Download PDF
Planta Med 2012; 78(10): 1020-1023
DOI: 10.1055/s-0031-1298622
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Paeciloside A, a New Antimicrobial and Cytotoxic Polyketide from Paecilomyces sp. Strain CAFT156[*]

Ferdinand Mouafo Talontsi
1   Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Göttingen, Germany
,
Timothee J. Nwemeguela Kenla
1   Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Göttingen, Germany
,
Birger Dittrich
2   Institute of Inorganic Chemistry, Georg-August University of Göttingen, Göttingen, Germany
,
Clovis Douanla-Meli
3   Institute of Biology, University of Kassel, Kassel, Germany
,
Hartmut Laatsch
1   Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Göttingen, Germany
› Author Affiliations
Further Information

Publication History

received 03 December 2011
revised 26 March 2012

accepted 02 May 2012

Publication Date:
12 June 2012 (online)

Also available at
    Permissions and Reprints

Abstract

Paeciloside A (1) and eight known compounds, acremoauxin A (2), farinosones A (3) and B (4), 1,5-dideoxy-3-C-methyl-arabitol (5), ergosterol, ergosterol peroxide, cerebroside C, and adenosine, were isolated from cultures of Paecilomyces sp. CAFT156, an endophytic fungus occurring in Enantia chlorantha Oliv (Annonaceae) leaves. The structure of the new compound 1 was elucidated using MS, UV, 1D and 2D NMR experiments, while its absolute configuration was established by subsequent single-crystal X-ray diffraction analysis using copper Kα radiation and invariom nonspherical scattering factors. Paeciloside A (1) and compounds 2, 4, and 5 displayed inhibitory effects on two gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus at a concentration of 40 µg per paper disk and moderate cytotoxicity towards brine shrimp larvae (Artemia salina). This study presents the first report on an endophytic fungus isolated from E. chlorantha Oliv and its natural products.

Key words

Enantia chlorantha - Annonaceae - Paecilomyces sp. - Trichocomaceae - antimicrobial - cytotoxicity

* Dedicated to Prof. Dr. Dr. Lutz F. Tietze on the occasion of his 70th birthday.


Supporting Information

 

  • References

  • 1 Strobel GA, Daisy B, Castillo U, Harper J. Natural products from endophytic microorganisms. J Nat Prod 2004; 67: 257-268
    CrossrefPubMedSearch in Google Scholar
  • 2 Strader CR, Pearce CJ, Oberlies NH. Fingolimod (FTY720): a recently approved multiple sclerosis drug based on a fungal secondary metabolite. J Nat Prod 2011; 74: 900-907
    CrossrefPubMedSearch in Google Scholar
  • 3 Kusari S, Spiteller M. Are we ready for industrial production of bioactive plant secondary metabolites utilizing endophytes?. Nat Prod Rep 2011; 28: 1203-1207
    CrossrefPubMedSearch in Google Scholar
  • 4 Laatsch H. AntiBase 2011, a data base for rapid dereplication and structure determination of microbial natural products. Weinheim: Wiley VCH; 2011. (Available at http://wwwuser.gwdg.de/~hlaatsc/antibase.htm)
    Search in Google Scholar
  • 5 Talontsi MF. Novel antimycotic epicoccolides, sordariones and further new zoosporicidal natural products from endophytic fungi inhabiting Cameroonian medicinal plants [dissertation]. Göttingen: Georg-August University of Göttingen; 2011
    PubMedSearch in Google Scholar
  • 6 Lindel T, Junker J, Köck M. 2D-NMR-guided constitutional analysis of organic compounds employing the computer program COCON. Eur J Org Chem 1999; 3: 573-577
    PubMedSearch in Google Scholar
  • 7 Dittrich B, Koritsanszky T, Luger P. A simple approach to nonspherical electron densities by using invarioms. Angew Chem Int Ed 2004; 43: 2718-2721
    CrossrefPubMedSearch in Google Scholar
  • 8 Hansen NK, Coppens P. Crystal physics, diffraction, theoretical and general crystallography. Acta Crystallogr A 1978; 34: 909-921
    CrossrefPubMedSearch in Google Scholar
  • 9 Dittrich B, Strumpel M, Schäfer M, Spackman MA, Koritsanszky T. Invarioms for improved absolute structure determination of light-atom crystal structures. Acta Crystallogr A 2006; 62: 217-223
    CrossrefPubMedSearch in Google Scholar
  • 10 Koritsanszky T, Richter T, Macchi P, Volkov A, Gatti C, Howard S, Mallinson PR, Farrugia L, Su ZW, Hansen NK. XD-computer program package for multipole refinement and topological analysis of electron densities from diffraction data. Berlin: Freie Universität Berlin; 2003
    Search in Google Scholar
  • 11 Subba RV, Seshadri TR. The isolation of montagnetol, a new phenolic compound from Roccella montagnei . Proc Indian Acad Sci Sect A 1941; 13: 199-202
    PubMedSearch in Google Scholar
  • 12 Manaktala SK, Neelakantan S, Seshadri TR. Synthesis of (±)-montagnetol and (±)-erythrin. Tetrahedron 1966; 22: 2373-2376
    CrossrefPubMedSearch in Google Scholar
  • 13 Sassa T, Yoshida N, Haruki E. Isolation and structural elucidation of acremoauxin A, a novel auxin derivative produced by Acremonium roseum I 4267. Agric Biol Chem 1989; 53: 3105-3107
    CrossrefPubMedSearch in Google Scholar
  • 14 Tang J, Gao H, Hong K, Jiang M, Zhou G, Wang N, Yao X. Secondary metabolites from a mangrove bacterium Bacillus sp. Chin J Med Chem 2008; 18: 206-209
    PubMedSearch in Google Scholar
  • 15 Cheng Y, Schmidt K, Riese U, Schubert B, Li Z, Hamburger M. Novel tetramic acids and pyridone alkaloids, militarinones B, C, and D, from the insect pathogenic fungus Paecilomyces militaris . J Nat Prod 2003; 66: 378-383
    CrossrefPubMedSearch in Google Scholar
  • 16 Reich HJ, Jautelat M, Messe MT, Weigert FJ, Roberts JD. Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of steroids. J Am Chem Soc 1969; 91: 7445-7454
    CrossrefPubMedSearch in Google Scholar
  • 17 Sgarbi DB, da Silva AJ, Carlos IZ, Silva CL, Angluster J, Alviano CS. Isolation of ergosterol peroxide and its reversion to ergosterol in the pathogenic fungus Sporothrix schenckii . Mycopathologia 1997; 139: 9-14
    CrossrefPubMedSearch in Google Scholar
  • 18 Koga J, Yamauchi T, Shimura M, Ogawa N, Oshima K, Umemura K, Kikuchi M, Ogasawara N. Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J Biol Chem 1998; 273: 31985-31991
    CrossrefPubMedSearch in Google Scholar
  • 19 Sajid I, Fotso-Fondja YCB, Shaaban KA, Hasnain S, Laatsch H. Antifungal and antibacterial activities of indigenous Streptomyces isolates from saline farmlands: prescreening, ribotyping and metabolic diversity. World J Microbiol Biotechnol 2009; 25: 2235-2241
    PubMedSearch in Google Scholar
  • 20 Ndongo JT, Shaaban M, Mbing NJ, Bikobo ND, Atchadé Ade T, Pegnyemb ED, Laatsch H. Phenolic dimers and an indole alkaloid from Campylospermum flavum (Ochnaceae). Phytochemistry 2011; 71: 1872-1878
    PubMedSearch in Google Scholar