色醇(英语:Tryptophol)是一种芳香醇,可诱导人类睡眠。它作为酒精发酵的副产品存在于葡萄酒中。它于1912年由费利克斯·埃尔利希首次描述。它也由昏睡病中的锥虫寄生虫产生。

色醇
Chemical structure of tryptophol
IUPAC名
2-(1H-Indol-3-yl)ethanol
2-(1H-3-吲哚基)乙醇
别名 吲哚-3-乙醇
吲哚乙醇
识别
CAS号 526-55-6  checkY
PubChem 10685
ChemSpider 10235
SMILES
 
  • C1=CC=C2C(=C1)C(=CN2)CCO
ChEBI 17890
性质
化学式 C10H11NO
摩尔质量 161.2 g·mol−1
熔点 59 °C(332 K)
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中易燃物的标签图案 《全球化学品统一分类和标签制度》(简称“GHS”)中有毒物质的标签图案
GHS提示词 danger
H-术语 H225, H300+310+330
P-术语 P210, P262, P280, P301+310+330, P302+352+310, P304+340+310
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。
色醇的紫外可见光谱。

它作为双硫仑治疗的副作用在肝脏中形成。[1]

自然产生

色醇可以在欧洲赤松[2]或种子中找到。[3] 它可由昏睡病(非洲锥虫病)中的锥虫寄生虫(布氏锥虫英语Trypanosoma brucei)产生。[1][4] 色醇存在于葡萄酒[5]啤酒中,作为酿酒酵母进行酒精发酵的次级产物[6]。 它也是一种由白色念珠菌产生的自身抗生素。[7] 它也可以从海绵Ircinia spiculosa英语Ircinia spiculosa中分离出来。[8]

代谢

它由费利克斯·埃尔利在1912年首次描述。埃尔利证明酵母主要通过分解二氧化碳和用羟基取代氨基来攻击天然氨基酸。通过该反应使得色氨酸生成色醇。[9]色氨酸首先脱氨基生成3-吲哚丙酮酸。然后通过吲哚丙酮酸脱羧酶将其脱羧[10]生成吲哚乙醛。后一种化合物通过乙醇脱氢酶转化为色醇。[11]

生物效应

色醇及其衍生物5-羟基色氨酸和5-甲氧基色氨酸可诱导小鼠睡眠。在250mg/kg剂量下,它会诱导持续不到一小时的睡眠样状态。[12]些化合物可能在生理睡眠机制中发挥作用。[13]它可能是血清素褪黑素的功能类似物,这些化合物参与睡眠调节。

色醇在体外显示出基因毒性[14] 色氨酸是酿酒酵母群聚感应分子。[15]它也存在于慢性锥虫病患者的血液中。出于这个原因,它可能是锥虫寄生虫的群聚感应分子。[14]

在锥虫感染的情况下,色氨酸会降低宿主的免疫反应。[16]

由于它是在摄入乙醇双硫仑治疗后在肝脏中形成,因此它也与酒精成瘾的研究有关。[1][12]吡唑和乙醇已被证明可抑制外源色醇转化为吲哚-3-乙酸,并增强色醇对小鼠的睡眠诱导低温作用。[17]

它是黄瓜下胚轴节段的生长促进剂。[18]

参见

参考资料

  1. ^ 1.0 1.1 1.2 Cornford, E. M.; Bocash, W. D.; Braun, L. D.; Crane, P. D.; Oldendorf, W. H.; MacInnis, A. J. Rapid distribution of tryptophol (3-indole ethanol) to the brain and other tissues. Journal of Clinical Investigation. 1979, 63 (6): 1241–1248. PMC 372073 . PMID 447842. doi:10.1172/JCI109419. 
  2. ^ Sandberg, Göran. Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. Needles. Planta. 1984, 161 (5): 398–403. PMID 24253838. S2CID 23500542. doi:10.1007/BF00394569. 
  3. ^ Sandberg, Goran; Ernstsen, Arild; Hamnede, Marianne. Dynamics of indole-3-acetic acid and indole-3-ethanol during development and germination of Pinus sylvestris seeds. Physiologia Plantarum. 1987, 71 (4): 411–418. doi:10.1111/j.1399-3054.1987.tb02876.x. 
  4. ^ Richard Seed, John; Seed, Thomas M.; Sechelski, John. The biological effects of tryptophol (indole-3-ethanol): Hemolytic, biochemical and behavior modifying activity. Comparative Biochemistry and Physiology C. 1978, 60 (2): 175–185. PMID 28889. doi:10.1016/0306-4492(78)90091-6. 
  5. ^ Gil, C.; Gómez-Cordovés, C. Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes. Food Chemistry. 1986, 22: 59–65. doi:10.1016/0308-8146(86)90009-9. 
  6. ^ Ribéreau-Gayon, P; Sapis, JC. On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation. Comptes Rendus de l'Académie des Sciences, Série D. 1965, 261 (8): 1915–6. PMID 4954284.  (Article in French)
  7. ^ Lingappa, BT; Prasad, M; Lingappa, Y; Hunt, DF; Biemann, K. Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans. Science. 1969, 163 (3863): 192–4. Bibcode:1969Sci...163..192L. PMID 5762768. S2CID 12430791. doi:10.1126/science.163.3863.192. 
  8. ^ Erdoğan, İlkay; Sener, B; Higa, T. Tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa. Biochemical Systematics and Ecology. 2000, 28 (8): 793–794. PMID 10856636. doi:10.1016/S0305-1978(99)00111-8. 
  9. ^ Richard W. Jackson (1930). A synthesis of tryptophol (PDF). Journal of Biological Chemistry: 659–662. [2022-10-02]. (原始内容存档 (PDF)于2019-07-20). 
  10. ^ Dickinson, JR; Salgado, LE; Hewlins, MJ. The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae. The Journal of Biological Chemistry. 2003, 278 (10): 8028–34. PMID 12499363. doi:10.1074/jbc.M211914200 . 
  11. ^ Pathway: tryptophan degradation VIII (to tryptophol) at BioCyc.org. [2022-10-02]. (原始内容存档于2022-10-07). 
  12. ^ 12.0 12.1 Cornford, Eain M.; Crane, Paul D.; Braun, Leon D.; Bocash, William D.; Nyerges, Anthony M.; Oldendorf, William H. Reduction in Brain Glucose Utilization Rate after Tryptophol (3-Indole Ethanol) Treatment. Journal of Neurochemistry. 1981, 36 (5): 1758–65. PMID 7241135. S2CID 9169087. doi:10.1111/j.1471-4159.1981.tb00428.x. 
  13. ^ Feldstein, A.; Chang, F.H.; Kucharski, J.M. Tryptophol, 5-hydroxytryptophol and 5-methoxytryptophol induced sleep in mice. Life Sciences. 1970, 9 (6): 323–9. PMID 5444013. doi:10.1016/0024-3205(70)90220-1. 
  14. ^ 14.0 14.1 Kosalec, Ivan; Ramić, Snježana; Jelić, Dubravko; Antolović, Roberto; Pepeljnjak, Stjepan; Kopjar, Nevenka. Assessment of Tryptophol Genotoxicity in Four Cell Lines in Vitro: A Pilot Study with Alkaline Comet Assay. Archives of Industrial Hygiene and Toxicology. 2011, 62 (1): 41–49 [2022-10-02]. PMID 21421532. doi:10.2478/10004-1254-62-2011-2090 . (原始内容存档于2021-03-06). 
  15. ^ Wuster, Arthur; Babu, M. Madan. Transcriptional control of the quorum sensing response in yeast. Molecular BioSystems. 2010, 6 (1): 134–41. PMID 20024075. doi:10.1039/B913579K. 
  16. ^ Ackerman, S. B.; Seed, J. R. The effects of tryptophol on immune responses and its implications toward trypanosome-induced immunosuppression. Experientia. 1976, 32 (5): 645–7. PMID 776647. S2CID 12695689. doi:10.1007/BF01990212. 
  17. ^ Seed, John Richard; Sechelski, John. Tryptophol levels in mice injected with pharmacological doses of tryptophol, and the effect of pyrazole and ethanol on these levels. Life Sciences. 1977, 21 (11): 1603–10. PMID 600013. doi:10.1016/0024-3205(77)90237-5. 
  18. ^ Rayle, DL; Purves, WK. Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings. Plant Physiology. 1967, 42 (4): 520–524. PMC 1086576 . PMID 16656532. doi:10.1104/pp.42.4.520.