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Toxins 2017, 9(2), 54; doi:10.3390/toxins9020054

Ustiloxin G, a New Cyclopeptide Mycotoxin from Rice False Smut Balls

1
Department of Plant Pathology, College of Plant Protection, China Agricultural University, Beijing 100193, China
2
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Science & Peking Union Medical College, Beijing 100050, China
3
Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Antonio Moretti
Received: 20 December 2016 / Accepted: 6 February 2017 / Published: 10 February 2017
(This article belongs to the Section Mycotoxins)
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Abstract

Ustiloxins were cyclopeptide mycotoxins from rice false smut balls (FSBs) that formed in rice spikelets infected by the fungal pathogen Ustilaginoidea virens. To investigate the chemical diversity of these metabolites and their bioactivities, one new cyclopeptide, ustiloxin G (1), together with four known congeners—ustiloxins A (2), B (3), D (4), and F (5)—were isolated from water extract of rice FSBs. Their structures were elucidated by analyses of their physical and spectroscopic data, including ultraviolet spectrometry (UV), infrared spectroscopy (IR), 1D and 2D nuclear magnetic resonance (NMR), and high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS). All the compounds were evaluated for their cytotoxic as well as radicle and germ elongation inhibitory activities. Ustiloxin B (3) showed the best activity against the cell line BGC-823 with an IC50 value of 1.03 µM, while ustiloxin G (1) showed moderate activity against the cell lines A549 and A375 with IC50 values of 36.5 µM and 22.5 µM, respectively. Ustiloxins A (2), B (3), and G (1) showed strong inhibition of radicle and germ elongation of rice seeds. When their concentrations were at 200 µg/mL, the inhibitory ratios of radicle and germ elongation were more than 90% and 50%, respectively, the same effect as that of positive control (glyphosate). They also induced abnormal swelling of the roots and germs of rice seedlings. View Full-Text
Keywords: ustiloxin G; cyclopeptide; mycotoxin; rice false smut disease; Villosiclava virens; rice false smut balls; cytotoxicity; phytotoxicity ustiloxin G; cyclopeptide; mycotoxin; rice false smut disease; Villosiclava virens; rice false smut balls; cytotoxicity; phytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wang, X.; Wang, J.; Lai, D.; Wang, W.; Dai, J.; Zhou, L.; Liu, Y. Ustiloxin G, a New Cyclopeptide Mycotoxin from Rice False Smut Balls. Toxins 2017, 9, 54.

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