Evolution of aromatic prenyltransferases in the biosynthesis of indole derivatives

Phytochemistry

Volumn 70, Issue 15-16, 2009, Pages 1746-1757

  Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Aspergillus; Biochemical characterisation; Catalytic promiscuity; Chemoenzymatic synthesis; Cyclic dipeptide; Diketopiperazine; Evolution; Heterologous overexpression; Indole alkaloid; Prenyltransferase

Indexed keywords

DIMETHYLALLYLTRANSFERASE; INDOLE ALKALOID;

CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; METABOLISM; MOLECULAR EVOLUTION; REVIEW;

DIMETHYLALLYLTRANSTRANSFERASE; EVOLUTION, MOLECULAR; INDOLE ALKALOIDS; MOLECULAR STRUCTURE;

ASPERGILLUS; ASPERGILLUS FUMIGATUS; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; FUNGI; NEOSARTORYA FISCHERI; SACCHAROMYCES CEREVISIAE;

EID: 67650410702     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.03.019     Document Type: Review

References (83)

1. Abe K., Gomi K., Hasegawa F., and Machida M. Impact of Aspergillus oryzae genomics on industrial production of metabolites. Mycopathologia 162 (2006) 143-153
2. Afiyatullov S.S., Kalinovskii A.I., Pivkin M.V., Dmitrenok P.S., and Kuznetsova T.A. Fumitremorgins from the marine isolate of the fungus Aspergillus fumigatus. Chem. Nat. Compd. 40 (2004) 615-617
3. Balibar C.J., Howard-Jones A.R., and Walsh C.T. Terrequinone A biosynthesis through l-tryptophan oxidation, dimerization and bisprenylation. Nat. Chem. Biol. 3 (2007) 584-592
4. Bohlmann J., Meyer-Gauen G., and Croteau R. Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc. Natl. Acad. Sci. USA 95 (1998) 4126-4133
5. Bok J.W., Hoffmeister D., Maggio-Hall L.A., Murillo R., Glasner J.D., and Keller N.P. Genomic mining for Aspergillus natural products. Chem. Biol. 13 (2006) 31-37
6. Bok J.W., Noordermeer D., Kale S.P., and Keller N.P. Secondary metabolic gene cluster silencing in Aspergillus nidulans. Mol. Microbiol. 61 (2006) 1636-1645
7. Bornscheuer U.T., and Kazlauskas R.J. Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew. Chem. Int. Ed. Engl. 43 (2004) 6032-6040
8. Botta B., Vitali A., Menendez P., Misiti D., and Delle M.G. Prenylated flavonoids: pharmacology and biotechnology. Curr. Med. Chem. 12 (2005) 717-739
9. Capon R.J., Skene C., Stewart M., Ford J., ÓHair R.A.J., Williams L., Lacey E., Gill J.H., Heiland K., and Friedel T. Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus. Org. Biomol. Chem. 1 (2003) 1856-1862
10. Chong Y.S., Su L.L., and Arulkumaran S. Current strategies for the prevention of postpartum haemorrhage in the third stage of labour. Curr. Opin. Obstet. Gynecol. 16 (2004) 143-150
11. Cole R.J., Kirksey J.W., Weinreb S.M., Singh P., Kim D., Clardy J., and Eickman N. Structures of rugulovasine-A and -B and 8-chlororugulovasine-A and -B. Tetrahedron Lett. 17 (1976) 3849-3852
12. Cramer Jr. R.A., Gamcsik M.P., Brooking R.M., Najvar L.K., Kirkpatrick W.R., Patterson T.F., Balibar C.J., Graybill J.R., Perfect J.R., Abraham S.N., and Steinbach W.J. Disruption of a nonribosomal peptide synthetase in Aspergillus fumigatus eliminates gliotoxin production. Eukaryot. Cell 5 (2006) 972-980
13. Cui C.B., Kakeya H., and Osada H. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures. J. Antibiot. 49 (1996) 534-540
14. Ding Y., Williams R.M., and Sherman D.H. Molecular analysis of a 4-dimethylallyltryptophan synthase from Malbranchea aurantiaca. J. Biol. Chem. 283 (2008) 16068-16076
15. Edwards D.J., and Gerwick W.H. Lyngbyatoxin biosynthesis: sequence of biosynthetic gene cluster and identification of a novel aromatic prenyltransferase. J. Am. Chem. Soc. 126 (2004) 11432-11433
16. Ellestad G.A., Mirando P., and Kunstmann M.P. Structure of the metabolite LL-S490ß from an unidentified Aspergillus species. J. Org. Chem. 38 (1973) 4204-4205
17. Fedorova N.D., Khaldi N., Joardar V.S., Maiti R., Amedeo P., Anderson M.J., Crabtree J., Silva J.C., Badger J.H., Albarraq A., Angiuoli S., Bussey H., Bowyer P., Cotty P.J., Dyer P.S., Egan A., Galens K., Fraser-Liggett C.M., Haas B.J., Inman J.M., Kent R., Lemieux S., Malavazi I., Orvis J., Roemer T., Ronning C.M., Sundaram J.P., Sutton G., Turner G., Venter J.C., White O.R., Whitty B.R., Youngman P., Wolfe K.H., Goldman G.H., Wortman J.R., Jiang B., Denning D.W., and Nierman W.C. Genomic islands in the pathogenic filamentous fungus Aspergillus fumigatus. PLoS. Genet. 4 (2008) e1000046
18. Finoli C., Vecchio A., Galli A., and Dragoni I. Roquefortine C occurrence in blue cheese. J. Food Prot. 64 (2001) 246-251
19. Frisvad J.C., Smedsgaard J., Larsen T.O., and Samson R.A. Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium. Stud. Mycol. 49 (2004) 201-241
20. Galagan J.E., Calvo S.E., Cuomo C., Ma L.J., Wortman J.R., Batzoglou S., Lee S.I., Basturkmen M., Spevak C.C., Clutterbuck J., Kapitonov V., Jurka J., Scazzocchio C., Farman M., Butler J., Purcell S., Harris S., Braus G.H., Draht O., Busch S., d'Enfert C., Bouchier C., Goldman G.H., Bell-Pedersen D., Griffiths-Jones S., Doonan J.H., Yu J., Vienken K., Pain A., Freitag M., Selker E.U., Archer D.B., Penalva M.A., Oakley B.R., Momany M., Tanaka T., Kumagai T., Asai K., Machida M., Nierman W.C., Denning D.W., Caddick M., Hynes M., Paoletti M., Fischer R., Miller B., Dyer P., Sachs M.S., Osmani S.A., and Birren B.W. Sequencing of Aspergillus nidulans and comparative analysis with A. Fumigatus and A. oryzae. Nature 438 (2005) 1105-1115
21. Gardiner D.M., Cozijnsen A.J., Wilson L.M., Pedras M.S., and Howlett B.J. The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans. Mol. Microbiol. 53 (2004) 1307-1318
22. Goadsby P.J. Migraine: diagnosis and management. Int. Med. J. 33 (2003) 436-442
23. Gröger D., and Floss H.G. Biochemistry of ergot alkaloids - achievements and challenges. In: Cordell G.A. (Ed). The Alkaloids, vol. 50 (Chemistry and Biology) (1998), Academic Press, San Diego 171-218
24. Grundmann A., Kuznetsova T., Afiyatullov S.S., and Li S.-M. FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B. ChemBioChem 9 (2008) 2059-2063
25. Grundmann A., and Li S.-M. Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus. Microbiology 151 (2005) 2199-2207
26. Haagen Y., Unsöld I., Westrich L., Gust B., Richard S.B., Noel J.P., and Heide L. A soluble, magnesium-independent prenyltransferase catalyzes reverse and regular C-prenylations and O-prenylations of aromatic substrates. FEBS Lett. 581 (2007) 2889-2893
27. Hayashi A., Fujioka S., Nukina M., Kawano T., Shimada A., and Kimura Y. Fumiquinones A and B, nematicidal quinones produced by Aspergillus fumigatus. Biosci. Biotechnol. Biochem. 71 (2007) 1697-1702
28. Hermansen K., Frisvad J.C., Emborg C., and Hansen J. Cyclopiazonic acid production by submerged cultures of Penicillium and Aspergillus strains. FEMS Microbiol. Lett. 21 (1984) 253-261
29. Jones M.G. The first filamentous fungal genome sequences: Aspergillus leads the way for essential everyday resources or dusty museum specimens?. Microbiology 153 (2007) 1-6
30. Keller N.P., Turner G., and Bennett J.W. Fungal secondary metabolism - from biochemistry to genomics. Nat. Rev. Microbiol. 3 (2005) 937-947
31. Kimura Y., Hamasaki T., Nakajima H., and Isogai A. Structure of aszonalenin, a new metabolite of Aspergillus zonatus. Tetrahedron Lett. 23 (1982) 225-228
32. Kozlovsky A.G., Adanin V.M., Dahse H.M., and Gräfe U. Rugulosuvines A and B, diketopiperazine alkaloids of Penicillium rugulosum and Penicillium piscarium fungi. Appl. Biochem. Microbiol. 37 (2001) 253-256
33. Kozlovsky A.G., Vinokurova N.G., Adanin V.M., Burkhardt G., Dahse H.M., and Gräfe U. New diketopiperazine alkaloids from Penicillium fellutanum. J. Nat. Prod. 63 (2000) 698-700
34. Kremer A., and Li S.-M. Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives. Appl. Microbiol. Biotechnol. 79 (2008) 951-961
35. Kremer A., and Li S.-M. Tryptophan aminopeptidase activity of several indole prenyltransferases from Aspergillus fumigatus. Chem. Biol. 15 (2008) 729-738
36. Kremer, A., Stec, S., Rigbers, O., Yin, W.-B., Grundmann, A., Hoffmeister, D., Li, S.-M. Catalytic promiscuity of prenyltransferases from fungi. Unpublished results.
37. Kremer A., Westrich L., and Li S.-M. A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization. Microbiology 153 (2007) 3409-3416
38. Kuzuyama T., Noel J.P., and Richard S.B. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435 (2005) 983-987
39. Li S.-M., and Unsöld I.A. Post genome research on the biosynthesis of ergot alkaloids. Planta Med. 72 (2006) 1117-1120
40. Liang P.H., Ko T.P., and Wang A.H. Structure, mechanism and function of prenyltransferases. Eur. J. Biochem. 269 (2002) 3339-3354
41. Ma H.Y., Song Y.C., Mao Y.Y., Jiang J.H., Tan R.X., and Luo L. Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings. Planta Med. 72 (2006) 387-392
42. MacDonald J.C., and Slater G.P. The utilization of tryptophan in the biosynthesis of echinulin. Can. J. Microbiol. 12 (1966) 455-463
43. Machida M., Asai K., Sano M., Tanaka T., Kumagai T., Terai G., Kusumoto K., Arima T., Akita O., Kashiwagi Y., Abe K., Gomi K., Horiuchi H., Kitamoto K., Kobayashi T., Takeuchi M., Denning D.W., Galagan J.E., Nierman W.C., Yu J., Archer D.B., Bennett J.W., Bhatnagar D., Cleveland T.E., Fedorova N.D., Gotoh O., Horikawa H., Hosoyama A., Ichinomiya M., Igarashi R., Iwashita K., Juvvadi P.R., Kato M., Kato Y., Kin T., Kokubun A., Maeda H., Maeyama N., Maruyama J., Nagasaki H., Nakajima T., Oda K., Okada K., Paulsen I., Sakamoto K., Sawano T., Takahashi M., Takase K., Terabayashi Y., Wortman J.R., Yamada O., Yamagata Y., Anazawa H., Hata Y., Koide Y., Komori T., Koyama Y., Minetoki T., Suharnan S., Tanaka A., Isono K., Kuhara S., Ogasawara N., and Kikuchi H. Genome sequencing and analysis of Aspergillus oryzae. Nature 438 (2005) 1157-1161
44. Maiya S., Grundmann A., Li X., Li S.-M., and Turner G. Identification of a hybrid PKS/NRPS required for pseurotin A biosynthesis in the human pathogen Aspergillus fumigatus. ChemBioChem 8 (2007) 1736-1743
45. Markert A., Steffan N., Ploss K., Hellwig S., Steiner U., Drewke C., Li S.-M., Boland W., and Leistner E. Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus. Plant Physiol. 147 (2008) 296-305
46. Nierman W.C., Pain A., Anderson M.J., Wortman J.R., Kim H.S., Arroyo J., Berriman M., Abe K., Archer D.B., Bermejo C., Bennett J., Bowyer P., Chen D., Collins M., Coulsen R., Davies R., Dyer P.S., Farman M., Fedorova N., Fedorova N., Feldblyum T.V., Fischer R., Fosker N., Fraser A., Garcia J.L., Garcia M.J., Goble A., Goldman G.H., Gomi K., Griffith-Jones S., Gwilliam R., Haas B., Haas H., Harris D., Horiuchi H., Huang J., Humphray S., Jimenez J., Keller N., Khouri H., Kitamoto K., Kobayashi T., Konzack S., Kulkarni R., Kumagai T., Lafton A., Latgèé J.P., Li W., Lord A., Lu C., Majoros W.H., May G.S., Miller B.L., Mohamoud Y., Molina M., Monod M., Mouyna I., Mulligan S., Murphy L., O'Neil S., Paulsen I., Penalva M.A., Pertea M., Price C., Pritchard B.L., Quail M.A., Rabbinowitsch E., Rawlins N., Rajandream M.A., Reichard U., Renauld H., Robson G.D., Rodriguez de Córdoba S., Rodriguez-Pena J.M., Ronning C.M., Rutter S., Salzberg S.L., Sanchez M., Sanchez-Ferrero J.C., Saunders D., Seeger K., Squares R., Squares S., Takeuchi M., Tekaia F., Turner G., Vazquez de Aldana C.R., Weidman J., White O., Woodward J., Yu J.H., Fraser C., Galagan J.E., Asai K., Machida M., Hall N., Barrell B., and Denning D.W. Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus. Nature 438 (2005) 1151-1156
47. Ohara K., Yamamoto K., Hamamoto M., Sasaki K., and Yazaki K. Functional characterization of OsPPT1, which encodes p-hydroxybenzoate polyprenyltransferase involved in ubiquinone biosynthesis in Oryza sativa. Plant Cell Physiol. 47 (2006) 581-590
48. Panaccione D.G., and Coyle C.M. Abundant respirable ergot alkaloids from the common airborne fungus Aspergillus fumigatus. Appl. Environ. Microbiol. 71 (2005) 3106-3111
49. Pel H.J., de Winde J.H., Archer D.B., Dyer P.S., Hofmann G., Schaap P.J., Turner G., de Vries R.P., Albang R., Albermann K., Andersen M.R., Bendtsen J.D., Benen J.A., van den Berg M., Breestraat S., Caddick M.X., Contreras R., Cornell M., Coutinho P.M., Danchin E.G., Debets A.J., Dekker P., van Dijck P.W., van Dijk A., Dijkhuizen L., Driessen A.J., d'Enfert C., Geysens S., Goosen C., Groot G.S., de Groot P.W., Guillemette T., Henrissat B., Herweijer M., van den Hombergh J.P., van den Hondel C.A., van der Heijden R.T., van der Kaaij R.M., Klis F.M., Kools H.J., Kubicek C.P., van Kuyk P.A., Lauber J., Lu X., van der Maarel M.J., Meulenberg R., Menke H., Mortimer M.A., Nielsen J., Oliver S.G., Olsthoorn M., Pal K., van Peij N.N., Ram A.F., Rinas U., Roubos J.A., Sagt C.M., Schmoll M., Sun J., Ussery D., Varga J., Vervecken W., van de Vondervoort P.J., Wedler H., Wosten H.A., Zeng A.P., van Ooyen A.J., Visser J., and Stam H. Genome sequencing and analysis of the versatile cell factory Aspergillus niger CBS 513.88. Nat. Biotechnol. 25 (2007) 221-231
50. Pojer F., Wemakor E., Kammerer B., Chen H., Walsh C.T., Li S.-M., and Heide L. CloQ, a prenyltransferase involved in clorobiocin biosynthesis. Proc. Natl. Acad. Sci. USA 100 (2003) 2316-2321
51. Raskin D.M., Seshadri R., Pukatzki S.U., and Mekalanos J.J. Bacterial genomics and pathogen evolution. Cell 124 (2006) 703-714
52. Ruan H.-L., Yin W.-B., Wu J.-Z., and Li S.-M. Reinvestigation of a cyclic dipeptide N-prenyltransferase reveals rearrangement of N-1 prenylated indole derivatives. ChemBioChem 9 (2008) 1044-1047
53. Rundberget T., Skaar I., and Flaoyen A. The presence of Penicillium and Penicillium mycotoxins in food wastes. Int. J. Food Microbiol. 90 (2004) 181-188
54. Sacchettini J.C., and Poulter C.D. Creating isoprenoid diversity. Science 277 (1997) 1788-1789
55. Sasaki K., Mito K., Ohara K., Yamamoto H., and Yazaki K. Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant Physiol. 146 (2008) 1075-1084
56. Schardl C.L., Panaccione D.G., and Tudzynski P. Ergot alkaloids - biology and molecular biology. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology 63 (2006), Academic Press, Amsterdam 45-86
57. Schneider P., Weber M., and Hoffmeister D. The Aspergillus nidulans enzyme TdiB catalyzes prenyltransfer to the precursor of bioactive asterriquinones. Fungal. Genet. Biol. 45 (2008) 302-309
58. Scott P.M., and Kennedy B.P.C. Analysis of blue cheese for roquefortine and other alkaloids from Penicillium roqueforti. J. Agric. Food Chem. 24 (1976) 865-868
59. Sekita S. Isocochliodinol and neocochliodinol, bis(3-indolyl)-benzoquinones from Chaetomium spp. Chem. Pharm. Bull. 31 (1983) 2998-3001
60. Smetanina O.F., Kalinovsky A.I., Khudyakova Y.V., Pivkin M.V., Dmitrenok P.S., Fedorov S.N., Ji H., Kwak J.Y., and Kuznetsova T.A. Indole alkaloids produced by a marine fungus isolate of Penicillium janthinellum Biourge. J. Nat. Prod. 70 (2007) 906-909
61. Stec E., Steffan N., Kremer A., Zou H., Zheng X., and Li S.-M. Two Lysine residues are responsible for the enzymatic activities of indole prenyltransferases from fungi. ChemBioChem 9 (2008) 2055-2058
62. Steffan N., Grundmann A., Yin W.-B., Kremer A., and Li S.-M. Indole prenyltransferases from fungi: a new enzyme group with high potential for the production of prenylated indole derivatives. Curr. Med. Chem. 16 (2009) 218-231
63. Steffan N., Unsöld I.A., and Li S.-M. Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus. ChemBioChem 8 (2007) 1298-1307
64. Stocking E.M., Williams R.M., and Sanz-Cervera J.F. Reverse prenyl transferases exhibit poor facial discrimination in the biosynthesis of paraherquamide A, brevianamide A, and austamide. J. Am. Chem. Soc. 122 (2000) 9089-9098
65. Takase S., Kawai Y., Uchida I., Tanaka H., and Aoki H. Structure of amauromine, a new hypotensive vasodilator produced by Amauroascus sp. Tetrahedron 41 (1985) 3037-3048
66. Tello M., Kuzuyama T., Heide L., Noel J.P., and Richard S.B. The ABBA family of aromatic prenyltransferases: broadening natural product diversity. Cell Mol. Life Sci. 65 (2008) 1459-1463
67. Tudzynski P., Correia T., and Keller U. Biotechnology and genetics of ergot alkaloids. Appl. Microbiol. Biotechnol. 57 (2001) 593-605
68. Unsöld I.A., and Li S.-M. Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus. Microbiology 151 (2005) 1499-1505
69. Unsöld I.A., and Li S.-M. Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: gene expression, purification and characterization of fumigaclavine C synthase FgaPT1. ChemBioChem 7 (2006) 158-164
70. Usui T., Kondoh M., Cui C.B., Mayumi T., and Osada H. Tryprostatin A, a specific and novel inhibitor of microtubule assembly. Biochem. J. 333 (1998) 543-548
71. van den Berg M.A., Albang R., Albermann K., Badger J.H., Daran J.M., Driessen A.J., Garcia-Estrada C., Fedorova N.D., Harris D.M., Heijne W.H., Joardar V., Kiel J.A., Kovalchuk A., Martin J.F., Nierman W.C., Nijland J.G., Pronk J.T., Roubos J.A., van der Klei I.J., van Peij N.N.M.E., Veenhuis M., von Dohren H., Wagner C., Wortman J., and Bovenberg R.A. Genome sequencing and analysis of the filamentous fungus Penicillium chrysogenum. Nat. Biotechnol. 26 (2008) 1161-1168
72. Vinokurova N.G., Ozerskaya S.M., Baskunov B.P., and Arinbasarov M.U. The Penicillium commune Thom and Penicillium clavigerum demelius fungi producing fumigaclavines A and B. Microbiology (Moscow) 72 (2003) 149-151
73. Wakana D., Hosoe T., Itabashi T., Nozawa K., Okada K., Takaki G.M., d C., Yaguchi T., Fukushima K., and Kawai K.I. Isolation of isoterrein from Neosartorya fischeri. Mycotoxins 56 (2006) 3-6
74. Wang J., Machado C., Panaccione D.G., Tsai H.F., and Schardl C.L. The determinant step in ergot alkaloid biosynthesis by an endophyte of perennial ryegrass. Fungal Genet. Biol. 41 (2004) 189-198
75. Wang Y., Gloer J.B., Scott J.A., and Malloch D. Terezines A-D: new amino acid-derived bioactive metabolites from the coprophilous fungus Sporormiella teretispora. J. Nat. Prod. 58 (1995) 93-99
76. Williams R.M., Stocking E.M., and Sanz-Cervera J.F. Biosynthesis of prenylated alkaloids derived from tryptophan. Topics Curr. Chem. 209 (2000) 97-173
77. Wu X.-F., Fei M.-J., Shu R.-G., Tan R.-X., and Xu Q. Fumigaclavine C, an fungal metabolite, improves experimental colitis in mice via downregulating Th1 cytokine production and matrix metalloproteinase activity. Int. Immunopharmacol. 5 (2005) 1543-1553
78. Xu M., Gessner G., Groth I., Lange C., Christner A., Bruhn T., Deng Z., Li X., Heinemann S.H., Grabley S., Bringmann G., Sattler I., and Lin W. Shearinines D-K, new indole triterpenoids from an endophytic Penicillium sp. (strain HKI0459) with blocking activity on large-conductance calcium-activated potassium channels. Tetrahedron 63 (2007) 435-444
79. Yamazaki M., Sasago K., and Miyaki K. Structure of fumitremorgin B (FTB), a tremorgenic toxin from Aspergillus fumigatus. J. Chem. Soc. Chem. Commun. 40 (1974) 8-409
80. Yin W.-B., Grundmann A., Cheng J., and Li S.-M. Acetylaszonalenin biosynthesis in Neosartorya fischeri: identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes by biochemical investigation. J. Biol. Chem. 284 (2009) 100-109
81. Yin W.-B., Ruan H.-L., Westrich L., Grundmann A., and Li S.-M. CdpNPT, an N-prenyltransferase from Aspergillus fumigatus: overproduction, purification and biochemical characterisation. ChemBioChem 8 (2007) 1154-1161
82. Zhao Y., Liu J., Wang J., Wang L., Yin H., Tan R., and Xu Q. Fumigaclavine C improves concanavalin A-induced liver injury in mice mainly via inhibiting TNF-alpha production and lymphocyte adhesion to extracellular matrices. J. Pharm. Pharmacol. 56 (2004) 775-782
83. Zou H., Zheng X., and Li S.-M. Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus. J. Nat. Prod. 72 (2009) 44-52