Fundamentals of Medicinal Chemistry

(Brent) #1
Consequently, their carbon skeletons usually contain five or multiples of five

carbon atoms. The structures of terpenes may also contain functional groups,

such as alcohols, ethers, esters and ketones.

Two isoprene units

α-Pinene

Myrcene (oil of bay)

Two isoprene units

Isoprene

Figure 1.25 The isoprene rule for classifying compounds as terpenes. To apply the rule one


ignores the double bonds (see myrcene) and in some cases it is also necessary to distort the


isoprene structure (seea-pinene)


Most terpenes are known by their historic trivial names, although systematic

names may be used for simple compounds. Terpenes are also classified

according to the number of carbon atoms in their structures (Table 1.5).

Table 1.5 The classification system for terpenes

Number of C atoms Classification

10 Monoterpene
15 Sesquiterpene
20 Diterpene
25 Sesterterpene
30 Triterpene
40 Tetraterpene

Monoterpenes are the main constituents of a group of compounds that are

known as theessential oils. They are extracted from plants and animals and have

been used as perfumes, medicines and spices for thousands of years (Figure 1.26).

1.5.6 Phospholipids


Most phospholipids are essentially disubstituted phosphates (Figure 1.27). They

may be initially classified as phosphatidyl compounds, plasmalogens, ether

phospholipids and sphingomyelins depending on the nature of the R 1 group

attached to the phosphate residue (Table 1.6).

LIPIDS 23

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