色醇

色醇
	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
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;
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（英語：Tryptophol）是一種芳香醇，可誘導人類睡眠。它作為酒精發酵的副產品存在於葡萄酒中。它於1912年由費利克斯·埃爾利希首次描述。它也由昏睡病中的錐蟲寄生蟲產生。

它作為二硫龍治療的副作用在肝臟中形成。^[1]

自然產生

色醇可以在歐洲赤松針^[2]或種子中找到。^[3] 它可由昏睡病（非洲錐蟲病）中的錐蟲寄生蟲（布氏錐蟲（英语：Trypanosoma brucei））產生。^[1]^[4] 色醇存在於葡萄酒^[5]和啤酒中，作為釀酒酵母進行酒精發酵的次級產物^[6]。它也是一種由白色念珠菌產生的自身抗生素。^[7] 它也可以從海綿Ircinia spiculosa（英语：Ircinia spiculosa）中分離出來。^[8]

代謝

它由費利克斯·埃爾利在1912年首次描述。埃爾利證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]

生物效應

色醇及其衍生物5-羥基色氨酸和5-甲氧基色氨酸可誘導小鼠睡眠。在250mg/kg劑量下，它會誘導持續不到一小時的睡眠樣狀態。^[12]些化合物可能在生理睡眠機制中發揮作用。^[13]它可能是血清素或褪黑素的功能類似物，這些化合物參與睡眠調節。

色醇在體外顯示出基因毒性。^[14] 色氨酸是釀酒酵母的群聚感應分子。^[15]它也存在於慢性錐蟲病患者的血液中。出於這個原因，它可能是錐蟲寄生蟲的群聚感應分子。^[14]

在錐蟲感染的情況下，色氨酸會降低宿主的免疫反應。^[16]

由於它是在攝入乙醇或二硫龍治療後在肝臟中形成，因此它也與酒精成癮的研究有關。^[1]^[12]吡唑和乙醇已被證明可抑制外源色醇轉化為吲哚-3-乙酸，並增強色醇對小鼠的睡眠誘導低溫作用。^[17]

它是黃瓜下胚軸節段的生長促進劑。^[18]

參見

參考資料

^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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)
^ 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.
^ 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.
^ 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）.
^ 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 .
^ Pathway: tryptophan degradation VIII (to tryptophol) at BioCyc.org. [2022-10-02]. （原始内容存档于2022-10-07）.
^ ^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.
^ 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.
^ ^14.0 ^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）.
^ 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.
^ 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.
^ 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.
^ 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.

[Cornford-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）.

[Cornford2-12] 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.

[Kosalec-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.

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