Labdane
Chemical compound
Labdane is a natural bicyclic diterpene. It forms the structural core for a wide variety of natural products collectively known as labdanes or labdane diterpenes. The labdanes were so named because the first members of the class were originally obtained from labdanum, a resin derived from the gum rockrose.
A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities. Natural labdanes in tree resin are believed to be the precursors of amber, which polymerise under great pressure.
01Biosynthesis
The enzyme (13E)-labda-7,13-dien-15-ol synthase produces the labdane, (13E)-labda-7,13-dien-15-ol, directly from geranylgeranyl pyrophosphate in the lycophyte Selaginella moellendorffii. The reaction proceeds in two steps: cyclisation and then hydrolysis, with pyrophosphate (PPi) as a byproduct.
geranylgeranyl pyrophosphate H2O PPi (13E)-labda-7,13-dien-15-ol02Example labdane derivatives
- Forskolin
- Galanolactone
- Isocupressic acid - is an abortifacient component of Cupressus macrocarpa.
- Medigenin
- Sclareol
- Stemodene
Sources and credits
This article is adapted from the Wikipedia article “Labdane”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Labdane.svg by Ed (Edgar181), Public domain
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