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Periwinkle yields novel compounds
Posted: Wednesday, January 28, 2009 2:52 pm
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By manipulating the complex biosynthetic pathways of the periwinkle plant, MIT chemists have genetically altered the plant to produce entirely new compounds, some of which could be used as drugs against cancer and other diseases. The researchers, led by Sarah O'Connor of the Department of Chemistry, has studied periwinkle for several years because it produces a variety of alkaloid compounds of pharmacological interest, including vinblastine, a drug commonly used to treat cancers such as Hodgkin's lymphoma.

Scientists have known for years how to get plants to resist pests and herbicides or to produce substances such as insecticides by inserting genes from other plants or animals. What is new, however, is the ability to induce plants to create new products by tinkering with the plants' own synthetic pathways.

O'Connor and her graduate student, Weerawat Runguphan, focused on an enzyme involved in an early step of the alkaloid synthesis pathway. The enzyme normally accepts a terpenoid called secologanin and tryptamine, an alkaloid, as substrates.

Another graduate student, Peter Bernhardt, engineered a mutant form of the enzyme that can accept tryptamine with a halogen (such as chlorine or bromine) attached. Runguphan grew genetically engineered plant cell cultures that produce the mutant enzyme and got them to synthesize several compounds that periwinkle plants would normally never produce.

The halogens could serve as points of attachment to add other novel chemical groups to the compounds, modifying their effectiveness and/or toxicity as drugs, said O'Connor.

Their work is reported in the Jan. 18 issue of Nature Chemical Biology.
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