Kumbicins A–D: Bis-Indolyl Benzenoids and Benzoquinones from an Australian Soil Fungus, Aspergillus kumbius
Heather J. Lacey A , Daniel Vuong A , John I. Pitt B , Ernest Lacey A and Andrew M. Piggott C D
+ Author Affiliations
- Author Affiliations
A Microbial Screening Technologies Pty Ltd, Smithfield, NSW 2164, Australia.
B Food and Nutrition Flagship, Commonwealth Scientific and Industrial Research Organisation (CSIRO), North Ryde, NSW 2113, Australia.
C Department of Chemistry and Biomolecular Sciences, Macquarie University, NSW 2109, Australia.
D Corresponding author. Email: andrew.piggott@mq.edu.au
Australian Journal of Chemistry 69(2) 152-160 https://doi.org/10.1071/CH15488
Submitted: 11 August 2015 Accepted: 12 November 2015 Published: 17 December 2015
Abstract
A soil survey conducted in southern Queensland, Australia, identified a novel isolate belonging to the genus Aspergillus subgenus Circumdati section Circumdati, Aspergillus kumbius FRR6049. Cultivation and fractionation of secondary metabolites from A. kumbius revealed a unique chemotype comprising three new bis-indolyl benzenoids, kumbicins A–C, and a new bis-indolyl benzoquinone, kumbicin D, along with the previously reported compounds asterriquinol D dimethyl ether, petromurins C and D, aspochracin, its N-demethyl analogue JBIR-15, and neohydroxyaspergillic acid. The structures of kumbicins A–D were assigned by detailed spectroscopic analysis. Kumbicin C was found to inhibit the growth of mouse myeloma cells (IC50 0.74 μg mL–1) and the Gram-positive bacterium Bacillus subtilis (MIC 1.6 μg mL–1).
References
[1] C. M. Visagie, J. Houbraken, R. A. Samson, J. C. Frisvad, S.-B. Hong, C. H. W. Klaassen, G. Perrone, K. A. Seifert, J. Varga, T. Yaguchi, Stud. Mycol. 2014, 78, 343.| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BC2Mvgt1Sqsw%3D%3D&md5=bd2b6cf2e4564e80022b2724d59de138CAS | 25505353PubMed |
[2] R. A. Samson, C. M. Visagie, J. Houbraken, S.-B. Hong, V. Hubka, C. H. W. Klaassen, G. Perrone, A. Susca, K. A. Seifert, J. B. Tanney, J. Varga, S. Kocsube, G. Szigeti, T. Yaguchi, J. C. Frisvad, Stud. Mycol. 2014, 78, 141.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BC2MzpsVKgsg%3D%3D&md5=98e8639e16800db6d38abe6eb1235554CAS | 25492982PubMed |
[3] G. Y. A. Tan, S. Robinson, E. Lacey, M. Goodfellow, Int. J. Syst. Evol. Microbiol. 2006, 56, 2297.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1WntbrN&md5=c22643ac63e6ac47c92dcf3c5baf799bCAS |
[4] G. Y. A. Tan, S. Robinson, E. Lacey, R. Brown, W. Kim, M. Goodfellow, Int. J. Syst. Evol. Microbiol. 2007, 57, 2562.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVKnsL3K&md5=2a5ae465524e83637e099d111fa851c5CAS |
[5] R. A. Mittermeier, P. Robles-Gil, C. G. Mittermeier, Megadiversity: Earth’s Biologically Wealthiest Nations 1997 (Cemex: Mexico).
[6] D. J. Collins, C. C. J. Culvenor, J. A. Lamberto, J. W. Loder, J. R. Price, Plants for Medicines: A Chemical and Pharmacological Survey of Plants in the Australian Region 1990 (CSIRO Publishing: Melbourne).
[7] E. Lacey, S. Tennant, Microbiol. Aust. 2003, 24, 34.
[8] A talented fungus produces >5 different metabolite classes and/or high levels of one or more major metabolites. Approximately 5 % of randomly assessed cultures can be assigned as talented.
[9] A. C. Whyte, B. K. Joshi, J. B. Gloer, D. T. Wicklow, P. F. Dowd, J. Nat. Prod. 2000, 63, 1006.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjs1Ogtrc%3D&md5=ab17c7ca8cca9ef10f63039a9dde2842CAS | 10924188PubMed |
[10] M. Ooike, K. Nozawa, S.-I. Udagawa, K.-I. Kawai, Can. J. Chem. 1997, 75, 625.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXkslKms70%3D&md5=29898870ce0a2e041a674676e96e3af5CAS |
[11] R. Myokei, A. Sakurai, C.-F. Chang, Y. Kodaira, N. Takahashi, S. Tamura, Agric. Biol. Chem. 1969, 33, 1491.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXisV2h&md5=de78d2cd2205f4cf17aa0a55cbb47115CAS |
[12] R. Myokei, A. Sakurai, C.-F. Chang, Y. Kodaira, N. Takahashi, S. Tamura, Tetrahedron Lett. 1969, 10, 695.
| Crossref | GoogleScholarGoogle Scholar |
[13] K. Motohashi, S. Inaba, M. Takagi, K. Shin-ya, Biosci. Biotechnol. Biochem. 2009, 73, 1898.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVyntLzE&md5=54d019e20104cdeddf00dab5b7fc95b0CAS | 19661713PubMed |
[14] U. Weiss, F. Strelitz, H. Flon, I. N. Asheshov, Arch. Biochem. Biophys. 1958, 74, 150.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1cXltFemtg%3D%3D&md5=29c0a72faf5806583070e6d7be4ccad6CAS | 13522233PubMed |
[15] F. S. de Guzman, D. R. Bruss, J. M. Rippentrop, K. B. Gloer, J. B. Gloer, J. Nat. Prod. 1994, 57, 634.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlsFaqs70%3D&md5=40f4ce609842f9b37cdabdff0ba88422CAS | 8064296PubMed |
[16] M. Ōki, in Topics in Stereochemistry (Eds N. L. Allinger, E. L. Eliel, S. H. Wilen) 1983, Vol. 14, pp. 1–81 (John Wiley & Sons, Inc.: Hoboken, NJ).
[17] J. W. Bok, D. Hoffmeister, L. A. Maggio-Hall, R. Murillo, J. D. Glasner, N. P. Keller, Chem. Biol. 2006, 13, 31.
| 1:CAS:528:DC%2BD28XmsV2ktw%3D%3D&md5=8a06e5e59ade0984a67e6a87819b8eeeCAS | 16426969PubMed |
[18] P. Schneider, M. Weber, D. Hoffmeister, Fungal Genet. Biol. 2008, 45, 302.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhslegtr4%3D&md5=d1120b14a03558b8177476988ffe18cdCAS | 18029206PubMed |
[19] C. J. Balibar, A. R. Howard-Jones, C. T. Walsh, Nat. Chem. Biol. 2007, 3, 584.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpt1ersL0%3D&md5=116dce33d860907f7687ee52f6c07c94CAS | 17704773PubMed |
[20] P. Schneider, M. Weber, K. Rosenberger, D. Hoffmeister, Chem. Biol. 2007, 14, 635.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmvVOgt7w%3D&md5=845352a3169d636917a98fc7bae47a1bCAS | 17584611PubMed |
[21] S. Tarcz, L. Ludwig, S.-M. Li, ChemBioChem 2014, 15, 108.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvVGqs7%2FL&md5=a7846a1772fc318df39631c78566b4e5CAS | 24302698PubMed |
[22] S. Bouhired, M. Weber, A. Kempf-Sontag, N. P. Keller, D. Hoffmeister, Fungal Genet. Biol. 2007, 44, 1134.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFKhsLvI&md5=804dbd542235bf327c65d7f8bae36b70CAS | 17291795PubMed |
[23] J.-P. Lumb, D. Trauner, Org. Lett. 2005, 7, 5865.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1Gju77K&md5=ed00ce734aee1251a205bf43ded9e58cCAS | 16354086PubMed |
[24] H.-P. Deng, D. Wang, K. J. Szabo, J. Org. Chem. 2015, 80, 3343.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjsFCgtbs%3D&md5=ff3db9efad589d970ef47fbffb608eb0CAS | 25728494PubMed |
[25] S. Shimizu, S. Koshimura, Chem. Pharm. Bull. 1990, 38, 2617.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhslWjsQ%3D%3D&md5=923fd583256e6604aa8fc1fd69b360e8CAS | 2285995PubMed |
[26] A. Kaji, R. Saito, M. Nomura, K.-I. Miyamoto, N. Kiriyama, Anticancer Res. 1997, 17, 3675.
| 1:CAS:528:DyaK1cXkvFOnsg%3D%3D&md5=022b81d3a29fd8fc3f173e7f73d8b354CAS | 9413222PubMed |
[27] A. Kaji, R. Saito, M. Nomura, K.-I. Miyamoto, N. Kiriyama, Biol. Pharm. Bull. 1998, 21, 945.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmtFGjtb4%3D&md5=82b38dab3027fd1bd36332fcb57abdceCAS | 9781844PubMed |
[28] O. Treutler, R. Ahlrichs, J. Chem. Phys. 1995, 102, 346.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXivVCkt7s%3D&md5=c5cb2d42f1c76cddaae335f908131a8aCAS |
[29] K. Eichkorn, O. Treutler, H. Öhm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 242, 652.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXnvFWkurk%3D&md5=aa2e1ce865c9d9f952c372ebbd3a03d3CAS |
[30] TURBOMOLE V6.6 2014 (TURBOMOLE GmbH: Karlsruhe). Available at: http://www.turbomole.com (accessed 11 August 2015).
[31] K. Eichkorn, F. Weigend, O. Treutler, R. Ahlrichs, Theor. Chem. Acc. 1997, 97, 119.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmvFCisbg%3D&md5=0148a2f9e85048419ce53bc54e7a560bCAS |
