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Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696
Phytochemistry ( IF 3.2 ) Pub Date : 2018-07-01 , DOI: 10.1016/j.phytochem.2018.04.001
Karoon Sadorn , Siriporn Saepua , Nattawut Boonyuen , Tanapong Boonruangprapa , Pranee Rachtawee , Pattama Pittayakhajonwut

Eleven previously undescribed compounds, including cytosporanthraxanthone, xanthoquinodins A7-A10, ketoxanthoquinodin A6, xanthoquinodins B6-B8, and spiroxanthoquinodins A and B, and one synthetically known compound, 2-methoxy pinselin, as well as ten known compounds, including xanthoquinodins A4-A6, B4, and B5, chrysophanol, physcion, (4S)-5-hydroxy-4-methoxy-α-tetralone, (4S)-4,8-dihydroxy-α-tetralone (or isosclerone), and gonytolide C were isolated from the fungus Cytospora eugeniae BCC42696. Their chemical structures were determined based on the analysis of NMR spectroscopic and mass spectrometric data. Moreover, the absolute configurations of the unknown compounds were established by using NOESY and NOEDIFF NMR experiments along with CD spectroscopic data. The isolated xanthoquinodins exhibited a broad range of antimalarial, antibacterial, and fungicidal activities as well as cytotoxicity. Xanthoquinodins A6, B4, and B5 showed strong activity to Plasmodium falciparum, K1 strain (IC50 0.52-0.92 μM) and displayed anti-Bacillus cereus (MIC 1.56 μg/mL). Xanthoquinodin A6 also showed anti-Curvularia lunata (MIC 3.13 μg/mL). In addition, xanthoquinodins A4, A6, B4, and B5 and ketoxanthoquinodin A6 showed cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells.

中文翻译:

来自真菌 Cytospora eugeniae BCC42696 的黄喹啉类似物的抗菌活性和细胞毒性

11 种以前未描述的化合物,包括胞孢蒽醌、黄喹啉 A7-A10、酮黄喹啉 A6、黄喹啉 B6-B8 和螺环蒽醌 A 和 B,以及一种合成已知化合物 2-甲氧基松香素,以及 10 种已知化合物,包括 A4-A4-A16 、B4 和 B5、大黄酚、physcion、(4S)-5-羟基-4-甲氧基-α-四氢萘酮、(4S)-4,8-​​二羟基-α-四氢萘酮(或异硬烯酮)和 gonytolide C 从真菌 Cytospora eugeniae BCC42696。它们的化学结构是基于核磁共振光谱和质谱数据的分析确定的。此外,未知化合物的绝对构型是通过使用 NOESY 和 NOEDIFF NMR 实验以及 CD 光谱数据建立的。分离出的黄喹啉具有广泛的抗疟、抗菌、和杀真菌活性以及细胞毒性。Xanthoquinodins A6、B4 和 B5 对恶性疟原虫 K1 菌株显示出很强的活性(IC50 0.52-0.92 μM)并显示出抗蜡样芽孢杆菌(MIC 1.56 μg/mL)。Xanthoquinodin A6 还显示出抗弯孢霉 (MIC 3.13 μg/mL)。此外,xanthoquinodins A4、A6、B4 和 B5 以及 ketoxanthoquinodin A6 对癌(MCF-7、KB、NCI-H187)和非癌 (Vero) 细胞均显示出细胞毒性。
更新日期:2018-07-01
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