Susilo R, Damm H, Rommelspacher H
Department of Neuropsychopharmacology, Free University, Berlin, F.R.G.
J Neurochem. 1988 Jun;50(6):1817-24. doi: 10.1111/j.1471-4159.1988.tb02483.x.
Tryptamine was degraded by incubation with rat brain homogenate to an unknown product. The reaction was stimulated by the nonionic detergents Triton X-100 and Lubrol PX and less by the zwitterionic detergent 3-[(3-cholamidopropyl)dimethylammonio]1-propanesulfonate (CHAPS). The same results were obtained with pig brain and bovine brain. The monoamine oxidase inhibitor pargyline inhibited the reaction strongly, indicating the participation of the enzyme on the reaction. Addition of 17,000 g supernatant from rat brain homogenate increased the formation effectively whereas phospholipids or chloroform/methanol (7:3) extract from the 17,000 g supernatant showed only little or no effect. Chromatographic and electrophoretic properties as well as the chemical reaction of the product with specific reagents suggest that the compound consists of an indole part and an amino acid part. The product could be identified by fast atom bombardment mass spectrometry and by comparison with the synthetic substance (4R)-2-(3-indolylmethyl)-1,3-thiazolidine-4-carboxylic acid. It is formed by the enzymatic oxidation of tryptamine producing indole-3-acetaldehyde which spontaneously cyclizes with free L-cysteine from the tissue. The results suggest that the reaction of biogenic aldehydes with brain macromolecules may proceed via an analogous reaction.
色胺与大鼠脑匀浆孵育后降解为一种未知产物。该反应受到非离子型去污剂Triton X - 100和Lubrol PX的刺激，而两性离子去污剂3 - [(3 - 胆酰胺丙基)二甲基铵基] - 1 - 丙烷磺酸盐(CHAPS)的刺激作用较小。猪脑和牛脑也得到了相同的结果。单胺氧化酶抑制剂帕吉林强烈抑制该反应，表明该酶参与了反应。添加大鼠脑匀浆17,000g上清液可有效增加产物的形成，而17,000g上清液中的磷脂或氯仿/甲醇(7:3)提取物的影响很小或无影响。产物的色谱和电泳性质以及与特定试剂的化学反应表明该化合物由吲哚部分和氨基酸部分组成。该产物可通过快原子轰击质谱法并与合成物质(4R)-2-(3 - 吲哚基甲基)-1,3 - 噻唑烷 - 4 - 羧酸进行比较来鉴定。它是由色胺的酶促氧化产生吲哚 - 3 - 乙醛，吲哚 - 3 - 乙醛与组织中的游离L - 半胱氨酸自发环化形成的。结果表明生物源性醛与脑大分子的反应可能通过类似的反应进行。
