Diversity of biologically active secondary metabolites from endophytic and saprotrophic fungi of the ascomycete order Xylariales

Natural Product Reports - Tập 35 Số 9 - Trang 992-1014
Soleiman E. Helaly1,2,3,4,5, Benjarong Thongbai1,6,7,3,4, Marc Stadler1,3,4,5
138124 Braunschweig
2Department of Chemistry, Faculty of Science, Aswan University, 81528 Aswan, Egypt
3Dept Microbial Drugs, Helmholtz Centre for Infection Research, Inhoffenstr. 7, 38124 Braunschweig, Germany
4Germany
5Helmholtz Centre for Infection Research
6Centre of Excellence in Fungal Research
7Centre of Excellence in Fungal Research, Mae Fah Luang University, Chiang Rai, 57100, Thailand

Tóm tắt

The diversity of secondary metabolites in the fungal order Xylariales is reviewed with special emphasis on correlations between chemical diversity and biodiversity as inferred from recent taxonomic and phylogenetic studies.

Từ khóa


Tài liệu tham khảo

Whalley, 1995, Can. J. Bot., 73, 802, 10.1139/b95-325

Stadler, 2006, Rev. Iberoam. Micol., 23, 160, 10.1016/S1130-1406(06)70037-7

Stadler, 2005, Recent Res. Dev. Phytochem., 9, 41

Maharachchikumbura, 2016, Fungal Divers., 79, 1, 10.1007/s13225-016-0369-6

Hongsanan, 2017, Fungal Divers., 84, 25, 10.1007/s13225-017-0384-2

Jaklitsch, 2016, Persoonia, 37, 82, 10.3767/003158516X690475

Wendt, 2018, Mycol. Progr., 17, 115, 10.1007/s11557-017-1311-3

Daranagama, 2018, Fungal Divers., 88, 1, 10.1007/s13225-017-0388-y

Voglmayr, 2018, Mycol. Progr., 17, 155, 10.1007/s11557-017-1329-6

Wijayawardene, 2017, Fungal Divers., 86, 1, 10.1007/s13225-017-0386-0

Senanayake, 2015, Fungal Divers., 73, 73, 10.1007/s13225-015-0340-y

Xu, 2010, Fungal Divers., 44, 15, 10.1007/s13225-010-0055-z

Davis, 2010, Org. Biomol. Chem., 8, 1785, 10.1039/b924169h

Xu, 2011, Tetrahedron Lett., 52, 21, 10.1016/j.tetlet.2010.10.131

Li, 2011, Org. Lett., 13, 2670, 10.1021/ol200770k

Hume, 2014, J. Org. Chem., 79, 5269, 10.1021/jo5008527

Wang, 2017, Fitoterapia, 120, 164, 10.1016/j.fitote.2017.06.013

Zhang, 2012, Org. Biomol. Chem., 10, 5307, 10.1039/c2ob25469g

Wei, 2013, Mar. Drugs, 11, 1050, 10.3390/md11041050

Hemberger, 2013, Chem.–Eur. J., 19, 15556, 10.1002/chem.201302204

Kesting, 2011, J. Nat. Prod., 74, 2206, 10.1021/np2005665

Akone, 2013, Tetrahedron Lett., 54, 6751, 10.1016/j.tetlet.2013.10.005

Wang, 2015, BMC Genomics, 16, 28, 10.1186/s12864-014-1190-9

Liu, 2009, J. Nat. Prod., 72, 1482, 10.1021/np900308s

Liu, 2010, Chem. Commun., 46, 460, 10.1039/B918330B

Wu, 2016, Org. Lett., 18, 1832, 10.1021/acs.orglett.6b00562

Liu, 2013, Fitoterapia, 85, 114, 10.1016/j.fitote.2013.01.010

Liu, 2013, J. Org. Chem., 78, 2992, 10.1021/jo302804h

Ballio, 1988, Phytochemistry, 27, 3117, 10.1016/0031-9422(88)80011-6

Evidente, 1986, J. Nat. Prod., 49, 593, 10.1021/np50046a006

Evidente, 1994, J. Nat. Prod., 57, 1720, 10.1021/np50114a017

Ballio, 1991, Phytochemistry, 30, 131, 10.1016/0031-9422(91)84113-7

Evidente, 1993, Phytochemistry, 33, 69, 10.1016/0031-9422(93)85398-B

Toshima, 1998, Tetrahedron Lett., 39, 9223, 10.1016/S0040-4039(98)02103-0

Tey-Rulh, 1991, Phytochemistry, 30, 471, 10.1016/0031-9422(91)83707-R

Smith, 2003, J. Nat. Prod., 66, 169, 10.1021/np020415t

Renaud, 1989, Helv. Chim. Acta, 72, 1262, 10.1002/hlca.19890720612

Molyneux, 2002, J. Agric. Food Chem., 50, 1393, 10.1021/jf011215a

Mahoney, 2005, J. Agric. Food Chem., 53, 8148, 10.1021/jf0510236

Lin, 2002, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 41, 1542

Pongcharoen, 2006, J. Nat. Prod., 69, 856, 10.1021/np0600649

Zhou, 2017, Nat. Prod. Res., 31, 1676, 10.1080/14786419.2017.1286486

Sun, 2012, Mar. Drugs, 10, 539, 10.3390/md10030539

Ciavatta, 2008, Tetrahedron, 64, 5365, 10.1016/j.tet.2008.03.016

Duncan, 2001, J. Am. Chem. Soc., 123, 554, 10.1021/ja002940p

Zhang, 2008, J. Nat. Prod., 71, 1078, 10.1021/np800095g

Clark, 2008, J. Am. Chem. Soc., 130, 12355, 10.1021/ja8012819

Duncan, 2003, Chem. Commun., 9, 316, 10.1039/b211889k

Rukachaisirikul, 2005, Chem. Pharm. Bull., 53, 238, 10.1248/cpb.53.238

Quang, 2005, Tetrahedron, 61, 1743, 10.1016/j.tet.2004.12.031

Cheng, 2012, Phytochem. Lett., 5, 467, 10.1016/j.phytol.2012.04.007

Cheng, 2011, Chem. Nat. Compd., 47, 527, 10.1007/s10600-011-9988-z

Song, 2014, Chem. Biodiversity, 11, 673, 10.1002/cbdv.201200286

Hsieh, 2010, Mol. Phylogenet. Evol., 54, 957, 10.1016/j.ympev.2009.12.015

Fournier, 2012, Mycol. Progr., 10, 33, 10.1007/s11557-010-0671-8

Guo, 2016, Org. Lett., 18, 3338, 10.1021/acs.orglett.6b01437

Cho, 2016, J. Chin. Chem. Soc., 63, 404, 10.1002/jccs.201500525

Intaraudom, 2009, Planta Med., 75, 1431, 10.1055/s-0029-1185698

Stadler, 2014, IMA Fungus, 5, 57, 10.5598/imafungus.2014.05.01.07

Gunawan, 1990, Eur. J. Org. Chem., 8, 825

Stadler, 2008, Mycol. Progr., 7, 53, 10.1007/s11557-008-0553-5

Anderson, 1984, J. Chem. Soc., Chem. Commun., 14, 917, 10.1039/c39840000917

Anderson, 1982, J. Chem. Soc., Perkin Trans. 1, 1, 215, 10.1039/P19820000215

Bodo, 1987, Tetrahedron Lett., 28, 2355, 10.1016/S0040-4039(00)96123-9

Kornsakulkarn, 2017, Tetrahedron, 73, 3505, 10.1016/j.tet.2017.05.030

Schlingmann, 2002, Tetrahedron, 58, 6825, 10.1016/S0040-4020(02)00746-9

Chinworrungsee, 2001, Bioorg. Med. Chem. Lett., 11, 1965, 10.1016/S0960-894X(01)00327-4

Daferner, 1999, Z. Naturforsch., C: J. Biosci., 54, 474, 10.1515/znc-1999-7-803

Vicente, 2009, Mycol. Res., 113, 754, 10.1016/j.mycres.2009.02.011

Chang, 2014, J. Nat. Prod., 77, 751, 10.1021/np400523k

L. E. Petrini , Rosellinia-a world monograph , J. Cramer , 2013

Scherkenbeck, 2002, Curr. Top. Med. Chem., 2, 759, 10.2174/1568026023393624

Kuhnert, 2017, Fungal Divers., 85, 1, 10.1007/s13225-016-0377-6

Stadler, 2014, Stud. Mycol., 77, 1, 10.3114/sim0016

Allport, 1958, J. Chem. Soc., 4090, 10.1039/jr9580004090

Allport, 1960, J. Chem. Soc., 654, 10.1039/jr9600000654

Sudarman, 2016, Tetrahedron, 72, 6450, 10.1016/j.tet.2016.08.054

Fukai, 2012, J. Nat. Prod., 75, 22, 10.1021/np2004193

Liu, 2017, RSC Adv., 7, 5381, 10.1039/C6RA27306H

Bitzer, 2008, Mycol. Res., 112, 251, 10.1016/j.mycres.2007.07.004

Stadler, 2010, Persoonia, 25, 11, 10.3767/003158510X524231

Stadler, 2010, Mycoscience, 51, 189, 10.1007/S10267-009-0028-9

Stadler, 2010, Mycol. Progr., 9, 169, 10.1007/s11557-009-0623-3

Anke, 1995, Can. J. Bot., 73, 932, 10.1139/b95-341

Kim, 2004, Curr. Microbiol., 49, 282, 10.1007/s00284-004-4349-9

Igarashi, 1993, J. Antibiot., 46, 1843, 10.7164/antibiotics.46.1843

Kuhnert, 2014, Fungal Divers., 64, 181, 10.1007/s13225-013-0264-3

Surup, 2015, Nat. Prod. Bioprospect., 5, 167, 10.1007/s13659-015-0065-3

Wiebach, 2015, Phytochemistry, 117, 1162

Wiebach, 2016, Nat. Prod. Commun., 11, 909

Kuhnert, 2015, Phytochemistry, 118, 68, 10.1016/j.phytochem.2015.08.004

Surup, 2017, Chem.–Eur. J., 24, 2200, 10.1002/chem.201704928

Intaraudom, 2017, Phytochemistry, 139, 8, 10.1016/j.phytochem.2017.03.008

Surup, 2014, Mycology, 5, 110, 10.1080/21501203.2014.929600

Cao, 2016, Pestic. Biochem. Physiol., 129, 7, 10.1016/j.pestbp.2015.10.002

Leman-Loubière, 2017, J. Nat. Prod., 80, 2850, 10.1021/acs.jnatprod.7b00714

Leman-Loubière, 2017, Front. Mar. Sci., 4, 399, 10.3389/fmars.2017.00399

E. B. Sir , L.Wendt and M.Stadler , unpublished data

Steglich, 1974, Phytochemistry, 13, 2874, 10.1016/0031-9422(74)80262-1

Stadler, 2008, North American Fungi, 3, 73, 10.2509/naf2008.003.0075

Quang, 2006, J. Nat. Prod., 69, 1198, 10.1021/np0602057

Sir, 2016, Mycol. Progr., 15, 42, 10.1007/s11557-016-1182-z

Bitzer, 2007, Chimia, 51, 332, 10.2533/chimia.2007.332

Quang, 2004, J. Nat. Prod., 67, 1152, 10.1021/np040063l

Hellwig, 2005, Mycol. Progr., 4, 39, 10.1007/s11557-006-0108-6

Sir, 2015, Mycol. Progr., 14, 1, 10.1007/s11557-015-1043-1

Quang, 2005, Tetrahedron, 61, 8451, 10.1016/j.tet.2005.06.077

Stadler, 2005, Mycologia, 97, 1129, 10.1080/15572536.2006.11832761

Svilar, 2012, Rapid Commun. Mass Spectrom., 26, 2612, 10.1002/rcm.6382

Quang, 2004, Phytochemistry, 65, 469, 10.1016/j.phytochem.2003.09.022

Kuhnert, 2015, Fungal Divers., 71, 165, 10.1007/s13225-014-0318-1

Kuhnert, 2014, Fungal Biol., 118, 242, 10.1016/j.funbio.2013.12.003

Fournier, 2010, Mycotaxon, 113, 209, 10.5248/113.209

Læssøe, 2010, Fungal Biol., 114, 481, 10.1016/j.funbio.2010.03.010

Hsieh, 2005, Mycologia, 97, 844, 10.1080/15572536.2006.11832776

Quang, 2005, Phytochemistry, 66, 797, 10.1016/j.phytochem.2005.02.006

Quang, 2006, Tetrahedron, 62, 6349, 10.1016/j.tet.2006.04.040

Surup, 2013, Phytochemistry, 95, 252, 10.1016/j.phytochem.2013.07.027

Quang, 2005, Planta Med., 71, 1058, 10.1055/s-2005-873129

Kuhnert, 2017, Phytochemistry, 137, 67, 10.1016/j.phytochem.2017.02.014

Surup, 2016, Tetrahedron Lett., 57, 2183, 10.1016/j.tetlet.2016.04.014

Stadler, 2007, Nat. Prod. Commun., 2, 287

Stadler, 2006, Mycol. Res., 110, 811, 10.1016/j.mycres.2006.03.013

Petrini, 1985, Sydowia, 38, 216

Polishook, 2001, Mycologia, 92, 1125, 10.2307/3761673

Bills, 2012, PLoS One, 7, e46687, 10.1371/journal.pone.0046687

Schoch, 2012, Proc. Natl. Acad. Sci. U. S. A., 109, 6241, 10.1073/pnas.1117018109

Pažoutová, 2013, Fungal Divers., 60, 107, 10.1007/s13225-013-0238-5

Raja, 2017, J. Nat. Prod., 80, 756, 10.1021/acs.jnatprod.6b01085

Hashimoto, 1998, Heterocycles, 2, 1067

Yang, 2017, Nat. Prod. Res., 29, 1

Barnes, 2016, Chem.–Eur. J., 13, 4551, 10.1002/chem.201504005

Liu, 2017, J. Asian Nat. Prod. Res., 10.1080/10286020.2017.1392512

Tarman, 2012, Phytochem. Lett., 5, 83, 10.1016/j.phytol.2011.10.006

Hu, 2014, Mar. Drugs, 12, 5563, 10.3390/md12115563

Zhang, 2008, Angew. Chem., Int. Ed., 47, 5823, 10.1002/anie.200801284

Zhang, 2011, J. Am. Chem. Soc., 133, 5931, 10.1021/ja110932p

Fang, 2012, Nat. Commun., 3, 1039, 10.1038/ncomms2031

Lu, 2018, J. Biosci. Bioeng., 125, 205, 10.1016/j.jbiosc.2017.08.018

Zhang, 2016, Org. Lett., 18, 6496, 10.1021/acs.orglett.6b03435

Cheng, 2013, Chem. Nat. Compd., 49, 446, 10.1007/s10600-013-0635-8

Cheng, 2012, Phytochem. Lett., 5, 219, 10.1016/j.phytol.2011.12.012

Maciel, 2018, J. Photochem. Photobiol., A, 178, 316, 10.1016/j.jphotobiol.2017.11.018

Ibrahim, 2017, Phytochemistry, 140, 16, 10.1016/j.phytochem.2017.04.009

Zheng, 2013, Steroids, 78, 896, 10.1016/j.steroids.2013.05.007

Zhao, 2015, Steroids, 102, 101, 10.1016/j.steroids.2015.08.004

Sawadsitang, 2015, Nat. Prod. Res., 29, 2033, 10.1080/14786419.2015.1017724

Sica, 2016, Front. Microbiol., 7, 544, 10.3389/fmicb.2016.00544

Cheng, 2015, Chem. Nat. Compd., 51, 515, 10.1007/s10600-015-1327-3

Arora, 2016, Phytomedicine, 23, 1312, 10.1016/j.phymed.2016.07.004

Jiménez-Romero, 2008, Pharm. Biol., 46, 700, 10.1080/13880200802215859

Song, 2012, Mar. Drugs, 10, 340, 10.3390/md10020340

Richardson, 2014, Fungal Ecol., 11, 107, 10.1016/j.funeco.2014.05.004

Sorres, 2015, Tetrahedron Lett., 56, 4596, 10.1016/j.tetlet.2015.06.022

Pongcharoen, 2008, Phytochemistry, 69, 1900, 10.1016/j.phytochem.2008.04.003

Nong, 2014, Nat. Prod. Commun., 9, 467

Yang, 2014, Nat. Prod. Res., 28, 967, 10.1080/14786419.2014.901318

Zou, 2015, J. Asian Nat. Prod. Res., 17, 705, 10.1080/10286020.2015.1054816

Wu, 2014, RSC Adv., 4, 54144, 10.1039/C4RA10365C

Kim, 2014, J. Chem. Res., 38, 722, 10.3184/174751914X14175406270662

Xu, 2015, Nat. Prod. Commun., 10, 1655

Lin, 2011, Helv. Chim. Acta, 94, 301, 10.1002/hlca.201000220

Dickschat, 2017, Nat. Prod. Rep., 34, 310, 10.1039/C7NP00003K

Strobel, 2001, Microbiology, 147, 2943, 10.1099/00221287-147-11-2943

Ezra, 2004, Microbiology, 150, 4023, 10.1099/mic.0.27334-0

Zhang, 2010, Fungal Biol., 114, 797, 10.1016/j.funbio.2010.07.006

Saxena, 2015, Ann. Microbiol., 65, 47, 10.1007/s13213-014-0834-y

Suwannarach, 2013, Ann. Microbiol., 63, 1341, 10.1007/s13213-012-0593-6

Stadler, 2013, Mycology, 4, 5, 10.1080/21501203.2013.782478

K. Seifert , G.Morgan-Jones , W.Gams and B.Kendrick , The genera of Hyphomycetes , CBS-KNAW Fungal Biodiversity Centre , Utrecht , 2011

Riyaz-Ul-Hassan, 2012, Microbiology, 158, 464

Riyaz-Ul-Hassan, 2013, J. Microbiol. Biotechnol., 23, 29, 10.4014/jmb.1208.04062

Ulloa-Benítez, 2016, J. Appl. Microbiol., 121, 380, 10.1111/jam.13174

Liarzi, 2016, PLoS One, 11, e0168242, 10.1371/journal.pone.0168242

Liarzi, 2016, PLoS One, 11, e0168437, 10.1371/journal.pone.0168437

Wang, 2018, Beilstein J. Org. Chem., 14, 135, 10.3762/bjoc.14.9

Dickschat, 2018, Beilstein J. Org. Chem., 14, 734, 10.3762/bjoc.14.62

Paungmoung, 2007, FEMS Microbiol. Lett., 274, 260, 10.1111/j.1574-6968.2007.00843.x

Amnuaykanjanasin, 2005, FEMS Microbiol. Lett., 251, 125, 10.1016/j.femsle.2005.07.038

Chan, 2015, BMC Genomics, 16, 966, 10.1186/s12864-015-2200-2

Büttner, 2017, Genome Announc., 5, e01076-17, 10.1128/genomeA.01076-17

Wu, 2017, Appl. Microbiol. Biotechnol., 101, 2603, 10.1007/s00253-017-8091-1

Wu, 2016, PLoS One, 11, e0146983, 10.1371/journal.pone.0146983

Shaw, 2015, J. Biol. Chem., 290, 8511, 10.1074/jbc.M114.636159

Qadri, 2017, Microb. Ecol., 73, 954, 10.1007/s00248-016-0901-y

Shaw, 2015, J. Biol. Chem., 290, 8511, 10.1074/jbc.M114.636159

Qadri, 2017, Microb. Ecol., 73, 954, 10.1007/s00248-016-0901-y

Weckwerth, 2000, Biol. Chem., 275, 17909, 10.1074/jbc.M001084200

Van de Bittner, 2018, J. Am. Chem. Soc., 140, 582, 10.1021/jacs.7b10909

Kudo, 2016, J. Antibiot., 69, 541, 10.1038/ja.2016.40

Skellam, 2017, Nat. Prod. Rep., 34, 1252, 10.1039/C7NP00036G