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Terpenoid

physical science Maturity 5-7 Next article →

Terpenoids, also known as isoprenoids, are a massive class of naturally occurring organic chemicals. They are derived from a small five-carbon compound called isoprene. While people sometimes use the word "terpenes" to describe the same thing, terpenoids are technically different. Terpenoids contain additional functional groups, which usually means they include oxygen atoms. When you combine these terpenoids with hydrocarbon terpenes, they form about 80,000 different compounds. This makes them the largest class of plant secondary metabolites. In fact, they represent about 60% of all known natural products found in nature.

These chemicals are built through specific biological processes. They often arise through a process called hydrolysis. This happens when water reacts with certain intermediate molecules. For example, terpenoids containing an alcohol group often come from the hydrolysis of carbocationic intermediates. These intermediates are produced from a molecule called geranyl pyrophosphate. Other types follow a similar pattern. Hydrolysis of intermediates from farnesyl pyrophosphate creates sesquiterpenoids. Meanwhile, hydrolysis from geranylgeranyl pyrophosphate results in diterpenoids. This step-by-step chemical building allows for incredible variety.

Scientists classify terpenoids based on how many isoprene units they contain. This determines their size and structure. Hemiterpenoids are the smallest, containing only one isoprene unit and five carbon atoms. Monoterpenoids have two units and ten carbon atoms, including substances like menthol and camphor. Sesquiterpenoids contain three units and fifteen carbon atoms. Diterpenoids consist of four units and twenty carbon atoms, such as ginkgolides. Sesterterpenoids have five units and twenty-five carbon atoms. Triterpenoids contain six units and thirty carbon atoms, which includes sterols. Tetraterpenoids have eight units and forty carbon atoms. Carotenoids are a specific type of tetraterpenoid derivative.

Beyond their size, terpenoids can also be classified by their shape. They can form different types of cyclic structures. These structures might be linear or acyclic, meaning they do not form rings. They can also be monocyclic, meaning they have one ring. Some are more complex, forming bicyclic, tricyclic, tetracyclic, or pentacyclic structures. Some even form macrocyclic structures, which are very large rings. To identify if terpenoids are present in a sample, scientists can use a specific method called the Salkowski test.

Terpenoids serve many vital roles in the natural world. In plants, they act as a defense system called prophylaxis against pathogens. They can also act as attractants. For instance, they might call in predators to eat herbivores that are attacking the plant. Plants also use them for their aromatic qualities. They provide the scent of eucalyptus and the flavors of cinnamon, cloves, and ginger. They even create colors, such as the yellow in sunflowers and the red in tomatoes. In animals, terpenoid precursors are used to biologically produce steroids and sterols.

Many well-known substances are actually terpenoids. This includes citral, menthol, and camphor. There is also salvinorin A, which is found in the plant Salvia divinorum. Scientists study ginkgolide and bilobalide from the Ginkgo biloba tree. Even the cannabinoids found in cannabis are terpenoids. In some cases, terpenoids are added to proteins through a process called isoprenylation. This process helps the proteins attach more easily to cell membranes.

Terpenoids even have a significant impact on the atmosphere. When trees release these chemicals, they enter the air and undergo changes. They are converted into various species like aldehydes, organic nitrates, epoxides, and hydroperoxides. This conversion is driven by short-lived free radicals, such as the hydroxyl radical, and also by ozone. These new species can dissolve into water droplets. This process contributes to the formation of aerosols and haze. This is why the Blue Ridge Mountains in the U.S. and the Blue Mountains in Australia appear blue from a distance. The trees essentially put the blue color into the atmosphere through their terpenoids.

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