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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/10 05:22:49」(JST)
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (December 2007) |
| β-Carboline |
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| Identifiers |
| CAS number |
244-63-3 Y |
| PubChem |
64961 |
| ChemSpider |
58486 Y |
| MeSH |
norharman |
| ChEBI |
CHEBI:109895 Y |
| ChEMBL |
CHEMBL275224 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H Y
Key: AIFRHYZBTHREPW-UHFFFAOYSA-N Y
InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
Key: AIFRHYZBTHREPW-UHFFFAOYAG
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| Properties |
| Molecular formula |
C11H8N2 |
| Molar mass |
168.20 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
β-Carboline (9H-pyrido[3,4-b]indole) also known as norharmane is a nitrogen containing heterocycle. It is also the prototype of a class of compounds known as β-carbolines.
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Contents
- 1 Pharmacology
- 2 Structure
- 3 Examples of β-carbolines
- 4 Occurrence in nature
- 5 See also
- 6 References
- 7 External links
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Pharmacology[edit]
β-Carboline alkaloids are widespread in plants and animals, and frequently act as benzodiazepine inverse agonists. As components of the liana Banisteriopsis caapi, the β-carbolines harmine, harmaline, and tetrahydroharmine play a pivotal role in the pharmacology of the indigenous hallucinogenic drug ayahuasca by preventing the breakdown of dimethyltryptamine in the gut by inhibiting monoamine oxidase, thus making it psychoactive upon oral administration. Some β-carbolines, notably tryptoline and pinoline, are formed naturally in the human body. The latter is implicated along with melatonin in the role of the pineal gland in regulating the sleep-wake cycle.[citation needed] β-carboline is a benzodiazepine receptor inverse agonist and can therefore have convulsive, anxiogenic and memory enhancing effects.[1]
Structure[edit]
β-Carboline belongs to the group of indole alkaloids and consist of pyridine ring that is fused to an indole skeleton.[2] The structure of β-carboline is similar to that of tryptamine, with the ethylamine chain re-connected to the indole ring via an extra carbon atom, to produce a three-ringed structure. The biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines.[3] Different levels of saturation are possible in the third ring, which is indicated here in the structural formula by colouring the optionally double bonds red and blue:
Examples of β-carbolines[edit]
Some of the more important β-carbolines are tabulated by structure below.
| Short Name |
Red Bond
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Blue Bond
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R1 |
R6 |
R7 |
Structure |
| β-Carboline |
×
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×
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H
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H
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H
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| Tryptoline |
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H
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H
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H
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| Pinoline |
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H
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OCH3
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H
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| Harmane |
×
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CH3
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H
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H
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| Harmine |
×
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×
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CH3
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H
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OCH3
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| Harmaline |
×
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CH3
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H
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OCH3
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| Tetrahydroharmine |
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CH3
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H
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OCH3
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Occurrence in nature[edit]
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This section may contain inappropriate or misinterpreted citations that do not verify the text. Please help improve this article by checking for inaccuracies. (help, talk, get involved!) (December 2007) |
Eight plant families are known to express 64 different kinds of β-carboline alkaloids. By dry weight, the seeds of Peganum harmala (Syrian Rue) contain between 0.16%[4] and 5.9%[5] β-carboline alkaloids.
As a result of the presence of β-carbolines in the cuticle of scorpions, their skin is known to fluoresce when exposed to certain wavelengths of ultraviolet light such as that produced by a blacklight.[6]
A group of β-carboline derivatives, termed eudistomins were extracted from ascidians (marine tunicates of the family Ascidiacea), like Ritterella sigillinoides,[7] Lissoclinum fragile [8] or Pseudodistoma aureum.[9]
See also[edit]
- Harmala alkaloid
- Tryptamine
References[edit]
- ^ Venault P, Chapouthier G (2007). "From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory". ScientificWorldJournal 7: 204–23. doi:10.1100/tsw.2007.48. PMID 17334612.
- ^ The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications. Ratsch, Christian. Park Street Press c. 2005
- ^ Baiget, Jessica; Llona-Minguez, Sabin; Lang, Stuart; MacKay, Simon P; Suckling, Colin J; Sutcliffe, Oliver B (2011). "Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine". Beilstein Journal of Organic Chemistry 7: 1407–11. doi:10.3762/bjoc.7.164. PMC 3201054. PMID 22043251.
- ^ Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (Aug 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal Chim Acta 575 (2): 290–9. doi:10.1016/j.aca.2006.05.093. PMID 17723604.
- ^ Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. (2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)". Food Chem Toxicol. 48 (3): 839–43. doi:10.1016/j.fct.2009.12.019. PMID 20036304.
- ^ Stachel SJ, Stockwell SA, Van Vranken DL (August 1999). "The fluorescence of scorpions and cataractogenesis". Chem. Biol. 6 (8): 531–9. doi:10.1016/S1074-5521(99)80085-4. PMID 10421760.
- ^ Lake RJ, Blunt JW, Munro MHG (1989). "Eudistomins From the New Zealand Ascidian Ritterella sigillinoides". Aust. J. Chem. 42 (7): 1201–1206. doi:10.1071/CH9891201.
- ^ Badre A, Boulanger A, Abou-Mansour E, Banaigs B, Combaut G, Francisco C (April 1994). "Eudistomin U and Isoeudistomin U, New Alkaloids from the Caribbean Ascidian Lissoclinum fragile". J. Nat. Prod. 57 (4): 528–533. doi:10.1021/np50106a016.
- ^ Davis RA, Carroll AR, Quinn RJ (June 1998). "Eudistomin V, a New β-Carboline from the Australian Ascidian Pseudodistoma aureum". J. Nat. Prod. 61 (7): 959–960. doi:10.1021/np9800452.
External links[edit]
- Beta-Carbolines at the US National Library of Medicine Medical Subject Headings (MeSH)
- TiHKAL #44
- TiHKAL in general
- Beta-carbolines in Coffee
- Farzin D, Mansouri N (July 2006). "Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test". Eur Neuropsychopharmacol 16 (5): 324–8. doi:10.1016/j.euroneuro.2005.08.005. PMID 16183262.
English Journal
- Rats With Different Thresholds to Clonic Convulsions Induced by DMCM Differ in the Binding of [(3)H]-MK-801 and [ (3)H]-Ouabain in the Membranes of Brain Regions.
- Contó MB, de Carvalho JG, Venditti MA.SourceDepartamento de Psicobiologia, Universidade Federal de São Paulo, Escola Paulista de Medicina (UNIFESP/EPM), Rua Botucatu 862, 1° andar, Vila Clementino, São Paulo, SP, 04023-062, Brazil, mmmarcos@uol.com.br.
- Neurochemical research.Neurochem Res.2012 Jul;37(7):1442-9. Epub 2012 Mar 1.
- Considering the putative participation of N-methyl-D-aspartate (NMDA) receptors and the Na(+), K(+)-ATPase enzymes in the susceptibility to convulsions induced by the benzodiazepine inverse agonist methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate (DMCM), the present study sought to determine
- PMID 22382813
- The antinociceptive activity of harmicine on chemical-induced neurogenic and inflammatory pain models in mice.
- Spindola HM, Vendramini-Costa DB, Rodrigues MT Jr, Foglio MA, Pilli RA, Carvalho JE.SourceCPQBA, University of Campinas, P.O. Box 6171, 13083-970 Campinas-SP, Brazil.
- Pharmacology, biochemistry, and behavior.Pharmacol Biochem Behav.2012 Jul;102(1):133-8. Epub 2012 Apr 6.
- Harmicine is a β-carboline alkaloid isolated and identified as a major active compound present in many plant species and marine invertebrates. This alkaloid exhibits a wide spectrum of pharmacological activities, including antispasmodic, antipyretic, and anticancer properties. This report described
- PMID 22507912
Japanese Journal
- FIRST TOTAL SYNTHESES OF 1,3-DISUBSTITUTED β-CARBOLINE ALKALOIDS, DICHOTOMIDE ？ AND MARINACARBOLINES A-D
- Tagawa Shinji,Choshi Tominari,Okamoto Asuka [他]
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 87(2), 357-367, 2013-02-01
- NAID 40019561674
- Influence of β-Carboline Produced from Glucose and Tryptophan on Protein Synthesis of Chicken Embryo Myoblasts
- Nishimagi Ryosuke,Kita Kazumi
- Journal of poultry science 49(4), 300-302, 2012-10
- NAID 40019455395
- Kitasetaline, a novel β-carboline alkaloid from Kitasatospora setae NBRC 14216^T(MICROBIAL PHYSIOLOGY AND BIOTECHNOLOGY)
- Aroonsri Aiyada,Kitani Shigeru,Ikeda Haruo,Nihira Takuya
- Journal of bioscience and bioengineering 114(1), 56-58, 2012-07
- … With the genetically modified Kitasatospora setae NBRC 14216^T strain, a new β-carboline alkaloid, kitasetaline (1), was produced on solid medium. …
- NAID 110009479365
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