Labdane

Labdane
Names
	IUPAC name Labdane
	Systematic IUPAC name (4aR,5S,6S,8aS)-1,1,4a,6-Tetramethyl-5-[(3R)-3-methylpentyl]decahydronaphthalene
Identifiers
CAS Number	561-90-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36505 ;
ChEMBL	ChEMBL1087749 ;
ChemSpider	7827634 ;
PubChem CID	9548711;
CompTox Dashboard (EPA)	DTXSID80429533 ;
	InChI InChI=1S/C20H38/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h15-18H,7-14H2,1-6H3/t15-,16+,17+,18+,20-/m1/s1 Key: LEWJAHURGICVRE-AISVETHESA-N ;
	SMILES C2CC([C@@H]1CC[C@@H]([C@@H]([C@@]1(C)C2)CC[C@H](C)CC)C)(C)C;
Properties
Chemical formula	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). Infobox references

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 (PP_i) as a byproduct.^[4]

geranylgeranyl pyrophosphate

H₂O

PP_i

Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

(13E)-labda-7,13-dien-15-ol

Example labdane derivatives

Forskolin
Galanolactone^[5]
Isocupressic acid - is an abortifacient component of Cupressus macrocarpa.^[6]
Medigenin
Sclareol
Stemodene

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.
↑ Mafu S, Hillwig ML, Peters RJ (September 2011). "A novel labda-7,13E-dien-15-ol-producing bifunctional diterpene synthase from Selaginella moellendorffii". ChemBioChem. 12 (13): 1984–7. doi:10.1002/cbic.201100336. PMC 3383829. 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. 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.

[1] 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.

[2] 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.

[3] Atta-Ur-Rahman, ed. (1988). Studies in Natural Product Chemistry : Bioactive Natural Products, Part F. ISBN 978-0-08-044001-9.

[4] Mafu S, Hillwig ML, Peters RJ (September 2011). "A novel labda-7,13E-dien-15-ol-producing bifunctional diterpene synthase from Selaginella moellendorffii". ChemBioChem. 12 (13): 1984–7. doi:10.1002/cbic.201100336. PMC 3383829. PMID 21751328.

[5] 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.

[6] 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.

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Labdane

Biosynthesis

Example labdane derivatives

See also

References