[关键词]
[摘要]
目的 研究海绵共附生链霉菌Streptomyces parvulus 162432的化学成分。方法 采用十八烷基硅烷键合硅胶填料(ODS)中压柱色谱和半制备高效液相色谱等技术进行分离纯化,得到的单体化合物采用HR-ESI-MS、NMR以及文献比对等方法进行鉴定,新化合物的绝对构型通过计算NMR和圆二色谱(ECD)确定。结果 从菌株Streptomyces parvulus 162432中分离纯化了9个环二肽类化合物,包括1个新化合物链霉菌二肽A(1)和8个已知化合物:环-(D-顺式-羟脯氨酸-L-苯丙氨酸)(2)、环-(D-脯氨酸-D-苯丙氨酸)(3)、环-(L-羟脯氨酸-L-亮氨酸)(4)、环-(L-羟脯氨酸-D-亮氨酸)(5)、环-(D-脯氨酸- L-亮氨酸)(6)、环-(L-脯氨酸-D-亮氨酸)(7)、环-(D-脯氨酸-L-异亮氨酸)(8)、环-(L-亮氨酸-D-缬氨酸)(9)。对分离得到的化合物1~9进行肿瘤细胞增殖细胞毒和抗菌活性评价,活性结果显示,化合物1~9在10 μg/mL下对肿瘤细胞增殖均未显示出明显的细胞毒活性;化合物9对苏云金芽孢杆菌显示抑菌活性,最小抑菌浓度(minimum inhibitory concentration,MIC)为25 μg/mL。结论 化合物1为新化合物,化合物2和4~9为首次从链霉菌Streptomyces parvulus中分离得到,化合物9具有一定的抗菌活性。
[Key word]
[Abstract]
Objective To reveal the secondary metabolites of a marine sponge associated Streptomyces parvulus 162432. Methods The organic extract and fractions were separated and purified by octadecylsilyl silica (ODS) medium-pressure column chromatography (MPLC) and semi-preparative high-performance liquid chromatography (HPLC). The obtained purified compounds were identified by high-resolution-electrospray-mass spectrometry (HR-ESI-MS), nuclear magnetic resonance spectroscopy (NMR) and literature data comparison. The absolute configuration of new compound was determined by NMR and electrostatic circular dichroism (ECD) calculations. Results Nine compounds were isolated from S. parvulus 162432, including one new compound streptomyces dipeptide A (1) and eight known compounds: cyclo-(D-cis-Hyp-L-Phe) (2), cyclo-(D-Pro-D-Phe) (3), cyclo-(L-Hyp-L-Leu) (4), cyclo-(L-Hyp-D-Leu) (5), cyclo-(D-Pro-L-Leu) (6), cyclo-(L-Pro-D-Leu) (7), cyclo-(D-Pro-L-Ile) (8), cyclo-(L-Leu-D-Val) (9). The cytotoxicity on tumor cell proliferation and antibacterial activities of the isolated compounds 1—9 were evaluated. None of compounds 1—9 showed significant cytotoxic activity on tumor cell proliferation at the concentration of 10 μg/mL; compound 9 showed antibacterial activity against Bacillus thuringiensis with the minimal inhibitory concentration (MIC) value of 25 μg/mL. Conclusion Compound 1 is a new compound, compound 2 and 4—9 are isolated from S. parvulus for the first time. Compound 9 showed antibacterial activity against B. thuringiensis.
[中图分类号]
R284.1
[基金项目]
国家重点研发计划项目(2022YFC2804100);国家自然科学基金项目(22137006);国家自然科学基金项目(82022068)