Chaetoglocins A–D, Four New Metabolites from the Endophytic Fungus Chaetomium globosum

Abstract

Chaetoglocins A–D (1–4), four new secondary metabolites, were isolated from the solid-fermentation culture of Chaetomium globosum (strain no. IFB-E036), an endophytic fungus residing inside the root of Cynodon dactylon. The structures of these compounds were elucidated on the basis of detailed spectroscopic evidence and by comparing spectroscopic data with those in the literature. Compounds 1 and 2 displayed antimicrobial activity against the gram-positive bacteria with minimum inhibitory concentrations (MIC) between 8 and 32 µg/mL.

Key words

Chaetomium globosum - Chaetomiaceae - secondary metabolites - endophyte - antibiotic

References

• 1 Miglia K J, McArthur E D, Redman R S, Rodriguez R J, Zak J C, Freeman D C. Genotype, soil type, and locale effects on reciprocal transplant vigor, endophyte growth, and microbial functional diversity of a narrow sagebrush hybrid zone in Salt Creek, Canyon, Utah.  Am J Bot. 2007;  94 425-436
• 2 Zhang H W, Song Y C, Tan R X. Biology and chemistry of endophytes.  Nat Prod Rep. 2006;  23 753-771
• 3 Strobel G, Daisy B, Castillo U, Harper J. Natural products from endophytic microorganisms.  J Nat Prod. 2004;  67 257-268
• 4 Gunatilaka A. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence.  J Nat Prod. 2006;  69 509-526
• 5 Von Arx J A, Guarro J, Figueras M J. The ascomycetes genus Chaetomium.  Nova Hedwigia Beih. 1986;  84 1-162
• 6 Schmann J, Hertweck C. Molecular basis of cytochalasan biosynthesis in fungi: gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing.  J Am Chem Soc. 2007;  129 9564-9565
• 7 Ge H M, Zhang W Y, Ding G, Saparpakorn P, Song Y C, Hannongbua S, Tan R X. Chaetoglobins A and B, two unusual alkaloids from endophytic Chaetomium globosum culture.  Chem Commun. 2008;  45 5978-5980
• 8 Jiao R H, Xu S, Liu J Y, Ge H M, Ding H, Xu C, Zhu H L, Tan R X. Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015.  Org Lett. 2006;  8 5709-5712
• 9 Ding G, Song Y C, Chen J R, Xu C, Ge H M, Wang X T, Tan R X. Chaetoglobosin U, a cytochalasan alkaloid from endophyte Chaetomium globosum IFB-E019.  J Nat Prod. 2006;  69 302-304
• 10 Urones J G, Marcos I S, Basabe P, Diez D, Garrido N M, Alonso C, Oliva I M, Lithgow A M, Moro R F, Sexmero M J, Lopez C. Compounds with the labdane skeleton from Halimium viscosum.  Phytochemistry. 1994;  35 713-719
• 11 Hernández-Hernández J D, Román-Marín L U, Cerda-García-Rojas C M, Joseph-Nathan P. Verticillane derivatives from Bursera suntui and Bursera kerberi.  J Nat Prod. 2005;  68 1598-1602
• 12 Huo J, Yang S P, Ding J, Yue J M. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum.  J Nat Prod. 2004;  67 1470-1475
• 13 Suárez-Gómez B, Souto M L, Cruz P G, Fernández J J, Norte M. New targets in diarrhetic shellfish poisoning control.  J Nat Prod. 2005;  68 596-599
• 14 Gao F, Mabry T J. Ten cis-clerodane-type diterpene lactones from Gutierrezia texana.  Phytochemistry. 1987;  26 209-216
• 15 Niedermeyer T H, Lindequist U, Mentel R, Gordes D, Schmidt E, Thurow K, Lalk M. Antiviral terpenoid constituents of Ganoderma pfeifferi.  J Nat Prod. 2005;  68 1728-1731
• 16 Pagani A, Navarrete C, Fiebich B L, Munoz E, Appendino G. Synthesis and biological evaluation of 12-aminoacylphorboids.  J Nat Prod. 2010;  73 447-451
• 17 Kim T H, Ito H, Hatano T, Hasegawa T, Akiba A, Machiguchi T, Yoshida T. Bisabolane- and santalane-type sesquiterpenoids from Santalum album of Indian origin.  J Nat Prod. 2005;  68 1805-1808
• 18 Suzuki S, Horii F, Kurosu H. Theoretical investigations of the γ-gauche effect on the ¹³C chemical shifts produced by oxygen atoms at the c position by quantum chemistry calculations.  J Mol Struct. 2009;  919 290-294
• 19 Ge H M, Shen Y, Zhu C H, Tan S H, Ding H, Song Y C, Tan R X. Penicidones A–C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.  Phytochemistry. 2008;  69 571-576
• 20 National Committee for Clinical Laboratory Standards (NCCLS) .Methods for dilution in antimicrobial susceptibility tests: approved standard M2-A5. Villanova; National Committee for Clinical Laboratory Standards 1993