Triterpene

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Triterpenoid
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Squalene: One of the most important triterpenes
Hopane: An example of a pentacyclic triterpene

Triterpenes are a class of

terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.[1][2]

Structures

Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified.[3] These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate.

Number of rings Examples
0 Squalene
1 Achilleol A [4]
2 Polypodatetraene
3 Malabaricane
4 Lanostane, Cucurbitacin
5 Hopane, Oleanane, Ursolic acid
6 Chamaecydin


Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols.

Triterpenoids

Cholesterol: one of the simplest but most important triterpenoids

By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms triterpene and triterpenoid often are used interchangeably.

Triterpenoids possess a rich chemistry and pharmacology (e.g. cholesterol) with several pentacyclic motifs. Lupane, oleanane and ursane show particular promise as anti-cancer agents.[5][6]

Steroids

Steroids feature a

steroid hormone receptors. Important sub-classes include sterols and cucurbitacins
.

Triterpenoid saponins

Triterpenoid saponins are triterpenes which belong to the saponin group of compounds, making them triterpenoid glycosides. They are produced by plants as part of their self-defense mechanism[7] with important sub-classes including ginsenosides[8] and eleutherosides
.

References

  1. ISBN 9783527609949
    .
  2. ISBN 978-3-540-66573-1
    .
  3. PMID 14751299
    .
  4. ISSN 0040-4039
    .
  5. PMID 19742422
    .
  6. PMID 8847885
    .
  7. PMID 21333312
    .
  8. PMID 10571242
    .
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