Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Author(s): Bin Zhang, Ting Zhang, Jianzhou Xu, Jian Lu, Panpan Qiu, Tingting Wang* and Lijian Ding*

DOI: 10.2174/1389557520666200826123248

DownloadDownload PDF Flyer Cite As
Marine Sponge-Associated Fungi as Potential Novel Bioactive Natural Product Sources for Drug Discovery: A Review

Page: [1966 - 2010] Pages: 45

  • * (Excluding Mailing and Handling)

Abstract

Marine sponge-associated fungi are promising sources of structurally interesting and bioactive secondary metabolites. Great plenty of natural products have been discovered from spongeassociated fungi in recent years. Here reviewed are 571 new compounds isolated from marine fungi associated with sponges in 2010-2018. These molecules comprised eight different structural classes, including alkaloids, polyketides, terpenoids, meroterpenoids, etc. Moreover, most of these compounds demonstrated profoundly biological activities, such as antimicrobial, antiviral, cytotoxic, etc. This review systematically summarized the structural diversity, biological function, and future potential of these novel bioactive natural products for drug discovery.

Keywords: Sponge-associated fungi, natural products, antimicrobial, antiviral, cytotoxic, lead drugs.

Graphical Abstract

[1]
Webster, N.S.; Taylor, M.W. Marine sponges and their microbial symbionts: Love and other relationships. Environ. Microbiol., 2012, 14(2), 335-346.
[http://dx.doi.org/10.1111/j.1462-2920.2011.02460.x ] [PMID: 21443739]
[2]
Hentschel, U.; Usher, K.M.; Taylor, M.W. Marine sponges as microbial fermenters. FEMS Microbiol. Ecol., 2006, 55(2), 167-177.
[http://dx.doi.org/10.1111/j.1574-6941.2005.00046.x ] [PMID: 16420625]
[3]
Schwartsmann, G.; Brondani da Rocha, A.; Berlinck, R.G.; Jimeno, J. Marine organisms as a source of new anticancer agents. Lancet Oncol., 2001, 2(4), 221-225.
[http://dx.doi.org/10.1016/S1470-2045(00)00292-8 ] [PMID: 11905767]
[4]
Hentschel, U.; Piel, J.; Degnan, S.M.; Taylor, M.W. Genomic insights into the marine sponge microbiome. Nat. Rev. Microbiol., 2012, 10(9), 641-654.
[http://dx.doi.org/10.1038/nrmicro2839] [PMID: 22842661]
[5]
Burlando, B.; Sabatini, M.A.; Gaino, E. Association between calcareous Clathrina cerebrum (Haeckel) and bacteria: Electron microscope study. J. Exp. Mar. Biol. Ecol., 1988, 116(1), 35-42.
[http://dx.doi.org/10.1016/0022-0981(88)90244-4]
[6]
Cheng, M.M.; Tang, X.L.; Sun, Y.T.; Song, D.Y.; Cheng, Y.J.; Liu, H.; Li, P.L.; Li, G.Q. Biological and chemical diversity of marine sponge-derived microorganisms over the last two decades from 1998 to 2017. Molecules, 2020, 25(4), 853.
[http://dx.doi.org/10.3390/molecules25040853] [PMID: 32075151]
[7]
Thomas, T.R.A.; Kavlekar, D.P. LokaBharathi, P.A. Marine drugs from sponge-microbe association--a review. Mar. Drugs, 2010, 8(4), 1417-1468.
[http://dx.doi.org/10.3390/md8041417] [PMID: 20479984]
[8]
Fan, L.; Reynolds, D.; Liu, M.; Stark, M.; Kjelleberg, S.; Webster, N.S.; Thomas, T. Functional equivalence and evolutionary convergence in complex communities of microbial sponge symbionts. Proc. Natl. Acad. Sci. USA, 2012, 109(27), E1878-E1887.
[http://dx.doi.org/10.1073/pnas.1203287109] [PMID: 22699508]
[9]
Fleming, A. On the antibacterial action of cultures of a Penicillium, with special reference to their use in the isolation of B. influenzæ. Br. J. Exp. Pathol., 1929, 10(3), 226-236.
[10]
Taylor, M.W.; Schupp, P.J.; Dahllöf, I.; Kjelleberg, S.; Steinberg, P.D. Host specificity in marine sponge-associated bacteria, and potential implications for marine microbial diversity. Environ. Microbiol., 2004, 6(2), 121-130.
[http://dx.doi.org/10.1046/j.1462-2920.2003.00545.x ] [PMID: 14756877]
[11]
Silber, J.; Kramer, A.; Labes, A.; Tasdemir, D. From discovery to production: biotechnology of marine fungi for the production of new antibiotics. Mar. Drugs, 2016, 14(7), 137.
[http://dx.doi.org/10.3390/md14070137] [PMID: 27455283]
[12]
Flórez, L.V.; Biedermann, P.H.; Engl, T.; Kaltenpoth, M. Defensive symbioses of animals with prokaryotic and eukaryotic microorganisms. Nat. Prod. Rep., 2015, 32(7), 904-936.
[http://dx.doi.org/10.1039/C5NP00010F] [PMID: 25891201]
[13]
Abdelmohsen, U.R.; Bayer, K.; Hentschel, U. Diversity, abundance and natural products of marine sponge-associated actinomycetes. Nat. Prod. Rep., 2014, 31(3), 381-399.
[http://dx.doi.org/10.1039/C3NP70111E] [PMID: 24496105]
[14]
Indraningrat, A.A.G.; Smidt, H.; Sipkema, D. Bioprospecting sponge-associated microbes for antimicrobial compounds. Mar. Drugs, 2016, 14(5), 87.
[http://dx.doi.org/10.3390/md14050087] [PMID: 27144573]
[15]
Kjer, J.; Debbab, A.; Aly, A.H.; Proksch, P. Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products. Nat. Protoc., 2010, 5(3), 479-490.
[http://dx.doi.org/10.1038/nprot.2009.233] [PMID: 20203665]
[16]
Debbab, A.; Aly, A.H.; Proksch, P. Bioactive secondary metabolites from endophytes and associated marine derived fungi. Fungal Divers., 2011, 49(1), 1-12.
[http://dx.doi.org/10.1007/s13225-011-0114-0]
[17]
Wang, J.; Wei, X.; Qin, X.; Lin, X.; Zhou, X.; Liao, S.; Yang, B.; Liu, J.; Tu, Z.; Liu, Y. Arthpyrones A-C, pyridone alkaloids from a sponge-derived fungus Arthrinium arundinis ZSDS1-F3. Org. Lett., 2015, 17(3), 656-659.
[http://dx.doi.org/10.1021/ol503646c] [PMID: 25606827]
[18]
Özkaya, F.C.; Ebrahim, W.; El-Neketi, M.; Tansel Tanrıkul, T.; Kalscheuer, R.; Müller, W.E.G.; Guo, Z.; Zou, K.; Liu, Z.; Proksch, P. Induction of new metabolites from sponge-associated fungus Aspergillus carneus by OSMAC approach. Fitoterapia, 2018, 131, 9-14.
[http://dx.doi.org/10.1016/j.fitote.2018.10.008] [PMID: 30312652]
[19]
Lee, Y.M.; Dang, H.T.; Li, J.; Zhang, P.; Hong, J.; Lee, C.O.; Jung, J.H. A cytotoxic fellutamide analogue from the sponge-derived fungus Aspergillus versicolor. Bull. Korean Chem. Soc., 2010, 31(10), 205-208.
[http://dx.doi.org/10.5012/bkcs.2010.31.01.205]
[20]
Ueda, J.Y.; Takagi, M.; Shin-ya, K. New xanthoquinodin-like compounds, JBIR-97, -98 and -99, obtained from marine sponge-derived fungus Tritirachium sp. SpB081112MEf2. J. Antibiot. (Tokyo), 2010, 63(10), 615-618.
[http://dx.doi.org/10.1038/ja.2010.92] [PMID: 20683450]
[21]
Song, F.; Ren, B.; Chen, C.; Yu, K.; Liu, X.; Zhang, Y.; Yang, N.; He, H.; Liu, X.; Dai, H.; Zhang, L. Three new sterigmatocystin analogues from marine-derived fungus Aspergillus versicolor MF359. Appl. Microbiol. Biotechnol., 2014, 98(8), 3753-3758.
[http://dx.doi.org/10.1007/s00253-013-5409-5] [PMID: 24458562]
[22]
Qi, J.; Shao, C.L.; Li, Z.Y.; Gan, L.S.; Fu, X.M.; Bian, W.T.; Zhao, H.Y.; Wang, C.Y. Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus. J. Nat. Prod., 2013, 76(4), 571-579.
[http://dx.doi.org/10.1021/np3007556] [PMID: 23477451]
[23]
Peng, J.; Jiao, J.; Li, J.; Wang, W.; Gu, Q.; Zhu, T.; Li, D. Pyronepolyene C-glucosides with NF-κB inhibitory and anti-influenza A viral (H1N1) activities from the sponge-associated fungus Epicoccum sp. JJY40. Bioorg. Med. Chem. Lett., 2012, 22(9), 3188-3190.
[http://dx.doi.org/10.1016/j.bmcl.2012.03.044] [PMID: 22487178]
[24]
Kong, X.; Ma, X.; Xie, Y.; Cai, S.; Zhu, T.; Gu, Q.; Li, D. Aromatic polyketides from a sponge-derived fungus Metarhizium anisopliae mxh-99 and their antitubercular activities. Arch. Pharm. Res., 2013, 36(6), 739-744.
[http://dx.doi.org/10.1007/s12272-013-0077-7] [PMID: 23463335]
[25]
Almeida, C.; Kehraus, S.; Prudêncio, M.; König, G.M. Marilones A-C, phthalides from the sponge-derived fungus Stachylidium sp. Beilstein J. Org. Chem., 2011, 7(1), 1636-1642.
[http://dx.doi.org/10.3762/bjoc.7.192] [PMID: 22238541]
[26]
Mosadeghzad, Z.; Zuriati, Z.; Asmat, A.; Gires, U.; Wickneswari, R.; Pittayakhajonwut, P.; Farahani, G.H.N. Chemical components and bioactivity of the marine-derived fungus Paecilomyces sp. collected from Tinggi Island, Malaysia. Chem. Nat. Compd., 2013, 49(4), 621-625.
[http://dx.doi.org/10.1007/s10600-013-0693-y]
[27]
Jansen, N.; Ohlendorf, B.; Erhard, A.; Bruhn, T.; Bringmann, G.; Imhoff, J.F. Helicusin E, isochromophilone X and isochromophilone XI: new chloroazaphilones produced by the fungus Bartalinia robillardoides strain LF550. Mar. Drugs, 2013, 11(3), 800-816.
[http://dx.doi.org/10.3390/md11030800] [PMID: 23481677]
[28]
Prompanya, C.; Dethoup, T.; Bessa, L.J.; Pinto, M.M.M.; Gales, L.; Costa, P.M.; Silva, A.M.S.; Kijjoa, A. New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013. Mar. Drugs, 2014, 12(10), 5160-5173.
[http://dx.doi.org/10.3390/md12105160] [PMID: 25317534]
[29]
Qin, C.; Lin, X.; Lu, X.; Wan, J.; Zhou, X.; Liao, S.; Tu, Z.; Xu, S.; Liu, Y. Sesquiterpenoids and xanthones derivatives produced by sponge-derived fungus Stachybotry sp. HH1 ZSDS1F1-2. J. Antibiot. (Tokyo), 2015, 68(2), 121-125.
[http://dx.doi.org/10.1038/ja.2014.97] [PMID: 25118104]
[30]
Figueroa, L.; Jiménez, C.; Rodríguez, J.; Areche, C.; Chávez, R.; Henríquez, M.; de la Cruz, M.; Díaz, C.; Segade, Y.; Vaca, I. 3-Nitroasterric acid derivatives from an antarctic sponge-derived Pseudogymnoascus sp. fungus. J. Nat. Prod., 2015, 78(4), 919-923.
[http://dx.doi.org/10.1021/np500906k] [PMID: 25732560]
[31]
Kim, H.; Yang, I.; Ryu, S.Y.; Won, D.H.; Giri, A.G.; Wang, W.; Choi, H.; Chin, J.; Hahn, D.; Kim, E.; Han, C.; Lee, J.; Nam, S.J.; Ho, W.K.; Kang, H. Acredinones A and B, voltage-dependent potassium channel inhibitors from the sponge-derived fungus Acremonium sp. F9A015. J. Nat. Prod., 2015, 78(3), 363-367.
[http://dx.doi.org/10.1021/np5007586] [PMID: 25689430]
[32]
Zhang, J.; Lin, X.P.; Li, L.C.; Zhong, B.L.; Liao, X.J.; Liu, Y.H.; Xu, S.H. Gliomasolides A-E, unusual macrolides from a sponge-derived fungus Gliomastix sp. ZSDS1-F7-2. RSC Adv., 2015, 5(67), 54645-54648.
[http://dx.doi.org/10.1039/C5RA08559D]
[33]
Kong, F.; Zhao, C.; Hao, J.; Wang, C.; Wang, W.; Huang, X.; Zhu, W. New α-glucosidase inhibitors from a marine sponge-derived fungus, Aspergillus sp. OUCMDZ-1583. RSC Adv., 2015, 5(84), 68852-68863.
[http://dx.doi.org/10.1039/C5RA11185D]
[34]
Wu, Q.; Wu, C.; Long, H.; Chen, R.; Liu, D.; Proksch, P.; Guo, P.; Lin, W. Varioxiranols A-G and 19-O-methyl-22-methoxypre-shamixanthone, PKS and hybrid PKS-derived metabolites from a sponge-associated Emericella variecolor fungus. J. Nat. Prod., 2015, 78(10), 2461-2470.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00578] [PMID: 26394166]
[35]
Prompanya, C.; Fernandes, C.; Cravo, S.; Pinto, M.M.; Dethoup, T.; Silva, A.M.; Kijjoa, A. A new cyclic hexapeptide and a new isocoumarin derivative from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. Mar. Drugs, 2015, 13(3), 1432-1450.
[http://dx.doi.org/10.3390/md13031432] [PMID: 25789601]
[36]
Yamada, T.; Umebayashi, Y.; Kawashima, M.; Sugiura, Y.; Kikuchi, T.; Tanaka, R. Determination of the chemical structures of tandyukisins B-D, isolated from a marine sponge-derived fungus. Mar. Drugs, 2015, 13(5), 3231-3240.
[http://dx.doi.org/10.3390/md13053231] [PMID: 26006715]
[37]
Wang, J.; Wang, Z.; Ju, Z.; Wan, J.; Liao, S.; Lin, X.; Zhang, T.; Zhou, X.; Chen, H.; Tu, Z.; Liu, Y. Cytotoxic cytochalasins from marine-derived fungus Arthrinium arundinis. Planta Med., 2015, 81(2), 160-166.
[http://dx.doi.org/10.1055/s-0034-1383403] [PMID: 25626143]
[38]
Yamazaki, H.; Rotinsulu, H.; Kaneko, T.; Murakami, K.; Fujiwara, H.; Ukai, K.; Namikoshi, M. A new dibenz[b,e]oxepine derivative, 1-hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a marine-derived fungus, Beauveria bassiana TPU942. Mar. Drugs, 2012, 10(12), 2691-2697.
[http://dx.doi.org/10.3390/md10122691] [PMID: 23342391]
[39]
Sureram, S.; Wiyakrutta, S.; Ngamrojanavanich, N.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P. Depsidones, aromatase inhibitors and radical scavenging agents from the marine-derived fungus Aspergillus unguis CRI282-03. Planta Med., 2012, 78(6), 582-588.
[http://dx.doi.org/10.1055/s-0031-1298228] [PMID: 22307935]
[40]
Jeon, J.E.; Julianti, E.; Oh, H.; Park, W.; Oh, D.C.; Oh, K.B.; Shin, J. Stereochemistry of hydroxy-bearing benzolactones: isolation and structural determination of chrysoarticulins A–C from a marine-derived fungus Chrysosporium articulatum. Tetrahedron Lett., 2013, 54(24), 3111-3115.
[http://dx.doi.org/10.1016/j.tetlet.2013.04.006]
[41]
Kotoku, N.; Higashimoto, K.; Kurioka, M.; Arai, M.; Fukuda, A.; Sumii, Y.; Sowa, Y.; Sakai, T.; Kobayashi, M. Xylarianaphthol-1, a novel dinaphthofuran derivative, activates p21 promoter in a p53-independent manner. Bioorg. Med. Chem. Lett., 2014, 24(15), 3389-3391.
[http://dx.doi.org/10.1016/j.bmcl.2014.05.083] [PMID: 24939757]
[42]
Wang, X.; Mou, Y.; Hu, J.; Wang, N.; Zhao, L.; Liu, L.; Wang, S.; Meng, D. Cytotoxic polyphenols from a sponge-associated fungus Aspergillus versicolor Hmp-48. Chem. Biodivers., 2014, 11(1), 133-139.
[http://dx.doi.org/10.1002/cbdv.201300115] [PMID: 24443433]
[43]
Wang, J.F.; Xu, F.Q.; Wang, Z.; Lu, X.; Wan, J.T.; Yang, B.; Zhou, X.F.; Zhang, T.Y.; Tu, Z.C.; Liu, Y. A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3. Nat. Prod. Res., 2014, 28(14), 1070-1074.
[http://dx.doi.org/10.1080/14786419.2014.905935] [PMID: 24735402]
[44]
Yamada, T.; Mizutani, Y.; Umebayashi, Y.; Inno, N.; Kawashima, M.; Kikuchi, T.; Tanaka, R. Tandyukisin, a novel ketoaldehyde decalin derivative, produced by a marine sponge-derived Trichoderma harzianum. Tetrahedron Lett., 2014, 55(3), 662-664.
[http://dx.doi.org/10.1016/j.tetlet.2013.11.107]
[45]
Zhao, D.L.; Shao, C.L.; Gan, L.S.; Wang, M.; Wang, C.Y. Chromone derivatives from a sponge-derived strain of the fungus Corynespora cassiicola. J. Nat. Prod., 2015, 78(2), 286-293.
[http://dx.doi.org/10.1021/np5009152] [PMID: 25594263]
[46]
Ueda, J.Y.; Hashimoto, J.; Inaba, S.; Takagi, M.; Shin-ya, K. JBIR-59, a new sorbicillinoid, from a marine-derived fungus Penicillium citrinum SpI080624G1f01. J. Antibiot. (Tokyo), 2010, 63(4), 203-205.
[http://dx.doi.org/10.1038/ja.2010.19] [PMID: 20203701]
[47]
Kawahara, T.; Takagi, M.; Shin-ya, K. JBIR-124: a novel antioxidative agent from a marine sponge-derived fungus Penicillium citrinum SpI080624G1f01. J. Antibiot. (Tokyo), 2012, 65(1), 45-47.
[http://dx.doi.org/10.1038/ja.2011.98] [PMID: 22008699]
[48]
Bringmann, G.; Lang, G.; Bruhn, T.; Schäffler, K.; Steffens, S.; Schmaljohann, R.; Wiese, J.; Imhoff, J.F. Sorbifuranones A–C, sorbicillinoid metabolites from Penicillium strains isolated from Mediterranean sponges. Tetrahedron, 2010, 66(52), 9894-9901.
[http://dx.doi.org/10.1016/j.tet.2010.10.057]
[49]
Chen, H.; Aktas, N.; Konuklugil, B.; Mandi, A.; Daletos, G.; Lin, W.; Dai, H.; Kurtan, T.; Proksch, P. A new fusarielin analogue from Penicillium sp. Isolated from the Mediterranean sponge Ircinia oros. Tetrahedron Lett., 2015, 56(39), 5317-5320.
[http://dx.doi.org/10.1016/j.tetlet.2015.07.072]
[50]
Wang, Y.; Lin, X.P.; Ju, Z.R.; Liao, X.J.; Huang, X.J.; Zhang, C.; Zhao, B.X.; Xu, S.H. Aspergchromones A and B, two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03. J. Asian Nat. Prod. Res., 2017, 19(7), 684-690.
[http://dx.doi.org/10.1080/10286020.2016.1231673 ] [PMID: 28276769]
[51]
Tian, Y.Q.; Lin, X.P.; Wang, Z.; Zhou, X.F.; Qin, X.C.; Kaliyaperumal, K.; Zhang, T.Y.; Tu, Z.C.; Liu, Y. Asteltoxins with antiviral activities from the marine sponge-derived fungus Aspergillus sp. SCSIO XWS02F40. Molecules, 2015, 21(1)E34
[http://dx.doi.org/10.3390/molecules21010034] [PMID: 26712735]
[52]
Buttachon, S.; May Zin, W.W.; Dethoup, T.; Gales, L.; Pereira, J.A.; Silva, A.M.; Kijjoa, A. Secondary metabolites from the culture of the marine sponge-associated fungi Talaromyces tratensis and Sporidesmium circinophorum. Planta Med., 2016, 82, 888-896.
[http://dx.doi.org/10.1055/s-0042-103687]
[53]
Long, H.; Cheng, Z.; Huang, W.; Wu, Q.; Li, X.; Cui, J.; Proksch, P.; Lin, W. Diasteltoxins A-C, asteltoxin-based dimers from a mutant of the sponge-associated Emericella variecolor fungus. Org. Lett., 2016, 18(18), 4678-4681.
[http://dx.doi.org/10.1021/acs.orglett.6b02313] [PMID: 27571434]
[54]
Zhao, Y.; Liu, D.; Proksch, P.; Yu, S.; Lin, W. Isocoumarin derivatives from the sponge‐associated fungus Peyronellaea glomerata with antioxidant activities. Chem. Biodivers., 2016, 13(9), 1186-1193.
[http://dx.doi.org/10.1002/cbdv.201600012] [PMID: 27450949]
[55]
Zhao, D.L.; Shao, C.L.; Wang, C.Y.; Wang, M.; Yang, L.J.; Wang, C.Y. Naphthalenones and depsidones from a sponge-derived strain of the fungus Corynespora cassiicola. Molecules, 2016, 21(2), 160.
[http://dx.doi.org/10.3390/molecules21020160] [PMID: 26828473]
[56]
Prompanya, C.; Dethoup, T.; Gales, L.; Lee, M.; Pereira, J.A.C.; Silva, A.M.S.; Pinto, M.M.M.; Kijjoa, A. New polyketides and new benzoic acid derivatives from the marine sponge-associated fungus Neosartorya quadricincta KUFA 0081. Mar. Drugs, 2016, 14(7), 134.
[http://dx.doi.org/10.3390/md14070134] [PMID: 27438842]
[57]
Suzue, M.; Kikuchi, T.; Tanaka, R.; Yamada, T. Tandyukisins E and F, Novel cytotoxic decalin derivatives isolated from a marine sponge-derived fungus. Tetrahedron Lett., 2016, 57(46), 5070-5073.
[http://dx.doi.org/10.1016/j.tetlet.2016.10.004]
[58]
Gu, B.B.; Tang, J.; Wang, S.P.; Sun, F.; Yang, F.; Li, L.; Xu, Y.; Lin, H.W. .Structure, absolute configuration, and variabletemperature 1H-NMR study of (±)-versiorcinols A–C, three racemates of diorcinol monoethers from the sponge-associated fungus Aspergillus versicolor 16F-11 RSC Adv., 2017, 7(79), 50254-50263..
[59]
Fang, F.; Zhao, J.; Ding, L.; Huang, C.; Naman, C.B.; He, S.; Wu, B.; Zhu, P.; Luo, Q.; Gerwick, W.H.; Yan, X.; Wang, Q.; Zhang, Z.; Cui, W. 5-Hydroxycyclopenicillone, a new beta-amyloid fibrillization inhibitor from a sponge-derived fungus Trichoderma sp. HPQJ-34. Mar. Drugs, 2017, 15(8), 260.
[http://dx.doi.org/10.3390/md15080260] [PMID: 28825620]
[60]
Kumla, D.; Shine Aung, T.; Buttachon, S.; Dethoup, T.; Gales, L.; Pereira, J.A.; Inácio, Â.; Costa, P.M.; Lee, M.; Sekeroglu, N.; Silva, A.M.S.; Pinto, M.M.M.; Kijjoa, A. A new dihydrochromone dimer and other secondary metabolites from cultures of the marine sponge-associated fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213. Mar. Drugs, 2017, 15(12), 375.
[http://dx.doi.org/10.3390/md15120375] [PMID: 29194412]
[61]
Noinart, J.; Buttachon, S.; Dethoup, T.; Gales, L.; Pereira, J.A.; Urbatzka, R.; Freitas, S.; Lee, M.; Silva, A.M.S.; Pinto, M.M.M.; Vasconcelos, V.; Kijjoa, A. A new ergosterol analog, a new bis-anthraquinone and anti-obesity activity of anthraquinones from the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. Mar. Drugs, 2017, 15(5), 139.
[http://dx.doi.org/10.3390/md15050139] [PMID: 28509846]
[62]
Zhao, Y.; Liu, D.; Proksch, P.; Yu, S.; Lin, W. Angupyrones A-E, α-pyrone analogues with ARE-activation from a sponge-associated fungus Truncatella angustata. Chem. Biodivers., 2017, 14(9)e1700236
[http://dx.doi.org/10.1002/cbdv.201700236] [PMID: 28599098]
[63]
Küppers, L.; Ebrahim, W.; El-Neketi, M.; Özkaya, F.C.; Mándi, A.; Kurtán, T.; Orfali, R.S.; Müller, W.E.G.; Hartmann, R.; Lin, W.; Song, W.; Liu, Z.; Proksch, P. Lactones from the sponge-derived fungus Talaromyces rugulosus. Mar. Drugs, 2017, 15(11), 359.
[http://dx.doi.org/10.3390/md15110359] [PMID: 29135916]
[64]
Liu, S.; Wang, H.; Su, M.; Hwang, G.J.; Hong, J.; Jung, J.H. New metabolites from the sponge-derived fungus Aspergillus sydowii J05B-7F-4. Nat. Prod. Res., 2017, 31(14), 1682-1686.
[http://dx.doi.org/10.1080/14786419.2017.1289205 ] [PMID: 28278674]
[65]
Wu, Z.; Li, Y.; Liu, D.; Ma, M.; Chen, J.; Lin, W. New resorcinol derivatives from a sponge-derived fungus Hansfordia sinuosae. Chem. Biodivers., 2017, 14(6)e1700059
[http://dx.doi.org/10.1002/cbdv.201700059] [PMID: 28374459]
[66]
Lei, H.; Lin, X.; Han, L.; Ma, J.; Dong, K.; Wang, X.; Zhong, J.; Mu, Y.; Liu, Y.; Huang, X. Polyketide derivatives from a marine-sponge-associated fungus Pestalotiopsis heterocornis. Phytochemistry, 2017, 142, 51-59.
[http://dx.doi.org/10.1016/j.phytochem.2017.06.009 ] [PMID: 28675830]
[67]
Wu, Z.H.; Li, Y.; Li, Y.; Ma, M.; Chen, J.L. Salicylic acid derivatives and phenylspirodrimanes from the sponge-associated fungus Hansfordia sinuosae. J. Asian Nat. Prod. Res., 2018, 20(10), 985-991.
[http://dx.doi.org/10.1080/10286020.2017.1367924 ] [PMID: 28832193]
[68]
Leman-Loubière, C.; Le Goff, G.; Retailleau, P.; Debitus, C.; Ouazzani, J. Sporothriolide-related compounds from the fungus Hypoxylon monticulosum CLL-205 isolated from a Sphaerocladina sponge from the Tahiti Coast. J. Nat. Prod., 2017, 80(10), 2850-2854.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00714] [PMID: 29043802]
[69]
Liu, J.T.; Wu, W.; Cao, M.J.; Yang, F.; Lin, H.W. Trienic α-pyrone and ochratoxin derivatives from a sponge-derived fungus Aspergillus ochraceopetaliformis. Nat. Prod. Res., 2018, 32(15), 1791-1797.
[http://dx.doi.org/10.1080/14786419.2017.1402325 ] [PMID: 29130337]
[70]
Pang, X.; Lin, X.; Tian, Y.; Liang, R.; Wang, J.; Yang, B.; Zhou, X.; Kaliyaperumal, K.; Luo, X.; Tu, Z.; Liu, Y. Three new polyketides from the marine sponge-derived fungus Trichoderma sp. SCSIO41004. Nat. Prod. Res., 2018, 32(1), 105-111.
[http://dx.doi.org/10.1080/14786419.2017.1338286 ] [PMID: 28592143]
[71]
Qiu, P.; Ding, L.; Su, D.; Shan, H. A new cyclopentenone derivative from the sponge-associated fungus Hypocrea koningii. Chem. Nat. Compd., 2018, 54(4), 631-633.
[http://dx.doi.org/10.1007/s10600-018-2433-9]
[72]
Gu, B.B.; Wu, Y.; Tang, J.; Jiao, W.H.; Li, L.; Sun, F.; Wang, S.P.; Yang, F.; Lin, H.W. Azaphilone and isocoumarin derivatives from the sponge-derived fungus Eupenicillium sp. 6A-9. Tetrahedron Lett., 2018, 59(36), 3345-3348.
[http://dx.doi.org/10.1016/j.tetlet.2018.06.057]
[73]
Kumla, D.; Pereira, J.A.; Dethoup, T.; Gales, L.; Freitas-Silva, J.; Costa, P.M.; Lee, M.; Silva, A.M.S.; Sekeroglu, N.; Pinto, M.M.M.; Kijjoa, A. Chromone derivatives and other constituents from cultures of the marine sponge-associated fungus Penicillium erubescens KUFA0220 and their antibacterial activity. Mar. Drugs, 2018, 16(8), 289.
[http://dx.doi.org/10.3390/md16080289] [PMID: 30127313]
[74]
Zhen, X.; Gong, T.; Wen, Y.H.; Yan, D.J.; Chen, J.J.; Zhu, P. Chrysoxanthones A-C, three new xanthone-chromanone heterdimers from sponge-associated Penicillium chrysogenum HLS111 treated with histone deacetylase inhibitor. Mar. Drugs, 2018, 16(10), 357.
[http://dx.doi.org/10.3390/md16100357] [PMID: 30275353]
[75]
Sun, Y.; Liu, J.; Li, L.; Gong, C.; Wang, S.; Yang, F.; Hua, H.; Lin, H. New butenolide derivatives from the marine sponge-derived fungus Aspergillus terreus. Bioorg. Med. Chem. Lett., 2018, 28(3), 315-318.
[http://dx.doi.org/10.1016/j.bmcl.2017.12.049] [PMID: 29295795]
[76]
Zhang, P.P.; Song, S.; Lang, J.J.; Jia, C.X.; Yan, S.J.; Liu, L.; Chen, S.H.; Li, J. A new diphenolic metabolite isolated from the marine-derived fungus Aspergillus niger 102. J. Asian Nat. Prod. Res., 2019, 21(8), 813-819.
[http://dx.doi.org/10.1080/10286020.2018.1488830 ] [PMID: 29962231]
[77]
Wu, Z.; Liu, D.; Huang, J.; Proksch, P.; Zhu, K.; Lin, W. Hansforesters A–M, polyesters from the sponge-associated fungus Hansfordia sinuosae with antibacterial activities. RSC Adv., 2018, 8(69), 39756-39768.
[http://dx.doi.org/10.1039/C8RA08606K]
[78]
Wang, J.; Xu, C.C.; Tang, H.; Su, L.; Chou, Y.; Soong, K.; Li, J.; Zhuang, C.L.; Luo, Y.P.; Zhang, W. Osteoclastogenesis inhibitory polyketides from the sponge-associated fungus Xylaria feejeensis. Chem. Biodivers., 2018, 15(12)e1800358
[http://dx.doi.org/10.1002/cbdv.201800358] [PMID: 30295992]
[79]
Wang, C.Y.; Hao, J.D.; Ning, X.Y.; Wu, J.S.; Zhao, D.L.; Kong, C.J.; Shao, C.L.; Wang, C.Y. Penicilazaphilones D and E: two new azaphilones from a sponge-derived strain of the fungus Penicillium sclerotiorum. RSC Adv., 2018, 8(8), 4348-4353.
[http://dx.doi.org/10.1039/C7RA13327H]
[80]
Liu, Y.; Ding, L.; Fang, F.; He, S. Penicillilactone A, a novel antibacterial 7-membered lactone derivative from the sponge-associated fungus Penicillium sp. LS54. Nat. Prod. Res., 2019, 33(17), 2466-2470.
[http://dx.doi.org/10.1080/14786419.2018.1452012 ] [PMID: 29553833]
[81]
Pang, X.; Lin, X.; Wang, P.; Zhou, X.; Yang, B.; Wang, J.; Liu, Y. Perylenequione derivatives with anticancer activities isolated from the marine sponge-derived fungus, Alternaria sp. SCSIO41014. Mar. Drugs, 2018, 16(8), 280.
[http://dx.doi.org/10.3390/md16080280] [PMID: 30110969]
[82]
Zhang, J.; Yang, Z.; Liang, Y.; Zhong, L.; Lin, H.; Zhong, B.; Li, L.; Xu, S.; Liu, Y. Four new C9 metabolites from the sponge-associated Fungus Gliomastix sp. ZSDS1-F7-2. Mar. Drugs, 2018, 16(7), 231.
[http://dx.doi.org/10.3390/md16070231] [PMID: 29987219]
[83]
Tian, Y.; Lin, X.; Zhou, X.; Liu, Y. Phenol derivatives from the sponge-derived fungus Didymellaceae sp. SCSIO F46. Front Chem., 2018, 6, 536.
[http://dx.doi.org/10.3389/fchem.2018.00536] [PMID: 30443544]
[84]
Du, X.; Liu, D.; Huang, J.; Zhang, C.; Proksch, P.; Lin, W. Polyketide derivatives from the sponge associated fungus Aspergillus europaeus with antioxidant and NO inhibitory activities. Fitoterapia, 2018, 130, 190-197.
[http://dx.doi.org/10.1016/j.fitote.2018.08.030] [PMID: 30193789]
[85]
Tian, Y.Q.; Lin, S.T.; Kumaravel, K.; Zhou, H.; Wang, S.Y.; Liu, Y.H. Polyketide-derived metabolites from the sponge-derived fungus Aspergillus sp. F40. Phytochem. Lett., 2018, 27, 74-77.
[http://dx.doi.org/10.1016/j.phytol.2018.06.009]
[86]
Meng, J.; Cheng, W.; Heydari, H.; Wang, B.; Zhu, K.; Konuklugil, B.; Lin, W. Sorbicillinoid-based Metabolites from a sponge-derived fungus Trichoderma saturnisporum. Mar. Drugs, 2018, 16(7), 226.
[http://dx.doi.org/10.3390/md16070226] [PMID: 29973484]
[87]
Pang, X.; Lin, X.; Yang, J.; Zhou, X.; Yang, B.; Wang, J.; Liu, Y. Spiro-phthalides and isocoumarins isolated from the marine sponge-derived fungus Setosphaeria sp. SCSIO41009. J. Nat. Prod., 2018, 81(8), 1860-1868.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00345] [PMID: 30091601]
[88]
Pang, X.; Lin, X.; Wang, J.; Liang, R.; Tian, Y.; Salendra, L.; Luo, X.; Zhou, X.; Yang, B.; Tu, Z.; Liu, Y. Three new highly oxygenated sterols and one new dihydroisocoumarin from the marine sponge-derived fungus Cladosporium sp. SCSIO41007. Steroids, 2018, 129, 41-46.
[http://dx.doi.org/10.1016/j.steroids.2017.12.001 ] [PMID: 29223616]
[89]
Ding, L.; Li, T.; Liao, X.; He, S.; Xu, S. Asperitaconic acids A-C, antibacterial itaconic acid derivatives produced by a marine-derived fungus of the genus Aspergillus. J. Antibiot. (Tokyo), 2018, 71(10), 902-904.
[http://dx.doi.org/10.1038/s41429-018-0079-2] [PMID: 29973682]
[90]
Ding, L.; Xu, P.; Li, T.; Liao, X.; He, S.; Xu, S. Asperfurandiones A and B, two antifungal furandione analogs from a marine-derived fungus Aspergillus versicolor. Nat. Prod. Res., 2019, 33(23), 3404-3408.
[http://dx.doi.org/10.1080/14786419.2018.1480622 ] [PMID: 29806501]
[91]
Gong, T.; Zhen, X.; Li, B.J.; Yang, J.L.; Zhu, P. Two new monoterpenoid α-pyrones from a fungus Nectria sp. HLS206 associated with the marine sponge Gelliodes carnosa. J. Asian Nat. Prod. Res., 2015, 17(6), 633-637.
[http://dx.doi.org/10.1080/10286020.2015.1040778 ] [PMID: 26001271]
[92]
Cohen, E.; Koch, L.; Thu, K.M.; Rahamim, Y.; Aluma, Y.; Ilan, M.; Yarden, O.; Carmeli, S. Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel. Bioorg. Med. Chem., 2011, 19(22), 6587-6593.
[http://dx.doi.org/10.1016/j.bmc.2011.05.045] [PMID: 21676619]
[93]
Yang, Z.; Si, L.; Liu, D.; Peter, P.; Zhou, D.; Lin, W. Truncateols A–N, new isoprenylated cyclohexanols from the sponge-associated fungus Truncatella angustata with anti-H1N1 virus activities. Tetrahedron, 2015, 71(18), 2708-2718.
[http://dx.doi.org/10.1016/j.tet.2015.03.033]
[94]
Sun, L.L.; Shao, C.L.; Chen, J.F.; Guo, Z.Y.; Fu, X.M.; Chen, M.; Chen, Y.Y.; Li, R.; de Voogd, N.J.; She, Z.G.; Lin, Y.C.; Wang, C.Y. New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from the sponge Xestospongia testudinaria. Bioorg. Med. Chem. Lett., 2012, 22(3), 1326-1329.
[http://dx.doi.org/10.1016/j.bmcl.2011.12.083] [PMID: 22225637]
[95]
Julianti, E.; Oh, H.; Jang, K.H.; Lee, J.K.; Lee, S.K.; Oh, D.C.; Oh, K.B.; Shin, J. Acremostrictin, a highly oxygenated metabolite from the marine fungus Acremonium strictum. J. Nat. Prod., 2011, 74(12), 2592-2594.
[http://dx.doi.org/10.1021/np200707y] [PMID: 22136576]
[96]
Li, D.; Xu, Y.; Shao, C.L.; Yang, R.Y.; Zheng, C.J.; Chen, Y.Y.; Fu, X.M.; Qian, P.Y.; She, Z.G.; de Voogd, N.J.; Wang, C.Y. Antibacterial bisabolane-type sesquiterpenoids from the sponge-derived fungus Aspergillus sp. Mar. Drugs, 2012, 10(1), 234-241.
[http://dx.doi.org/10.3390/md10010234] [PMID: 22363233]
[97]
Acirc; Pinheiro, n.; Dethoup, T.; Bessa, J.; Silva, A.M.S.; Kijjoa, A. A new bicyclic sesquiterpene from the marine sponge associated fungus Emericellopsis minima. Phytochem. Lett., 2012, 5(1), 68-70.
[http://dx.doi.org/10.1016/j.phytol.2011.10.002]
[98]
Zhu, H.; Hua, X.X.; Gong, T.; Pang, J.; Hou, Q.; Zhu, P. Hypocreaterpenes A and B, cadinane-type sesquiterpenes from a marine-derived fungus, Hypocreales sp. Phytochem. Lett., 2013, 6(3), 392-396.
[http://dx.doi.org/10.1016/j.phytol.2013.04.008]
[99]
Wu, Z.; Liu, D.; Proksch, P.; Guo, P.; Lin, W. Punctaporonins H-M: caryophyllene-type sesquiterpenoids from the sponge-associated fungus Hansfordia sinuosae. Mar. Drugs, 2014, 12(7), 3904-3916.
[http://dx.doi.org/10.3390/md12073904] [PMID: 24983636]
[100]
Wang, J.F.; Lin, X.P.; Qin, C.; Liao, S.R.; Wan, J.T.; Zhang, T.Y.; Liu, J.; Fredimoses, M.; Chen, H.; Yang, B.; Zhou, X.F.; Yang, X.W.; Tu, Z.C.; Liu, Y.H. Antimicrobial and antiviral sesquiterpenoids from sponge-associated fungus, Aspergillus sydowii ZSDS1-F6. J. Antibiot. (Tokyo), 2014, 67(8), 581-583.
[http://dx.doi.org/10.1038/ja.2014.39] [PMID: 24736857]
[101]
Liu, Y.; Li, X.M.; Meng, L.H.; Jiang, W.L.; Xu, G.M.; Huang, C.G.; Wang, B.G. Bisthiodiketopiperazines and acorane sesquiterpenes produced by the marine-derived fungus Penicillium adametzioides AS-53 on different culture media. J. Nat. Prod., 2015, 78(6), 1294-1299.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00102] [PMID: 26039736]
[102]
Liu, S.; Dai, H.; Konuklugil, B.; Orfali, R.S.; Lin, W.; Kalscheuer, R.; Liu, Z.; Proksch, P. Phenolic bisabolanes from the sponge-derived fungus Aspergillus sp. Phytochem. Lett., 2016, 18, 187-191.
[http://dx.doi.org/10.1016/j.phytol.2016.10.015]
[103]
Yong, L.; Dong, L.; Cheng, Z.; Proksch, P.; Lin, W. Cytotoxic trichothecene-type sesquiterpenes from the sponge-derived fungus Stachybotrys chartarum with tyrosine kinase inhibition. RSC Adv., 2017, 7(12), 7259-7267.
[http://dx.doi.org/10.1039/C6RA26956G]
[104]
Yamada, T.; Suzue, M.; Arai, T.; Kikuchi, T.; Tanaka, R. Trichodermanins C-E, new diterpenes with a fused 6-5-6-6 ring system produced by a marine sponge-derived fungus. Mar. Drugs, 2017, 15(6), 169.
[http://dx.doi.org/10.3390/md15060169] [PMID: 28598397]
[105]
Liu, H.B.; Edrada-Ebel, R.A.; Ebel, R.; Wang, Y.; Schulz, B.; Draeger, S.; Müller, W.E.G.; Wray, V.; Lin, W.H.; Proksch, P. Ophiobolin sesterterpenoids and pyrrolidine alkaloids from the sponge-derived fungus Aspergillus ustus. Helv. Chim. Acta, 2011, 94(4), 623-631.
[http://dx.doi.org/10.1002/hlca.201000283]
[106]
Zhou, Y.; Mándi, A.; Debbab, A.; Wray, V.; Schulz, B.; Müller, W.E.G.; Lin, W.H.; Proksch, P.; Kurtán, T.; Aly, A.H. New austalides from the sponge-associated fungus Aspergillus sp. Eur. J. Org. Chem., 2011, 2011(30), 6009-6019.
[http://dx.doi.org/10.1002/ejoc.201100670]
[107]
Zhang, G.; Wu, G.; Zhu, T.; Kurtán, T.; Mándi, A.; Jiao, J.; Li, J.; Qi, X.; Gu, Q.; Li, D. Meroterpenoids with diverse ring systems from the sponge-associated fungus Alternaria sp. JJY-32. J. Nat. Prod., 2013, 76(10), 1946-1957.
[http://dx.doi.org/10.1021/np4005757] [PMID: 24128115]
[108]
Ma, X.; Li, L.; Zhu, T.; Ba, M.; Li, G.; Gu, Q.; Guo, Y.; Li, D. Phenylspirodrimanes with anti-HIV activity from the sponge-derived fungus Stachybotrys chartarum MXH-X73. J. Nat. Prod., 2013, 76(12), 2298-2306.
[http://dx.doi.org/10.1021/np400683h] [PMID: 24308675]
[109]
Li, Y.; Wu, C.; Liu, D.; Proksch, P.; Guo, P.; Lin, W. Chartarlactams A-P, phenylspirodrimanes from the sponge-associated fungus Stachybotrys chartarum with antihyperlipidemic activities. J. Nat. Prod., 2014, 77(1), 138-147.
[http://dx.doi.org/10.1021/np400824u] [PMID: 24387683]
[110]
Gomes, N.M.; Bessa, L.J.; Buttachon, S.; Costa, P.M.; Buaruang, J.; Dethoup, T.; Silva, A.M.S.; Kijjoa, A. Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi Neosartorya paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis. Mar. Drugs, 2014, 12(2), 822-839.
[http://dx.doi.org/10.3390/md12020822] [PMID: 24477284]
[111]
Zhou, Y.; Debbab, A.; Wray, V.; Lin, W.H.; Schulz, B.; Trepos, R.; Pile, C.; Hellio, C.; Proksch, P.; Aly, A.H. Marine bacterial inhibitors from the sponge‐derived fungus Aspergillus sp. Tetrahedron Lett., 2014, 55(17), 2789-2792.
[http://dx.doi.org/10.1016/j.tetlet.2014.02.062]
[112]
Lin, Z.; Ma, X.; Wei, H.; Li, D.; Gu, Q.; Zhu, T. Spicarins A–D from acetylated extract of fungus Spicaria elegans KLA03. RSC Adv., 2015, 5(44), 35262-35266.
[http://dx.doi.org/10.1039/C5RA01923K]
[113]
Suciati; Fraser, J.A.; Lambert, L.K.; Pierens, G.K.; Bernhardt, P.V.; Garson, M.J. Secondary metabolites of the sponge-derived fungus Acremonium persicinum. J. Nat. Prod., 2013, 76(8), 1432-1440.
[http://dx.doi.org/10.1021/np4002114] [PMID: 23883432]
[114]
Peng, J.; Zhang, X.; Wang, W.; Zhu, T.; Gu, Q.; Li, D. Austalides S-U, new meroterpenoids from the sponge-derived fungus Aspergillus aureolatus HDN14-107. Mar. Drugs, 2016, 14(7), 131.
[http://dx.doi.org/10.3390/md14070131] [PMID: 27428982]
[115]
Gu, B.B.; Wei, W.; Liu, L.Y.; Jie, T.; Zeng, Y.J.; Wang, S.P.; Fan, S.; Lei, L.; Fan, Y.; Lin, H.W. 3, 5‐dimethylorsellinic acid derived meroterpenoids from Eupenicillium sp. 6A‐9, a fungus isolated from the marine sponge Plakortis simplex. Eur. J. Org. Chem., 2018, 2018, 48-59.
[http://dx.doi.org/10.1002/ejoc.201701335]
[116]
Dong, L.; Yong, L.; Li, X.; Cheng, Z.; Jian, H.; Proksch, P.; Lin, W. Chartarolides A-C, novel meroterpenoids with antitumor activities. Tetrahedron Lett., 2017, 58(19), 1826-1829.
[http://dx.doi.org/10.1016/j.tetlet.2017.03.079]
[117]
Elissawy, A.M.; Ebada, S.S.; Ashour, M.L.; Özkaya, F.C.; Ebrahim, W.; Singab, A.N.B.; Proksch, P. Spiroarthrinols a and B, two novel meroterpenoids isolated from the sponge-derived fungus Arthrinium sp. Phytochem. Lett., 2017, 20, 246-251.
[http://dx.doi.org/10.1016/j.phytol.2017.05.008]
[118]
Zhang, J.; Yuan, B.; Liu, D.; Gao, S.; Proksch, P.; Lin, W. Brasilianoids A–F, new meroterpenoids from the sponge-associated fungus Penicillium brasilianum. Front Chem., 2018, 6, 314.
[http://dx.doi.org/10.3389/fchem.2018.00314] [PMID: 30101144]
[119]
Shin, H.J.; Choi, B.K.; Trinh, P.T.H.; Lee, H.S.; Kang, J.S.; Van, T.T.T.; Lee, H.S.; Lee, J.S.; Lee, Y.J.; Lee, J. Suppression of RANKL-induced osteoclastogenesis by the metabolites from the marine fungus Aspergillus flocculosus isolated from a sponge Stylissa sp. Mar. Drugs, 2018, 16(1), 14.
[http://dx.doi.org/10.3390/md16010014] [PMID: 29304006]
[120]
Zhao, Y.; Liu, D.; Proksch, P.; Zhou, D.; Lin, W. Truncateols O-V, further isoprenylated cyclohexanols from the sponge-associated fungus Truncatella angustata with antiviral activities. Phytochemistry, 2018, 155, 61-68.
[http://dx.doi.org/10.1016/j.phytochem.2018.07.017 ] [PMID: 30077121]
[121]
Özkaya, F.C.; Ebrahim, W.; Klopotowski, M.; Liu, Z.; Janiak, C.; Proksch, P. Isolation and X-ray structure analysis of citreohybridonol from marine-derived Penicillium atrovenetum. Nat. Prod. Res., 2018, 32(7), 840-843.
[http://dx.doi.org/10.1080/14786419.2017.1311893 ] [PMID: 28391714]
[122]
Zhou, Y.; Debbab, A.; Mándi, A.; Wray, V.; Schulz, B.; Müller, W.E.G.; Kassack, M.; Lin, W.H.; Kurtán, T.; Proksch, P. Alkaloids from the sponge-associated fungus Aspergillus sp. Eur. J. Org. Chem., 2013, 2013(5), 894-906.
[http://dx.doi.org/10.1002/ejoc.201201220]
[123]
Liu, Y.; Li, X.M.; Meng, L.H.; Wang, B.G. N-Formyllapatin A, a new N-formylspiroquinazoline derivative from the marine-derived fungus Penicillium adametzioides AS-53. Phytochem. Lett., 2014, 10, 145-148.
[http://dx.doi.org/10.1016/j.phytol.2014.08.018]
[124]
Ma, X.; Peng, J.; Wu, G.; Zhu, T.; Li, G.; Gu, Q.; Li, D. Speradines B-D, oxygenated cyclopiazonic acid alkaloids from the sponge-derived fungus Aspergillus flavus MXH-X104. Tetrahedron, 2015, 71(21), 3522-3527.
[http://dx.doi.org/10.1016/j.tet.2015.03.050]
[125]
Almeida, C.; Part, N.; Bouhired, S.; Kehraus, S.; König, G.M. Stachylines A-D from the sponge-derived fungus Stachylidium sp. J. Nat. Prod., 2011, 74(1), 21-25.
[http://dx.doi.org/10.1021/np1005345] [PMID: 21162532]
[126]
Almeida, C.; Hemberger, Y.; Schmitt, S.M.; Bouhired, S.; Natesan, L.; Kehraus, S.; Dimas, K.; Gütschow, M.; Bringmann, G.; König, G.M. Marilines A-C: novel phthalimidines from the sponge-derived fungus Stachylidium sp. Chemistry, 2012, 18(28), 8827-8834.
[http://dx.doi.org/10.1002/chem.201103278] [PMID: 22711513]
[127]
Li, Y.; Liu, D.; Shan, C.; Peter, P.; Lin, W. Isoindolinone-type alkaloids from the sponge-derived fungus Stachybotrys chartarum. Tetrahedron, 2014, 70(39), 7010-7015.
[http://dx.doi.org/10.1016/j.tet.2014.07.047]
[128]
Cao, Q.X.; Wei, J.H.; Deng, R.; Feng, G.K.; Zhu, X.F.; Lan, W.J.; Li, H.J. Two new pyripyropenes from the marine fungus Fusarium lateritium 2016F18‐1. Chem. Biodivers., 2017, 14(3)e1600298
[http://dx.doi.org/10.1002/cbdv.201600298] [PMID: 27804218]
[129]
Zhou, R.; Liao, X.; Li, H.; Li, J.; Feng, P.; Zhao, B.; Xu, S. Isolation and synthesis of misszrtine A: A novel indole alkaloid from marine sponge-associated Aspergillus sp. SCSIO XWS03F03. Front Chem., 2018, 6, 212.
[http://dx.doi.org/10.3389/fchem.2018.00212] [PMID: 29951479]
[130]
Buttachon, S.; Ramos, A.A.; Inácio, Â.; Dethoup, T.; Gales, L.; Lee, M.; Costa, P.M.; Silva, A.M.S.; Sekeroglu, N.; Rocha, E.; Pinto, M.M.M.; Pereira, J.A.; Kijjoa, A. Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus Aspergillus candidus KUFA0062. Mar. Drugs, 2018, 16(4), 119.
[http://dx.doi.org/10.3390/md16040119] [PMID: 29642369]
[131]
Gu, B.B.; Jiao, F.R.; Wu, W.; Jiao, W.H.; Li, L.; Sun, F.; Wang, S.P.; Yang, F.; Lin, H.W. Preussins with inhibition of IL-6 expression from Aspergillus flocculosus 16D-1, a fungus isolated from the marine sponge Phakellia fusca. J. Nat. Prod., 2018, 81(10), 2275-2281.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00662] [PMID: 30350993]
[132]
Tian, Y.Q.; Lin, S.N.; Zhou, H.; Lin, S.T.; Wang, S.Y.; Liu, Y.H. Protuboxepin C and protuboxepin D from the sponge-derived fungus Aspergillus sp. SCSIO XWS02F40. Nat. Prod. Res., 2018, 32(21), 2510-2515.
[http://dx.doi.org/10.1080/14786419.2017.1423303 ] [PMID: 29313378]
[133]
Chen, Y.; Chen, R.; Xu, J.; Tian, Y.; Xu, J.; Liu, Y. Two new altenusin/thiazole hybrids and a new benzothiazole derivative from the marine sponge-derived fungus Alternaria sp. SCSIOS02F49. Molecules, 2018, 23(11), 2844.
[http://dx.doi.org/10.3390/molecules23112844] [PMID: 30388842]
[134]
Yin, J.; Zhang, C.; Huang, J.; Zhang, J.; Dong, L.; Jian, H.; Proksch, P.; Lin, W. Violaceimides A-E, sulfur-containing metabolites from a sponge-associated fungus Aspergillus violaceus. Tetrahedron Lett., 2018, 59(33), 3157-3160.
[http://dx.doi.org/10.1016/j.tetlet.2018.05.085]
[135]
Pruksakorn, P.; Arai, M.; Kotoku, N.; Vilchèze, C.; Baughn, A.D.; Moodley, P.; Jacobs, W.R., Jr; Kobayashi, M. Trichoderins, novel aminolipopeptides from a marine sponge-derived Trichoderma sp., are active against dormant mycobacteria. Bioorg. Med. Chem. Lett., 2010, 20(12), 3658-3663.
[http://dx.doi.org/10.1016/j.bmcl.2010.04.100] [PMID: 20483615]
[136]
Panizel, I.; Yarden, O.; Ilan, M.; Carmeli, S. Eight new peptaibols from sponge-associated Trichoderma atroviride. Mar. Drugs, 2013, 11(12), 4937-4960.
[http://dx.doi.org/10.3390/md11124937] [PMID: 24335521]
[137]
Kawahara, T.; Takagi, M.; Shin-Ya, K. Three new depsipeptides, JBIR-113, JBIR-114 and JBIR-115, isolated from a marine sponge-derived Penicillium sp. fS36. J. Antibiot. (Tokyo), 2012, 65(3), 147-150.
[http://dx.doi.org/10.1038/ja.2011.126] [PMID: 22186594]
[138]
El Maddah, F.; Kehraus, S.; Nazir, M.; Almeida, C.; König, G.M. Insights into the biosynthetic origin of 3-(3-Furyl)alanine in Stachylidium sp. 293 K04 tetrapeptides. J. Nat. Prod., 2016, 79(11), 2838-2845.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00601] [PMID: 27786475]
[139]
Ding, L.J.; Yuan, W.; Liao, X.J.; Han, B.N.; Wang, S.P.; Li, Z.Y.; Xu, S.H.; Zhang, W.; Lin, H.W. Oryzamides A-E, cyclodepsipeptides from the sponge-derived fungus Nigrospora oryzae PF18. J. Nat. Prod., 2016, 79(8), 2045-2052.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00349] [PMID: 27489998]
[140]
May Zin, W.W.; Buttachon, S.; Dethoup, T.; Fernandes, C.; Cravo, S.; Pinto, M.M.M.; Gales, L.; Pereira, J.A.; Silva, A.M.S.; Sekeroglu, N.; Kijjoa, A. New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702. Mar. Drugs, 2016, 14(7), 136.
[http://dx.doi.org/10.3390/md14070136] [PMID: 27447650]
[141]
Liu, J.; Gu, B.; Yang, L.; Yang, F.; Lin, H. New anti-inflammatory cyclopeptides from a sponge-derived fungus Aspergillus violaceofuscus. Front Chem., 2018, 6, 226.
[http://dx.doi.org/10.3389/fchem.2018.00226] [PMID: 29963550]
[142]
Elsebai, M.F.; Rempel, V.; Schnakenburg, G.; Kehraus, S.; Müller, C.E.; König, G.M. Identification of a potent and selective cannabinoid CB1 receptor antagonist from Auxarthron reticulatum. ACS Med. Chem. Lett., 2011, 2(11), 866-869.
[http://dx.doi.org/10.1021/ml200183z] [PMID: 24900275]
[143]
Gomes, N.M.; Dethoup, T.; Singburaudom, N.; Gales, L.; Silva, A.M.S.; Kijjoa, A. Eurocristatine, a new diketopiperazine dimer from the marine sponge-associated fungus Eurotium cristatum. Phytochem. Lett., 2012, 5(4), 717-720.
[http://dx.doi.org/10.1016/j.phytol.2012.07.010]
[144]
Chen, C.J.; Zhou, Y.Q.; Liu, X.X.; Zhang, W.J.; Hu, S.S.; Lin, L.P.; Huo, G.M.; Jiao, R.H.; Tan, R.; Ge, H.M. Antimicrobial and anti-inflammatory compounds from a marine fungus Pleosporales sp. Tetrahedron Lett., 2015, 56(45), 6183-6189.
[http://dx.doi.org/10.1016/j.tetlet.2015.09.079]
[145]
Yan, B.F.; Fang, S.T.; Li, W.Z.; Liu, S.J.; Wang, J.H.; Xia, C.H. A new minor diketopiperazine from the sponge-derived fungus Simplicillium sp. YZ-11. Nat. Prod. Res., 2015, 29(21), 2013-2017.
[http://dx.doi.org/10.1080/14786419.2015.1027890 ] [PMID: 25835596]
[146]
Cho, K.H.; Sohn, J.H.; Oh, H. Isolation and structure determination of a new diketopiperazine dimer from marine-derived fungus Aspergillus sp. SF-5280. Nat. Prod. Res., 2018, 32(2), 214-221.
[http://dx.doi.org/10.1080/14786419.2017.1346642 ] [PMID: 28670919]
[147]
Li, B.; Huang, Q.X.; Gao, D.; Liu, D.; Ji, Y.B.; Liu, H.G.; Lin, W.H. New C13 lipids from the marine-derived fungus Trichoderma harzianum. J. Asian Nat. Prod. Res., 2015, 17(5), 468-474.
[http://dx.doi.org/10.1080/10286020.2015.1042371 ] [PMID: 26031203]
[148]
Li, J.L.; Zhang, P.; Lee, Y.M.; Hong, J.; Yoo, E.S.; Bae, K.S.; Jung, J.H. Oxygenated hexylitaconates from a marine sponge-derived fungus Penicillium sp. Chem. Pharm. Bull. (Tokyo), 2011, 59(1), 120-123.
[http://dx.doi.org/10.1248/cpb.59.120] [PMID: 21212560]
[149]
Harms, H.; Kehraus, S.; Nesaei-Mosaferan, D.; Hufendieck, P.; Meijer, L.; König, G.M. Aβ-42 lowering agents from the marine-derived fungus Dichotomomyces cejpii. Steroids, 2015, 104, 182-188.
[http://dx.doi.org/10.1016/j.steroids.2015.09.012 ] [PMID: 26440473]
[150]
Gu, B.B.; Wu, W.; Jiao, F.R.; Jiao, W.H.; Li, L.; Sun, F.; Wang, S.P.; Yang, F.; Lin, H.W. Aspersecosteroids A and B, two 11(9→10)-abeo-5,10-secosteroids with a dioxatetraheterocyclic ring system from Aspergillus flocculosus 16D-1. Org. Lett., 2018, 20(24), 7957-7960.
[http://dx.doi.org/10.1021/acs.orglett.8b03530] [PMID: 30512956]
[151]
Kong, F.D.; Huang, X.L.; Ma, Q.Y.; Xie, Q.Y.; Wang, P.; Chen, P.W.; Zhou, L.M.; Yuan, J.Z.; Dai, H.F.; Luo, D.Q.; Zhao, Y.X. Helvolic acid derivatives with antibacterial activities against Streptococcus agalactiae from the marine-derived fungus Aspergillus fumigatus HNMF0047. J. Nat. Prod., 2018, 81(8), 1869-1876.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00382] [PMID: 30070829]
[152]
Ding, L.J.; Gu, B.B.; Jiao, W.H.; Yuan, W.; Li, Y.X.; Tang, W.Z.; Yu, H.B.; Liao, X.J.; Han, B.N.; Li, Z.Y.; Xu, S.H.; Lin, H.W. New furan and cyclopentenone derivatives from the sponge-associated fungus Hypocrea Koningii PF04. Mar. Drugs, 2015, 13(9), 5579-5592.
[http://dx.doi.org/10.3390/md13095579] [PMID: 26343687]
[153]
San-martin, A.; Rovirosa, J.; Vaca, I.; Vergara, K.; Acevedo, L.; Vina, D.; Orallo, F.; Chamy, M.C. New butyrolactone from a marine-derived fungus Aspergillus sp. J. Chil. Chem. Soc., 2010, 56(1), 625-627.
[http://dx.doi.org/10.4067/S0717-97072011000100023]
[154]
Wiese, J.; Ohlendorf, B.; Blümel, M.; Schmaljohann, R.; Imhoff, J.F. Phylogenetic identification of fungi isolated from the marine sponge Tethya aurantium and identification of their secondary metabolites. Mar. Drugs, 2011, 9(4), 561-585.
[http://dx.doi.org/10.3390/md9040561] [PMID: 21731550]
[155]
Ding, L.J.; Yuan, W.; Li, Y.X.; Liao, X.J.; Sun, H.; Peng, Q.; Han, B.N.; Lin, H.W.; Li, Z.Y.; Yang, F.; Xu, S.H. Hypocrol A, a new tyrosol derivative from a sponge-derived strain of the fungus Hypocrea koningii. Nat. Prod. Res., 2016, 30(14), 1633-1638.
[http://dx.doi.org/10.1080/14786419.2015.1129333 ] [PMID: 26828743]
[156]
Rotinsulu, H.; Yamazaki, H.; Sugai, S.; Iwakura, N.; Wewengkang, D.S.; Sumilat, D.A.; Namikoshi, M. Cladosporamide A, a new protein tyrosine phosphatase 1B inhibitor, produced by an Indonesian marine sponge-derived Cladosporium sp. J. Nat. Med., 2018, 72(3), 779-783.
[http://dx.doi.org/10.1007/s11418-018-1193-y] [PMID: 29508256]