Chemistry:Labdane
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.[1][2]
A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities.[3] Natural labdanes in tree resin are believed to be the precursors of amber, which polymerise under great pressure.
Biosynthesis
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.[4]
- REDIRECT Template:Chemical reaction
Example labdane derivatives
- Forskolin
- Galanolactone[5]
- Isocupressic acid - is an abortifacient component of Cupressus macrocarpa.[6]
- Medigenin
- Sclareol
- Stemodene
See also
References
- ↑ Cocker, J. D.; Halsall, T. G.; Bowers, A. (1956). "The chemistry of gum labdanum. I. Some acidic constituents". Journal of the Chemical Society: 4259–62. doi:10.1039/jr9560004259.
- ↑ Cocker, J. D.; Halsall, T. G. (1956). "The chemistry of gum labdanum. II. The structure of labdanolic acid". Journal of the Chemical Society: 4262–71. doi:10.1039/jr9560004262.
- ↑ Atta-Ur-Rahman, ed (1988). Studies in Natural Product Chemistry : Bioactive Natural Products, Part F. ISBN 978-0-08-044001-9.
- ↑ "A novel labda-7,13E-dien-15-ol-producing bifunctional diterpene synthase from Selaginella moellendorffii". ChemBioChem 12 (13): 1984–7. September 2011. doi:10.1002/cbic.201100336. PMID 21751328.
- ↑ Kenmogne, Marguerite; Prost, Elise; Harakat, Dominique; Jacquier, Marie-José; Frédérich, Michel; Sondengam, Lucas B.; Zèches, Monique; Waffo-Téguo, Pierre (1 March 2006). "Five labdane diterpenoids from the seeds of Aframomum zambesiacum". Phytochemistry 67 (5): 433–438. doi:10.1016/j.phytochem.2005.10.015. PMID 16321410. Bibcode: 2006PChem..67..433K.
- ↑ Parton, K; Gardner, D; Williamson, N.B (1996). "Isocupressic acid, an abortifacient component of Cupressus macrocarpa". New Zealand Veterinary Journal 44 (3): 109–111. doi:10.1080/00480169.1996.35946. PMID 16031906. https://zenodo.org/record/1234401.
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