Abstract
In our screening for antitubercular agents, five naphtho-γ-pyrones including two new naphtho-γ-pyrones glycosides, indigotides G and H (1 and 2), and two diphenyl ethers were isolated from the extract of a sponge-derived fungus Metarhizium anisopliae mxh-99. Their structures were established on the basis of chemical and spectroscopic evidence. The antitubercular activities of all the compounds were evaluated against Mycobacterium phlei. The known isochaetochromin B2 (6) and ustilaginoidin D (7) exhibited the highest activity with MICs 50.0 μg/mL.
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Asai, T., T. Yamamoto, Y.M. Chung, F.R. Chang, Y.C. Wu, K. Yamashita, and Y. Oshima. 2012. Aromatic polyketide glycosides from an entomopathogenic fungus, Cordyceps indigotica. Tetrahedron Letters 53: 277–280.
Bunyapaiboonsri, T., S. Yoiprommarat, K. Intereya, and K. Kocharin. 2007. New diphenyl ethers from the insect pathogenic fungus Cordyceps sp. BBC 1861. Chemical & Pharmaceutical Bulletin 55: 304–307.
Chiang, Y.M., K.M. Meyer, M. Praseuth, S.E. Baker, K.S. Bruno, and C.C.C. Wang. 2011. Characterization of a polyketide synthase in Aspergillus niger whose product is a precursor for both dihydroxynaphthalene (DHN) melanim and naphtho-γ-pyrone. Fungal Genetics and Biology 48: 430–437.
Gautschi, J.T., T. Amagata, A. Amagata, F.A. Valeriote, S.L. Mooberry, and P. Crews. 2004. Expanding the strategies in natural product studies of marine-derived fungi: A chemical investigation of Penicillium obtained from deep water sediment. Journal of Natural Products 67: 362–367.
Ghosal, S., K. Biswas, and D.K. Chakrabarti. 1979. Toxic naphtho-γ-pyrones from Aspergillus niger. Journal of Agriculture and Food Chemistry 27: 1347–1351.
Graham, J.G., H. Zhang, S.L. Pendland, B.D. Santarsiero, A.D. Mesecar, F. Cabieses, and N.R. Farnsworth. 2004. Antimycobacterial naphthopyrones from Senna oblique. Journal of Natural Products 67: 225–227.
Huang, H.B., Z.E. Xiao, X.J. Feng, C.H. Huang, X. Zhu, J.H. Ju, M.F. Li, Y.C. Lin, L. Liu, and Z.G. She. 2011. Cytotoxic naphtho-γ-pyrones from the mangrove endophytic fungus Aspergillus tubingensis (GX1-5E). Helvetica Chimica Acta 94: 1732–1740.
Ikeda, S., M. Sugita, A. Yoshimura, T. Sumizawa, H. Douzono, Y. Nagata, and S. Akiyama. 1990. Aspergillus species strain M39 produces two naphtho-γ-pyrones that reverse drug resistance in human KB cells. International Journal of Cancer 45: 508–513.
Itabashi, T., K. Nozawa, S. Nakajima, and K. Kawai. 1993. A new azaphilone, falconensin H, from Emericella falconensis. Chemical & Pharmaceutical Bulletin 41: 2040–2041.
Koyama, K., and S. Natori. 1987. Chaetochromins B, C and D, bis(naphtho-γ-pyrone) derivatives from Chaetomium gracile. Chemical & Pharmaceutical Bulletin 35: 578–584.
Koyama, K., and S. Natori. 1988. Further characterization of seven bis(naphtho-γ-pyrone) congeners of ustilaginoidins, coloring matters of Claviceps virens (Ustilaginoidea virens). Chemical & Pharmaceutical Bulletin 36: 146–152.
Lienhardt, C., P. Glaziou, M. Uplekar, K. Lonnroth, H. Getahun, and M. Raviglione. 2012. Global tuberculosis control: Lessons learnt and future prospects. Nature Reviews Microbiology 10: 407–416.
Macias, M., A. Gamboa, M. Ulloa, R.A. Toscano, and R. Mata. 2001. Phytotoxic naphthopyranone derivatives from the coprophilous fungus Guanomyces polythrix. Phytochemistry 58: 751–758.
Macias, M., M. Ulloa, A. Gamboa, and R. Mata. 2000. Phytotoxic compounds from the new coprophilous fungus Guanomyces polythrix. Journal of Natural Products 63: 757–761.
Ohkawa, Y., K. Miki, T. Suzuki, K. Nishio, T. Sugita, K. Kinoshita, K. Takahashi, and K. Koyama. 2010. Antiangiogenic metabolites from a marine-derived fungus, Hypocrea vinosa. Journal of Natural Products 73: 579–582.
Shaaban, M., K.A. Shaaban, and M.S. Abdel-Aziz. 2012. Seven naphtho-γ-pyrones from the marine-derived fungus Alternaria alternata: Structure elucidation and biological properties. Organic and Medicinal Chemistry Letters 2: 9–16.
Singh, S.B., D.L. Zink, G.F. Bills, A. Teran, K.C. Silverman, R.B. Lingham, P. Felock, and D.J. Hazuda. 2003. Four novel bis-(naphtho-γ-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase. Bioorganic & Medicinal Chemistry Letters 13: 713–717.
Ugaki, N., H. Yamazaki, R. Uchida, and H. Tomoda. 2012. New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: II. structure elucidation. Journal of Antibiotics 65: 21–24.
Villemagne, B., C. Crauste, M. Flipo, A.R. Baulard, B. Deprez, and N. Willand. 2012. Tuberculosis: The drug development pipeline at a glance. European Journal of Medicinal Chemistry 51: 1–16.
Wang, Q., F. Song, X. Xiao, P. Huang, L. Li, A. Monte, W.M. Abdel-Mageed, J. Wang, H. Guo, W. He, F. Xie, H. Dai, M. Liu, C. Chen, H. Xu, M. Liu, A.M. Piggott, X. Liu, R.J. Capon, and L. Zhang. 2012. Abyssomicins from the south china sea deep-sea sediment Verrucosispora sp.: Natural thioether Michael addition adducts as antitubercular prodrugs. Angewandte Chemie International Edition 51: 1–5.
Zaika, L.L. 1988. Spices and herbs: Their antimicrobial activity and its determination. Journal of Food Safety 9: 97–118.
Zhan, J., Kamal B. Gunaherath, G.M. Kithsiri, E.M. Wijeratne, and A.A. Leslie Gunatilaka. 2007. Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis. Phytochemistry 68: 368–372.
Zhang, Y., S. Ling, Y. Fang, T. Zhu, Q. Gu, and W.M. Zhu. 2008. Isolation, structure elucidation, and antimycobacterial properties of dimeric naphtho-γ-pyrones from the marine-derived fungus Aspergillus carbonarius. Chemistry & Biodiversity 5: 93–100.
Acknowledgments
This work was supported by the Chinese National Science Fund (No. 41176120), Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (No. BS2010HZ027), Specialized Research Fund for the Doctoral Program of Higher Education (No. 20100132120026), the Public Projects of State Oceanic Administration (No. 2010418022-3), and the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT0944).
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Kong, X., Ma, X., Xie, Y. et al. Aromatic polyketides from a sponge-derived fungus Metarhizium anisopliae mxh-99 and their antitubercular activities. Arch. Pharm. Res. 36, 739–744 (2013). https://doi.org/10.1007/s12272-013-0077-7
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DOI: https://doi.org/10.1007/s12272-013-0077-7