Bioactive Bis-naphtho-γ-pyrones from Rice False Smut Pathogen Ustilaginoidea virens

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 13, 2015, Pages 3501-3508

  Lu, Shiqiong ^a   Sun, Weibo ^a   Meng, Jiajia ^a   Wang, Ali ^a   Wang, Xiaohan ^a   Tian, Jin ^a   Fu, Xiaoxiang ^a   Dai, Jungui ^b   Liu, Yang ^c   Lai, Daowan ^a   Zhou, Ligang ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b INSTITUTE OF MATERIA MEDICA   (China)

^c INSTITUTE OF PLANT PROTECTION   (China)

Author keywords

Bis naphtho pyrone; Mycotoxin; Rice false smut; Rice false smut pathogen; Ustilaginoidea virens; Ustilaginoidin; Villosiclava virens

Indexed keywords

BACTERIA; BIOCHEMISTRY; CELL CULTURE; DICHROISM; FLUORINE; MASS SPECTROMETRY; STEREOCHEMISTRY;

MYCOTOXIN; RICE FALSE SMUT; USTILAGINOIDEA; USTILAGINOIDIN; VILLOSICLAVA VIRENS;

CHEMICAL COMPOUNDS;

FUNGI; USTILAGINOIDEA VIRENS;

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; MYCOTOXIN; NAPHTHALENE DERIVATIVE; PYRONE DERIVATIVE;

BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; FEMALE; FERMENTATION; GROWTH, DEVELOPMENT AND AGING; HUMAN; HYPOCREALES; METABOLISM; MICROBIOLOGY; OVARY TUMOR; PLANT DISEASE; PLANT SEED; RICE; TUMOR CELL LINE;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FEMALE; FERMENTATION; HUMANS; HYPOCREALES; MOLECULAR STRUCTURE; MYCOTOXINS; NAPHTHALENES; ORYZA SATIVA; OVARIAN NEOPLASMS; PLANT DISEASES; PYRONES; SEEDS;

EID: 84926483197     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b00694     Document Type: Article

References (38)

1. Tanaka, E.; Ashizawa, T.; Sonoda, R.; Tanaka, C. Villosiclava virens gen. nov., comb. nov., teleomorph of Ustilaginoidea virens, the causal agent of rice false smut Mycotaxon 2008, 106, 491 - 501
2. Hu, M.; Luo, L.; Wang, S.; Liu, Y.; Li, J. Infection processes of Ustilaginoidea virens during artificial inoculation of rice panicles Eur. J. Plant Pathol. 2014, 139, 67 - 77
3. Tang, Y. X.; Jin, J.; Hu, D. W.; Yong, M. L.; Xu, Y.; He, L. P. Elucidation of the infection process of Ustilaginoidea virens (teleomorph: Villosiclava virens) in rice spikelets Plant Pathol. 2013, 62, 1 - 8
4. Shibata, S.; Ogihara, Y.; Ohta, A. Metabolic products of fungi. XXII. On ustilaginoidins. (2). The structure of ustilaginoidin A Chem. Pharm. Bull. 1963, 11, 1179 - 1182
5. Shibata, S.; Ogihara, Y. Metabolic products of fungi. XXIII. Ustilaginoidins. 3. The structure of ustilaginoidins B and C Chem. Pharm. Bull. 1963, 11, 1576 - 1578
6. Koyama, K.; Natori, S. Further characterization of seven bis(naphtho-γ-pyrone) congeners of ustilaginoidins, pigments of Claviceps virens (Ustilaginoidea virens) Chem. Pharm. Bull. 1988, 36, 146 - 152
7. Shibata, S.; Ogihara, Y. Absolute configurations of ustilaginoidins Tetrahedron Lett. 1963, 4, 1777 - 1780
8. Koyama, K.; Natori, S.; Iitaka, Y. Absolute configurations of chaetochromin A and related bis(naphtho-γ-pyrone) mold metabolites Chem. Pharm. Bull. 1987, 35, 4049 - 4055
9. Lu, S.; Tian, J.; Sun, W.; Meng, J.; Wang, X.; Fu, X.; Wang, A.; Lai, D.; Liu, Y.; Zhou, L. Bis-naphtho-γ-pyrones from fungi and their bioactivities Molecules 2014, 19, 7169 - 7188
10. 1H long-range coupling to the structure elucidation Chem. Pharm. Bull. 1980, 28, 2428 - 2435
11. Koyama, K.; Natori, S. Chaetochromins B, C, and D; bis(naphtho-γ-pyrone) derivatives from Chaetomium gracile Chem. Pharm. Bull. 1987, 35, 578 - 584
12. 2, a new bis(naphthodihydropyran-4-one) with antimicrobial and immunological activities from fungus Chaetomium microcephalum Arch. Pharmacal Res. 2014, 37, 575 - 579
13. Zhang, Q.; Li, H. Q.; Zong, S. C.; Gao, J. M.; Zhang, A. L. Chemical and bioactive diversities of the genus Chaetomium secondary metabolites Mini Rev. Med. Chem. 2012, 12, 127 - 148
14. Singh, S. B.; Zink, D. L.; Bills, G. F.; Teran, A.; Silverman, K. C.; Lingham, R. B.; Felock, P.; Hazuda, D. J. Four novel bis-(naphtho-γ-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase Bioorg. Med. Chem. Lett. 2003, 13, 713 - 717
15. Ugaki, N.; Matsuda, D.; Yamazaki, H.; Nonaka, K.; Masuma, R.; Omura, S.; Tomoda, H. New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: I. Taxonomy, fermentation, isolation, and biological properties J. Antibiot. 2012, 65, 15 - 19
16. Kong, X.; Ma, X.; Xie, Y.; Cai, S.; Zhu, T.; Gu, Q.; Li, D. Aromatic polyketides from a sponge-derived fungus Metarhizium anisopliae mxh-99 and their antitubercular activities Arch. Pharmacal Res. 2013, 36, 739 - 744
17. Ohtsubo, K. Oral toxicity of chaetochromin, a new mycotoxin produced by Chaetomium virescens, to mice Mycotoxins 1980, 28 - 29
18. Ito, Y.; Ohtsubo, K. Exencephaly in mice induced by feeding chaetochromin containing diet Mycotoxins 1982, 22 - 23
19. Ohtsubo, K. Hematopoietic injury and liver necrosis in the mice fed chaetochromin-containing moldy rice diet Mycotoxins 1982, 25 - 27
20. Ito, Y.; Ohtsubo, K. Teratogenicity of oral chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp., to mice embryo Bull. Environ. Contam. Toxicol. 1987, 39, 299 - 303
21. Ohtsubo, K. Myocardial and hepatic necrosis and bone marrow suppression in mice induced by single administration of chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp J. Toxicol. Pathol. 1989, 2, 163 - 174
22. Tsuchiya, T.; Sekita, S.; Koyama, K.; Natori, S.; Takahashi, A. Effect of chaetochromin A, chaetochromin D, and ustilaginoidin A, bis(naphtho-γ-pyrone) derivatives, on the mouse embryo limb bud and midbrain cells in culture Cong. Anom. 1987, 27, 245 - 250
23. Koyama, K.; Ominato, K.; Natori, S.; Tashiro, T.; Tsuruo, T. Cytotoxicity and antitumor activities of fungal bis-(naphtho-γ-pyrone) derivatives J. Pharmacobiodyn. 1988, 11, 630 - 635
24. Kawai, K.; Hisada, K.; Mori, S.; Nozawa, Y.; Koyama, K.; Natori, S. The impairing effect of chaetochromin A and related mycotoxins on mitochondrial respiration Mycotoxins 1991, 31 - 35
25. Mori, S.; Kawai, K.; Nozawa, Y.; Koyama, K.; Natori, S. The impairing effects of chaetochromin D on mitochondrial respiration and structure Mycotoxin Res. 1993, 9, 85 - 93
26. Kawai, K.; Mori, S.; Hisada, K.; Nozawa, Y.; Koyama, K.; Natori, S. The induction of mitochondrial swelling by chaetochromin A, a bis-(naphtho-γ-pyrone) mycotoxin from Chaetomium gracile Mycotoxins 1991, 25 - 29
27. Mori, S.; Kawai, K.; Nozawa, Y.; Koyama, K.; Natori, S. Induction of mitochondrial swelling by chaetochromin A, a bis-(naphtho-γ-pyrone) mycotoxin from Chaetomaum gracale II. Relationship with uncoupling effect Mycotoxins 1991, 33 - 37
28. Ishii, R.; Horie, M.; Koyama, K.; Ishikawa, Y.; Kitanaka, S. Inhibitory effects of fungal bis-(naphtho-γ-pyrone) derivatives on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-γ Biol. Pharm. Bull. 2005, 28, 786 - 790
29. Ugaki, N.; Yamazaki, H.; Uchida, R.; Tomoda, H. New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: II. Structure elucidation J. Antibiot. 2012, 65, 21 - 24
30. Xu, L.; Zhou, L.; Zhao, J.; Li, J.; Li, X.; Wang, J. Fungal endophytes from Dioscorea zingiberensis rhizomes and their antibacterial activity Lett. Appl. Microbiol. 2008, 46, 68 - 72
31. Xu, L.; Wang, X.-H.; Luo, R.-Y.; Lu, S.-Q.; Guo, Z.-J.; Wang, M.-A.; Liu, Y.; Zhou, L.-G. Secondary metabolites of rice sheath blight pathogen Rhizoctonia solani Kühn and their biological activities J. Integr. Agric. 2015, 14, 80 - 87
32. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55 - 63
33. Aliferis, K. A.; Jabaji, S. Metabolite composition and bioactivity of Rhizoctonia solani sclerotial exudates J. Agric. Food. Chem. 2010, 58, 7604 - 7615
34. Koyama, K.; Natori, S. Biosynthesis of chaetochromin A, a bis-(naphtho-γ-pyrone), in Chaetomium spp Chem. Pharm. Bull. 1989, 37, 2022 - 2025
35. Frandsen, R. J. N.; Nielsen, N. J.; Maolanon, N.; Soerensen, J. C.; Olsson, S.; Nielsen, J.; Giese, H. The biosynthetic pathway for aurofusarin in Fusarium graminearum reveals a close link between the naphthoquinones and naphthopyrones Mol. Microbiol. 2006, 61, 1069 - 1080
36. Shan, T.; Tian, J.; Wang, X.; Mou, Y.; Mao, Z.; Lai, D.; Dai, J.; Peng, Y.; Zhou, L.; Wang, M. Bioactive spirobisnaphthalenes from the endophytic fungus Berkleasmium sp J. Nat. Prod. 2014, 77, 2151 - 2160
37. 16 from Coniothyrium sp.: Isolation, structure elucidation, and biological activity Liebigs Ann. Chem. 1994, 1994, 1099 - 1108
38. Fan, J.; Guo, X. Y.; Huang, F.; Li, Y.; Liu, Y. F.; Li, L.; Xu, Y. J.; Zhao, J. Q.; Xiong, H.; Yu, J. J.; Wang, W. Epiphytic colonization of Ustilaginoidea virens on biotic and abiotic surfaces implies the widespread presence of primary inoculum for rice false smut disease Plant Pathol. 2014, 63, 937 - 945