来自耐辐射红球菌的抗衣原体二聚吲哚衍生物。
Antichlamydial Dimeric Indole Derivatives from Marine Actinomycete Rubrobacter radiotolerans.
作者信息
Li Jian Lin, Chen Dandan, Huang Lei, Ni Min, Zhao Yu, Fan Huizhou, Bao Xiaofeng
机构信息
School of Pharmacy, Nantong University, Nantong, China.
Department of Pharmacy, The Second People's Hospital of Nantong, Nantong, China.
出版信息
Planta Med. 2017 Jun;83(9):805-811. doi: 10.1055/s-0043-100382. Epub 2017 Jan 17.
Abstract
Chlamydiae are widely distributed pathogens of human populations, which can lead to serious reproductive and other health problems. In our search for novel antichlamydial metabolites from marine derived-microorganisms, one new () and two known () dimeric indole derivatives were isolated from the sponge-derived actinomycete . The chemical structures of these metabolites were elucidated by NMR spectroscopic data as well as CD calculations. All three metabolites suppressed chlamydial growth in a concentration-dependent manner. Among them, compound exhibited the most effective antichlamydial activity with IC values of 46.6 ~ 96.4 µM in the production of infectious progeny. Compounds appeared to target the mid-stage of the chlamydial developmental cycle by interfering with reticular body replication, but not directly inactivating the infectious elementary body.
摘要
衣原体是广泛传播的人类病原体，可导致严重的生殖及其他健康问题。在我们从海洋来源微生物中寻找新型抗衣原体代谢产物的过程中，从海绵来源的放线菌中分离出一种新的（）和两种已知的（）二聚吲哚衍生物。这些代谢产物的化学结构通过核磁共振光谱数据以及圆二色计算得以阐明。所有三种代谢产物均以浓度依赖的方式抑制衣原体生长。其中，化合物在感染性后代产生方面表现出最有效的抗衣原体活性，其半数抑制浓度值为46.6至96.4 μM。化合物似乎通过干扰网状体复制靶向衣原体发育周期的中期，而不是直接使感染性原体失活。
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PLoS One. 2016 Jun 9;11(6):e0157306. doi: 10.1371/journal.pone.0157306. eCollection 2016.
2
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J Med Chem. 2016 Mar 10;59(5):2094-108. doi: 10.1021/acs.jmedchem.5b01759. Epub 2016 Feb 22.
3
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