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Journal of Integrative Agriculture  2015, Vol. 14 Issue (1): 80-87    DOI: 10.1016/S2095-3119(14)60905-9
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Secondary metabolites of rice sheath blight pathogen Rhizoctonia solani Kühn and their biological activities
 XU Liang, WANG Xiao-han, LUO Rui-ya, LU Shi-qiong, GUO Ze-jian, WANG Ming-an, LIU Yang, ZHOU Li-gang
1、Key Laboratory of Plant Pathology, Ministry of Agriculture/Department of Plant Pathology, College of Agronomy and
Biotechnology, China Agricultural University, Beijing 100193, P.R.China
2、Institute of Agro-Products Processing and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, P.R.China
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摘要  Eight compounds were isolated from the fermentation cultures of rice sheath blight pathogen Rhizoctonia solani Kühn. They were identified as ergosterol (1), 6β-hydroxysitostenone (2), sitostenone (3), m-hydroxyphenylacetic acid (4), methyl m-hydroxyphenylacetate (5), m-hydroxymethylphenyl pentanoate (6), (Z)-3-methylpent-2-en-1,5-dioic acid (7) and 3-methoxyfuran-2-carboxylic acid (8) by means of physicochemical and spectroscopic analysis. Among them, 2, 3, 5–8 were isolated from R. solani for the first time. All the compounds were evaluated for their biological activities. 4–6 and 8 showed their inhibitory activities on the radical and germ elongation of rice seeds. 1, 4 and 7 showed moderate antibacterial activity to some bacteria. 4, 7 and 8 exhibited weak inhibitory activities on spore germination of Magnaporthe oryzae. 8 showed moderate antioxidant activity with the 1,1-diphenyl-2-picryhydrazyl (DPPH) and β-carotene-linoleic acid assays. This is the first time to reveal compounds 5, 6 and 8 from rice sheath blight pathogen R. solani to have in vitro phytotoxic activity.

Abstract  Eight compounds were isolated from the fermentation cultures of rice sheath blight pathogen Rhizoctonia solani Kühn. They were identified as ergosterol (1), 6β-hydroxysitostenone (2), sitostenone (3), m-hydroxyphenylacetic acid (4), methyl m-hydroxyphenylacetate (5), m-hydroxymethylphenyl pentanoate (6), (Z)-3-methylpent-2-en-1,5-dioic acid (7) and 3-methoxyfuran-2-carboxylic acid (8) by means of physicochemical and spectroscopic analysis. Among them, 2, 3, 5–8 were isolated from R. solani for the first time. All the compounds were evaluated for their biological activities. 4–6 and 8 showed their inhibitory activities on the radical and germ elongation of rice seeds. 1, 4 and 7 showed moderate antibacterial activity to some bacteria. 4, 7 and 8 exhibited weak inhibitory activities on spore germination of Magnaporthe oryzae. 8 showed moderate antioxidant activity with the 1,1-diphenyl-2-picryhydrazyl (DPPH) and β-carotene-linoleic acid assays. This is the first time to reveal compounds 5, 6 and 8 from rice sheath blight pathogen R. solani to have in vitro phytotoxic activity.
Keywords:  rice sheath blight       Rhizoctonia solani Kühn       secondary metabolites       bioactivities       in vitro phytotoxic activity  
Received: 10 February 2014   Accepted:
Fund: 

This work was co-financed by the grants from the National Basic Research Program of China (2013GB127800) and the National Natural Science Foundation of China (31271996).

Corresponding Authors:  ZHOU Li-gang, Tel: +86-10-62731199, Fax: +86-10-62731062,E-mail: lgzhou@cau.edu.cn     E-mail:  lgzhou@cau.edu.cn
About author:  XU Liang, E-mail: 1baf2006@163.com

Cite this article: 

XU Liang, WANG Xiao-han, LUO Rui-ya, LU Shi-qiong, GUO Ze-jian, WANG Ming-an, LIU Yang, ZHOU Li-gang. 2015. Secondary metabolites of rice sheath blight pathogen Rhizoctonia solani Kühn and their biological activities. Journal of Integrative Agriculture, 14(1): 80-87.

Adachi T, Inagaki K. 1988. Phytotoxin producued by Rhizoctoniaoryzae Ryker et Gooch. Agricultural and BiologicalChemistry, 52, 2625.

Aliferis K A, Jabaji S. 2010a. 1H NMR and GC-MS metabolicfingerprinting of developmental stages of Rhizoctonia solanisclerotia. Metabolomics, 6, 96–108.

Aliferis K A, Jabaji S. 2010b. Metabolite composition andbioactivity of Rhizoctonia solani sclerotial exudates. Journalof Agricultural and Food Chemistry, 58, 7604–7615.

Aoki H, Sassa T, Tamura T. 1963. Phytotoxic metabolites ofRhizoctonia solani. Nature, 200, 575.

Boukaew S, Klinmanee C, Prasertsan P. 2013. Potential forthe integration of biological and chemical control of sheathblight disease caused by Rhizoctonia solani on rice. WorldJournal of Microbiology and Biotechnology, 29, 1885–1893.

Cui Y, Liu P, Chen R. 2002. Studies on the chemical constituentsof Spatholobus suberectus Dunn. Acta PharmaceuticaSinica, 37, 784–787.

Eizenga G C, Lee F N, Rutger J N. 2002. Screening Oryzaspecies plants for rice sheath blight resistance. PlantDisease, 86, 808–812.

Fiori A C G, Schwan-Estrada K R F, Stangarlin J R, VidaJ B, Scapim C A, Cruz M E S, Pascholati S F. 2000.Antifungal activity of leaf extracts and essential oils of somemedicinal plants against Didymella bryoniae. Journal ofPhytopathology, 148, 483–487.

Kan S, Chen G, Han C, Chen Z, Song X, Ren M, Jiang H. 2011.Chemical constituents from the roots Xanthium sibiricum.Natural Product Research, 25, 1243–1249.

Langfied R D, Scarano F J, Heitzman M E, Kondo M, HammondG B, Neto C C. 2004. Use of a modified microplatebioassay method to investigate antibacterial activity in thePeruvian medicinal plant Peperomia galioides. Journal ofEthnopharmacology, 94, 279–281.

Li J, Fu X, Tan C, Zeng Y, Wang Q, Zhao P. 2011. Two newchroman derivations from the endophytic Peniclllium sp.DCS523. Molecules, 16, 686–693.

Li X, Sun G, Zheng Y, Lin W, Sattler I. 2007. Isolation andstructures of two steroids from mangrove endophytePenicillium sp. Natural Product Research and Development,19, 420–422.

Liu H, Wang J, Zhao J, Lu S, Wang J, Jiang W, Ma Z, Zhou L. 2009. Isoquinoline alkaloids from Macleaya cordataactive against plant microbial pathogens. Natural ProductCommunications, 4, 1557–1560.

Ma Y M, Li Y, Liu J Y, Song Y C, Tan R X. 2004. Anti-Helicobacter pylori metabolites from Rhizoctonia sp. Cy064,an endophytic fungus in Cynodon dactylon. Fitoterapia,75, 451–456.

Mandava N B, Orellana R G, Warthen J D, Worley J F, DutkyS R, Finegold H, Weathington B C. 1980. Phytotoxinsin Rhizoctonia solani: isolation and biological activity ofm-hydroxy and m-methoxyphenylacetic acids. Journal ofAgricultural and Food Chemistry, 28, 71–75.

Pedras M S, Yu Y, Liu J, Tandron-Moya Y A. 2005. Metabolitesproduced by the phytopathogenic fungus Rhizoctoniasolani: isolation, chemical structure determination,syntheses and bioactivity. Zeitschrift für Naturforschung C(Journal of Biosciences), 60, 717–722.

Qiao D, Ke C, Hu B, Luo J, Ye H, Sun Y, Yan X, Zeng X. 2009.Antioxidant activities of polysaccharides from Hyriopsiscumingii. Carbohydrate Polymers, 78, 199–204.

Sakuma M. 1998. Probit analysis of preference data. AppliedEntomology and Zoology, 33, 339–347.

Smith J D, Kidwell K K, Evans M A, Cook R J, Smiley R W. 2003.Assessment of spring wheat genotypes for disease reactionto Rhizoctonia solani AG-8 in controlled environment anddirect-seeded field evaluations Crop Science, 43, 694–700.

Sriram S, Raguchander T, Babu S, Nandakumar R, ShanmugamV, Vidhyasekaran P, Balasubramanian P, Samiyappan R.2000. Inactivation of phytotoxin produced by the rice sheathblight pathogen Rhizoctonia solani. Canadian Journal ofMicrobiology, 46, 520–524.

Tsuge T, Harimoto Y, Akimitsu K, Ohtani K, Kodama M, AkagiY, Egusa M, Yamamoto M, Otani H. 2013. Host-selectivetoxins produced by the plant pathogenic fungus Alternariaalternata. FEMS Microbiology Reviews, 37, 44–46.

Velazhahan R, Vidhyasekaran P. 2000. Isolation of an elicitorfrom Rhizoctonia solani, the rice sheath blight pathogenwhich activates phenylpropanoid metabolism in suspensionculturedrice cells. Zeitschrift fur Pflanzenkrankheiten undPflanzenschutz, 107, 135–144.

Vidhyasekaran P, Ponmalar T R, Samiyappan R, VelazhahanR, Vimala R, Ramanthan A, Paranidharan V, MuthukrishnanS. 1997. Host-specific toxin production by Rhizoctoniasolani, the rice sheath blight pathogen. Phytopathology,87, 1258–1263.

Vilgalys R, Cubeta M A. 1994. Molecular systematics andpopulation biology of rhizoctonia. Annual Review ofPhytopathology, 32, 135–155.

Wang J, Lou J, Luo C, Zhou L, Wang L. 2012. Phenoliccompounds from Halimodendron halodendron (Pall.)Voss and their antimicrobial and antioxidant activities.International Journal of Molecular Sciences, 13, 11349–11364.

Wang Q, Ma Y, Zuo B, Qin Q. 1996. Zeolite-catalyzed friedelcraftsreaction of anisole with carboxylic acids. ChineseJournal of Catalysis, 17, 425–428.

Woodhall J W, Lees A K, Edwards S G, Jenkinson P. 2008.Infection of potato by Rhizoctonia solani: Effect ofanastomosis group. Plant Pathology, 57, 897–905.

Zhao J, Mou Y, Shan T, Li Y, Zhou L, Wang M, Wang J. 2010.Antimicrobial metabolites from the endophytic fungusPichia guilliermondii isoalted from Paris polyphylla var.yunnanensis. Molecules, 15, 7961–7970.

Zuo S M, Zhang Y F, Chen Z X, Chen X J, Pan X B. 2010.Current progress in genetics and breeding in resistance torice sheath blight. Scientia Sinica (Vitae), 40, 1014–1023.(in Chinese)
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