PRODUCTS OF ISOPRENE METABOLISM

Acetoacetyl-CoA + Acetyl-CoA
CH 2COOCH3C(OH)CH 2COSCoA

3-OH-3-methylglutaryl-CoA
1.1.1.32

Ergot Alkaloids (fungi)

PHYTYL SIDE CHAINS

HO CH3
CH3 O CH3 O CH3 CH3

CH2COOCH 3C(OH)CH 2CH2OH

Mevalonate
2.7.1.36 2.7.4.2

Natural Rubber

Isoprene blue haze Isopentenyl adenosine

a-Tocopherol (Vitamin E)

CH2COOCH 3C(OH)CH 2CH 2OP-O-P

Plant Monoterpenes
CH2OH

Diphospho mevalonate
4.1.1.33

Phylloquinone (Vitamin K)

CH 3 CH 3C = CHCH 2OP-O-P

CH 2 CH3C.CH 2CHOP-O-P
5.3.3.2

Geraniol
Perfumes
OH

Limonene
Colour s
CHO

Chlorophyll side chain

CH 2OP-O-P

Dimethylallyl- P-O-P
(C5)

Isopentenyl-P-O-P
(C5)
2.5.1.1

Phytyl-P-O-P
O CH3O CH3O
CH3
2.5.1.10

Geranyl- P-O-P
(C10)

CH2 OP-O-P

Menthol
Dolichol

Citronellal
Insect Hormones

Flavours
Zingiberene (ginger)

CH2OP-O-P

Ubiquinone (Coenzyme Q) Menaquinone (Vitamin K2) Plastoquinone

Gibberellins - Plant growth hormones

Farnesyl-P-O-P
2.5.1.29

Hopanoids

(C15)

2. 1. 5. 21

CH2OP-O-P

Geranyl-geranyl-PP
(C20)
2.5.1.32

Squalene
(C30)
1.14.99.7 5.4.99.7

CAROTENOIDS
Colour

Phytoene
(C 40)

HO

Lanosterol
(C30)

Lycopene
Colour
(C 40)

HO

Zymosterol

Light harvesting pigments in Photosynthesis

B-CAROTENE i
(C 40)

HO

Xanthophylls
1.13.11.21

To brain -

VISION LIGHT

Desmosterol

HO

Metarhodopsin
COO-

Rhodopsin

CHOLESTEROL
Ergosterol (yeast)

Opsin
CHO

STEROIDS
Progesterone

Retinoate
1.2.1.36

Pregnenolone

trans-Retinal
1.1.1.105

5.2.1.3

Retinol esters
2.3.1.76 3.1.1.21

Light

11-cis-Retinal CHO

Aldosterone
CH2OH

Testosterone

trans-Retinol Dark (Vitamin A)

5.2.1.7

11-cis-Retinol CH2OH

Calciferol (Vitamin D)
Cortisol

Finasteride
Dihydrotestosterone Estradiol

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 addition, 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.
Designed by Donald Nicholson

c 2002 IUBMB