関: carboline

WordNet

to remain unmolested, undisturbed, or uninterrupted -- used only in infinitive form; "let her be"
work in a specific place, with a specific subject, or in a specific function; "He is a herpetologist"; "She is our resident philosopher" (同)follow
have life, be alive; "Our great leader is no more"; "My grandfather lived until the end of war" (同)live
be identical to; be someone or something; "The president of the company is John Smith"; "This is my house"
happen, occur, take place; "I lost my wallet; this was during the visit to my parents house"; "There were two hundred people at his funeral"; "There was a lot of noise in the kitchen"
have the quality of being; (copula, used with an adjective or a predicate noun); "John is rich"; "This is not a good answer"
occupy a certain position or area; be somewhere; "Where is my umbrella?" "The toolshed is in the back"; "What is behind this behavior?"
spend or use time; "I may be an hour"
stake on the outcome of an issue; "I bet $100 on that new horse"; "She played all her money on the dark horse" (同)wager, play
the act of gambling; "he did it on a bet" (同)wager
maintain with or as if with a bet; "I bet she will be there!" (同)wager
second in order of importance; "the candidate, considered a beta male, was perceived to be unable to lead his party to victory"
the 2nd letter of the Greek alphabet
preliminary or testing stage of a software or hardware product; "a beta version"; "beta software"
beets (同)genus Beta

PrepTutorEJDIC

《連結語として補語を伴なって…『である』,…だ,…です / 《位置・場所を表す語句を伴って》(…に)『ある』,いる(occupy a place or situation) / 〈物事が〉『存在する』,ある(exist);〈生物が〉生存する,生きている(live) / 行われる,起こる,発生する(take place, occur) / 存続する,そのままでいる(remain as before) / 《『be to』 do》 / …する予定である,…することになっている / …すべきだ / 《受動態の不定詞を伴って》…できる / 《命令》…するのだ / 《条件節に》…する意図がある / 《『if…were to』 do》…するとしたなら / 《『be』 do『ing』》《進行形》 / 《進行中の動作》…している,しつつある / 《近い未来》…しようとしている,するつもり / 《動作の反復》(いつも)…している / 《『be』+『他動詞の過去分詞』》《受動態》…される,されている / 《『be』+『自動詞の過去分詞』》《完了形》…した[状態にある]
『かけ』・(…との)かけ《+『with』+『名』》 / かけた物(金) / かけの対象 / 〈金・物〉'を'『かける』 / (かけ事・ゲームなどで)〈人〉‘と'『かけをする』《+『名』〈人〉+『on』+『名』》 / (…に)『かける』《+『on』(『against』)+『名』(one's do『ing』)》
ベータ(ギリシア語アルファベットの第2文字;B,β;英語のB,b に遭当)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/16 17:47:35」(JST)

wiki en

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.

Pharmacology

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 psychedelic drug ayahuasca by preventing the breakdown of dimethyltryptamine in the gut by reversibly inhibiting monoamine oxidase, thus making it psychoactive upon oral administration. Some β-carbolines, notably tryptoline and pinoline, may be formed naturally in the human body. The latter is possibly 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] 9-methyl-β-carbolines appear to induce DNA damage when exposed to ultra-violet light.^[2]

Structure

β-Carboline belongs to the group of indole alkaloids and consist of pyridine ring that is fused to an indole skeleton.^[3] 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.^[4] 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

Some of the more important β-carbolines are tabulated by structure below.

Short Name	Red Bond	Blue Bond	R1	R6	R7	Structure
β-Carboline	×	×	H	H	H
Tryptoline			H	H	H
Pinoline			H	OCH₃	H
Harmane	×		CH₃	H	H
Harmine	×	×	CH₃	H	OCH₃
Harmaline	×		CH₃	H	OCH₃
Tetrahydroharmine			CH₃	H	OCH₃

Occurrence in nature

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%^[5] and 5.9%^[6] 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.^[7]

A group of β-carboline derivatives, termed eudistomins were extracted from ascidians (marine tunicates of the family Ascidiacea), like Ritterella sigillinoides,^[8] Lissoclinum fragile ^[9] or Pseudodistoma aureum.^[10] Nostocarboline was isolated from freshwater cyanobacterium.

References

^ 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.
^ Vignoni M, Rasse-Suriani FA, Butzbach K, Erra-Balsells R, Epe B, Cabrerizo FM (2013). "Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines". Org Biomol Chem 11: 5300–9. doi:10.1039/c3ob40344k. PMID 23842892.
^ 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

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.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. β-ラクタマーゼ阻害剤、カルバペネム系、およびモノバクタム系抗菌薬の併用 combination beta lactamase inhibitors carbapenems and monobactams
2. 喘息におけるβ刺激剤：急性期投与および予防的使用 beta agonists in asthma acute administration and prophylactic use
3. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
4. β-ラクタム系抗生物質：作用機序、耐性および有害作用 beta lactam antibiotics mechanisms of action and resistance and adverse effects
5. β遮断剤中毒 beta blocker poisoning

English Journal

Inhibitory profiles of chilli pepper and capsaicin on heterocyclic amine formation in roast beef patties.

Zeng M1, Zhang M1, He Z1, Qin F1, Tao G1, Zhang S1, Gao Y2, Chen J3.
Food chemistry.Food Chem.2017 Apr 15;221:404-411. doi: 10.1016/j.foodchem.2016.10.061. Epub 2016 Oct 14.
The inhibitory profiles of chilli pepper and capsaicin, as well as their relationship to the formation of heterocyclic amines (HAs) in roast beef patties were investigated using ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) combined with principal component analysis (
PMID 27979221

Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea.

Olmedo GM1, Cerioni L1, González MM2, Cabrerizo FM2, Rapisarda VA1, Volentini SI3.
Food microbiology.Food Microbiol.2017 Apr;62:9-14. doi: 10.1016/j.fm.2016.09.011. Epub 2016 Sep 16.
β-carbolines (βCs) are alkaloids widely distributed in nature that have demonstrated antimicrobial properties. Here, we tested in vitro six βCs against Penicillium digitatum and Botrytis cinerea, causal agents of postharvest diseases on fruit and vegetables. Full aromatic βCs (harmine, harmol,
PMID 27889171

Isolation of a new β-carboline alkaloid from aerial parts of Triclisia sacleuxii and its antibacterial and cytotoxicity effects.

Samita F1, Ochieng CO1, Owuor PO1, Manguro LO1, Midiwo JO2.
Natural product research.Nat Prod Res.2017 Mar;31(5):529-536. doi: 10.1080/14786419.2016.1201666. Epub 2016 Jul 3.
A new β-carboline alkaloid named sacleuximine A (1) together with known compounds palmatine (2), isotetrandrine (3), trans-N-feruloyltyramine (4), trans-N-caffeoyltyramine (5), yangambin (6), syringaresinol (7), sesamin (8), (+) epi-quercitol (9), 4-hydroxybenzaldehyde (10), β-sitosterol (11), que
PMID 27373319

Japanese Journal

Influence of β-Carboline Produced from Glucose and Tryptophan on Protein Synthesis of Chicken Embryo Myoblasts

The journal of poultry science 49(4), 300-302, 2012-10-25
NAID 10031120758

The .BETA.-Carboline Alkaloid Harmol Induces Cell Death via Autophagy but Not Apoptosis in Human Non-small Cell Lung Cancer A549 Cells

Biological and Pharmaceutical Bulletin 34(8), 1264-1272, 2011
NAID 130000936597

銅触媒による多成分反応を用いたインドール及びイソキノリン縮環型含窒素複素環構築法の開発

薬学雑誌 130(7), 925-936, 2010
NAID 130000308757

Related Pictures

★リンクテーブル★

リンク元	「β-カルボリン」「βカルボリン」
関連記事	「carboline」「beta」「be」

「β-カルボリン」

β-Carboline
Names
	IUPAC name 9H-β-carboline
	Other names 9H-pyrido[3,4-b]indole
Identifiers
CAS Number	244-63-3
ChEBI	CHEBI:109895
ChEMBL	ChEMBL275224
ChemSpider	58486
IUPHAR/BPS	8222
Jmol interactive 3D	Image
MeSH	norharman
PubChem	64961
	InChI InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H Key: AIFRHYZBTHREPW-UHFFFAOYSA-N ; 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 ;
	SMILES c2cncc3nc1ccccc1c23 ;
Properties
Chemical formula	C11H8N2
Molar mass	168.20 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references