mono-unsaturated fatty acids

-PUFA: poly-unsaturated fatty acids

-Naturally occurring Fatty Acids are cis not trans

-Industrial production of MUFA + PUFA fats/oils – yield trans isomer fats. omega (last) = w

The position of the C=C double bond can be denoted:

-In relation to the C number (1 st C is the C atom of the COO-)

-In relation to the omega C atom e.g. w3 would be 3 carbons back from the omega carbon.

Saturated fat – no C=C double bonds

Palmitic Acid = C16

Stearic Acid = C18

-solid at room temperature.

Unsaturated fat – contains C=C double bonds

Oleic acid = monounsaturated fatty acid ---> trans isomer = Elaidic acid

Linoleic acid = polyunsaturated fatty acid (more than 1 C=C double bond – 2 double bonds)

-Unsaturated fats allow membrane to be more fluid.

-They bend and pack in a less ordered way.

-liquid at room temperature.

EPA: Eicosapentaenoic acid – 5 double bonds

DHA: Docosahexenoic acid – 6 double bonds

Essential fatty acids

PU fatty acids that have more than 2 C=C bonds at least 1 of which is beyond C9.

-Linolenic acid (C18:3) – omega 3 fatty acid

-Converted to arachidonic acid – ARA (C20:4)

-Linoleic acid (C18:2) – omega 6 fatty acid

-Converted to eicosapentaenoic acid (C20:5) – EPA

-ARA and EPA are used to synthesise eicosanoids.

Eicosanoids (prostaglandins and leukotrienes)

-Derived from C20 PUFAs – ARA, ESA and EPA.

-Synthesis pathways

-cyclooxygenase (COX) pathway – prostaglandins and thromboxane.

-lipoxygenase (LOX) pathway – leukotriene.

-Bind specific plasma membrane receptors.

-Functions as local signalling molecules.

-Play important roles in:

*Inflammation – COX2 inhibtors are widely prescribed NSAIDs e.g. aspirin

*Regulation of vascular tone,

Triacylglycerides

-3C alcohol = Glycerol.

-Stored in adipose tissue

-1g of triglycerides yields 38kJ of energy.

-No solvation – takes up less space than CHO.

Lipases: cleave ester bonds of triglycerides to release fatty acids.

GlyceroPhospholipids (GPLs)

-Simplest GPL is phosphatidate.

-It is glycerol 3 phosphate esterified with 2 FA (diacylglycerol) with phosphate group attached to the 3 rd OH group.

Polar alcohol compounds can be esterified to the PO4 group

-Choline – Phosphatidylcholine – major component of biological membranes.

-Serine

-Ethanolamine

-Inositol ---> sugar alcohol – makes neurotransmitters and steroid hormones bind to their receptors in the brain, important in cell signal transduction.

-Glycerol: C3 alcohol.

GPLs are composed of fatty acid, glycerol, phosphate and alcohol.

-Phospholipases breakdown GPLs.

Phospholipase A2 (snake venom) - cleaves the SN-2 acyl chain , releasing arachidonic acid .

-Lysolecithin:- breakdown product of this reaction, biological detergent, dissolves the membranes of red blood cells causing them of rupture.

GPL Properties

-Amphipathic molecules.

-Polar PO4 and alcohol groups: polar head

-Non-polar hydrophobic FA chains: non-polar tail

-Integral to the role of GPL in biological membranes.

Cholesterol increases membrane fluidity deep in membrane.

Cholesterol decreases membrane fluidity near surface.

Glycolipids

-Main class is Glycosphingolipids – simplest glycosphingolipid is a ceramide.

-They’re abundant in nerve cell membranes.

-Nerve impulse transmission.

-Cell-cell recognition.

-Molecular recognition – binds glycoprotein hormones & bacterial toxins.

-Sphingolipidoses: defects glycosphingolipid metabolism – fatal neurological disorders.

-Membrane lipids based on an 18C amino alcohol rather than glycerol.

-Parent compound is ceramide.

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