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Labdane: Difference between revisions

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Revision as of 18:44, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 14:05, 3 May 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name 
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{{chembox {{chembox
| verifiedrevid = 443913051 | verifiedrevid = 443914554
|ImageFile=labdane.png | ImageFile=labdane.svg
|ImageSize=150px | ImageSize=150px
| IUPACName=Labdane
|IUPACName=(4aR,5S,6S,8aS)- 1,1,4a,6-tetramethyl-5- decalin
| SystematicName=(4a''R'',5''S'',6''S'',8a''S'')-1,1,4a,6-Tetramethyl-5-decahydronaphthalene
|OtherNames= | OtherNames=
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7827634 | 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 | 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
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LEWJAHURGICVRE-AISVETHESA-N | StdInChIKey = LEWJAHURGICVRE-AISVETHESA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=561-90-0 | CASNo=561-90-0
| PubChem=9548711 | PubChem=9548711
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1087749 | ChEMBL = 1087749
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
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| SMILES = C2CC(1CC((1(C)C2)CC(C)CC)C)(C)C | SMILES = C2CC(1CC((1(C)C2)CC(C)CC)C)(C)C
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>20</sub>H<sub>38</sub> | C=20|H=38
| Appearance=
| MolarMass=278.516
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Labdane''' is a natural bicyclic ]. It forms the structural core for a wide variety of ]s collectively known as ''labdanes'' or ''labdane diterpenes''. The labdanes were so named because the first members of the class were originally obtained from ], a resin derived from ] plants.<ref>{{cite journal|author=Cocker, J. D.; Halsall, T. G.; Bowers, A.|title=The chemistry of gum labdanum. I. Some acidic constituents|journal=Journal of the Chemical Society|year=1956|pages=4259–62}}</ref><ref>{{cite journal|author=Cocker, J. D.; 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}}</ref> '''Labdane''' is a natural bicyclic ]. It forms the structural core for a wide variety of ]s collectively known as ''labdanes'' or ''labdane diterpenes''. The labdanes were so named because the first members of the class were originally obtained from ], a resin derived from the ].<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>''Studies in Natural Product Chemistry : Bioactive Natural Products, Part F'', Atta-Ur-Rahman (Editor), ISBN 978-0080440019</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>


== Example labdane derivatives==
⚫ ==See also==
⚫ * ]
* ] * ]
* ]<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 }}</ref>
* ] - is an abortifacient component of '']''.<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| year = 1996| last1 = Parton| first1 = K| last2 = Gardner| first2 = D| last3 = Williamson| first3 = N.B| url = https://zenodo.org/record/1234401}}</ref>
*]
*]
* ] * ]

⚫ == See also ==
⚫ * ]


==References== ==References==
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