Terpenoid
From Wikipedia, the free encyclopedia
The terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures which differ from one another not only in functional groups, but also in their basic carbon skeletons. These lipids can be found in all classes of living things, and are the largest group of natural products.
Plant terpenoids are extensively used for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial, antineoplastic and other pharmaceutical effects. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves and ginger and the color of yellow flowers. Well-known terpenoids include citral, menthol, camphor and the cannabinoids found in the Cannabis plant.
The steroids and sterols in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to proteins, e.g. to enhance their attachment to the cell membrane; this is known as isoprenylation.
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[edit] Structure and classification
Terpenes are hydrocarbons resulting from the combination of several isoprene units. Terpenoids can be thought of as modified terpenes, where methyl groups have been moved or removed, or oxygen atoms added. (Some authors use the term "terpene" more broadly, to include the terpenoids.) Just like terpenes, the terpenoids can be classified according to the number of isoprene units used:
- Monoterpenoids, 2 isoprene units
- Sesquiterpenoids, 3 isoprene units
- Diterpenoids, 4 isoprene units
- Sesterterpenoids, 5 isoprene units
- Triterpenoids, 6 isoprene units
- Tetraterpenoids, 8 isoprene units
- Polyterpenoids with a larger number of isoprene units
Terpenoids can also be classified according to the number of cyclic structures they contain.
[edit] Biosynthesis
There are two metabolic pathways of creating terpenoids:
[edit] Mevalonic acid pathway
Many organisms manufacture terpenoids through the HMG-CoA reductase pathway, the pathway that also produces cholesterol. The reactions take place in the cytosol. The pathway was discovered in the 1950s.
[edit] MEP/DOXP pathway
The MEP/DOXP pathway, also known as 2-C-methyl-D-erythritol 4-phosphate/deoxy-xylulose phosphate pathway, mevalonic acid independent pathway, or non-mevalonate pathway takes place in the plastids of plants and apicomplexan protozoa as well as in many bacteria. It was discovered in the late 1980s.
Pyruvate is converted by DOXP synthase (DXS) to 1-Deoxy-D-xylulose-5-P and by DOXP reductase (DXR) to 2-C-Methyl-D-erythritol-4-P (MEP) and in multiple steps via (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP).
DMAPP is a common metabolite in both pathways and an exchange of DMAPP would be possible.
Out of this intermediate, isoprene, monoterpenoids (10-carbon) diterpenoids (20-carbon), carotenoids (40-carbon), chlorophylls and plastoquinone-9 (45-carbon) are formed.
Intermediates are geranyl pyrophosphate (GPP) and geranylgeranyl pyrophosphate (GGPP). Both intermediates can also be found in the MVA pathway.
Although both pathways, MVA and MEP, operate independently under normal conditions, interactions between them have been reported repeatedly.
| Organism | Pathways |
|---|---|
| Eubacteria | MVA + MEP |
| Archaea | MVA |
| Green Algae | MEP |
| Plants | MVA + MEP |
| Animals | MVA |
| Fungi | MVA |
