Abstract
Mellamide, a novel indole amide, was isolated from a fermentation of Aspergillus melleus using silica gel and high-performance liquid chromatographic methods. This allowed its separation from three known antiparasitic compounds (ochratoxin A, viomellin and xanthomegnin) also present in the potent extract. The structure was elucidated by 1H, 13C, COSY, DEPT, HMQC and HMBC NMR experiments. HR-FTMS aided in the molecular weight and formula determination. Mellamide showed in vitro insecticidal activity in bioassays against larvae of Lucilia sericata and Aedes egypti with LD90 of 1,000 and 50 μg/ml, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chabala JC, Mrozik H, Tolman RL, Eskola P, Lusi A, Peterson LH, Woods MF, Fisher MH, Campbell WC, Ergerton JR, Ostlind D (1980) Ivermectin, a new broad-spectrum antiparasitic agent. J Med Chem 23:1134–1136
Cui CB, Kayeya H, Osada H (1996) Novel mammalian cell cycle inhibitors, tryptostatins A, B and other diketopiperaazines produced by Aspergillus fumigatus II. J Antibiot 49:534–540
Henrick CA, Staal CB, Siddall JB (1973) Alkyl 3,7,11-trimethyl-2,4-dodecadienoates, a new class of potent insect growth regulators with juvenile hormone activity. J Agric Food Chem 213:354–359
Kagamizono T, Sakai N, Arai K, Kobinata K, Osada H (1997) Terpeptin, a novel mammalian cell cycle inhibitor, produced by Aspergillus terreus 95F-1. Tetrahedron Lett 38:1223–1226
Michael B, Meinke PT, Shoop W (2001) Comparison of ivermectin, doramectin, selamectin and eleven intermediates in a nematode larval development assay. J Parasitol 87:692–696
Ondeyka JG, Goegelman RT, Schaeffer JM, Keleman L, Zitano L (1990) Novel antinematodal and antiparasitic agents from Penicillium charlesii. I fermentation, isolation and biological activity. J Antibiot 43:1375–1380
Ondeyka JG, Helms GL, Hensens OD, Goetz MA, Zink DL, Tsipouras A, Shoop WL, Slayton L, Dombrowski AW, Polishook JD, Ostlind DA, Tsou NN, Ball RG, Singh SB (1997) Nodulisporic acid A, a novel and potent insecticide from a Nodulisporium sp. Isolation, structure determination, and chemical transformations. J Am Chem Soc 119:8809–8816
Ostlind DA, Felcetto T, Misura A, Ondeyka JG, Smith S, Goetz M, Shoop W, Mickle W (1997) Discovery of a novel indole diterpene insecticide using first instars of Lucilia sericata. Med Vet Entomol 11:407–408
Simpson TJ (1977)13C Nuclear magnetic resonance spectra and biosynthetic studies of xanthomegnin and related pigments from Aspergillus sulpureus and melleus. J Chem Soc Perkin Trans 1:592–595
Singh PD, Johnson JH, Aklonis CA, Bush K, Fisher SM, O'Sullivan J (1985) Two new inhibitors of Phospholipase A, produced by Penicillum chermesinum. J Antibiot 37:706–712
Toske SG, Jensen PR, Kauffman CA, Fenical W (1998) Aspergillamide A and B: modified cytotoxic tripeptides produced by a marine fungus of the genus Aspergillus. Tetrahedron 54:13459–13466
Xiao H, Marquardt RR, Frohlich AA, Ling YZ (1995) Synthesis and structural elucidation of analogs of ochratoxin A. J Agric Food Chem 43:524–530
Acknowledgements
We thank Bruce Michael for running the Haemonchus contortus assay during the screening and providing the bioassay-guided fractionation support, and Marta Arocho for the initial library extract preparation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ondeyka, J.G., Dombrowski, A.W., Polishook, J.P. et al. Isolation and insecticidal activity of mellamide from Aspergillus melleus . J IND MICROBIOL BIOTECHNOL 30, 220–224 (2003). https://doi.org/10.1007/s10295-003-0048-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10295-003-0048-y