Clerodane diterpene

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Clerodane diterpenes, sometimes referred to as clerodane diterpenoids, are a large group of secondary metabolites that have been isolated from several hundreds of different plant species, as well as fungi, bacteria and marine sponges.[1] They are bicyclic terpenes that contain 20 carbons and a decalin core.

Classification

The clerodane diterpenes are classified into four groups trans-cis (TC), trans-trans (TT), cis-cis (CC), and cis-trans (TC) based on the relative stereochemistry at the decalin junction (trans or cis) and the relative stereochemistry of the substituents at C-8 and C-9 (trans or cis). The absolute stereochemistry of the clerodanes is classified as neo (shown below) or ent-neo (enantiomeric to neo). The neo-clerodanes share the same absolute stereochemistry as clerodin. Approximately 25% of clerodanes have the 5:10 cis ring junction. The remaining 75% have a trans 5:10 ring junction.[2]

The clerodane skeleton contains 20 carbons and a decalin core. There are four additional distinctions that refer to the stereochemistry of the decalin ring junction and the substituents on the C-8 and C-9 carbons.

Biosynthesis

They are structurally related to the bicyclic

anthelminthic properties, others like ajugarins are repellent to herbivore predators (mostly insects and their larvae) or have a very bitter taste, such as gymnocolin
.

Some examples for clerodanes are ajugarins I to V extracted from

hallucinogenic properties such as salvinorin A, a trans-neoclerodane diterpene from Salvia divinorum.[4]

See also

References

  1. PMID 27433555
    .
  2. PMID 1436738
    .
  3. PMID 17534496
    .
  4. PMID 17190459
    .

External links
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