Chapter 20 Lipids.

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Presentation transcript:

Chapter 20 Lipids

Lipids Bioorganic compounds that are generally insoluble in water (hydrophobic). Waxes and Fats Prostaglandins Terpenoids Steroids

Waxes Esters of long-chain carboxylic acids with long chain alcohols Spermaceti from sperm whale oil mp 42–47oC

Waxes Esters of long-chain carboxylic acids with long chain alcohols Beeswax mp 60–82oC Major components:

Fats Esters of long-chain carboxylic acids with glycerol Fats = glycerides long-chain carboxylic acids = fatty acids glycerol a triglyceride

Fats Trimyristin

Common Saturated Fatty Acids Lauric acid (dodecanoic acid) Myristic acid (tetradecanoic acid) Palmitic acid (hexadecanoic acid) Stearic acid (octadecanoic acid)

Common Unsaturated Fatty Acids Oleic acid (cis-9-octadecenoic acid) Linoleic acid (cis,cis-9,12-octadecadienoic acid) Linolenic acid (cis,cis,cis-9,12,15- octadecatrienoic acid)

Common Unsaturated Fatty Acids Note that these unsaturated fatty acids are cis. This tends to lower the melting points of the corresponding fats. Tristearin (mp ~55oC) Triolein (mp ~5oC)

Olestra® (Sucrose Polyester) Non-absorbable lipid. Substitute for fat in foods to reduce cholesterol. Mixture of hexa-, hepta-, and octa-fatty acid esters of sucrose.

Lipophilic Vitamins Vitamin A (Retinol) Vitamin D3 (Cholecalciferol) Vitamin E (a-Tocopherol) Vitamin K (Phylloquinone)

Hydrolysis of Fats This process is called saponification.

Hydrolysis of Fats This process is called saponification.

Soap Sodium stearate:

Soap A soap micelle: Greasy dirt

Sodium dodecyl sulfate Detergents hydrophobic hydrophilic Sodium dodecyl sulfate

Detergents Alkyl benzene sulfonate detergents hydrophilic hydrophobic Non-biodegradable hydrophilic hydrophobic

Poly(ethyleneglycol) hydrophilic Detergents Non-ionic detergents less sudsing (suitable for use in dishwashers). clean synthetic fibers better. hydrophobic Poly(ethyleneglycol) hydrophilic

Phosphoglycerides Fats in which glycerol is esterified to two fatty acids and to phosphoric acid: Phosphoric acid esterified with another alcohol: phosphatidic acid (a phosphoglyceride) choline ethanolamine

Phosphoglycerides a phosphatidyl choline (a lecithin) a phosphatidyl ethanolamine (a cephalin)

Phosphoglycerides Major components of cell membranes hydrophobic hydrophilic A bilayer of phosphoglycerides

Prostaglandins Monocyclic hydroxy-fatty acids. Widespread occurrence in mammalian tissues. Potent physiological activities. Derived biosynthetically from arachidonic acid: prostaglandin E2 arachidonic acid prostaglandin F2a

Terpenoids and Other Isoprenoids Made up of several “isoprene units” isoprene

Terpenoids and Other Isoprenoids Monoterpenes C10 compounds composed of two isoprene units. geraniol menthol b-pinene camphor

Terpenoids and Other Isoprenoids Sesquiterpenes C15 (three isoprene units) bisabolene farnesol b-santalol a-humulene

Terpenoids and Other Isoprenoids Diterpenes C20 (four isoprene units) retinal abietic acid

Terpenoids and Other Isoprenoids Triterpenes C30 (six isoprene units) squalene friedelin betulin

Terpenoids and Other Isoprenoids Tetraterpenes (Carotenoids) C40 (eight isoprene units) lycopene b-carotene

Steroids Tetracyclic natural products related to terpenes.

Steroids Cholesterol Precursor to sex hormones, vitamins, etc.

Steroids Stigmasterol The most abundant plant sterol.

Steroids Progesterone Secreted by corpus luteum during latter half of menstrual cycle. Antiovulatory activity – if pregnant, secretion continues.

Steroids Testosterone Principal hormone of the testes. Converted to dihydrotestosterone (responsible for male secondary sex characteristics, including male pattern baldness).

Steroids Estradiol Mammalian estrogenic hormone produced by ovaries by aromatization of testosterone. Triggers production of gonadotropins leading to ovulation.

Steroids Norethindrone (“mini pill”) Antiovulatory activity. Compare structure with progesterone: norethindrone progesterone

Steroids Methandrostenolone (dianabol) An anabolic (growth promoting) steroid. Now banned. acne liver tumors  sperm count testicular atrophy

Steroids Androstenedione Compare structure with testosterone. A testosterone precursor. Allegedly used by Mark McGwire and Barry Bonds Compare structure with testosterone.

Steroids Androstenedione Compare structure with testosterone. A testosterone precursor. Allegedly used by Mark McGwire and Barry Bonds Compare structure with testosterone. androstenedione testosterone

Steroids Cortisone A natural glucocorticoid. Anti-inflammatory activity. Arthritis Asthma

Steroids Hydrocortisone Principal glucocorticoid hormone produced by adrenal cortex.

Steroids Betamethasone betamethasone hydrocortisone Synthetic glucocorticoid. Much stronger than hydrocortisone. betamethasone hydrocortisone

Steroids Aldosterone A mineralocorticoid steroid. Regulates absorption of Na+, Cl- by kidneys; water balance in body.

Sample Problem The compound to the right has been isolated from the leaves of Leonotis ocymifolia. What type of lipid is it? Locate the isoprene units in the compound. It has 20 carbon atoms and it follows the isoprene rule – it is a diterpenoid.