Cytotoxic Secondary Metabolites from a Sea-Derived Fungal Strain of Hypoxylon rubiginosum FS521

doi:10.6023/cjoc201912012

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1367-1371.DOI: 10.6023/cjoc201912012 Previous Articles Next Articles

海洋真菌赤褐炭团菌FS521的次级代谢产物研究

张捷^a,b, 陈玉婵^a, 刘昭明^a, 郭波红^b, 高晓霞^b, 刘洪新^a, 章卫民^a

a 广东省微生物研究所广东省科学院华南应用微生物国家重点实验室广东省菌种保藏与应用重点实验室广东省微生物应用新技术公共实验室;
b 广东药科大学药学院广州 510006

收稿日期:2019-12-09 修回日期:2020-01-05 发布日期:2020-01-15
通讯作者: 刘洪新, 章卫民 E-mail:liuhx@gdim.cn;wmzhang@gdim.cn
基金资助:
国家自然科学基金（No.41906106，31272087）、广州市珠江科技新星（No.201806010080）、广东省自然科学基金研究团队（No.2016A030312014）和广东省科学院（No.2019GDASYL-0103007）资助项目.

Cytotoxic Secondary Metabolites from a Sea-Derived Fungal Strain of Hypoxylon rubiginosum FS521

Zhang Jie^a,b, Chen Yuchan^a, Liu Zhaoming^a, Guo Bohong^b, Gao Xiaoxia^b, Liu Hongxin^a, Zhang Weimin^a

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou 510070;
b School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006

Received:2019-12-09 Revised:2020-01-05 Published:2020-01-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 41906106, 31272087), the Pearl River Science and Technology New Star Fund of Guangzhou Province (No. 201806010080), the Team Project of the Natural Science Foundation of Guangdong Province (No. 2016A030312014), and the Project of Science and Technology Development of Guangdong Academy of Sciences (No. 2019GDASYL-0103007).

1. 201367S.pdf(1507KB)

Abstract

One new compound, named hypoxone A (1), together with two new natural products 4,8-dimethoxy-1-naphthol (2) and 1'-hydroxy-4',8,8'-trimethoxy[2,2']binaphthalenyl-1,4-dione (3), and fourteen known derivatives 4~17 were isolated from the broth extract of the marine fungus Hypoxylon rubiginosum FS521, which was isolated from a deep-sea sediment sample. Their structures were elucidated by interpretation of spectroscopic analysis and comparison with previously published data for the known ones. Moreover, compounds 1~4 were evaluated for their in vitro cytotoxic activities against SF-268, MCF-7, HepG-2, and A549 tumor cell lines, and compound 3 exhibited potent cytotoxic activity with IC₅₀ values of 1.85, 3.21, 2.53, and 5.09 mmol·L^-1, respectively.

Key words: marine fungus, Hypoxylon rubiginosum, cytotoxicity, polyketides

Cite this article

Zhang Jie, Chen Yuchan, Liu Zhaoming, Guo Bohong, Gao Xiaoxia, Liu Hongxin, Zhang Weimin. Cytotoxic Secondary Metabolites from a Sea-Derived Fungal Strain of Hypoxylon rubiginosum FS521[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1367-1371.

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[1] Koyama. K.; Kuramochi, D.; Kinoshiita, K.; Takahashi, T. J. Nat. Prod. 2002, 65, 1489.
[2] Gu, W.; Ge, H. M.; Song, Y. C.; Ding, H.; Zhu, L.; Zhao, X. A.; Tan, R. X. J. Nat. Prod. 2007, 70, 114.
[3] Quang, D. N.; Hashimoto, T.; Tanaka, M.; Stadler, M.; Asakawa, Y. Phytochemistry 2004, 65, 269.
[4] Quang, D. N.; Hashimoto, T.; Stadler, M.; Radulovic, N.; Asakawa, Y. Planta Med. 2005, 71, 1058.
[5] Edwards, R. L.; Maitland, D. J.; Whalley, A. J. S. J. Chem. Soc., Perkin Trans. 1 1989, 57.
[6] Liu, H. X.; Tan, H. B.; Chen, K.; Zhao, L. Y.; Chen, Y. C.; Li, S. N.; Li, H. H.; Zhang, W. M. Org. Biomol. Chem. 2019, 17, 2346.
[7] Liu, H. X.; Tan, H. B.; Wang, W. X.; Zhang, W. G.; Chen, Y. C.; Li, S. N.; Liu, Z. M.; Li, H. H.; Zhang, W. M. Org. Chem. Front. 2019, 6, 591.
[8] Liu, H. X.; Tan, H. B.; Chen, Y. C.; Guo, X. Y.; Wang, W. X.; Guo, H.; Liu, Z. M.; Zhang, W. M. Org. Lett. 2019, 21, 1063.
[9] Liu, H. X.; Tan, H. B.; Liu, Y.; Chen, Y. C.; Li, S. N.; Sun, Z. H.; Li, H. H.; Qiu, S. X.; Zhang, W. M. Fitoterapia 2017, 117, 1.
[10] Kögl F.; Becker H.; Detzel, A; de Voss, G. Justus Liebigs Ann. Chem. 1928, 465, 211.
[11] Rukachisirikul, V.; Sommart, U.; Phongpaichit, S. Chem. Pharm. Bull. 2007, 55, 1316.
[12] Talapatra, S. K.; Karmcharya, B.; De, S. C.; Talapatra, B. Phytochemistry 1988, 27, 3929.
[13] Chang, C. W.; Chang, H. S. Cheng, M. J.; Liu, T. W.; Hsieh, S. Y.; Yuan, G. F.; Chen, I. S. Chem. Biodiversity 2014, 11, 949.
[14] Chen, P.; Wu, J.; Dai, H. F.; Xie, X. C.; Mei, W. L. Chin. J. Med. Chem. 2008, 18, 279.
[15] Kamisuki, S.; Ishimaru, C.; Onoda, K.; Kuriyama, I.; Ida, N.; Sugawara, F.; Yoshida, H.; Mizushina, Y. Bioorg. Med. Chem. 2007, 15, 3109.
[16] Allport, D. C.; Bu'Lock, J. D. J. Chem. Soc. 1960, 1960, 654.
[17] Nadeau, A. K.; Sorensen, J. L. Tetrahedron Lett. 2011, 52, 1697.
[18] Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608.
[19] Li, Y. J.; Lv, S. W.; Wang, Y. H.; An F. T.; Liu, J.; Wang R.; Zhao, J. H. Inf. Trad. Chin. Med. 2003, 20, 25.
[20] Zhao, Q.; Wang, C. X.; Yu, Y.; Wang, G. Q.; Zheng, Q. C.; Chen, G. D.; Lian, Y. Y.; Lin, F.; Guo, L. D.; Gao, H. J. Asian Nat. Prod. Res. 2015, 17, 567.
[21] Lakhrissi, M.; Chapleur, Y. J. Org. Chem. 1994, 59, 5752.
[22] Zhang, Q. J.; Dong, J. Y.; Cui, Q.; Li, S. S.; Cui, J. H. Synth. Commun. 2017, 47, 536.
[23] Takeya, T.; Kondo, H.; Otsuka, T.; Tomita, K.; Okamoto, I.; Tamura, O. Org. Lett. 2007, 9, 2807.
[24] Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107.

海洋真菌赤褐炭团菌FS521的次级代谢产物研究

Cytotoxic Secondary Metabolites from a Sea-Derived Fungal Strain of Hypoxylon rubiginosum FS521

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