Products of Isoprene Metabolism

PRODUCTS OF ISOPRENE METABOLISM

Acetoacetyl-CoA + Acetyl-CoA

CH2COO-

CH3C(OH)CH 2COSCoA 3-OH-3-methylglutaryl-CoA Ergot Alkaloids (fungi) 1.1.1.32

CH2COO- CH C(OH)CH CH OH 3 2 2 n PHYTYL SIDE CHAINS Mevalonate Natural Rubber CH3 Isoprene blue haze HO 2.7.1.36 CH3 2.7.4.2 Isopentenyl adenosine CH3 O CH COO- CH3 2 a-Tocopherol (Vitamin E) CH3C(OH)CH 2CH2OP-O-P Plant Monoterpenes CH2OH O Diphospho mevalonate CH3 4.1.1.33 O CH CH2 Phylloquinone (Vitamin K) 3 Geraniol Limonene CH3C.CH2CHOP-O-P CH3C = CHCH 2OP-O-P 5.3.3.2 P-O-P Isopentenyl-P-O-P Chlorophyll side chain Dimethylallyl- Perfumes Colour s (C5) (C5)

2.5.1.1 OH CHO CH2OP-O-P Menthol Phytyl-P-O-P CH2 OP-O-P Citronellal Flavours Geranyl-P-O-P (C10) Dolichol Insect Hormones Zingiberene (ginger) O CH OP-O-P 2.5.1.10 2 CH3 CH3O Gibberellins - Plant growth hormones CH3O n O Ubiquinone Hopanoids + (Coenzyme Q) Farnesyl-P-O-P 2.5.1.29 (C15)

2. 5. Menaquinone 1. 21 (Vitamin K2) CH2OP-O-P Plastoquinone Geranyl-geranyl-PP (C20) Squalene 2.5.1.32 (C30)

1.14.99.7 5.4.99.7 Phytoene CAROTENOIDS (C 40) HO Lanosterol (C30) Colour

Lycopene HO (C 40) Colour Zymosterol

Light harvesting B-CAROTENE pigments in i HO Photosynthesis (C 40)

To brain - VISION Desmosterol Xanthophylls

1.13.11.21 LIGHT HO Rhodopsin Metarhodopsin CHOLESTEROL STEROIDS COO- Opsin Retinoate CHO Ergosterol Pregnenolone Progesterone 5.2.1.3 (yeast) trans-Retinal 11-cis-Retinal CHO 1.2.1.36 Light Retinol esters 1.1.1.105 Aldosterone Testosterone 2.3.1.76 CH2OH Calciferol Finasteride 3.1.1.21 5.2.1.7 trans-Retinol 11-cis-Retinol CH2OH (Vitamin D) Dark Estradiol (Vitamin A) Cortisol Dihydro- testosterone

These two minimaps are designed to stimulate the imagination and hopefully create excitement and an awareness that we are dealing with REAL- LIFE METABOLISM. The facing one is entitled Isoprene Metabolism and is a traditional biochemical pathways map but is itself interesting because it shows that two very differing types of products- one mainly open-chain (carotenoid) and the other ringed (steroid )- can arise from the same source. The facing map Isoprene Products is identical except that, in additio n, it highlights and pictures the real- -life significance of some of these products They include natural rubber; plant and insect hormones and the side chains of many vitamins and of chlorophyll. They provide colour, smell and flavour in many plant pr oducts such as carrots, lemons or roses. They include some of the vital reactions that can convert light into vision and, in a different pathway, the steroids including estrogens and testosterones with all their implications. Many of the sensual and sexual pleasures of life can thus be seen to derive from the same, simple 5-carbon compound isoprene. This is real-life metabolism.