{{chembox | verifiedrevid = 443914554 | ImageFile=labdane.svg | ImageSize=150px | IUPACName=Labdane | SystematicName=(4a''R'',5''S'',6''S'',8a''S'')-1,1,4a,6-Tetramethyl-5-[(3''R'')-3-methylpentyl]decahydronaphthalene | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7827634 | InChI = 1/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 | InChIKey = LEWJAHURGICVRE-AISVETHEBV | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LEWJAHURGICVRE-AISVETHESA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo=561-90-0 | PubChem=9548711 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1087749 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 36505 | SMILES = C2CC([C@@H]1CC[C@@H]([C@@H]([C@@]1(C)C2)CC[C@H](C)CC)C)(C)C }} |Section2={{Chembox Properties | C=20|H=38 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }}
'''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.<ref>{{cite journal|author1=Cocker, J. D. |author2=Halsall, T. G. |author3=Bowers, A. |title=The chemistry of gum labdanum. I. Some acidic constituents|journal=Journal of the Chemical Society|year=1956|pages=4259–62|doi=10.1039/jr9560004259 }}</ref><ref>{{cite journal|author1=Cocker, J. D. |author2=Halsall, T. G. |title=The chemistry of gum labdanum. II. The structure of labdanolic acid|journal=Journal of the Chemical Society|year=1956|pages=4262–71|doi=10.1039/jr9560004262 }}</ref>
A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities.<ref>{{cite book | title = Studies in Natural Product Chemistry : Bioactive Natural Products, Part F | editor = Atta-Ur-Rahman | isbn = 978-0-08-044001-9| year = 1988 }}</ref> Natural labdanes in tree resin are believed to be the precursors of amber, which polymerise under great pressure.
== Example labdane derivatives== * Forskolin * Galanolactone<ref>{{cite journal |last1=Kenmogne |first1=Marguerite |last2=Prost |first2=Elise |last3=Harakat |first3=Dominique |last4=Jacquier |first4=Marie-José |last5=Frédérich |first5=Michel |last6=Sondengam |first6=Lucas B. |last7=Zèches |first7=Monique |last8=Waffo-Téguo |first8=Pierre |title=Five labdane diterpenoids from the seeds of Aframomum zambesiacum |journal=Phytochemistry |date=1 March 2006 |volume=67 |issue=5 |pages=433–438 |doi=10.1016/j.phytochem.2005.10.015 |pmid=16321410 |bibcode=2006PChem..67..433K }}</ref> * Isocupressic acid - is an abortifacient component of ''Cupressus macrocarpa''.<ref>{{Cite journal | doi = 10.1080/00480169.1996.35946| pmid = 16031906| title = Isocupressic acid, an abortifacient component of ''Cupressus'' macrocarpa| journal = New Zealand Veterinary Journal| volume = 44| issue = 3| pages = 109–111| year = 1996| last1 = Parton| first1 = K| last2 = Gardner| first2 = D| last3 = Williamson| first3 = N.B| url = https://zenodo.org/record/1234401}}</ref> *Medigenin *Sclareol * Stemodene
== See also == * Abietane
==References== {{reflist}}
Category:Diterpenes Category:Decalins