Biosynthesis of cocaine

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The discovery of the first enzyme in the pathway sheds new light on the evolution of alkaloid formation. Cocaine is one of the most commonly used and abused plant-derived drugs in the world, but we have almost no modern information on how plants produce this complex alkaloid. Researchers from the Max Planck Institute for Chemical Ecology in Jena, Germany, have just discovered a key reaction in cocaine formation in the coca plant from South America, and identified the responsible enzyme. This enzyme was shown to belong to the aldo-keto-reductase protein family revealing some exciting new insights into the evolution of cocaine biosynthesis. Alkaloids constitute a very large group of natural nitrogen-containing compounds with diverse effects on the human organism. A large variety of plant-produced alkaloids have strong pharmacological effects, and are used as toxins, stimulants, pharmaceuticals or recreational drugs, including caffeine, nicotine, morphine, quinine, strychnine, atropine and cocaine. Atropine, used to dilate the pupils of the eye, and the addictive drug cocaine are both tropane alkaloids which possess two distinctive, inter-connecting five- and seven-membered rings. Plants commonly produce tropane and other alkaloids for protection against herbivores and other enemies. Species in seven plant families are known to produce tropane alkaloids, including the Brassicaceae mustard family , Solanaceae nightshade or potato family and Erythroxylaceae coca family. These families are not closely related to each other. For example, it is assumed that the last common ancestor of the Erythroxylaceae and the Solanaceae lived about million years ago. But how similar are the tropane alkaloid biosynthetic pathways in these families? Was there a single original tropane alkaloid pathway which was lost in most other plant families during the course of evolution? Or, did tropane alkaloid biosynthesis arise independently on several different occasions? Native tribes in South America have been cultivating coca and chewing its leaves for at least years for their stimulant and hunger-suppressing properties. Although the formation of cocaine has not been investigated in the last 40 years, the biosynthesis of the related tropane alkaloid, atropine, from belladonna Solanaceae is well-established. In the penultimate step, a ketone function is reduced to an alcohol residue. Among this group of enzymes are also many alcohol-degrading dehydrogenases in animals. To find the corresponding enzyme in cocaine biosynthesis, Jan Jirschitzka, a PhD student in the group, searched the genome of the coca plant to look for SDR-like proteins. However, all the SDR genes that he cloned and expressed did not show any activity for the key reaction in cocaine formation. AKR enzymes are known in plants and also mammals, amphibians, yeast, protozoa, and bacteria. They are involved in the formation of steroid hormones, for example. The second result is that the MecgoR gene, as well as the protein, is highly active in the very young leaves of coca plants, but not in the roots. Atropine, on the other hand, is synthesized exclusively in the roots of belladonna, from where it is transported into the green organs of the plant. Based on these results, the Max Planck researchers conclude that the tropane alkaloid pathways in coca and belladonna evolved completely independently. Elucidation of the MecgoR-catalysed step in cocaine biosynthesis represents a major success, but the researchers are now continuing to investigate other important steps in the cocaine pathway. Also of interest is to learn how cocaine is stored in leaf tissue in such high amounts. Homepage Research Research News How plants make cocaine. How plants make cocaine The discovery of the first enzyme in the pathway sheds new light on the evolution of alkaloid formation. Coca plant Erythroxylum coca and the molecular structure of cocaine grey: Immunolabeling green areas of MecgoR, the enzyme catalysing the penultimate step of cocaine biosynthesis. The picture shows the strong accumulation of the enzyme in a cross section of a very young E. Open in new window. Go to Editor View.

Biosynthesis of cocaine