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The Chemistry of Medicinal Plants

Basic Structure of the Carotenoids: Lycopene

Lycopene is the biosynthetic precursor of all the other carotenoids. The lycopene molecule represents the basic structure of these oil-soluble compounds. It is composed of forty carbon atoms (and their associated hydrogens) arranged in a long structure with alternating single and double bonds:


Lycopene
Lycopene
A series of alternating single and double carbon-carbon bonds is referred to as being conjugated; in carotenoids, this conjugated series of double bonds makes up the chromophore which is the part of the molecule that absorbs and gives off certain wavelengths of light, generating the colors we perceive. This chromophore not only gives carotenoids their rich colors, but it also contributes to their antioxidant properties by helping to stabilize the molecule so that it can 'donate' an electron which is used to quench a free radical. You'll notice that the lycopene molecule is quite symmetrical (with one half upside down relative to the other); this is characteristic of the carotenoids in general.

The carbon atoms of the lycopene molecule are numbered as follows: carbon # 1 is on the far left and carbon # 1' (one prime) is on the far right. The left side of the molecule contains carbons 1 through 20 and the right side, like an upside-down mirror image, contains carbons 1' through 20'. There are forty carbons all together. This total of 40 is why the carotenoids are also known as tetraterpenes: in terpene nomenclature, one group of ten carbons = mono as in monoterpene; two groups of ten carbons = di (diterpenes); three groups of ten carbons = tri (triterpenes); and four groups of ten carbons = tetra (tetraterpenes). So lycopene and all of the carotenoids which are derived from it are classified as tetraterpenes.

Accumulating evidence suggests that lycopene (the red pigment in ripe tomatoes) is a strong antioxidant and can help to prevent prostate cancer, lung cancer, stomach cancer, and possibly other cancers including those of the bladder, breast, cervix, pancreas, colon & rectum, and oral cavity.1,2 It works synergistically with other carotenoid compounds.

Updated: 1/31/12   Herbal Constituents (C) 2012 Lisa Ganora,  Louisville, CO   U.S.A.