Tremorgenic and neurotoxic paspaline-derived indole-diterpenes: biosynthetic diversity, threats and applications.
Biosynthesis
Drug discovery
Food and feed safety
Fungal secondary metabolite
Heterologous production
Indole-diterpene
Mycotoxin
Journal
Applied microbiology and biotechnology
ISSN: 1432-0614
Titre abrégé: Appl Microbiol Biotechnol
Pays: Germany
ID NLM: 8406612
Informations de publication
Date de publication:
Feb 2019
Feb 2019
Historique:
received:
30
10
2018
accepted:
20
12
2018
revised:
15
12
2018
pubmed:
8
1
2019
medline:
29
5
2019
entrez:
8
1
2019
Statut:
ppublish
Résumé
Indole-diterpenes (IDTs) such as the aflatrems, janthitrems, lolitrems, paspalitrems, penitrems, shearinines, sulpinines, and terpendoles are biogenetically related but structurally varied tremorgenic and neurotoxic mycotoxins produced by fungi. All these metabolites derive from the biosynthetic intermediate paspaline, a frequently occurring IDT on its own right. In this comprehensive review, we highlight the similarities and differences of the IDT biosynthetic pathways that lead to the generation of the main paspaline-derived IDT subgroups. We survey the taxonomic distribution and the regulation of IDT production in various fungi and compare the organization of the known IDT biosynthetic gene clusters. A detailed assessment of the highly diverse biological activities of these mycotoxins leads us to emphasize the significant losses that paspaline-derived IDTs cause in agriculture, and compels us to warn about the various hazards they represent towards human and livestock health. Conversely, we also describe the potential utility of these versatile molecules as lead compounds for pharmaceutical drug discovery, and examine the prospects for their industrial scale manufacture in genetically manipulated IDT producers or domesticated host microorganisms in synthetic biological production systems.
Identifiants
pubmed: 30613899
doi: 10.1007/s00253-018-09594-x
pii: 10.1007/s00253-018-09594-x
pmc: PMC6384164
mid: NIHMS1008551
doi:
Substances chimiques
Diterpenes
0
Indoles
0
Mycotoxins
0
Neurotoxins
0
paspaline
11024-56-9
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
1599-1616Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM114418
Pays : United States
Organisme : European Union and the European Social Fund
ID : EFOP-3.6.1-16-2016-00022
Organisme : Ministry of Human Capacities in Hungary
ID : Higher Education Institutional Excellence Program
Organisme : U.S. National Institutes of Health
ID : NIGMS 5R01GM114418
Références
J Agric Food Chem. 1998 Feb 16;46(2):590-598
pubmed: 10554283
Mol Microbiol. 2001 Feb;39(3):754-64
pubmed: 11169115
J Parasitol. 2001 Apr;87(2):419-23
pubmed: 11318575
Curr Opin Microbiol. 2001 Oct;4(5):540-5
pubmed: 11587930
Appl Microbiol Biotechnol. 2001 Dec;57(5-6):593-605
pubmed: 11778866
Can Vet J. 2002 May;43(5):372-4
pubmed: 12001505
J Am Chem Soc. 2002 Jun 19;124(24):7055-60
pubmed: 12059229
J Chromatogr A. 2002 Jul 26;964(1-2):189-97
pubmed: 12198847
Trends Microbiol. 2003 Jan;11(1):30-6
pubmed: 12526852
Chem Biol. 2003 Feb;10(2):131-7
pubmed: 12618185
Toxicol Appl Pharmacol. 1976 Feb;35(2):311-20
pubmed: 1265748
Toxicon. 2003 Jun;41(7):933-5
pubmed: 12782095
Mini Rev Med Chem. 2003 Sep;3(6):576-84
pubmed: 12871160
Mol Genet Genomics. 2003 Oct;270(1):9-23
pubmed: 12884010
Appl Microbiol Biotechnol. 1992 Feb;36(5):569-72
pubmed: 1368061
Nature. 1960 Jul 16;187:238-9
pubmed: 13794048
Int J Food Microbiol. 2003 Nov 15;88(1):69-77
pubmed: 14527787
Alkaloids Chem Biol. 2003;60:51-163
pubmed: 14593856
J Food Prot. 2003 Nov;66(11):2123-9
pubmed: 14627292
Int J Food Microbiol. 2004 Jan 15;90(2):181-8
pubmed: 14698099
Mycopathologia. 1992 Dec;120(3):177-82
pubmed: 1494361
J Vet Diagn Invest. 2004 Jul;16(4):340-2
pubmed: 15305749
Toxicology. 2004 Oct 1;202(3):199-211
pubmed: 15337583
Appl Environ Microbiol. 2004 Nov;70(11):6875-83
pubmed: 15528556
Toxicol Lett. 2005 Mar 15;155(3):421-6
pubmed: 15649626
J Agric Food Chem. 2004 Dec 15;52(25):7507-13
pubmed: 15675796
Med J Aust. 2005 Jun 6;182(11):582-4
pubmed: 15938687
Mycopathologia. 2005 Jun;159(4):571-7
pubmed: 15983744
Mol Genet Genomics. 2005 Aug;274(1):13-29
pubmed: 15991026
FEMS Microbiol Ecol. 2005 Jun 1;53(1):51-60
pubmed: 16329929
Fungal Genet Biol. 2006 Oct;43(10):679-93
pubmed: 16765617
J Agric Food Chem. 2006 Jun 28;54(13):4582-7
pubmed: 16787001
Rapid Commun Mass Spectrom. 2006;20(18):2649-59
pubmed: 16912987
J Antibiot (Tokyo). 2007 Jan;60(1):43-51
pubmed: 17390588
J Biol Chem. 2007 Jun 8;282(23):16829-37
pubmed: 17428785
Anal Bioanal Chem. 2007 Nov;389(5):1505-23
pubmed: 17874237
Mycol Res. 2008 Feb;112(Pt 2):184-99
pubmed: 18262778
Curr Top Med Chem. 2008;8(10):888-904
pubmed: 18673173
J Pharmacol Exp Ther. 2008 Dec;327(3):657-64
pubmed: 18801945
Clin Cancer Res. 2008 Dec 1;14(23):7583-7
pubmed: 19047082
Drug Chem Toxicol. 2009;32(1):26-37
pubmed: 19514936
Mol Genet Genomics. 2009 Sep;282(3):257-71
pubmed: 19529962
Anal Bioanal Chem. 2009 Nov;395(5):1355-72
pubmed: 19669641
Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Jan;27(1):72-88
pubmed: 19753495
Appl Environ Microbiol. 2009 Dec;75(23):7469-81
pubmed: 19801473
Med Mycol. 2010 Feb;48(1):188-96
pubmed: 19886763
J Agric Food Chem. 2009 Dec 9;57(23):11112-9
pubmed: 19891432
Ann Agric Environ Med. 2009;16(2):325-31
pubmed: 20047270
J Infect Dis. 2010 Jul 1;202(1):171-5
pubmed: 20497051
Bioorg Med Chem Lett. 2010 Oct 1;20(19):5677-80
pubmed: 20797856
Aust Vet J. 2010 Oct;88(10):393-5
pubmed: 20854295
Toxicon. 2011 Apr;57(5):686-94
pubmed: 21300077
Eukaryot Cell. 2011 Dec;10(12):1660-9
pubmed: 21666076
Neurochem Int. 2011 Dec;59(7):1074-81
pubmed: 21924313
N Z Vet J. 2012 Jan;60(1):56-60
pubmed: 22175431
PLoS One. 2011;6(12):e29290
pubmed: 22195040
Invest Ophthalmol Vis Sci. 2012 May 17;53(6):3059-66
pubmed: 22427579
J Pharmacol Exp Ther. 2012 Aug;342(2):453-60
pubmed: 22580348
J Environ Sci Health A Tox Hazard Subst Environ Eng. 2012;47(11):1659-64
pubmed: 22702826
FEBS Lett. 2012 Jul 30;586(16):2563-9
pubmed: 22750140
Bioorg Med Chem. 2012 Oct 1;20(19):5678-98
pubmed: 22902032
N Z Vet J. 2012 Nov;60(6):315-28
pubmed: 22913513
N Z Vet J. 2013 Mar;61(2):87-97
pubmed: 22913546
N Z Vet J. 2013 Jan;61(1):11-7
pubmed: 22984816
Toxicon. 2012 Dec 15;60(8):1428-35
pubmed: 23085423
Chem Biol. 2012 Dec 21;19(12):1611-9
pubmed: 23261604
J Am Chem Soc. 2013 Jan 30;135(4):1260-3
pubmed: 23311903
ACS Chem Biol. 2013 Apr 19;8(4):840-8
pubmed: 23387427
PLoS Genet. 2013;9(2):e1003323
pubmed: 23468653
Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(8):1402-6
pubmed: 23721156
Am J Physiol Cell Physiol. 2013 Sep 15;305(6):C609-22
pubmed: 23804200
J Nat Prod. 2013 Jul 26;76(7):1328-36
pubmed: 23886345
Toxins (Basel). 2013 Aug 14;5(8):1422-46
pubmed: 23949005
Appl Environ Microbiol. 2013 Dec;79(23):7298-304
pubmed: 24038699
Eur J Med Chem. 2013;70:594-606
pubmed: 24211635
Food Microbiol. 2014 Feb;37:78-95
pubmed: 24230476
Medchemcomm. 2013 Oct;4(10):null
pubmed: 24273638
Invest Ophthalmol Vis Sci. 2014 Apr 07;55(4):2157-65
pubmed: 24609622
Chembiochem. 2014 May 5;15(7):934-8
pubmed: 24648249
J Microbiol Biotechnol. 2014 Aug;24(8):1081-7
pubmed: 24759426
Rapid Commun Mass Spectrom. 2014 Jul 30;28(14):1621-34
pubmed: 24895259
Metabolites. 2012 Jan 05;2(1):39-56
pubmed: 24957367
Toxins (Basel). 2014 Jun 23;6(6):1916-28
pubmed: 24960201
Chembiochem. 2014 Sep 22;15(14):2076-80
pubmed: 25087641
Mycotoxin Res. 2014 Nov;30(4):213-20
pubmed: 25109845
J Chromatogr A. 2014 Oct 3;1362:145-56
pubmed: 25175039
Toxicon. 2014 Dec 15;92:129-32
pubmed: 25448387
PLoS One. 2015 Feb 13;10(2):e0117231
pubmed: 25680199
Angew Chem Int Ed Engl. 2015 May 4;54(19):5748-52
pubmed: 25831977
Toxins (Basel). 2015 Jul 23;7(8):2701-22
pubmed: 26213965
J Chromatogr. 1989 Dec 8;483:153-68
pubmed: 2625435
J Anim Sci. 2015 Aug;93(8):4098-109
pubmed: 26440189
J Am Chem Soc. 2015 Nov 4;137(43):13724-7
pubmed: 26469304
Plant Mol Biol. 2016 Apr;90(6):665-75
pubmed: 26542393
Clin Orthop Relat Res. 1989 Jul;(244):3-6
pubmed: 2663289
Microbiol Res. 2016 Jan;182:150-61
pubmed: 26686623
Anal Bioanal Chem. 2016 May;408(12):3083-91
pubmed: 26886743
Toxins (Basel). 2016 Feb 15;8(2):47
pubmed: 26891327
J Nat Prod. 2016 Aug 26;79(8):2066-74
pubmed: 27462726
Org Lett. 2016 Oct 7;18(19):5026-5029
pubmed: 27632559
Mar Drugs. 2016 Nov 09;14(11):
pubmed: 27834847
Sci Rep. 2016 Dec 12;6:38747
pubmed: 27941917
Toxins (Basel). 2016 Dec 24;9(1):
pubmed: 28029129
Mol Cell Proteomics. 2017 Mar;16(3):428-437
pubmed: 28062800
Anal Chem. 2016 Dec 20;88(24):12461-12469
pubmed: 28193030
J Agric Food Chem. 2017 Jul 5;65(26):5266-5277
pubmed: 28571312
Toxins (Basel). 2017 Jul 01;9(7):
pubmed: 28671569
Anal Bioanal Chem. 2017 Aug;409(21):5101-5112
pubmed: 28674820
Toxicology. 2017 Dec 1;392:64-70
pubmed: 29037868
J Am Chem Soc. 2018 Jan 17;140(2):582-585
pubmed: 29283570
J Agric Food Chem. 2018 Feb 7;66(5):1264-1269
pubmed: 29338236
Chemistry. 2018 Mar 20;24(17):4445-4452
pubmed: 29356159
Appl Microbiol Biotechnol. 2018 Apr;102(7):3255-3266
pubmed: 29457197
ACS Synth Biol. 2018 Apr 20;7(4):1018-1029
pubmed: 29620866
Mar Drugs. 2018 May 11;16(5):null
pubmed: 29751615
J Nat Prod. 2018 Jul 27;81(7):1682-1686
pubmed: 30011204
Food Microbiol. 2018 Dec;76:396-404
pubmed: 30166166
Appl Microbiol Biotechnol. 2018 Nov;102(22):9481-9515
pubmed: 30293194
J Ethnopharmacol. 1988 Dec;24(2-3):345-8
pubmed: 3075677
J Antibiot (Tokyo). 1988 Dec;41(12):1868-72
pubmed: 3209479
Mycopathologia. 1988 Dec;104(3):157-62
pubmed: 3237243
Int J Food Microbiol. 1988 Aug;7(1):9-17
pubmed: 3275314
Aust Vet J. 1988 Mar;65(3):82-5
pubmed: 3401148
J Chromatogr. 1987 Apr 17;392:333-47
pubmed: 3597582
J Chromatogr. 1987 Aug 28;404(1):195-214
pubmed: 3680432
Folia Microbiol (Praha). 1971;16(1):35-40
pubmed: 4322929
Can J Microbiol. 1974 Aug;20(8):1159-62
pubmed: 4425383
Mycopathologia. 1979 May 31;67(2):107-9
pubmed: 481557
Res Vet Sci. 1978 Jan;24(1):49-56
pubmed: 625600
J Gen Microbiol. 1984 May;130(5):1293-8
pubmed: 6470667
Appl Environ Microbiol. 1983 Dec;46(6):1301-10
pubmed: 6660869
J Agric Food Chem. 1983 May-Jun;31(3):655-7
pubmed: 6886222
N Z Vet J. 1981 Oct;29(10):185-6
pubmed: 6950332
N Z Vet J. 1981 Oct;29(10):189-90
pubmed: 6950333
Mycopathologia. 1981 Oct 10;76(1):55-8
pubmed: 7312021
Appl Environ Microbiol. 1980 Jan;39(1):272-3
pubmed: 7356319
Biochemistry. 1994 May 17;33(19):5819-28
pubmed: 7514038
Appl Environ Microbiol. 1979 Jan;37(1):172-3
pubmed: 760635
J Antibiot (Tokyo). 1995 Jan;48(1):5-11
pubmed: 7868389
Can J Neurol Sci. 1993 Aug;20(3):237-9
pubmed: 8221391
J S Afr Vet Assoc. 1996 Mar;67(1):36-7
pubmed: 8786617
J Agric Food Chem. 1977 Sep-Oct;25(5):1197-1201
pubmed: 893851
J Biol Chem. 1998 Oct 9;273(41):26747-54
pubmed: 9756918
J Biol Chem. 1998 Oct 9;273(41):26755-64
pubmed: 9756919
Bioorg Med Chem Lett. 1998 Feb 3;8(3):289-94
pubmed: 9871672