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格兰菌素的有机催化活性及其在杀菌功能中的作用。

Organocatalytic activity of granaticin and its involvement in bactericidal function.

机构信息

Life Science Research Center, College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, 252-0880, Japan.

出版信息

Sci Rep. 2022 Apr 29;12(1):7046. doi: 10.1038/s41598-022-10877-7.

DOI:10.1038/s41598-022-10877-7
PMID:35487928
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9054759/
Abstract

We previously discovered that actinorhodin, a benzoisochromanequinone antibiotic produced by Streptomyces coelicolor A3(2), serves as a catalyst facilitating the oxidation of ascorbic acid and cysteine (PNAS 48:17,152, 2014). In the present study, we screened for similar ascorbic acid-oxidizing activity in the culture broth of various Streptomyces spp., and discovered marked activity in the culture broth of Streptomyces vietnamensis. The principle active compound was granaticin, a pigmented antibiotic that is structurally related to actinorhodin. The absence of any metals in the purified granaticin fraction indicated that granaticin was an organocatalyst. Granaticin catalyzed the oxidation of L-ascorbic acid, generating L-dehydroascorbic acid and hydrogen peroxide (HO) at a 1:1 stoichiometric ratio, with 15 times higher reactivity than that of actinorhodin at an optimum pH of 7.0. Granaticin also oxidizes sulfhydryl compounds, including L-cysteine and glutathione. Growth inhibitory assays demonstrated that knockout mutants of the catalase gene exhibit high sensitivity to granaticin. The results suggest that the bactericidal activity of granaticin is exerted by the oxidation of sulfhydryl groups of cellular components and the toxicity of HO generated during the oxidation reaction.

摘要

我们之前发现，放线紫红素是一种由变红红链霉菌 A3(2) 产生的苯并异香豆素醌类抗生素，它作为一种催化剂，促进抗坏血酸和半胱氨酸的氧化（PNAS 48:17,152, 2014）。在本研究中，我们筛选了各种链霉菌属的发酵液中是否具有类似的抗坏血酸氧化活性，发现越南链霉菌的发酵液中具有显著的活性。主要的活性化合物是格兰地辛，一种与放线紫红素结构相关的色素抗生素。在纯化的格兰地辛部分中没有任何金属，表明格兰地辛是一种有机催化剂。格兰地辛催化 L-抗坏血酸的氧化，以 1:1 的化学计量比生成 L-脱氢抗坏血酸和过氧化氢（HO），在最佳 pH 值为 7.0 时，其反应活性比放线紫红素高 15 倍。格兰地辛还氧化巯基化合物，包括 L-半胱氨酸和谷胱甘肽。生长抑制试验表明，过氧化氢酶基因的敲除突变体对格兰地辛表现出高度的敏感性。结果表明，格兰地辛的杀菌活性是通过细胞成分的巯基氧化和氧化反应中生成的 HO 的毒性来发挥的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/7328742ec09e/41598_2022_10877_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/6962dcac5970/41598_2022_10877_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/45e735427100/41598_2022_10877_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/67fd65e3a806/41598_2022_10877_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/85178e72792d/41598_2022_10877_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/56503ab90267/41598_2022_10877_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/6257b2c74db4/41598_2022_10877_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/de7502b0e38c/41598_2022_10877_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/7328742ec09e/41598_2022_10877_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/6962dcac5970/41598_2022_10877_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/45e735427100/41598_2022_10877_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/67fd65e3a806/41598_2022_10877_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/85178e72792d/41598_2022_10877_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/56503ab90267/41598_2022_10877_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/6257b2c74db4/41598_2022_10877_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/de7502b0e38c/41598_2022_10877_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d76c/9054759/7328742ec09e/41598_2022_10877_Fig8_HTML.jpg

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