Chromatographic analysis of a crude ethyl acetate (EtOAc) extract derived from a solid rice culture incubated at 40°C to mimic the natural ecological niche of the extremophilic fungus Botryotrichum piluliferum strain WESH19 yielded a new natural butenolide compound (1) together with three known metabolites (2–4). Chemical structures of the isolated metabolites were confirmed by HR-ESI-MS along with 1D and 2D NMR spectroscopic analyses. Compounds 1–3 revealed pronounced antimicrobial activities against Staphylococcus aureus (ATCC 700699), Enterococcus faecalis (ATCC 29212), and Enterococcus faecium (ATCC 35667), while their antifungal activities were assessed against the extremophilic fungus Penicillium simplicissimum strain WSH17 (GenBank Acc. No. MN055685). This study adds another example of how extreme environmental conditions may influence secondary metabolism of the inhabiting fungi.
Similar content being viewed by others
References
G. F. Bills and J. B. Gloer, Biologically Active Secondary Metabolites from the Fungi, in: The Fungal Kingdom, J. Heitman, B. J. Howlett, P. W. Crous, E. H. Stukenbrock, T. Y. James, and N. A. R. Gow (eds.), American Society of Microbiology, Sterling, USA, 2017, pp. 1087–1119.
R. Orellana, C. Macaya, G. Bravo, F. Dorochesi, A. Cumsille, R. Valencia, C. Rojas, and M. Seeger, Front. Microbiol., 9, 2309 (2018).
R. Maheshwari, G. Bharadwaj, and M. K. Bhat, Microbiol. Mol. Biol. Rev., 64, 461 (2000).
A. T. Bull, Actinobacteria of the Extremobiosphere, in: Extremophiles, K. Horikosh (ed.), Springer, Japan,Tokyo, 2011, pp. 1203–1240.
P. M. Leung, S. K. Bay, D. V. Meier, E. Chiri, D. A. Cowan, O. Gillor, D. Woebken, and C. Greening, mSystems, 5, e-00495-19 (2020).
S. C. Cary, I. R. McDonald, J. E. Barrett, and D. A. Cowan, Nat. Rev. Microbiol., 8, 129 (2010).
S. B. Pointing and J. Belnap, Nat. Rev. Microbiol., 10, 551 (2012).
G. Wang and D. Or, ISME J., 7, 395 (2013).
T. P. Makhalanyane, A. Valverde, E. Gunnigle, A. Frossard, J. B. Ramond, and D. A. Cowan, FEMS Microbiol. Rev., 39, 203 (2015).
J. P. Schimel, Annu. Rev. Ecol. Evol. S., 49, 409 (2018).
E. F. DeLong, Nat. Rev. Microbiol., 5, 755 (2007).
T. K. Mohanta and H. Bae, Biol. Proc. Online, 17, 8 (2015).
S. S. Ebada and W. Ebrahim, Phytochem. Lett., 36, 95 (2020).
I. Uchida, Y. Itoh, T. Namiki, M. Nishikawa, and M. Hashimoto, Tetrahedron Lett., 27, 2015 (1986).
T. Namiki, M. Nishikawa, Y. Itoh, I. Uchida, and M. Hashimoto, J. Antibiot., 40, 1400 (1987).
X. Niu, H.-M. Dahse, K.-D. Menzel, O. Lozach, G. Walther, L. Meijer, S. Grabley, and I. Sattler, J. Nat. Prod., 71, 689 (2008).
H. Chen, G. Daletos, M. S. Abdel-Aziz, D. Thomy, H. Dai, H. Broetz-Oesterhelt, W. Lin, and P. Proksch, Phytochem. Lett., 12, 35 (2015).
R. R. Parvatkar, C. D’Souza, A. Tripathi, and C. G. Naik, Phytochemistry, 70, 128 (2009).
T. Namiki, Y. Baba, Y. Suzuki, M. Nishikawa, K. Sawada, Y. Itoh, T. Oku, Y. Kitaura, and M. Hashimoto, Chem. Pharm. Bull., 36, 1404 (1988).
N. Okamura, H. Haraguchi, K. Hashimoto, and A. Yagi, Phytochemistry, 34, 1005 (1993).
W.-J. Lan, W. Liu, W.-L. Liang, Z. Xu, X. Le, J. Xu, C.-K. Lam, D.-P. Yang, H.-J. Li, and L.-Y. Wang, Mar. Drugs, 12, 4188 (2014).
M. M. S. Nagia, M. M. El-Metwally, M. Shaaban, S. M. El-Zalabani, and A. G. Hanna, Org. Med. Chem. Lett., 2, 9 (2012).
R. K. Pettit, Mar. Biotechnol., 13, 1 (2011).
A. Jaouani, M. Neifar, V. Prigione, A. Ayari, I. Sbissi, S. Ben Amor, S. Ben Tekaya, G. C. Varese, A. Cherif, and M. Gtari, BioMed Res. Int., 2014, 1 (2014).
B. van den Burg, Curr. Opin. Microbiol., 6, 213 (2003).
N. Kostadinova, E. Krumova, S. Tosi, Pashova, and M. Angelova, Biotechnol. Biotechnol. Equip., 23, 267 (2009).
S. S. Ebada and W. Ebrahim, S. Afr. J. Bot., 133 (2020).
Clinical and Laboratory Standards Institute (CLSI), Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, CLSI Document M27-A3. 3rd Edn., Clinical and Laboratory Standards Institute, Wayne, Pennsylvania, 2008.
Clinical and Laboratory Standards Institute (CLSI), Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standard, 9th Edn., Clinical and Laboratory Standards Institute, Wayne, Pennsylvania, 2012.
W. Ebrahim, F. C. Ozkaya, and S. S. Ebada, S. Afr. J. Bot., 133, 40 (2020).
Acknowledgment
The authors are gratefully indebted to Dr. Dalia E. El-Badan (Botany and Microbiology Department, Faculty of Science, Alexandria University, Alexandria, Egypt) for valuable microbiological discussions in this study.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2021, pp. 559–562.
Rights and permissions
About this article
Cite this article
Ebrahim, W., Ebada, S.S. Antimicrobial Metabolites from Extremophilic Fungus Botryotrichum piluliferum Strain WESH19. Chem Nat Compd 57, 654–658 (2021). https://doi.org/10.1007/s10600-021-03443-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-021-03443-6