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首页> 外文期刊>Biochemical and Biophysical Research Communications >Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases
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Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases

机译：色氨酸衍生的天然存在的四氢-β-咔啉生物碱被血红素过氧化物酶氧化为生物活性的β-咔啉生物碱

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摘要

β-Carbolines are indole alkaloids that occur in plants, foods, and endogenously in mammals and humans, and which exhibit potent biological, psychopharmacological and toxicological activities. They form from naturally-occurring tetrahydro-β-carboline alkaloids arising from tryptophan by still unknown way and mechanism. Results in this research show that heme peroxidases catalyzed the oxidation of tetrahydro-β-carbolines (i.e. 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid) into aromatic β-carbolines (i.e. norharman and harman, respectively). This oxidation followed a typical catalytic cycle of peroxidases through redox intermediates I, II, and ferric enzyme. Both, plant peroxidases (horseradish peroxidase, HRP) and mammalian peroxidases (myeloperoxidase, MPO and lactoperoxidase, LPO) catalyzed the oxidation in an efficient manner as determined by kinetic parameters (VMAX and KM). Oxidation of tetrahydro-β-carbolines was inhibited by peroxidase inhibitors such as sodium azide, ascorbic acid, hydroxylamine and excess of H2O 2. The formation of aromatic β-carbolines by heme peroxidases can help to explain the presence and activity of these compounds in biological systems.
机译：β-咔啉是吲哚生物碱，存在于植物，食物中，并在哺乳动物和人类中内源性存在，并表现出强大的生物学，心理药理和毒理学活性。它们由色氨酸产生的天然存在的四氢-β-咔啉生物碱以未知的方式和机制形成。研究结果表明，血红素过氧化物酶催化四氢-β-咔啉（即1,2,3,4-四氢-β-咔啉-3-羧酸和1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸）转变为芳香族的β-咔啉（分别为norharman和harman）。该氧化遵循过氧化物酶通过氧化还原中间体I，II和铁酶的典型催化循环。植物过氧化物酶（辣根过氧化物酶，HRP）和哺乳动物过氧化物酶（髓过氧化物酶，MPO和乳过氧化物酶，LPO）均以动力学参数（VMAX和KM）确定的有效方式催化氧化。过氧化酶抑制剂（如叠氮化钠，抗坏血酸，羟胺和过量的H2O）抑制了四氢-β-咔啉的氧化。血红素过氧化物酶形成芳香族β-咔啉可以帮助解释这些化合物在生物中的存在和活性。系统。

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