New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2

被引:8
作者
Hu, Jin-Shan [1 ,2 ]
He, Yu-Pei [1 ]
Zhou, Feng-Guo [1 ]
Wu, Ping-Ping [1 ]
Chen, Le-Yi [1 ]
Ni, Cheng [1 ]
Zhang, Ze-Kun [1 ]
Xiao, Xi-Ji [1 ]
An, Lin-Kun [3 ]
He, Xi-Xin [1 ]
Zhang, Cui-Xian [1 ]
机构
[1] Guangzhou Univ Chinese Med, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
[2] First Compulsory Isolated Detoxificat Ctr Shenzhen, Municipal Bur Justice, Shenzhen 518024, Peoples R China
[3] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
基金
中国国家自然科学基金;
关键词
A; versicolor CGF 9-1-2; IDAs; inhibitory effect; molecular docking; soft coral-associated epiphytic fungus; MARINE; BIOSYNTHESIS; TDP1;
D O I
10.1002/cbdv.202300301
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Two new indole diketopiperazine alkaloids (IDAs), (+)19-epi-sclerotiamide (1) and (-)19-epi-sclerotiamide (2), along with 13 known analogs (3-15), were isolated from a soft coral-associated epiphytic fungus Aspergillus versicolor CGF 9-1-2. The structures of two new compounds were established based on the combination of HR-ESI-MS, 1D and 2D NMR spectroscopy, optical rotation measurements and quantum chemical C-13-NMR, the absolute configurations were determined by experimental and electronic circular dichroism (ECD) calculations. The results of molecular docking showed that all the compounds had a good binding with TDP1, TDP2, TOP1, TOP2, Ache, NLRP3, EGFR, EGFR L858R, EGFR T790M and EGFR T790/L858. Biological evaluation of compounds 3, 6, 8, 11 showed that 3 exerted a strong inhibitory effect on TDP2 with a rate of 81.72 %.
引用
收藏
页数:8
相关论文
共 37 条
[31]   Probing Indole Diketopiperazine-Based Hybrids as Environmental-Induced Products from Aspergillus sp. EGF 15-0-3 [J].
Wei, Xia ;
Su, Jun-Cheng ;
Hu, Jin-Shan ;
He, Xi-Xin ;
Lin, Shuang-Jun ;
Zhang, Dong-Mei ;
Ye, Wen-Cai ;
Chen, Min-Feng ;
Lin, Hou-Wen ;
Zhang, Cui-Xian .
ORGANIC LETTERS, 2022, 24 (01) :158-163
[32]   New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus sp. EGF 15-0-3 [J].
Wei, Xia ;
Feng, Chan ;
Wang, Si-Yu ;
Zhang, Dong-Mei ;
Li, Xiao-Hui ;
Zhang, Cui-Xian .
CHEMISTRY & BIODIVERSITY, 2020, 17 (05)
[33]   Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum [J].
Whyte, AC ;
Gloer, JB ;
Wicklow, DT ;
Dowd, PF .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (11) :1093-1095
[34]  
[吴东阳 Wu Dongyang], 2020, [中草药, Chinese Traditional and Herbal Drugs], V51, P4338
[35]   Bacterial Biosynthesis and Maturation of the Didemnin Anti-cancer Agents [J].
Xu, Ying ;
Kersten, Roland D. ;
Nam, Sang-Jip ;
Lu, Liang ;
Al-Suwailem, Abdulaziz M. ;
Zheng, Huajun ;
Fenical, William ;
Dorrestein, Pieter C. ;
Moore, Bradley S. ;
Qian, Pei-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (20) :8625-8632
[36]   The synthesis of furoquinolinedione and isoxazoloquinolinedione derivatives as selective Tyrosyl-DNA phosphodiesterase 2 (TDP2) inhibitors [J].
Yang, Hao ;
Zhu, Xiao-Qing ;
Wang, Wenjie ;
Chen, Yu ;
Hu, Zhu ;
Zhang, Yu ;
Hu, De-Xuan ;
Yu, Le-Mao ;
Agama, Keli ;
Pommier, Yves ;
An, Lin-Kun .
BIOORGANIC CHEMISTRY, 2021, 111
[37]   Dual DNA topoisomerase 1 and tyrosyl-DNA phosphodiesterase 1 inhibition for improved anticancer activity [J].
Zakharenko, Alexandra ;
Dyrkheeva, Nadezhda ;
Lavrik, Olga .
MEDICINAL RESEARCH REVIEWS, 2019, 39 (04) :1427-1441