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Aryl-enclosed polyketides from mangrove sediment associated bacterium Bacillus amyloliquefaciens attenuating pro-inflammatory 5-lipoxygenase
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2020-08-28 , DOI: 10.1007/s00044-020-02618-0
Kajal Chakraborty , Lakshmi Rajan , Prima Francis

Two aryl-enclosed polyketides were identified from the ethyl acetate extract of mangrove sediment associated bacterium Bacillus amyloliquefaciens, and were characterized as 1-(8-hydroxy-1-oxoisochroman-3-yl)propyl 4′-(6′-hydroxy-8′-oxotetrahydrofuran-5′-yl)acetate (compound 1) and 6′a-(3′-(1′-(8-hydroxy-1-oxoisochroman-3-yl)propoxy)-3′-oxoethyl)-8′-oxotetrahydrofuran-6′-yl butyrate (compound 2) by detailed spectroscopic techniques encompassing two-dimensional nuclear magnetic resonance and mass spectroscopic experiments. Polyketide compound 2 bearing oxotetrahydrofuran-6′-yl butyrate moiety exhibited potential antioxidant activities against the free radicals, 2,2-diphenyl-1-picrylhydrazyl radical and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid (IC50 1.01 and 1.22 mM, respectively), and were found to be significantly greater than those displayed by polyketide 1 and standard (α-tocopherol IC50 1.45–1.63 mM, p < 0.05). Compound 2 also exhibited greater anti-inflammatory properties as determined by 5-LOX inhibitory assay (IC50 1.11 mM) than those displayed by compound 1 (IC50 1.23 mM) and standard (ibuprofen IC50 4.50 mM). Greater electronic parameters of compound 2 could further support its greater bioactive potentials.



中文翻译:

来自红树林沉积物相关细菌解淀粉芽孢杆菌的芳基封闭聚酮化合物减弱促炎性5-脂氧合酶

从红树林沉积物解淀粉芽孢杆菌的乙酸乙酯提取物中鉴定出两个芳基包围的聚酮化合物,并将其表征为1-(8-羟基-1-氧代异色满-3-基)丙基4'-(6'-羟基-8) '-氧四氢呋喃-5'-基)乙酸酯(化合物1)和6'a-(3'-(1'-(8-羟基-1-氧代异色满-3-基)丙氧基)-3'-氧代乙基)-8 '-氧四氢呋喃-6'-丁酸丁酯(化合物2)通过详细的光谱技术,包括二维核磁共振和质谱实验。聚酮化合物2带有氧代四氢呋喃-6'-丁酸基酯部分显示出对自由基,2,2-二苯基-1-吡啶并肼基和2,2'-叠氮基-双-3-乙基苯并噻唑啉-6-磺酸的潜在抗氧化活性(IC 50 1.01和分别为1.22 mM和0.32 mM),并且发现它们显着大于聚酮化合物1和标准品所显示的值(α-生育酚IC 50 1.45–1.63 mM,p  <0.05)。通过5-LOX抑制分析(IC 50 1.11 mM)测定的化合物2还显示出比化合物1(IC 50 1.23 mM)和标准品(布洛芬IC 50)更高的抗炎特性。4.50 mM)。化合物2的更大电子参数可以进一步支持其更大的生物活性潜力。

更新日期:2020-09-16
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