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. 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.
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| IUPAC name
Labdane
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| Systematic IUPAC name
(4aR,5S,6S,8aS)-1,1,4a,6-Tetramethyl-5-[(3R)-3-methylpentyl]decahydronaphthalene | |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C20H38 | |
| Molar mass | 278.524 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
Example labdane derivatives
[edit]- Forskolin
- Galanolactone[4]
- Isocupressic acid - is an abortifacient component of Cupressus macrocarpa.[5]
- Medigenin
- Sclareol
- Stemodene
See also
[edit]References
[edit]- ^ 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.
- ^ 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. Bibcode:2006PChem..67..433K. doi:10.1016/j.phytochem.2005.10.015. PMID 16321410.
- ^ 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.