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Article | Open Access

Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka

Pamoda B. Ratnaweeraa,b, David E. Williamsc, E. Dilip de Silvaa( ), Ravi L.C. Wijesunderad, Doralyn S. Dalisayc, Raymond J. Andersenc
Department of Chemistry, University of Colombo, Colombo 03, Sri Lanka
Department of Science and Technology, Uva Wellassa University, Badulla, Sri Lanka
Department of Chemistry and Department of Earth, Ocean and Atmospheric Sciences, University of British Columbia, Vancouver, BC, Canada
Department of Plant Sciences, University of Colombo, Colombo 03, Sri Lanka
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Abstract

An endophytic fungus was isolated from surface sterilized leaf segments of Anoectochilus setaceus, an orchid endemic to Sri Lanka, and was identified as Xylaria sp. by morphological characters and DNA sequencing. Bioassay-guided chromatographic fractionation of the organic extract of a laboratory culture of this fungus led to the isolation of the known antibacterial helvolic acid. Helvolic acid was active against the Gram-positive bacteria, Bacillus subtilis [minimal inhibitory concentrations (MIC), 2 µg mL−1] and methicillin-resistant Staphylococcus aureus (MIC, 4 µg mL−1).

Keywords

rainforestantibacterialendophytic fungiXylariaAnoectochilus setaceushelvolic acid

References

 

Aly AH, Debbab A, Proksch P. 2011. Fungal endophytes: unique plant inhabitants with great promises. Appl Microbiol Biotechnol. 90:1829–1845. doi:10.1007/s00253-011-3270-y
Crossref Google Scholar
 

Brunner F, Petrini O. 1992. Taxonomy of some Xylaria species and Xylariaceous endophytes by isozyme electrophoresis. Mycological Res. 96:723–733. doi:10.1016/S0953-7562(09)80440-1
Crossref Google Scholar
 

Chain E, Florey HW, Jennings MA, Williams TI. 1943. Helvolic acid, an antibiotic produced by Aspergillus fumigatus, mut. helvola Yuill. Br J Exp Pathol. 24:108–119.
Google Scholar
 

Espada A, Rivera-Sagredo A, de la Fuente JM, Hueso-Rodríguez JA, Elson SW. 1997. New cytochalasins from the fungus Xylaria hypoxylon. Tetrahedron. 53:6485–6492. doi:10.1016/S0040-4020(97)00305-0
Crossref Google Scholar
 

Feng C, Ma Y. 2010. Isolation and anti-phytopathogenic activity of secondary metabolites from Alternaria sp. FL25, an endophytic fungus in Ficus carica*. Chin J Applied Environ Biol. 16:76–78. doi:10.3724/SP.J.1145.2010.00076
Crossref Google Scholar
 

Fujimoto H, Negishi E, Yamaguchi K, Nishi N, Yamazaki M. 1996. Isolation of new tremorgenic metabolites from an Ascomycete, Corynascus setosus. Chem Pharm Bull. 44:1843–1848. doi:10.1248/cpb.44.1843
Crossref Google Scholar
 
IUCN Sri Lanka and the Ministry of Environment and Natural Resources. 2007. The 2007 red list of threatened fauna and flora of Sri Lanka. Colombo: The World Conservation Union (IUCN) and Ministry of Environment and Natural Resources, xiii + 148pp.
 
Jayaweera DMA. 1982. Medicinal plants (indigenous and exotic) used in Ceylon, Part 4. Colombo: The National Science Council of Sri Lanka; p. 159.
 

Joong-Hyeop P, Choi GJ, Lee HB, Kim KM, Jung HS, Lee SW, Jang KS, Cho KY, Kim JC. 2005. Griseofulvin from Xylaria sp. Strain F0010, an endophytic fungus of Abies holophylla and its antifungal activity against plant pathogenic fungi. J Microbiol Biotechnol. 15:112–117.
Google Scholar
 
Kariyawasam GK, Mithrasena YJPK, Fernando THPS, Wijesundara RLC, Wijesundara WSS. 2012. A new cost effective method for extracting genomic DNA from fungi. Abstracts of papers, 5th Annual sessions of Institute of Biochemistry, Molecular Biology and Biotechnology, Colombo; 2012 Apr 27. Colombo: Institute of Biochemistry, Molecular Biology and Biotechnology; 5: 49.
 

Lee S, Kinoshita H, Ihara F, Igarashi Y, Nihira T. 2008. Identification of novel derivative of helvolic acid from Metarhizium anisopliae grown in medium with insect component. J Biosci Bioeng. 105:476–480. doi:10.1263/jbb.105.476
Crossref Google Scholar
 

Li Y, Hu Z, Lu C, Shen Y. 2010. Four new terpenoids from Xylaria sp. 101. Helvetica Chimica Acta. 93:796–802. doi:10.1002/hlca.200900296
Crossref Google Scholar
 

Lin Y, Wu X, Feng S, Jiang G, Luo J, Zhou S, Vrijmoed LLP, Jones EBG, Krohn K, Steingröver K, Zsila F. 2001. Five unique compounds: xyloketals from mangrove fungus Xylaria sp. from the South China Sea coast. J Org Chem. 66:6252–6256. doi:10.1021/jo015522r
Crossref Google Scholar
 

Liu X, Dong M, Chen X, Jiang M, Lv X, Zhou J. 2008. Antimicrobial activity of an endophytic Xylaria sp.YX-28 and identification of its antimicrobial compound 7-amino-4-methylcoumarin. Appl Microbiol Biotechnol. 78:241–247. doi:10.1007/s00253-007-1305-1
Crossref Google Scholar
 
National Committee for Clinical Laboratory Standards. 2002. Performance standards for antimicrobial susceptibility testing, Twelfth informational supplement, M100-S12. Wayne(PA): National Committee for Clinical Laboratory Standards.
 
National Committee for Clinical Laboratory Standards. 2003. Performance standards for antimicrobial disc susceptibility tests, Approved Standard, document M2-A8. 8th ed. Wayne (PA): National Committee for Clinical Laboratory Standards.
 

Okuda S, Nakayama Y, Tsuda K. 1966. Studies on microbial products. Ⅰ. 7-desacetoxyhelvolic acid and helvolinic Acid. Chem Pharm Bull. 14:436–441. 10.1248/cpb.14.436
Crossref Google Scholar
 

Oliveira CM, Regasini LO, Silva GH, Pfenning LH, Young MCM, Berlinck RGS, Bolzani VS, Araujo AR. 2011. Dihydroisocoumarins produced by Xylaria sp. and Penicillium sp., endophytic fungi associated with Piper aduncum and Alibertia macrophylla. Phytochemistry Lett. 4:93–96. doi:10.1016/j.phytol.2010.11.003
Crossref Google Scholar
 

Qin L, Li B, Guan J, Zhang G. 2009. In vitro synergistic antibacterial activities of helvolic acid on multi-drug resistant Staphylococcus aureus. Nat Prod Res. 23:309–318. doi:10.1080/14786410801972813
Crossref Google Scholar
 

Radji M, Sumiati A, Rachmayani R, Elya B. 2011. Isolation of fungal endophytes from Garcinia mangostana and their antibacterial activity. Afr J Biotechnol. 10:103–107.
Google Scholar
 

Schulz B, Boyle C, Draeger S, Rommert A, Krohn K. 2001. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol. Res. 106:996–1004.
Crossref Google Scholar
 
Soca-Chafre G, Hidalgo-Lara ME, Hernandez-Rodriguez CH, Marsch-Moreno R, Esparza-Garcia F, Escamilla-Slva E, Valenzuela-Encinas C, Rivera-Orduna FN, Flores-Cotera LB. 2009. NCBI GenBank: EU715609 [Internet]. Available from: http://www.ncbi.nlm.nih.gov/nuccore/EU715609
 

Strobel G, Daisy B. 2003. Bioprospecting for microbial endophytes and their natural products. Microbiol Mol Biol Rev. 67:491–502. doi:10.1128/MMBR.67.4.491-502.2003
Crossref Google Scholar
 

Strobel G, Daisy B, Castillo U, Harper J. 2004. Natural products from endophytic microorganisms. J Nat Prod. 67:257–268. doi:10.1021/np030397v
Crossref Google Scholar
 

Suryanarayanan TS, Thirunavukkarasu N, Govindarajulu MB, Sasse F, Jansen R, Murali TS. 2009. Fungal endophytes and bioprospecting. Fungal Biol Rev. 23:9–19. doi:10.1016/j.fbr.2009.07.001
Crossref Google Scholar
 

Tschen JS, Chen L, Hsieh S, Wu T. 1997. Isolation and phytotoxic effects of helvolic acid from plant pathogenic fungus Sarocladium oryzae. Bot Bull Acad Sinica. 38:251–256.
Google Scholar
 

von Daehne W, Lorch H, Godtfredsen WO. 1968. Microbiological transformations of fusidane-type antibiotics a correlation between fusidic acid and helvolic acid. Tetrahedron Lett. 9:4843–4846. doi:10.1016/S0040-4039(00)72771-7
Crossref Google Scholar
 

Wei JC. 1979. Identification handbook of fungi. Shanghai (China): Science and Technology Press.
 

Zhang M, Wang W, Fang Y, Zhu T, Gu Q, Zhu W. 2008. Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi. J Nat Prod. 71:985–989. doi:10.1021/np700737g
Crossref Google Scholar
 

Zhao J, Mou Y, Shan T, Li Y, Lu S, Zhou L. 2012. Preparative separation of helvolic acid from the endophytic fungus Pichia guilliermondii Ppf9 by high-speed counter-current chromatography. World J Microbiol Biotechnol. 28:835–840. doi:10.1007/s11274-011-0878-0
Crossref Google Scholar
Mycology
Volume 5 Issue 1,
March 2014
Pages 23-28
DOI: 10.1080/21501203.2014.892905
Cite this article:
Ratnaweera PB, Williams DE, de Silva ED, et al. Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka. Mycology, 2014, 5(1): 23-28. https://doi.org/10.1080/21501203.2014.892905

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Received: 30 December 2013
Accepted: 31 January 2014
Published: 25 March 2014
© 2014 The Author(s).

This is an open-access article distributed under the terms of the Creative Commons Attribution License http://creativecommons.org/licenses/by/3.0/, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The moral rights of the named author(s) have been asserted.
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