Abraham

Ando

Boot

Burgess

Cueto

Cámara

Fayos

Frey-Klett

Frisvad

Gibson

Gros

Hong

Jones

Kobayashi

Kronvall

Mansson

Nonaka

Nozawa

Okoro

Park

Pettit

Rateb

Sanchez

Santhanam

Schroeckh

Seya

Shirling

Sonnenbichler

Wang

Watts

Xiang-qian

Yamazaki

Zhang

Zuck

English

Mostafa E. Rateb

Irene Hallyburton

Wael E. Houssen

Alan T. Bull

Michael Goodfellow

Rakesh Santhanam

Marcel Jaspars

Rainer Ebel

Crossref

RSC Advances

Induction of diverse secondary metabolites in Aspergillus fumigatus by microbial co-culture

An established culture of Aspergillus fumigatus MBC-F1-10 proved to be very receptive to external stimuli and reacted with the production of secondary metabolites which were undetectable when the fungus was grown under standard conditions. Firstly, co-cultivation with the type strain of Streptomyces bullii, an isolate from hyper-arid Atacama desert soil, led to the isolation of ergosterol 1, seven metabolites belonging to the diketopiperazine alkaloids; brevianamide F 2, spirotryprostatin A 3, 6-methoxy spirotryprostatin B 4, fumitremorgin C and its 12,13-dihydroxy derivative (5–6), fumitremorgin B 7, and verruculogen 8, in addition to 11-O-methylpseurotin A 9 and its new isomer 11-O-methylpseurotin A210. In an independent experiment, addition of N-butyryl-DL-homoserine lactone to the culture medium led to the production of emestrins A and B (11–12). Neither microbe produced these compounds when cultured alone. The structures of all compounds were elucidated using NMR spectroscopic techniques and mass spectrometric analysis. The isolated compounds were tested for their potential antibacterial and antiprotozoal activities

Rateb, Mostafa E.

Hallyburton, Irene

Houssen, Wael E.

Bull, Alan T.

Goodfellow, Michael

Santhanam, Rakesh

Jaspars, Marcel

Ebel, Rainer

Kent Academic Repository

Rateb, M.

Hallyburton, I.

Houssen, W.

Bull, A.

Goodfellow, M.

Santhanam, R.

Jaspars, M.

Ebel, R.

MPG.PuRe

S1  Supporting Information Induction of diverse secondary metabolites in Aspergillus fumigatus by microbial co-culture Mostafa E. Rateb1,2, Irene Hallyburton3, Wael E. Houssen1,4, Alan T. Bull5, Michael Goodfellow6, Rakesh Santhanam6, Marcel Jaspars1, and Rainer Ebel1*   1Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, AB24 3UE, Scotland, U.K. 2Pharmacognosy Department, Faculty of Pharmacy, Beni-Suef University, Salah Salem St., 62111, Beni-Suef, Egypt. 3Drug Discovery Unit, Division of Biological Chemistry and Drug Discovery, College of Life Sciences, University of Dundee, Sir James Black Centre, Dundee, DD1 5EH, U.K. 4Institute of Medical Sciences, University of Aberdeen, Ashgrove Road West, Aberdeen AB25 2ZD, Scotland, UK 5School of Biosciences, University of Kent, Canterbury, Kent CT2 7NJ, UK 6School of Biology, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK     * To whom correspondence should be addressed. Tel.: +44 (0)1224 272930. Fax: +44 (0)1224 272921. Email: r.ebel@abdn.ac.uk              Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S2  Table of content Content Page Table S1. NMR spectroscopic data for 9 and 10 (CDCl3, 400 MHz at 298 ºK) S3 Fig. S1. Induction of cryptic biogenetic pathways in Aspergillus fumigatus MBC-F1-10 by different strategies S4 Fig. S2. HRESIMS spectrum of 9 S5 Fig. S3. 1H NMR spectrum of 9 in CDCl3 S6 Fig. S4. 13C NMR spectrum of 9 in CDCl3 S7 Fig. S5. HSQC spectrum of 9 S8 Fig. S6. COSY spectrum of 9 S9 Fig. S7. HMBC spectrum of 9 S10 Fig. S8. NOESY spectrum of 9 S11 Fig. S9. HRESIMS spectrum of 10 S12 Fig. S10. 1H NMR spectrum of 10 in CDCl3 S13 Fig. S11. 13C NMR spectrum of 10 in CDCl3 S14 Fig. S12. HSQC spectrum of 10 S15 Fig. S13. COSY spectrum of 10 S16 Fig. S14. HMBC spectrum of 10 S17 Fig. S15. NOESY spectrum of 10 S18 Fig. S16. 1H NMR spectrum of 10 in DMSO-d6  S19 Fig. S17. 13C NMR spectrum of 10 in DMSO-d6 S20               Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S3  Table S1. NMR spectroscopic data for 9 and 10 (CDCl3, 400 MHz at 298 K):  Atom 9 10 13C NMR of  related compounds δH, mult. (J in Hz) δC, mult δC, multa δH, mult. (J in Hz) δC, mult δH, multb (J in Hz) δC, multb δC, multc δC, multd 2  186.6, C 187.3, C*  184.4, C  186.8, C 186.8, C 187.6, C 3  113.4, C 113.6, C  113.3, C  111.4, C 111.6, C 111.3, C 4  197.7, C 198.0, C  198.1, C  199.8, C 196.7, C 200.0, C 5  91.8, C 92.3, C  88.5, C  88.2, C 92.4, C 88.2, C 6  166.1, C 167.2, C*  167.9, C  167.5, C 166.6, C 167.7, C 8  90.0, C 92.0, C  95.4, C  97.0, C 91.1, C 97.1, C 9 4.63, s 74.1, CH 75.0, CH 4.78, s 76.5, CH 4.62 (d, 6.2) 75.6, CH 75.0, CH 75.7, CH 10 4.69 (d, 5.7) 70.5, CH 69.7, CH 4.56 (d, 6.4) 70.3, CH 4.48 (t, 5.4) 70.4, CH 72.0, CH 72.8, CH 11 4.32 (dd, 5.2, 9.2) 77.6, CH 77.3, CH 4.28 (dd, 6.5, 9.1) 77.6, CH 4.17 (dd, 5.5, 9.3) 77.1, CH 68.3, CH 68.3, CH 12 5.33 (ddt, 10.9, 9.5, 1.3) 124.1, CH 125.1, CH 5.27 (t, 10.7) 124.7, CH 5.31 (t, 10.9) 125.6, CH 128.4, CH 129.0, CH 13 5.83, m 140.1, CH 138.4, CH 5.82, m 140.3, CH 5.62, m 136.9, CH 134.0, CH 133.8, CH 14 2.11, m 21.4, CH2 20.8, CH2  2.10, m 21.4, CH2 20.4, m 1.97, m 20.7, CH2 20.6, CH2 20.7, CH2 15 0.96 (t, 7.5) 14.3, CH3 13.1, CH3 0.98 (t, 7.5) 14.3, CH3 0.87 (t, 7.6) 14.1, CH3 14.1, CH3 14.2, CH3 16 1.75, s 5.8, CH3 4.3, CH3 1.77, s 5.8, CH3 1.64, s 5.6, CH3 5.6, CH3 5.7, CH3 17  194.6, C 195.8, C  193.3, C  194.7, C 196.4, C 194.8, C 18  132.5, C 133.5, C  134.0, C  134.8, C 133.6, C 134.7, C 19/23 8.29(dd, 1.2, 8.5) 130.7, CH 130.2, CH 8.21 (d, 7.9) 129.9, CH 8.11 (d, 7.7) 129.6, CH 130.2, CH 129.7, CH 20/22 7.49 (t, 8.0) 128.9, CH 128.1, CH 7.47 (t, 7.8) 128.7, CH 7.52 (t, 7.8) 128.3, CH 128.4, CH 128.4, CH 21 7.46 (t, 7.6) 134.8, CH 133.7, CH 7.60 (t, 7.2) 134.0, CH 7.63 (t, 7.6) 133.1, CH 133.6, CH 133.2, CH 8-OMe 3.38, s 51.9, CH3 51.0, CH3 3.29, s 51.6, CH3 3.12, s 51.4, CH3 51.7, CH3 51.5, CH3 11-OMe 3.31, s 56.8, CH3 55.4, CH3 3.25, s 56.7, CH3 3.15, s 55.7, CH3 --- --- 9-OH      6.09 (d, 6.2)    10-OH      5.75 (d, 5.8)    NH-7 7.67, br s   7.40, br s  9.89, s    a Reported 13C NMR data of 11-O-methylpseurotin A (9) in CD3OD.44   b NMR data of 7.10 in DMSO-d6. cReported 13C NMR data of pseurotin A in acetone-d6.45  dReported 13C NMR data of pseurotin A2  in DMSO-d6.46   *The 13C shifts were interchanged as they were wrongly reported.        Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S4     Fig. S1. Induction of cryptic biogenetic pathways in Aspergillus fumigatus MBC-F1-10 by different strategies  Aspergillus fumigatus MBC-F1-10fermentation in the presence of N-butyryl-homoserine lactoneco-cultivation with Streptomyces sp. C2diketopiperazine derivatives 2-8pseurotin derivatives 9 and 10 emestrin A (11) and B (12)Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S5     atd51 #36 RT: 0.41 AV: 1 NL: 2.12E7F: FTMS + p ESI Full ms [100.00-2000.00]420 430 440 450 460 470 480 490 500 510 520m/z05101520253035404550556065707580859095100Relative Abundance446.1807468.1624436.1364 463.2073484.1367 523.3017428.1703448.1865514.2333421.1242 440.2175470.2286478.2071 498.1070 505.3523453.2470[M+H]+[M+Na]+Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S6  Fig. S2. HRESIMS spectrum of 9   19,23NH2120,221312109118-OMe11-OMe141615Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S7  Fig. S3. 1H NMR spectrum of 9   19,2342120,221312109118-OMe11-OMe141615172618 358Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S8   Fig. S4. 13C NMR spectrum of 9   19,232120,2213 12109118-OMe11-OMe141615151516 1614148-OMe8-OMe11-OMe11-OMe21 2119,2319,2320,2220,22131312121111101099Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S9  Fig. S5. HSQC spectrum of 9    Fig. S6. COSY spectrum of 9   19,232120,2213 12 118-OMe11-OMe14161510919,232120,221312118-OMe14161510911-OMe19/2022/23 21/20,2212/1312/1110/913/1414/15Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S10     19,232120,2213 12 118-OMe11-OMe141615109NH-7151411-OMe8-OMe109118531220,2219,23 1821136217419/2319,23/2119,23/17NH-7/9NH-7/521/19,23 20/2220,22/1820,22/2113/1513/1112/1410/1110/310/1210/29/89/179/411/11-OMe11/1011/1311/28-Ome/811-Ome/1114/1214/1316/316/216/415/139/5Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S11  Fig. S7. HMBC spectrum of 9    Fig. S8. NOESY spectrum of 9 19,232120,2213 12 118-OMe11-OMe141615109NH-719,232120,221312118-OMe14161510911-OMeNH-721/8-OMeNH-7/913/1516/12 16/10 16/1114/1112/11-OMe11/1211/1010/1213/128-Ome/19,239/19,23Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S12     atd48 #41 RT: 0.47 AV: 1 NL: 3.55E7F: FTMS + p ESI Full ms [100.00-2000.00]390 400 410 420 430 440 450 460 470 480 490 500 510 520m/z05101520253035404550556065707580859095100Relative Abundance446.1809414.1547468.1626484.1367399.1914514.1559432.1653 465.1544410.1704454.1470471.2699486.6705493.3133424.1870 443.2513[M+H]+[M+Na]+Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S13  Fig. S9. HRESIMS spectrum of 10    19,23NH2120,221312109118-OMe11-OMe141615Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S14  Fig. S10. 1H NMR spectrum of 10    19,2342120,2213 12 109118-OMe11-OMe141615172 618 358Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S15  Fig. S11. 13C NMR spectrum of 10    Fig. S12. HSQC spectrum of 10  19,232120,2213 12109118-OMe11-OMe141615151516 1614148-OMe8-OMe11-OMe11-OMe21 2119,2319,2320,2220,22131312 121111101099Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S16     19,232120,2213 12 118-OMe11-OMe14161510919,232120,221312118-OMe14161510911-OMe19/2022/23 21/20,2212/1312/1110/913/1414/15NH-7NH-7Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S17  Fig. S13. COSY spectrum of 10   Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S18   Fig. 14. HMBC spectrum of 10  19,232120,2213 12 118-OMe11-OMe1416 15109NH-7151411-OMe8-OMe109118531220,2219,231821136217419/2319,23/2119,23/17NH-7/521/19,2320/2220,22/1813/1112/1410/1110/310/1210/29/89/411/11-OMe11/1011/1311/28-Ome/811-Ome/1114/1214/1316/316/216/415/139/614/15Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S19   Fig. S15. NOESY spectrum of 10   19,232120,2213 12 118-OMe11-OMe141615109NH-719,232120,221312118-OMe14161510911-OMeNH-721/8-OMe13/1516/10 16/1114/1112/11-OMe11/1210/1213/128-Ome/19,239/19,239/8-OMe11/11-OMeElectronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S20   Fig. S16. 1H NMR spectrum of 10 in DMSO-d6    Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013S21   Fig. S17. 13C NMR spectrum of 10 in DMSO-d6   Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2013

Rateb, Mostafa

Houssen, Wael E

Bull, Alan

The Open University

Induction of diverse secondary metabolites in Aspergillus fumigatus by microbial co-culture

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Crossref

Kent Academic Repository

MPG.PuRe

MPG.PuRe

The Open University