New Ustilaginoidins from Rice False Smut Balls Caused by Villosiclava virens and Their Phytotoxic and Cytotoxic Activities

文献类型： 外文期刊

第一作者： Sun, Weibo

作者： Sun, Weibo;Wang, Ali;Xu, Dan;Wang, Weixuan;Meng, Jiajia;Lai, Daowan;Zhou, Ligang;Dai, Jungui;Dai, Jungui;Liu, Yang

作者机构：

关键词： bis-naphtho-gamma-pyrones;ustilaginoidins;rice false smut balls;Villosiclava virens;phytotoxic activity;cytotoxicity

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.279； 五年影响因子：5.269 ）

ISSN：

年卷期：

页码：

收录情况： SCI

摘要： Ustilaginoidins are a class of bis-naphtho-gamma-pyrones, typically produced by Villosiclava virens, the pathogen of the rice false smut (RFS), which has been one of the most destructive rice fungal diseases. Previously, we found that ustilaginoidins identified from the culture of V. virens on rice medium were less polar than those reported from the RFS balls in general. In this study, we reinvestigated the high-performance liquid chromatography with diode array detection and high-resolution mass spectrometry (HPLC-DAD-HRMS) profile of the ethyl acetate (EtOAc) extract of the RFS balls and found several interesting peaks that correspond to new ustilaginoidins. As a result, eight new and polar congeners, named ustilaginoidins Q-T (1-4), 2,3-dihydroustilaginoidin T (5), and ustilaginoidins U-W (6-8), were isolated. In addition, 17 known ustilaginoidins, including ustilaginoidins K-N (9-12), ustilaginoidin P (13), ustilaginoidin E1 (14), isochaetochromin B2 (15), and ustilaginoidins A-J (16-25), were re-isolated. The structures of the new compounds were elucidated by comprehensive analysis of the spectroscopic data. Ustilaginoidins Q (1) and R (2) feature an uncommon 2-hydroxypropyl-substituted skeleton and biogenetically incorporate one more acetate unit than common ustilaginoidins. Ustilaginoidin W (8) is a rare formate-containing bis-naphtho-gamma-pyrone. Ustilaginoidins R (2), U (6), B (17), and I (24) showed moderate inhibitory activities toward the radicle or germ elongation of rice seeds. Ustilaginoidins R (2), S (3), V (7), W (8), B (17), C (18), and H-J (23-25) were cytotoxic to the tested human cancer cell lines (HCT116, NCI-H1650, BGC823, Daoy, and HepG2), with IC50 values in the range of 4.06-44.1 mu M.

分类号： R15`S

  • 相关文献

[1]Preparative Separation of Main Ustilaginoidins from Rice False Smut Balls by High-Speed Counter-Current Chromatography. Sun, Weibo,Dong, Xuejiao,Xu, Dan,Meng, Jiajia,Fu, Xiaoxiang,Wang, Xiaohan,Lai, Daowan,Zhou, Ligang,Liu, Yang. 2016

[2]Main Ustilaginoidins and Their Distribution in Rice False Smut Balls. Meng, Jiajia,Sun, Weibo,Mao, Ziling,Xu, Dan,Wang, Xiaohan,Lu, Shiqiong,Lai, Daowan,Zhou, Ligang,Zhang, Guozhen,Liu, Yang. 2015

[3]Ustiloxin G, a New Cyclopeptide Mycotoxin from Rice False Smut Balls. Wang, Xiaohan,Wang, Jian,Lai, Daowan,Wang, Weixuan,Zhou, Ligang,Dai, Jungui,Dai, Jungui,Liu, Yang. 2017

[4]The Contents of Ustiloxins A and B along with Their Distribution in Rice False Smut Balls. Wang, Xiaohan,Fu, Xiaoxiang,Lin, Fengke,Sun, Weibo,Meng, Jiajia,Wang, Ali,Lai, Daowan,Zhou, Ligang,Liu, Yang. 2016

[5]Frequency distribution of sensitivity of Ustilaginoidea virens to four EBI fungicides, prochloraz, difenoconazole, propiconazole and tebuconazole, and their efficacy in controlling rice false smut in Anhui Province of China. Chen, Yu,Zhang, Yong,Yang, Xue,Wang, Wen-Xiang,Zhang, Ai-Fang,Gao, Tong-Chun,Chen, Yu,Zhang, Yong,Yang, Xue,Wang, Wen-Xiang,Zhang, Ai-Fang,Gao, Tong-Chun,Yao, Jian,Li, Yun-Fei,Chen, Yu,Zhang, Yong,Yang, Xue,Wang, Wen-Xiang,Zhang, Ai-Fang,Gao, Tong-Chun. 2013

[6]Determination and Analysis of Ustiloxins A and B by LC-ESI-MS and HPLC in False Smut Balls of Rice. Shan, Tijiang,Sun, Weibo,Liu, Hao,Gao, Shan,Lu, Shiqiong,Wang, Mingan,Sun, Wenxian,Zhou, Ligang,Chen, Zhiyi,Wang, Shu. 2012

[7]Bioactive Bis-naphtho-gamma-pyrones from Rice False Smut Pathogen Ustilaginoidea virens. Lu, Shiqiong,Sun, Weibo,Meng, Jiajia,Wang, Ali,Wang, Xiaohan,Tian, Jin,Fu, Xiaoxiang,Lai, Daowan,Zhou, Ligang,Dai, Jungui,Dai, Jungui,Liu, Yang.

[8]Development of a Monoclonal Antibody-Based icELISA for the Detection of Ustiloxin B in Rice False Smut Balls and Rice Grains. Fu, Xiaoxiang,Wang, Ali,Wang, Xiaohan,Lin, Fengke,He, Lishan,Lai, Daowan,Zhou, Ligang,Wang, Baoming,Liu, Yang,Li, Qing X.. 2015

[9]A monoclonal antibody-based enzyme-linked immunosorbent assay for detection of ustiloxin A in rice false smut balls and rice samples. Fu, Xiaoxiang,Wang, Xiaohan,Cui, Yongliang,Wang, Ali,Lai, Daowan,Wang, Baomin,Zhou, Ligang,Liu, Yang,Li, Qing X..

[10]Characterization of mating-type loci in rice false smut fungus Villosiclava virens. Yu, Jun-jie,Yu, Mi-na,Yin, Xiao-le,Meng, Xiang-kun,Zhao, Jie,Huang, Lei,Liu, Yong-feng,Sun, Wen-xian,Huang, Li. 2015

[11]Development and application of an allele-specific PCR assay for detecting T409C mutation of cyp51 gene linked with tebuconazole resistance in Villosiclava virens (rice false smut). Shi, Niu-Niu,Ruan, Hong-Chun,Chen, Fu-Ru,Yang, Xiu-Juan,Dai, Yu-Li,Gan, Lin,Du, Yi-Xin,Zhang, Yu-Long.

[12]Simple and rapid detection of rice false smut pathogen Ustilaginoidea virens in rice seeds. Chen, Yu,Wang, Wen-Xiang,Yang, Xue,Zhang, Ai-Fang,Yao, Jian,Li, Yun-Fei,Chen, Yu,Wang, Wen-Xiang,Yang, Xue,Zhang, Ai-Fang,Chen, Yu,Wang, Wen-Xiang,Yang, Xue,Zhang, Ai-Fang.

[13]De novo sequencing and transcriptome analysis of Ustilaginoidea virens by using Illumina paired-end sequencing and development of simple sequence repeat markers. Yu, Mina,Yu, Junjie,Nie, Yafeng,Chen, Zhiyi,Yin, Xiaole,Liu, Yongfeng,Gu, Chenhao.

[14]Fabrication and stabilization of biocompatible selenium nanoparticles by carboxylic curdlans with various molecular properties. Yan, Jing-Kun,Qiu, Wen-Yi,Wang, Yao-Yao,Wang, Wen-Han,Yang, Yan,Zhang, He-Nan,Wang, Wen-Han,Yang, Yan,Zhang, He-Nan. 2018

[15]Anti-Phytopathogenic and Cytotoxic Activities of Crude Extracts and Secondary Metabolites of Marine-Derived Fungi. Zhao, Dong-Lin,Wang, Dan,Tian, Xue-Ying,Li, Yi-Qiang,Zhang, Cheng-Sheng,Cao, Fei. 2018

[16]Optimization of Catechin Nanoliposomes and Evaluation of Their Antioxidant Activity and Cytotoxicity. Wu, Zhipan,Guan, Rongfa,Liu, Mingqi,Xiao, Chaogeng,Lyu, Fei,Cao, Guozhou,Gao, Jianguo. 2017

[17]Cytotoxicity, oxidative stress, and genotoxicity in human hepatocyte and embryonic kidney cells exposed to ZnO nanoparticles. Guan, Rongfa,Kang, Tianshu,Liu, Mingqi,Lu, Fei,Zhang, Zhiguo,Shen, Haitao. 2012

[18]A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria. Dong, Wen-Hua,Mei, Wen-Li,Zhao, You-Xing,Zeng, Yan-Bo,Wang, Hui,Dai, Hao-Fu,Dong, Wen-Hua,Mei, Wen-Li,Zhao, You-Xing,Zeng, Yan-Bo,Wang, Hui,Dai, Hao-Fu. 2011

[19]Dimeric sesquiterpenoid-4&ITH&IT-chromone derivatives from agarwood of &ITAquilaria crassna&IT and their cytotoxicity. Yang, Yang,Chen, Hui-Qin,Kong, Fan-Dong,Zhou, Li-Man,Li, Wei,Dong, Wen-Hua,Mei, Wen-Li,Dai, Hao-Fu,Yang, Yang,Chen, Zhi-Bao. 2018

[20]Screening of microorganisms from Antarctic surface water and cytotoxicity metabolites from Antarctic microorganisms. Zheng, Lanhong,Yang, Kangli,Sun, Mi,Zhu, Jiancheng,Lv, Mei,Kang, Daole,Wang, Wei,Xing, Mengxin,Li, Zhao,Liu, Jia. 2016

作者其他论文 更多>>

微信小程序