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从浅黄链霉菌BC 01中分离出的三种生物活性化合物的纯化、结构解析及其生物活性

Purification and structural elucidation of three bioactive compounds isolated from Streptomyces coelicoflavus BC 01 and their biological activity.

作者信息

Raghava Rao Kothagorla Venkata, Mani Palla, Satyanarayana Botcha, Raghava Rao Tamanam

机构信息

Department of Biochemistry, Andhra University, Visakhapatnam, Andhra Pradesh, 530 003, India.

Department of Organic Chemistry, Andhra University, Visakhapatnam, 530 003, India.

出版信息

3 Biotech. 2017 May;7(1):24. doi: 10.1007/s13205-016-0581-9. Epub 2017 Apr 11.

DOI:10.1007/s13205-016-0581-9
PMID:28401462
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5388647/
Abstract

The strain Streptomyces coelicoflavus BC 01 was isolated from mangrove soil and used as inoculum for submerged fermentation. The fermented broth was extracted with ethyl acetate, the crude extract was subjected to silica gel column chromatography and the homogeneity of the isolated fractions was determined by TLC and then subjected to RP-HPLC for their purity. The purification steps led to the isolation of three pure bioactive compounds named as BC 01_C1, BC 01_C2 and BC 01_C3. The chemical structure of these three compounds was established on the basis of their spectroscopic studies like UV, IR, H and C NMR and GC-MS data by comparison with reference data from literature. The structure of the compound BC 01_C1 was established as 5-amino-2-(6-(2-hydroxyethyl)-3-oxononyl) cyclohex-2-enone. The compound BC 01_C2 was established as8-(aminomethyl)-7-hydroxy-1-(1-hydroxy-4-(hydroxylmethoxy)-2,3-dimethylbutyl)-2-methyl dodecahydro phenanthren-9(1H)-one and the compound BC 01_C3 was established as1-((E)-2-ethylhex-1-en-1-yl)2-((E)-2-ethylidenehexyl)cyclohexane-1,2-dicarboxylate. The MIC values of the three isolated compounds (BC 01_C1, BC 01_C2 and BC 01_C3) were found between 12.5-75 μg/ml for bacteria and 50-125 μg/ml for fungi used in this study. These compounds also possess in vitro antioxidant and anti-inflammatory activities.

摘要

从红树林土壤中分离出天蓝色链霉菌BC 01菌株,并将其用作深层发酵的接种物。发酵液用乙酸乙酯萃取,粗提物进行硅胶柱色谱分离,通过薄层色谱法测定分离组分的均一性,然后用反相高效液相色谱法测定其纯度。经过纯化步骤,分离出三种纯的生物活性化合物,分别命名为BC 01_C1、BC 01_C2和BC 01_C3。通过与文献参考数据比较,基于紫外、红外、氢和碳核磁共振以及气相色谱-质谱数据等光谱研究确定了这三种化合物的化学结构。化合物BC 01_C1的结构确定为5-氨基-2-(6-(2-羟乙基)-3-氧代壬基)环己-2-烯酮。化合物BC 01_C2的结构确定为8-(氨甲基)-7-羟基-1-(1-羟基-4-(羟基甲氧基)-2,3-二甲基丁基)-2-甲基十二氢菲-9(1H)-酮,化合物BC 01_C3的结构确定为1-((E)-2-乙基己-1-烯-1-基)2-((E)-2-亚乙基己基)环己烷-1,2-二羧酸酯。在本研究中使用该三种分离化合物(BC 01_C1、BC 01_C2和BC 01_C3)对细菌的最小抑菌浓度值在12.5 - 75μg/ml之间,对真菌的最小抑菌浓度值在50 - 125μg/ml之间。这些化合物还具有体外抗氧化和抗炎活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/71decaf2f407/13205_2016_581_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/798eb1947748/13205_2016_581_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/7abf44c33796/13205_2016_581_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/71decaf2f407/13205_2016_581_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/798eb1947748/13205_2016_581_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/7abf44c33796/13205_2016_581_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/76c7/5388647/71decaf2f407/13205_2016_581_Fig3_HTML.jpg

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