TMKS8A, an antibacterial and cytotoxic chlorinated alpha-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces

Zhang Zhiwei; Sibero Mada Triandala; Kai Akiho; Fukaya Keisuke; Urabe Daisuke; Igarashi Yasuhiro

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TMKS8A, an antibacterial and cytotoxic chlorinated alpha-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces

机译：TMKS8A，一种抗菌和细胞毒性氯化α-Lapachone，来自Streptomyces属的海绵衍生的放线菌网

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TMKS8A (1), a new chlorinated alpha-lapachone derivative, along with five known related metabolites, A80915 C (2), SF2415B1 (3), chlorinated dihydroquinone 3 (4), SF2415B3 (5), and A80915 C (6), were identified from the culture extract of Streptomyces sp. TMKS8, which was isolated from a sea slug, Paromoionchis tumidus. The structure of 1 was determined by the analysis of NMR and MS spectral data, assisted by NMR chemical shift prediction using DFT-based calculation. The absolute configuration was determined to be R by comparison of experimental and calculated ECD spectra. Compound 1 displayed antimicrobial activity against Gram-positive bacteria with MIC values ranging from 6.25 to 12.5 mu g ml(-1) and cytotoxicity against murine leukemia P388 cells with IC50 9.8 mu M.

机译：TMKS8A（1）是一种新的氯化α-拉帕酮衍生物，以及五种已知的相关代谢物，即A80915 C（2）、SF2415B1（3）、氯化二氢醌3（4）、SF2415B3（5）和A80915 C（6），均从链霉菌属TMKS8的培养提取物中鉴定出来，该菌株是从一种海蛞蝓，即猪耳旁孔菌中分离出来的。通过核磁共振和质谱数据的分析，以及基于DFT计算的核磁共振化学位移预测，确定了1的结构。通过比较实验和计算的ECD光谱，确定绝对构型为R。化合物1对革兰氏阳性菌具有抗菌活性，MIC值范围为6.25至12.5μg ml（-1），对小鼠白血病P388细胞具有细胞毒性，IC50为9.8μM。

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《The Journal of Antibiotics: An International Journal》 |2021年第7期|共6页
作者
Zhang Zhiwei; Sibero Mada Triandala; Kai Akiho; Fukaya Keisuke; Urabe Daisuke; Igarashi Yasuhiro;
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Toyama Prefectural Univ Biotechnol Res Ctr Dept Biotechnol 5180 Kurokawa Imizu Toyama 9390398;

Diponegoro Univ Fac Fisheries &

Marine Sci Dept Marine Sci Semarang 50275 Central Java;

Toyama Prefectural Univ Biotechnol Res Ctr Dept Biotechnol 5180 Kurokawa Imizu Toyama 9390398;

Toyama Prefectural Univ Biotechnol Res Ctr Dept Biotechnol 5180 Kurokawa Imizu Toyama 9390398;

Toyama Prefectural Univ Biotechnol Res Ctr Dept Biotechnol 5180 Kurokawa Imizu Toyama 9390398;

Toyama Prefectural Univ Biotechnol Res Ctr Dept Biotechnol 5180 Kurokawa Imizu Toyama 9390398;

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正文语种 eng
中图分类药学;
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2. Characterization of cytotoxic compound from marine sediment derived actinomycete Streptomyces avidinii strain SU4 [J] . Sudha S, Masilamani Selvam M 亚太热带生物医学杂志（英文版） . 2012,第010期
3. Characterization of cytotoxic compound from marine sediment derived actinomycete Streptomyces avidinii strain SU4 [J] . Sudha, S, Masilamani, 亚太热带生物医学杂志：英文版 . 2012,第010期
4. lsolation and characterization of marine-derived actinomycetes with cytotoxic activity from the Red Sea coast [J] . Mohamed Saleh Abdelfattah, Usama Wahid Hawas, Lamia Taha Abou El-Kassema, 亚太热带生物医学杂志（英文版） . 2016,第008期
5. Isolation and characterization of marine-derived actinomycetes with cytotoxic activity from the Red Sea coast [J] . Mohamed Saleh Abdelfattah, Mohammed Ismail Youssef Elmallah, Usama Wahid Hawas, 亚太热带生物医学杂志：英文版 . 2016,第008期
6. Chlorinated bis-indole alkaloids from deep-sea derived Streptomyces sp. SCSIO 11791 with antibacterial and cytotoxic activities [J] . Song Yongxiang, Yang Jiafan, Yu Jianchen, The Journal of Antibiotics: An International Journal . 2020,第8期

机译：来自深海衍生的链霉菌SP的氯化双吲哚生物碱。 SCSIO 11791具有抗菌和细胞毒性活动
7. Marmycins A and B,Cytotoxic Pentacyclic C-Glycosides from a Marine Sediment-Derived Actinomycete Related to the Genus Streptomyces [J] . Glenroy D.A.Martin, Lik T.Tan, Paul R.Jensen Journal of natural products . 2007,第9期

机译：Marmycins A和B，来自海洋沉积物的放线菌与链霉菌属相关的细胞毒性五环C-糖苷
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机译：Daryamides A-C，来自链霉菌属菌株CNQ-085的海洋来源的放线菌的细胞毒性弱的聚酮化合物。
9. Characterization of cytotoxic compound from marine sediment derived new actinomycete Streptomyces coelicolor strain SU5 [C] . Sudha. S, Masilamani Selvam. M Green Technology and Environmental Conservation (GTEC 2011), 2011 International Conference on . 2011

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机译：缩回：来自海洋的放线菌星海链霉菌的新型生物碱具有广谱抗菌和细胞毒活性
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机译：来自红海海洋放射瘤素链霉菌的抗微生物氯化3-苯基丙酸衍生物Crefromyces Coelicolor Ly001

TMKS8A, an antibacterial and cytotoxic chlorinated alpha-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces

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