| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:39:10 UTC |
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| Updated at | 2020-11-18 16:35:11 UTC |
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| CannabisDB ID | CDB000479 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | (-)-Aristolene |
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| Description | Aristolene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ).. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. Aristolene is possibly neutral. It has been identified in cannabis (PMID: 26657499 ), the essential oil from Pelargonium graveolens (rose geranium) (13.19% relative to total oil constituents) (PMID: 26854645 ), the essential oil from Ferula communis (giant fennel) leaf (8.5% relative to total oil constituents) (DOI: 10.1002/ffj.1405), and the dry fruit essential oil from Vitex negundo (Chinese chaste tree) (8% relative to total oil constituents) (PMID: 20046787 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1aS,7S,7aS,7bS)-1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene |
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| Traditional Name | (1aS,7S,7aS,7bS)-1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene |
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| CAS Registry Number | 6831-16-9 |
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| SMILES | C[C@H]1CCCC2=CC[C@H]3[C@@H](C3(C)C)[C@]12C |
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| InChI Identifier | InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3/t10-,12-,13-,15+/m0/s1 |
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| InChI Key | FOBXOZMHEKILEY-GZCFXPHUSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesquiterpenoids |
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| Direct Parent | Aristolane sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Aristolane sesquiterpenoid
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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Not Available | | Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| General References | - Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
- Juarez ZN, Bach H, Sanchez-Arreola E, Bach H, Hernandez LR: Protective antifungal activity of essential oils extracted from Buddleja perfoliata and Pelargonium graveolens against fungi isolated from stored grains. J Appl Microbiol. 2016 May;120(5):1264-70. doi: 10.1111/jam.13092. Epub 2016 Apr 4. [PubMed:26854645 ]
- Khokra SL, Prakash O, Jain S, Aneja KR, Dhingra Y: Essential Oil Composition and Antibacterial Studies of Vitex negundo Linn. Extracts. Indian J Pharm Sci. 2008 Jul-Aug;70(4):522-6. doi: 10.4103/0250-474X.44610. [PubMed:20046787 ]
- Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
- Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
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