Download PDF
Planta Med 2011; 77(3): 277-280
DOI: 10.1055/s-0030-1250292
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

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

Hui Ming Ge1 , Qiang Zhang1 , Su Hai Xu1 , Zhi Kai Guo1 , Yong Chun Song1 , Wu Yang Huang1 , Ren Xiang Tan1
  • 1Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing, P. R. China
Further Information

Publication History

received May 19, 2010 revised July 27, 2010

accepted August 5, 2010

Publication Date:
02 September 2010 (online)

    Permissions and Reprints

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
    CrossrefPubMedGoogle Scholar
  • 2 Zhang H W, Song Y C, Tan R X. Biology and chemistry of endophytes.  Nat Prod Rep. 2006;  23 753-771
    CrossrefPubMedGoogle Scholar
  • 3 Strobel G, Daisy B, Castillo U, Harper J. Natural products from endophytic microorganisms.  J Nat Prod. 2004;  67 257-268
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 5 Von Arx J A, Guarro J, Figueras M J. The ascomycetes genus Chaetomium.  Nova Hedwigia Beih. 1986;  84 1-162
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 12 Huo J, Yang S P, Ding J, Yue J M. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum.  J Nat Prod. 2004;  67 1470-1475
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 14 Gao F, Mabry T J. Ten cis-clerodane-type diterpene lactones from Gutierrezia texana.  Phytochemistry. 1987;  26 209-216
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar

Prof. Dr. R. X. Tan

State Key Laboratory of Pharmaceutical Biotechnology
Institute of Functional Biomolecules
Nanjing University

Nanjing 210093

P. R. China

Phone: + 86 25 83 59 29 45

Fax: + 86 25 83 30 27 28

Email: rxtan@nju.edu.cn

      >