An Updated Review of Secondary Metabolites from Marine Fungi

Page: [602 - 642] Pages: 41

  • * (Excluding Mailing and Handling)

Abstract

Marine fungi are valuable and richest sources of novel natural products for medicinal and pharmaceutical industries. Nutrient depletion, competition or any other type of metabolic stress which limits marine fungal growth promotes the formation and secretion of secondary metabolites. Generally secondary metabolites can be produced by many different metabolic pathways and include antibiotics, cytotoxic and cyto-stimulatory compounds. Marine fungi produce many different types of secondary metabolites that are of commercial importance. This review paper deals with around 187 novel compounds and 212 other known compounds with anticancer and antibacterial activities with a special focus on the period from 2011-2019. Furthermore, this review highlights the sources of organisms, chemical classes and biological activities (anticancer and antibacterial) of metabolites, that were isolated and structurally elucidated from marine fungi to throw a helping hand for novel drug development.

Keywords: Marine fungi, secondary metabolites, anticancer, antibacterial, novel drugs, natural product

Graphical Abstract

[1]
Abe, M.; Imai, T.; Ishii, N.; Usui, M.; Okuda, T.; Oki, T. Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539. Biosci. Biotechnol. Biochem., 2005, 69(6), 1202-1205.
[http://dx.doi.org/10.1271/bbb.69.1202] [PMID: 15973055]
[2]
Adler, J.H.; Young, M.; Nes, W.R. Determination of the absolute configuration at C-20 and C-24 of ergosterol in Ascomycetes and Basidiomycetes by proton magnetic resonance spectroscopy. Lipids, 1977, 12(4), 364-366.
[http://dx.doi.org/10.1007/BF02533639] [PMID: 853879]
[3]
Afiyatullov, S.S.; Kalinovskii, A.I.; Pivkin, M.V.; Dmitrenok, P.S.; Kuznetsova, T.A. Alkaloids from the marine isolate of the fungus Aspergillus fumigatus. Chem. Nat. Compd., 2005, 41(2), 236-238.
[http://dx.doi.org/10.1007/s10600-005-0122-y]
[4]
Amagata, T.; Amagata, A.; Tenney, K.; Valeriote, F.A.; Lobkovsky, E.; Clardy, J.; Crews, P. Unusual C25 steroids produced by a sponge-derived Penicillium citrinum. Org. Lett., 2003, 5(23), 4393-4396.
[http://dx.doi.org/10.1021/ol0356800] [PMID: 14602008]
[5]
Amagata, T.; Minoura, K.; Numata, A. Cytotoxic metabolites produced by a fungal strain from a Sargassum alga. J. Antibiot. (Tokyo), 1998, 51(4), 432-434.
[http://dx.doi.org/10.7164/antibiotics.51.432] [PMID: 9630866]
[6]
Amir-Heidari, B.; Micklefield, J. NMR confirmation that tryptophan dehydrogenation occurs with syn stereochemistry during the biosynthesis of CDA in Streptomyces coelicolor. J. Org. Chem., 2007, 72(23), 8950-8953.
[http://dx.doi.org/10.1021/jo701660v] [PMID: 17929869]
[7]
An, C.Y.; Li, X.M.; Li, C.S.; Xu, G.M.; Wang, B.G. Prenylated indolediketopiperazine peroxides and related homologues from the marine sediment-derived fungus Penicillium brefeldianum SD-273. Mar. Drugs, 2014, 12(2), 746-756.
[http://dx.doi.org/10.3390/md12020746] [PMID: 24473173]
[8]
Andersen, R.J.; Wolfe, M.S.; Faulkner, D.J. Autotoxic antibiotic production by a marine Chromobacterium. Mar. Biol., 1974, 27(4), 281-285.
[http://dx.doi.org/10.1007/BF00394363]
[9]
Ayent, A.G.; Hanson, J.R.; Truneh, A. Metabolites of Gliocladium flavofuscum. Phytochemistry, 1992, 32(1), 197-198.
[http://dx.doi.org/10.1016/0031-9422(92)80131-W]
[10]
Belofsky, G.N.; Jensen, P.R.; Renner, M.K.; Fenical, W. New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron, 1998, 54(9), 1715-1724.
[http://dx.doi.org/10.1016/S0040-4020(97)10396-9]
[11]
Bose, A.K.; Das, K.G.; Funke, P.T.; Kugajevsky, I.; Shukla, O.P.; Khanchandani, K.S.; Suhadolnik, R.J. Biosynthetic studies on gliotoxin using stable isotopes and mass spectral methods. J. Am. Chem. Soc., 1968, 90(4), 1038-1041.
[http://dx.doi.org/10.1021/ja01006a034] [PMID: 5688814]
[12]
Brade, W.; Vasella, A. Synthesis of Naphtho [2, 3‐b] pyrandiones:(-)- Cryptosporin. Helv. Chim. Acta, 1989, 72(8), 1649-1657.
[http://dx.doi.org/10.1002/hlca.19890720802]
[13]
Bunyapaiboonsri, T.; Yoiprommarat, S.; Intereya, K.; Kocharin, K. New diphenyl ethers from the insect pathogenic fungus Cordyceps sp. BCC 1861. Chem. Pharm. Bull. (Tokyo), 2007, 55(2), 304-307.
[http://dx.doi.org/10.1248/cpb.55.304] [PMID: 17268106]
[14]
Cafieri, F.; Fattorusso, E.; Gavagnin, M.; Santacroce, C. 3β, 5α, 6β-Trihydroxysterols from the Mediterranean bryozoan Myriapora truncata. J. Nat. Prod., 1985, 48(6), 944-947.
[http://dx.doi.org/10.1021/np50042a010]
[15]
Cao, F.; Yang, J.K.; Liu, Y.F.; Zhu, H.J.; Wang, C.Y. Pleosporalone A, the first azaphilone characterized with aromatic A-ring from a marine-derived Pleosporales sp. fungus. Nat. Prod. Res., 2016, 30(21), 2448-2452.
[http://dx.doi.org/10.1080/14786419.2016.1198352] [PMID: 27385435]
[16]
Chen, X.W.; Li, C.W.; Cui, C.B.; Hua, W.; Zhu, T.J.; Gu, Q.Q. Nine new and five known polyketides derived from a deep sea-sourced Aspergillus sp. 16-02-1. Mar. Drugs, 2014, 12(6), 3116-3137.
[http://dx.doi.org/10.3390/md12063116] [PMID: 24871461]
[17]
Chen, Z.; Song, Y.; Chen, Y.; Huang, H.; Zhang, W.; Ju, J. Cyclic heptapeptides, cordyheptapeptides C-E, from the marine-derived fungus Acremonium persicinum SCSIO 115 and their cytotoxic activities. J. Nat. Prod., 2012, 75(6), 1215-1219.
[http://dx.doi.org/10.1021/np300152d] [PMID: 22642609]
[18]
Cheng, Z.; Xu, W.; Liu, L.; Li, S.; Yuan, W.; Luo, Z.; Zhang, J.; Cheng, Y.; Li, Q. Peniginsengins BE, New farnesylcyclohexenones from the deep sea-derived fungus Penicillium sp. YPGA11. Mar. Drugs, 2018, 16(10), 358.
[http://dx.doi.org/10.3390/md16100358] [PMID: 30275364]
[19]
Choo, S.J.; Park, H.R.; Ryoo, I.J.; Kim, J.P.; Yun, B.S.; Kim, C.J.; Shin-ya, K.; Yoo, I.D. Deoxyverrucosidin, a novel GRP78/BiP down-regulator, produced by Penicillium sp. J. Antibiot. (Tokyo), 2005, 58(3), 210-213.
[http://dx.doi.org/10.1038/ja.2005.26] [PMID: 15895531]
[20]
Chung, Y.M.; Wei, C.K.; Chuang, D.W.; El-Shazly, M.; Hsieh, C.T.; Asai, T.; Oshima, Y.; Hsieh, T.J.; Hwang, T.L.; Wu, Y.C.; Chang, F.R. An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii. Bioorg. Med. Chem., 2013, 21(13), 3866-3872.
[http://dx.doi.org/10.1016/j.bmc.2013.04.004] [PMID: 23647825]
[21]
Clark, B.; Capon, R.J.; Lacey, E.; Tennant, S.; Gill, J.H. Quinolactacins revisited: From lactams to imide and beyond. Org. Biomol. Chem., 2006, 4(8), 1512-1519.
[http://dx.doi.org/10.1039/b600959j] [PMID: 16604219]
[22]
Cole, R.J.; Kirksey, J.W.; Cox, R.H.; Clardy, J. Structure of the tremor-producing indole, TR-2. J. Agric. Food Chem., 1975, 23(5), 1015-1018.
[http://dx.doi.org/10.1021/jf60201a017] [PMID: 1159175]
[23]
Cui, C.B.; Kakeya, H.; 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. (Tokyo), 1996, 49(6), 534-540.
[http://dx.doi.org/10.7164/antibiotics.49.534] [PMID: 8698635]
[24]
da Rocha, M.W.; Resck, I.S.; Caldas, E.D. Purification and full characterisation of citreoviridin produced by Penicillium citreonigrum in yeast extract sucrose (YES) medium. Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess., 2015, 32(4), 584-595.
[http://dx.doi.org/10.1080/19440049.2014.961177] [PMID: 25190053]
[25]
Dai, J.; Carté, B.K.; Sidebottom, P.J.; Sek Yew, A.L.; Ng, S.; Huang, Y.; Butler, M.S. Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. J. Nat. Prod., 2001, 64(1), 125-126.
[http://dx.doi.org/10.1021/np000381u] [PMID: 11170686]
[26]
Dai, M.C.; Tabacchi, R.; Satumin, C. Nitrogen-containing aromatic compound from the culture medium of Penicillium chrysogenum Thom. CHIMIA Int. J. Chem., 1993, 47(6), 226-229.
[27]
Dettrakul, S.; Kittakoop, P.; Isaka, M.; Nopichai, S.; Suyarnsestakorn, C.; Tanticharoen, M.; Thebtaranonth, Y. Antimycobacterial pimarane diterpenes from the Fungus Diaporthe sp. Bioorg. Med. Chem. Lett., 2003, 13(7), 1253-1255.
[http://dx.doi.org/10.1016/S0960-894X(03)00111-2] [PMID: 12657257]
[28]
Ding, Z.; Zhang, L.; Fu, J.; Che, Q.; Li, D.; Gu, Q.; Zhu, T. Phenylpyropenes E and F: New meroterpenes from the marine-derived fungus Penicillium concentricum ZLQ-69. J. Antibiot. (Tokyo), 2015, 68(12), 748-751.
[http://dx.doi.org/10.1038/ja.2015.64] [PMID: 26058567]
[29]
Dong, J.Y.; He, H.P.; Shen, Y.M.; Zhang, K.Q. Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum. J. Nat. Prod., 2005, 68(10), 1510-1513.
[http://dx.doi.org/10.1021/np0502241] [PMID: 16252916]
[30]
Dorner, J.W.; Cole, R.J.; Springer, J.P.; Cox, R.H.; Cutler, H.; Wicklow, D.T. Isolation and identification of two new biologically active norditerpene dilactones from Aspergillus wentii. Phytochemistry, 1980, 19(6), 1157-1161.
[http://dx.doi.org/10.1016/0031-9422(80)83075-5]
[31]
Du, L.; Li, D.; Zhu, T.; Cai, S.; Wang, F.; Xiao, X.; Gu, Q. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron, 2009, 65(5), 1033-1039.
[http://dx.doi.org/10.1016/j.tet.2008.11.078]
[32]
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]
[33]
Fan, Y.Q.; Li, P.H.; Chao, Y.X.; Chen, H.; Du, N.; He, Q.X.; Liu, K.C. Alkaloids with cardiovascular effects from the marine-derived fungus Penicillium expansum Y32. Mar. Drugs, 2015, 13(10), 6489-6504.
[http://dx.doi.org/10.3390/md13106489] [PMID: 26506361]
[34]
Fan, Z.; Sun, Z.H.; Liu, Z.; Chen, Y.C.; Liu, H.X.; Li, H.H.; Zhang, W.M. Dichotocejpins A–C: New diketopiperazines from a deep-sea-derived fungus Dichotomomyces cejpii FS110. Mar. Drugs, 2016, 14(9), 1-9.
[http://dx.doi.org/10.3390/md14090164] [PMID: 27618072]
[35]
Fang, G.U.O. Sheng, xiang Yang; Li, Liu.; Yong, Wang. Chemical constituents and their toxic activity from the endophytic fungus Phomopsis sp. KY-12, isolated from Pleioblastus amarus. Nat. Prod. Res. Develop., 2014, 26(9), 1389-1392.
[36]
Feng, Y.; Blunt, J.W.; Cole, A.L.; Munro, M.H. Novel cytotoxic thiodiketopiperazine derivatives from a Tilachlidium sp. J. Nat. Prod., 2004, 67(12), 2090-2092.
[http://dx.doi.org/10.1021/np030326w] [PMID: 15620259]
[37]
Franzén, J.; Fisher, A. Asymmetric alkaloid synthesis: A one-pot organocatalytic reaction to quinolizidine derivatives. Angew. Chem. Int. Ed. Engl., 2009, 48(4), 787-791.
[http://dx.doi.org/10.1002/anie.200805130] [PMID: 19090516]
[38]
Fredimoses, M.; Zhou, X.; Ai, W.; Tian, X.; Yang, B.; Lin, X.; Xian, J.Y.; Liu, Y. Westerdijkin A, a new hydroxyphenylacetic acid derivative from deep sea fungus Aspergillus westerdijkiae SCSIO 05233. Nat. Prod. Res., 2015, 29(2), 158-162.
[http://dx.doi.org/10.1080/14786419.2014.968154] [PMID: 25325177]
[39]
Fremlin, L.J.; Piggott, A.M.; Lacey, E.; Capon, R.J. Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor. J. Nat. Prod., 2009, 72(4), 666-670.
[http://dx.doi.org/10.1021/np800777f] [PMID: 19245260]
[40]
Fuchser, J.; Zeeck, A. Aspinolides and aspinonene/aspyrone co-metabolites, new pentaketides produced by Aspergillus ochraceus. Liebigs Ann., 1997, 1, 87-95.
[http://dx.doi.org/10.1002/jlac.199719970114]
[41]
Fujii, Y.; Asahara, M.; Ichinoe, M.; Nakajima, H. Fungal melanin inhibitor and related compounds from Penicillium decumbens. Phytochemistry, 2002, 60(7), 703-708.
[http://dx.doi.org/10.1016/S0031-9422(02)00196-6] [PMID: 12127587]
[42]
Fujimoto, H.; Negishi, E.; Yamaguchi, K.; Nishi, N.; Yamazaki, M. Isolation of new tremorgenic metabolites from an Ascomycete, Corynascus setosus. Chem. Pharm. Bull. (Tokyo), 1996, 44(10), 1843-1848.
[http://dx.doi.org/10.1248/cpb.44.1843]
[43]
Fujimoto, H.; Nozawa, M.; Okuyama, E.; Ishibashi, M. Six new constituents from an Ascomycete, Chaetomium quadrangulatum, found in a screening study focused on monoamine oxidase inhibitory activity. Chem. Pharm. Bull. (Tokyo), 2003, 51(3), 247-251.
[http://dx.doi.org/10.1248/cpb.51.247] [PMID: 12612405]
[44]
Fujimoto, H.; Sumino, M.; Okuyama, E.; Ishibashi, M. Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum. J. Nat. Prod., 2004, 67(1), 98-102.
[http://dx.doi.org/10.1021/np0302201] [PMID: 14738397]
[45]
Gao, H.; Zhang, L.; Zhu, T.; Gu, Q.; Li, D. Unusual pyrrolyl 4-quinolinone alkaloids from the marine-derived fungus Penicillium sp. ghq208. Chem. Pharm. Bull. (Tokyo), 2012, 60(11), 1458-1460.
[http://dx.doi.org/10.1248/cpb.c12-00487] [PMID: 22971874]
[46]
Gao, H.; Zhou, L.; Cai, S.; Zhang, G.; Zhu, T.; Gu, Q.; Li, D. Diorcinols B-E, new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60. J. Antibiot. (Tokyo), 2013, 66(9), 539-542.
[http://dx.doi.org/10.1038/ja.2013.40] [PMID: 23677033]
[47]
Gao, X.W.; Liu, H.X.; Sun, Z.H.; Chen, Y.C.; Tan, Y.Z.; Zhang, W.M. Secondary metabolites from the deep-sea derived fungus Acaromyces ingoldii FS121. Molecules, 2016, 21(4), 1-7.
[http://dx.doi.org/10.3390/molecules21040371] [PMID: 27023495]
[48]
Greshock, T.J.; Grubbs, A.W.; Tsukamoto, S.; Williams, R.M. A concise, biomimetic total synthesis of stephacidin A and notoamide B. Angew. Chem. Int. Ed. Engl., 2007, 46(13), 2262-2265.
[http://dx.doi.org/10.1002/anie.200604378] [PMID: 17304610]
[49]
Grundmann, A.; Li, S.M. Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus. Microbiology, 2005, 151(Pt 7), 2199-2207.
[http://dx.doi.org/10.1099/mic.0.27962-0] [PMID: 16000710]
[50]
Guo, W.; Peng, J.; Zhu, T.; Gu, Q.; Keyzers, R.A.; Li, D. Sorbicillamines A-E, nitrogen-containing sorbicillinoids from the deep-sea-derived fungus Penicillium sp. F23-2. J. Nat. Prod., 2013, 76(11), 2106-2112.
[http://dx.doi.org/10.1021/np4006647] [PMID: 24215398]
[51]
Guo, W.; Zhang, Z.; Zhu, T.; Gu, Q.; Li, D. Penicyclones A–E, antibacterial polyketides from the deep-sea-derived fungus Penicillium sp. F23-2. J. Nat. Prod., 2015, 78(11), 2699-2703.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00655] [PMID: 26540093]
[52]
Hamasaki, T.; Sato, Y.; Hatsuda, Y. Isolation of new metabolites from Aspergillus sydowi and structure of sydowic acid. Agric. Biol. Chem., 1975, 39(12), 2337-2340.
[http://dx.doi.org/10.1271/bbb1961.39.2337]
[53]
Hamasaki, T.; Nagayama, K.; Hatsuda, Y. Two new metabolites, sydonic acid and hydroxysydonic acid, from Aspergillus sydowi. Agric. Biol. Chem., 1978, 42(1), 37-40.
[http://dx.doi.org/10.1271/bbb1961.42.37]
[54]
Hamasaki, T.; Sato, Y.; Hatsuda, Y. Structure of sydowinin A, sydowinin B, and sydowinol, metabolites from Aspergillus sydowi. Agric. Biol. Chem., 1975, 39(12), 2341-2345.
[http://dx.doi.org/10.1271/bbb1961.39.2341]
[55]
Harmange, J.C.; Figadère, B.; Hocquemiller, R. Enantiospecific preparation of the lactone fragment of murisolin. Tetrahedron Asymmetry, 1991, 2(5), 347-350.
[http://dx.doi.org/10.1016/S0957-4166(00)82115-1]
[56]
Harrington, P.M.; Singh, B.K.; Szamosi, I.T.; Birk, J.H. Synthesis and herbicidal activity of cyperin. J. Agric. Food Chem., 1995, 43(3), 804-808.
[http://dx.doi.org/10.1021/jf00051a046]
[57]
Hashida, J.; Niitsuma, M.; Iwatsuki, M.; Mori, M.; Ishiyama, A.; Namatame, M.; Nishihara-Tsukashima, A.; Nonaka, K.; Ui, H.; Masuma, R.; Otoguro, K.; Yamada, H.; Shiomi, K.; Omura, S. Pyrenocine I, a new pyrenocine analog produced by Paecilomyces sp. FKI-3573. J. Antibiot. (Tokyo), 2010, 63(9), 559-561.
[http://dx.doi.org/10.1038/ja.2010.65] [PMID: 20588297]
[58]
Healy, P.C.; Hocking, A.; Tran-Dinh, N.; Pitt, J.I.; Shivas, R.G.; Mitchell, J.K.; Kotiw, M.; Davis, R.A. Xanthones from a microfungus of the genus Xylaria. Phytochemistry, 2004, 65(16), 2373-2378.
[http://dx.doi.org/10.1016/j.phytochem.2004.07.019] [PMID: 15381010]
[59]
Herath, H.M.; Herath, W.H.; Carvalho, P.; Khan, S.I.; Tekwani, B.L.; Duke, S.O.; Tomaso-Peterson, M.; Nanayakkara, N.P. Biologically active tetranorditerpenoids from the fungus Sclerotinia homoeocarpa causal agent of dollar spot in turfgrass. J. Nat. Prod., 2009, 72(12), 2091-2097.
[http://dx.doi.org/10.1021/np900334k] [PMID: 19928902]
[60]
Hikino, H.; Nabetani, S.; Takemoto, T. Structure and biosynthesis of chrysogine, a metabolite of Penicillium chrysogenum. Yakugaku Zasshi, 1973, 93(5), 619-623.
[http://dx.doi.org/10.1248/yakushi1947.93.5_619] [PMID: 4199763]
[61]
Hodge, R.P.; Harris, C.M.; Harris, T.M. Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin. J. Nat. Prod., 1988, 51(1), 66-73.
[http://dx.doi.org/10.1021/np50055a008] [PMID: 3373229]
[62]
Hu, H.; Zhu, B.; Gong, B. Studies on new bioactive compounds from Aspergillus versicolor. SIPI-17-SIPI-1-2, 3 and 4. Zhongguo Yaoxue Zazhi (Beijing), 1999, 34, 337-339.
[63]
Hu, X.; Xia, Q.W.; Zhao, Y.Y.; Zheng, Q.H.; Liu, Q.Y.; Chen, L.; Zhang, Q.Q. Speradines F-H, three new oxindole alkaloids from the marine-derived fungus Aspergillus oryzae. Chem. Pharm. Bull. (Tokyo), 2014, 62(9), 942-946.
[http://dx.doi.org/10.1248/cpb.c14-00312] [PMID: 24966178]
[64]
Imran, M.; Liviu, M.; Latif, S.; Mahmood, Z.; Naimat, I.; Zaman, S.S.; Fatima, S. Antibacterial Co (II), Ni (II), Cu (II) and Zn (II) complexes with biacetyl-derived Schiff bases. J. Serb. Chem. Soc., 2010, 75(8), 1075-1084.
[http://dx.doi.org/10.2298/JSC091026098I]
[65]
Isaka, M.; Jaturapat, A.; Rukseree, K.; Danwisetkanjana, K.; Tanticharoen, M.; Thebtaranonth, Y. Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species. J. Nat. Prod., 2001, 64(8), 1015-1018.
[http://dx.doi.org/10.1021/np010006h] [PMID: 11520217]
[66]
Iwamoto, C.; Yamada, T.; Ito, Y.; Minoura, K.; Numata, A. Cytotoxic cytochalasans from a Penicillium species separated from a marine alga. Tetrahedron, 2001, 57(15), 2997-3004.
[http://dx.doi.org/10.1016/S0040-4020(01)00153-3]
[67]
Kaouadji, M.; Steiman, R.; Seigle-Murandi, F.; Krivobok, S.; Sage, L. Gliotoxin: Uncommon 1H couplings and revised 1H-and 13C-NMR assignments. J. Nat. Prod., 1990, 53(3), 717-719.
[http://dx.doi.org/10.1021/np50069a032]
[68]
Kettering, M.; Sterner, O.; Anke, T. Antibiotics in the chemical communication of fungi. Z. Natforsch. C J. Biosci., 2004, 59(11-12), 816-823.
[http://dx.doi.org/10.1515/znc-2004-11-1209] [PMID: 15666540]
[69]
Kim, H.S.; Park, I.Y.; Park, Y.J.; Lee, J.H.; Hong, Y.S.; Lee, J.J. A novel dihydroxanthenone, AGI-B4 with inhibition of VEGF-induced endothelial cell growth. J. Antibiot. (Tokyo), 2002, 55(7), 669-672.
[http://dx.doi.org/10.7164/antibiotics.55.669] [PMID: 12243460]
[70]
Kim, K.S.; Cui, X.; Lee, D.S.; Sohn, J.H.; Yim, J.H.; Kim, Y.C.; Oh, H. Anti-inflammatory effect of neoechinulin a from the marine fungus Eurotium sp. SF-5989 through the suppression of NF-кB and p38 MAPK Pathways in lipopolysaccharide-stimulated RAW264.7 macrophages. Molecules, 2013, 18(11), 13245-13259.
[http://dx.doi.org/10.3390/molecules181113245] [PMID: 24165583]
[71]
Kim, Y.K.; Tomoda, H.; Nishida, H.; Sunazuka, T.; Obata, R.; Omura, S. Pyripyropenes, novel inhibitors of acyl-CoA: Cholesterol acyltransferase produced by Aspergillus fumigatus. II. Structure elucidation of pyripyropenes A, B, C and D. J. Antibiot. (Tokyo), 1994, 47(2), 154-162.
[http://dx.doi.org/10.7164/antibiotics.47.154] [PMID: 8150710]
[72]
Kimura, Y.; Tani, K.; Kojima, A.; Sotoma, G.; Okada, K.; Shimada, A. Cyclo-(l-tryptophyl-l-phenylalanyl), a plant growth regulator produced by the fungus Penicillium sp. Phytochemistry, 1996, 41(3), 665-669.
[http://dx.doi.org/10.1016/0031-9422(95)00693-1] [PMID: 8987583]
[73]
Kirby, G.W.; Rao, G.V.; Robins, D.J. New co-metabolites of gliotoxin in Gliocladium virens. J. Chem. Soc. Perkin Transact., 1988, 1(2), 301-304.
[http://dx.doi.org/10.1039/p19880000301]
[74]
Kirby, G.W.; Robins, D.J.; Sefton, M.A.; Talekar, R.R. Biosynthesis of bisdethiobis (methylthio) gliotoxin, a new metabolite of Gliocladium deliquescens. J. Chem. Soc. Perkin Transact., 1980, 1, 119-121.
[http://dx.doi.org/10.1039/p19800000119]
[75]
Kito, K.; Ookura, R.; Yoshida, S.; Namikoshi, M.; Ooi, T.; Kusumi, T. Pentaketides relating to aspinonene and dihydroaspyrone from a marine-derived fungus, Aspergillus ostianus. J. Nat. Prod., 2007, 70(12), 2022-2025.
[http://dx.doi.org/10.1021/np070301n] [PMID: 17994702]
[76]
Kozlovsky, A.G.; Zhelifonova, V.P.; Antipova, T.V.; Adanin, V.M.; Novikova, N.D.; Deshevaya, E.A.; Grafe, U. Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocyllin X and questiomycin A. Appl. Biochem. Microbiol., 2004, 40(3), 291-295.
[http://dx.doi.org/10.1023/B:ABIM.0000025954.82316.b4]
[77]
Kudo, S.; Murakami, T.; Miyanishi, J.; Tanaka, K.; Takada, N.; Hashimoto, M. Isolation and absolute stereochemistry of optically active sydonic acid from Glonium sp. (Hysteriales, Ascomycota). Biosci. Biotechnol. Biochem., 2009, 73(1), 203-204.
[http://dx.doi.org/10.1271/bbb.80535] [PMID: 19129640]
[78]
Kuramata, M. Fujioka, S.; Shimada, A.; Kawano, T.; Kimura, Y.; Citrinolactones, A. B and C, and sclerotinin C, plant growth regulators from Penicillium citrinum. Biosci. Biotechnol. Biochem., 2007, 71(2), 499-503.
[http://dx.doi.org/10.1271/bbb.60538] [PMID: 17284855]
[79]
Kwon, O.E.; Rho, M.C.; Song, H.Y.; Lee, S.W.; Chung, M.Y.; Lee, J.H.; Kim, Y.H.; Lee, H.S.; Kim, Y.K. Phenylpyropene A and B, new inhibitors of acyl-CoA: Cholesterol acyltransferase produced by Penicillium griseofulvum F1959. J. Antibiot. (Tokyo), 2002, 55(11), 1004-1008.
[http://dx.doi.org/10.7164/antibiotics.55.1004] [PMID: 12546421]
[80]
Lee, S.U.; Asami, Y.; Lee, D.; Jang, J.H.; Ahn, J.S.; Oh, H. Protuboxepins A and B and protubonines A and B from the marine-derived fungus Aspergillus sp. SF-5044. J. Nat. Prod., 2011, 74(5), 1284-1287.
[http://dx.doi.org/10.1021/np100880b] [PMID: 21366228]
[81]
Lee, Y.M.; Li, H.; Hong, J.; Cho, H.Y.; Bae, K.S.; Kim, M.A.; Kim, D.K.; Jung, J.H. Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor. Arch. Pharm. Res., 2010, 33(2), 231-235.
[http://dx.doi.org/10.1007/s12272-010-0207-4] [PMID: 20195823]
[82]
Li, C.S.; Li, X.M.; Gao, S.S.; Lu, Y.H.; Wang, B.G. Cytotoxic anthranilic acid derivatives from deep sea sediment-derived fungus Penicillium paneum SD-44. Mar. Drugs, 2013, 11(8), 3068-3076.
[http://dx.doi.org/10.3390/md11083068] [PMID: 23966037]
[83]
Li, D.L.; Li, X.M.; Li, T.G.; Dang, H.Y.; Wang, B. Dioxopiperazine alkaloids produced by the marine mangrove derived endophytic fungus Eurotium rubrum. Helv. Chim. Acta, 2008, 91(10), 1888-1893.
[http://dx.doi.org/10.1002/hlca.200890202]
[84]
Li, D.; Chen, L.; Zhu, T.; Kurtán, T.; Mándi, A.; Zhao, Z.; Gu, Q. Chloctanspirones A and B, novel chlorinated polyketides with an unprecedented skeleton, from marine sediment derived fungus Penicillium terrestre. Tetrahedron, 2011, 67(41), 7913-7918.
[http://dx.doi.org/10.1016/j.tet.2011.08.037]
[85]
Li, X.B.; Zhou, Y.H.; Zhu, R.X.; Chang, W.Q.; Yuan, H.Q.; Gao, W.; Zhang, L.L.; Zhao, Z.T.; Lou, H.X. Identification and biological evaluation of secondary metabolites from the endolichenic fungus Aspergillus versicolor. Chem. Biodivers., 2015, 12(4), 575-592. a
[http://dx.doi.org/10.1002/cbdv.201400146] [PMID: 25879502]
[86]
Li, X.D.; Li, X.M.; Xu, G.M.; Zhang, P.; Wang, B.G. Antimicrobial phenolic bisabolanes and related derivatives from Penicillium aculeatum SD-321, a deep-sea sediment-derived fungus. J. Nat. Prod., 2015, 78(4), 844-849.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00004] [PMID: 25763602]
[87]
Li, X.D.; Li, X.M.; Yin, X.L.; Li, X.; Wang, B.G. Antimicrobial sesquiterpenoid derivatives and monoterpenoids from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. Mar. Drugs, 2019, 17(10), 1-12.
[http://dx.doi.org/10.3390/md17100563] [PMID: 31569593]
[88]
Li, X. D.; Li, X.; Li, X. M.; Xu, G. M.; Zhang, P.; Meng, L. H.; Wang, B. G. Tetranorlabdane diterpenoids from the deep-sea sediment-derived fungus Aspergillus wentii SD-310. Planta medica, 2016, 82(09/10), 877-881.
[89]
Li, Y.; Ye, D.; Chen, X.; Lu, X.; Shao, Z.; Zhang, H.; Che, Y. Breviane spiroditerpenoids from an extreme-tolerant Penicillium sp. isolated from a deep sea sediment sample. J. Nat. Prod., 2009, 72(5), 912-916.
[http://dx.doi.org/10.1021/np900116m] [PMID: 19326880]
[90]
Li, Y.; Ye, D.; Shao, Z.; Cui, C.; Che, Y. A sterol and spiroditerpenoids from a Penicillium sp. isolated from a deep sea sediment sample. Mar. Drugs, 2012, 10(2), 497-508.
[http://dx.doi.org/10.3390/md10020497] [PMID: 22412815]
[91]
Liang, X.; Zhang, X.Y.; Nong, X.H.; Wang, J.; Huang, Z.H.; Qi, S.H. Eight linear peptides from the deep-sea-derived fungus Simplicillium obclavatum EIODSF 020. Tetrahedron, 2016, 72(22), 3092-3097.
[http://dx.doi.org/10.1016/j.tet.2016.04.032]
[92]
Limbadri, S.; Luo, X.; Lin, X.; Liao, S.; Wang, J.; Zhou, X.; Yang, B.; Liu, Y. Bioactive novel indole alkaloids and steroids from deep sea-derived fungus Aspergillus fumigatus SCSIO 41012. Molecules, 2018, 23(9), 1-9.
[http://dx.doi.org/10.3390/molecules23092379] [PMID: 30231470]
[93]
Lin, A.; Wu, G.; Gu, Q.; Zhu, T.; Li, D. New eremophilane-type sesquiterpenes from an Antarctic deepsea derived fungus, Penicillium sp. PR19 N-1. Arch. Pharm. Res., 2014, 37(7), 839-844.
[http://dx.doi.org/10.1007/s12272-013-0246-8] [PMID: 24078435]
[94]
Lin, X.; Zhou, X.; Wang, F.; Liu, K.; Yang, B.; Yang, X.; Peng, Y.; Liu, J.; Ren, Z.; Liu, Y. A new cytotoxic sesquiterpene quinone produced by Penicillium sp. F00120 isolated from a deep sea sediment sample. Mar. Drugs, 2012, 10(1), 106-115.
[http://dx.doi.org/10.3390/md10010106] [PMID: 22363223]
[95]
Little, A.; Porco, J.A. Jr Total syntheses of graphisin A and sydowinin B. Org. Lett., 2012, 14(11), 2862-2865.
[http://dx.doi.org/10.1021/ol301107m] [PMID: 22621405]
[96]
Liu, B.; Wang, H.F.; Zhang, L.H.; Liu, F.; He, F.J.; Bai, J.; Pei, Y.H. Isolation of a new compound from Penicillium oxalicum. Chem. Nat. Compd., 2016, 52(5), 821-823.
[http://dx.doi.org/10.1007/s10600-016-1786-1]
[97]
Liu, H.; Zhang, L.; Chen, Y.; Li, S.; Tan, G.; Sun, Z.; Pan, Q.; Ye, W.; Li, H.; Zhang, W. Cytotoxic pimarane-type diterpenes from the marine sediment-derived fungus Eutypella sp. FS46. Nat. Prod. Res., 2017, 31(4), 404-410.
[http://dx.doi.org/10.1080/14786419.2016.1169418] [PMID: 27050657]
[98]
Liu, F.A.; Lin, X.; Zhou, X.; Chen, M.; Huang, X.; Yang, B.; Tao, H. Xanthones and quinolones derivatives produced by the deep-sea-derived fungus Penicillium sp. SCSIO Ind16F01. Molecules, 2017, 22(12), 1-7.
[http://dx.doi.org/10.3390/molecules22121999] [PMID: 29215585]
[99]
Liu, Y.F.; Yue, Y.F.; Feng, L.X.; Zhu, H.J.; Cao, F. Asperienes A-D. Bioactive sesquiterpenes from the marine-derived fungus Aspergillus flavus. Mar. Drugs, 2019, 17(10), 1-10.
[http://dx.doi.org/10.3390/md17100550] [PMID: 31561527]
[100]
Lu, Z.; Zhu, H.; Fu, P.; Wang, Y.; Zhang, Z.; Lin, H.; Liu, P.; Zhuang, Y.; Hong, K.; Zhu, W. Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum. J. Nat. Prod., 2010, 73(5), 911-914.
[http://dx.doi.org/10.1021/np100059m] [PMID: 20415462]
[101]
Macías, F.A.; Varela, R.M.; Simonet, A.M.; Cutler, H.G.; Cutler, S.J.; Ross, S.A.; Hill, R.A. (+)-Brevione A. The first member of a novel family of bioactive spiroditerpenoids isolated from Penicillium brevicompactum Dierckx. Tetrahedron Lett., 2000, 41(15), 2683-2686.
[http://dx.doi.org/10.1016/S0040-4039(00)00223-9]
[102]
Macías, F.A.; Varela, R.M.; Simonet, A.M.; Cutler, H.G.; Cutler, S.J.; Dugan, F.M.; Hill, R.A. Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx. J. Org. Chem., 2000, 65(26), 9039-9046.
[http://dx.doi.org/10.1021/jo0011078] [PMID: 11149849]
[103]
Macías, M.; Gamboa, A.; Ulloa, M.; Toscano, R.A.; Mata, R. Phytotoxic naphthopyranone derivatives from the coprophilous fungus Guanomyces polythrix. Phytochemistry, 2001, 58(5), 751-758.
[http://dx.doi.org/10.1016/S0031-9422(01)00278-3] [PMID: 11672740]
[104]
Matsunaga, K.; Shizuri, Y.; Yamamura, S.; Kawai, K.; Furukawa, H. Isolation and structure of citreoindole, a new metabolite of hybrid strain KO 0052 derived from Penicillium citreo-viride B. IFO 6200 and 4692. Tetrahedron Lett., 1991, 32(47), 6883-6884.
[http://dx.doi.org/10.1016/0040-4039(91)80433-7]
[105]
Meng, J.; Geng, R.; Zhou, C. Benzene and imidazoles drug research progress. Zhongguo Xin Yao Zazhi, 2009, 18, 1505-1514.
[106]
Moreau, S.; Cacan, M.; Lablache-Combier, A. Eremofortin C.A new metabolite obtained from Penicillium roqueforti cultures and from biotransformation of PR toxin. J. Org. Chem., 1977, 42(15), 2632-2634.
[http://dx.doi.org/10.1021/jo00435a023] [PMID: 874620]
[107]
Nagasawa, H.; Isogai, A.; Suzuki, A.; Tamura, S. Structures of isoechinulins A, B and C, new indole metabolites from Aspergillus ruber. Tetrahedron Lett., 1976, 17(19), 1601-1604.
[http://dx.doi.org/10.1016/S0040-4039(01)91627-2]
[108]
Nakada, T.; Sudo, S.; Kosemura, S.; Yamamura, S. Two new metabolites of hybrid strains KO 0201 and 0211 derived from Penicillium citreo-viride B. IFO 6200 and 4692. Tetrahedron Lett., 1999, 40(37), 6831-6834.
[http://dx.doi.org/10.1016/S0040-4039(99)01408-2]
[109]
Niu, Z.; Chen, Y.; Guo, H.; Li, S.N.; Li, H.H.; Liu, H.X.; Liu, Z.; Zhang, W. Cytotoxic polyketides from a deep-sea sediment derived fungus Diaporthe phaseolorum FS431. Molecules, 2019, 24(17), 1-9.
[http://dx.doi.org/10.3390/molecules24173062] [PMID: 31443573]
[110]
Noda, N.; Kubota, S.; Miyata, Y.; Miyahara, K. Optically active N-acetyldopamine dimer of the crude drug “Zentai,” the cast-off shell of the Cicada, Cryptotympana sp. Chem. Pharm. Bull. (Tokyo), 2000, 48(11), 1749-1752.
[http://dx.doi.org/10.1248/cpb.48.1749] [PMID: 11086906]
[111]
Oh, D.C.; Jensen, P.R.; Kauffman, C.A.; Fenical, W. Libertellenones A-D: Induction of cytotoxic diterpenoid biosynthesis by marine microbial competition. Bioorg. Med. Chem., 2005, 13(17), 5267-5273.
[http://dx.doi.org/10.1016/j.bmc.2005.05.068] [PMID: 15993608]
[112]
Oleinikova, G.K.; Denisenko, V.A.; Slinkina, N.N.; Afiyatullov, S.S. Secondary metabolites of the marine fungus Aspergillus ustus KMM 4640. Chem. Nat. Compd., 2012, 48(3), 467-469.
[http://dx.doi.org/10.1007/s10600-012-0276-3]
[113]
Peng, J.; Gao, H.; Li, J.; Ai, J.; Geng, M.; Zhang, G.; Zhu, T.; Gu, Q.; Li, D. Prenylated indole diketopiperazines from the marine-derived fungus Aspergillus versicolor. J. Org. Chem., 2014, 79(17), 7895-7904.
[http://dx.doi.org/10.1021/jo5010179] [PMID: 25089636]
[114]
Peng, J.; Zhang, X.Y.; Tu, Z.C.; Xu, X.Y.; Qi, S.H. Alkaloids from the deep-sea-derived fungus Aspergillus westerdijkiae DFFSCS013. J. Nat. Prod., 2013, 76(5), 983-987.
[http://dx.doi.org/10.1021/np400132m] [PMID: 23701598]
[115]
Peng, J.; Lin, T.; Wang, W.; Xin, Z.; Zhu, T.; Gu, Q.; Li, D. Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp. PJX-41. J. Nat. Prod., 2013, 76(6), 1133-1140.
[http://dx.doi.org/10.1021/np400200k] [PMID: 23758051]
[116]
Peng, J.; Zhang, X.; Du, L.; Wang, W.; Zhu, T.; Gu, Q.; Li, D. Sorbicatechols A and B, antiviral sorbicillinoids from the marine-derived fungus Penicillium chrysogenum PJX-17. J. Nat. Prod., 2014, 77(2), 424-428.
[http://dx.doi.org/10.1021/np400977e] [PMID: 24495078]
[117]
Phillipson, D.W.; O’Sullivan, J.; Johnson, J.H.; Bolgar, M.S.; Kahle, A.D. Lanomycin and glucolanomycin, antifungal agents produced by Pycnidiophora dispersa. II. Structure elucidation. J. Antibiot. (Tokyo), 1992, 45(3), 313-319.
[http://dx.doi.org/10.7164/antibiotics.45.313] [PMID: 1577659]
[118]
Phonkerd, N.; Kanokmedhakul, S.; Kanokmedhakul, K.; Soytong, K.; Prabpai, S.; Kongsearee, P. Bis-spiro-azaphilones and azaphilones from the fungi Chaetomium cochliodes VTh01 and C. cochliodes CTh05. Tetrahedron, 2008, 64(40), 9636-9645.
[http://dx.doi.org/10.1016/j.tet.2008.07.040]
[119]
Pongcharoen, W.; Rukachaisirikul, V.; Phongpaichit, S.; Rungjindamai, N.; Sakayaroj, J. Pimarane diterpene and cytochalasin derivatives from the endophytic fungus Eutypella scoparia PSU-D44. J. Nat. Prod., 2006, 69(5), 856-858.
[http://dx.doi.org/10.1021/np0600649] [PMID: 16724861]
[120]
Qin, J.C.; Zhang, Y.M.; Gao, J.M.; Bai, M.S.; Yang, S.X.; Laatsch, H.; Zhang, A.L. Bioactive metabolites produced by Chaetomium globosum, an endophytic fungus isolated from Ginkgo biloba. Bioorg. Med. Chem. Lett., 2009, 19(6), 1572-1574.
[http://dx.doi.org/10.1016/j.bmcl.2009.02.025] [PMID: 19246197]
[121]
Quang, D.N.; Hashimoto, T.; Nomura, Y.; Wollweber, H.; Hellwig, V.; Fournier, J.; Stadler, M.; Asakawa, Y. Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata. Phytochemistry, 2005, 66(7), 797-809.
[http://dx.doi.org/10.1016/j.phytochem.2005.02.006] [PMID: 15797606]
[122]
Rahaim, R.J., Jr; Maleczka, R.E., Jr Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates. Synthesis, 2006, 2006(19), 3316-3340.
[http://dx.doi.org/10.1055/s-2006-950231]
[123]
Rahbaek, L.; Breinholt, J.; Circumdatins, D.; Circumdatins, D. E, and F: Further fungal benzodiazepine analogues from Aspergillus ochraceus. J. Nat. Prod., 1999, 62(6), 904-905.
[http://dx.doi.org/10.1021/np980495u] [PMID: 10395516]
[124]
Rahbæk, L.; Christophersen, C.; Frisvad, J.; Bengaard, H.S.; Larsen, S.; Rassing, B.R.; Insulicolide, A. A new nitrobenzoyloxy-substituted sesquiterpene from the marine fungus Aspergillus insulicola. J. Nat. Prod., 1997, 60(8), 811-813.
[http://dx.doi.org/10.1021/np970142f]
[125]
Rank, C.; Phipps, R.K.; Harris, P.; Frisvad, J.C.; Gotfredsen, C.H.; Larsen, T.O. epi-Aszonalenins A, B, and C from Aspergillus novofumigatus. Tetrahedron Lett., 2006, 47(34), 6099-6102.
[http://dx.doi.org/10.1016/j.tetlet.2006.06.086]
[126]
Rho, M.C.; Lee, H.S.; Chang, K.T.; Song, H.Y.; Kwon, O.E.; Lee, S.W.; Ko, J.S.; Hong, S.G.; Kim, Y.K. Phenylpyropene C, a new inhibitor of acyl-CoA: Cholesterol acyltransferase produced by Penicillium griseofulvum F1959. J. Antibiot. (Tokyo), 2002, 55(2), 211-214.
[http://dx.doi.org/10.7164/antibiotics.55.211] [PMID: 12003004]
[127]
Sarubbi, E.; Seneci, P.F.; Angelastro, M.R.; Peet, N.P.; Denaro, M.; Islam, K. Peptide aldehydes as inhibitors of HIV protease. FEBS Lett., 1993, 319(3), 253-256.
[http://dx.doi.org/10.1016/0014-5793(93)80557-B] [PMID: 8458418]
[128]
Sassa, T.; Tomizuka, K.; Ikeda, M.; Miura, Y. Isolation of a new root growth-stimulating substance from a fungus. Agric. Biol. Chem., 1973, 37(5), 1221-1222.
[http://dx.doi.org/10.1080/00021369.1973.10860822]
[129]
Sato, H.; Konoma, K.; Sakamura, S. Phytotoxins produced by onion pink root fungus, Pyrenochaeta terrestris. Agric. Biol. Chem., 1979, 43(11), 2409-2411.
[130]
Shang, Z.; Li, X.; Meng, L.; Li, C.; Gao, S.; Huang, C.; Wang, B. Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118. Chin. J. Oceanol. Limnol., 2012, 30(2), 305-314.
[http://dx.doi.org/10.1007/s00343-012-1075-1]
[131]
Shao, C.L.; Wang, C.Y.; Gu, Y.C.; Wei, M.Y.; Pan, J.H.; Deng, D.S.; She, Z.G.; Lin, Y.C. Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp. Bioorg. Med. Chem. Lett., 2010, 20(11), 3284-3286.
[http://dx.doi.org/10.1016/j.bmcl.2010.04.043] [PMID: 20452770]
[132]
Shao, C.; She, Z.; Guo, Z.; Peng, H.; Cai, X.; Zhou, S.; Gu, Y.; Lin, Y. 1H and 13C NMR assignments for two anthraquinones and two xanthones from the mangrove fungus (ZSUH-36). Magn. Reson. Chem., 2007, 45(5), 434-438.
[http://dx.doi.org/10.1002/mrc.1974] [PMID: 17372958]
[133]
Shintani, R.; Hayashi, T. Rhodium-catalyzed asymmetric 1,4-addition of sodium tetraarylborates to β,β-disubstituted α,β-unsaturated esters. Org. Lett., 2011, 13(2), 350-352.
[http://dx.doi.org/10.1021/ol102674z] [PMID: 21128681]
[134]
Shizuri, Y.; Nagahama, M.; Yamamura, S.; Kawai, K.; Kawai, N.; Furukawa, H. Isolation and structures of citreovirenone and citreovirone. Chem. Lett., 1986, 15(7), 1129-1132.
[http://dx.doi.org/10.1246/cl.1986.1129]
[135]
Shizuri, Y.; Shigemori, H.; Sato, R.; Yamamura, S.; Kawai, K.; Furukawa, H. Four new metabolites produced by Penicillium Citreo-viride B. on addition of NaBr. Chem. Lett., 1988, 17(8), 1419-1422.
[http://dx.doi.org/10.1246/cl.1988.1419]
[136]
Smetanina, O.F.; Yurchenko, A.N.; Afiyatullov, S.S.; Kalinovsky, A.I.; Pushilin, M.A.; Khudyakova, Y.V.; Yurchenko, E.A. Oxirapentyns B–D produced by a marine sediment-derived fungus Isaria felina (DC.). Fr. Phytochem. Lett., 2012, 5(1), 165-169.
[http://dx.doi.org/10.1016/j.phytol.2011.12.002]
[137]
Smith, W.B. The carbon‐13 spectra of steroids on the way to ecdysone. Org. Magnet. Resonance, 1977, 9(11), 644-648.
[http://dx.doi.org/10.1002/mrc.1270091108]
[138]
Ström, K.; Sjögren, J.; Broberg, A.; Schnürer, J. Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo (L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid. Appl. Environ. Microbiol., 2002, 68(9), 4322-4327.
[http://dx.doi.org/10.1128/AEM.68.9.4322-4327.2002] [PMID: 12200282]
[139]
Sun, C.; Ge, X.; Mudassir, S.; Zhou, L.; Yu, G.; Che, Q.; Zhang, G.; Peng, J.; Gu, Q.; Zhu, T.; Li, D. New glutamine-containing azaphilone alkaloids from deep-sea-derived fungus Chaetomium globosum HDN151398. Mar. Drugs, 2019, 17(5), 1-11.
[http://dx.doi.org/10.3390/md17050253] [PMID: 31035362]
[140]
Sun, H.F.; Li, X.M.; Meng, L.; Cui, C.M.; Gao, S.S.; Li, C.S.; Huang, C.G.; Wang, B.G. Asperolides A-C, tetranorlabdane diterpenoids from the marine alga-derived endophytic fungus Aspergillus wentii EN-48. J. Nat. Prod., 2012, 75(2), 148-152.
[http://dx.doi.org/10.1021/np2006742] [PMID: 22283451]
[141]
Sun, L.; Li, D.; Tao, M.; Chen, Y.; Dan, F.; Zhang, W. Scopararanes C-G: New oxygenated pimarane diterpenes from the marine sediment-derived fungus Eutypella scoparia FS26. Mar. Drugs, 2012, 10(3), 539-550.
[http://dx.doi.org/10.3390/md10030539] [PMID: 22611352]
[142]
Sun, Y.; Takada, K.; Takemoto, Y.; Yoshida, M.; Nogi, Y.; Okada, S.; Matsunaga, S. Gliotoxin analogues from a marine-derived fungus, Penicillium sp., and their cytotoxic and histone methyltransferase inhibitory activities. J. Nat. Prod., 2012, 75(1), 111-114.
[http://dx.doi.org/10.1021/np200740e] [PMID: 22148349]
[143]
Swathi, J.; Narendra, K.; Sowjanya, K.M.; Satya, A.K. Marine fungal metabolites as a rich source of bioactive compounds. Afr. J. Biochem. Res., 2013, 7(10), 184-196.
[http://dx.doi.org/10.5897/AJBR12.068]
[144]
Swathi, J.; Narendra, K.; Sowjanya, K.M.; Satya, A.K. Evaluation of biologically active molecules isolated from obligate marine fungi. Mintage J. Pharm. Med. Sci, 2013, 2, 45-47.
[145]
Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata, A. Fumiquinazolines A–G, novel metabolites of a fungus separated from a Pseudolabrus marine fish. J. Chem. Soc. Perkin Transact., 1995, 1(18), 2345-2353.
[http://dx.doi.org/10.1039/P19950002345]
[146]
Takahashi, M.; Koyama, K.; Natori, S. Four new azaphilones from Chaetomium globosum var. flavo-viridae. Chem. Pharm. Bull. (Tokyo), 1990, 38(3), 625-628.
[http://dx.doi.org/10.1248/cpb.38.625]
[147]
Tang, X.X.; Liu, S.Z.; Yan, X.; Tang, B.W.; Fang, M.J.; Wang, X.M.; Wu, Z.; Qiu, Y.K. Two new cytotoxic compounds from a deep-sea Penicillum citreonigrum XT20-134. Mar. Drugs, 2019, 17(9), 1-11.
[http://dx.doi.org/10.3390/md17090509] [PMID: 31470583]
[148]
Teng, X.C.; Zhuang, Y.B.; Wang, Y.; Liu, P.P.; Xu, Z.H.; Zhu, W.M. Secondary metabolites from Penicillium sp. gxwz406 symbiotic with the gorgonian Echinogorgia flora. Chin. J. Mar. Drugs, 2010, 29, 11-15.
[149]
TimTec Compound Libraries. Harmony Business Park Building; Newark, USA, 2010.
[150]
Tomoda, H.; Tabata, N.; Yang, D.J.; Namatame, I.; Tanaka, H.; Omura, S.; Kaneko, T. Pyripyropenes, novel ACAT inhibitors produced by Aspergillus fumigatus. IV. Structure elucidation of pyripyropenes M to R. J. Antibiot. (Tokyo), 1996, 49(3), 292-298.
[http://dx.doi.org/10.7164/antibiotics.49.292] [PMID: 8626247]
[151]
Tomoda, H.; Tabata, N.; Yang, D.J.; Takayanagi, H.; Nishida, H.; Omura, S.; Kaneko, T. Pyripyropenes, Novel ACAT inhibitors produced by Aspergillus fumigatus. III. Structure elucidation of pyripyropenes E to L. J. Antibiot. (Tokyo), 1995, 48(6), 495-503.
[http://dx.doi.org/10.7164/antibiotics.48.495] [PMID: 7622436]
[152]
Trisuwan, K.; Rukachaisirikul, V.; Borwornwiriyapan, K.; Phongpaichit, S.; Sakayaroj, J. Benzopyranone, benzophenone, and xanthone derivatives from the soil fungus Penicillium citrinum PSU-RSPG95. Tetrahedron Lett., 2014, 55(7), 1336-1338.
[http://dx.doi.org/10.1016/j.tetlet.2014.01.017]
[153]
Trisuwan, K.; Rukachaisirikul, V.; Kaewpet, M.; Phongpaichit, S.; Hutadilok-Towatana, N.; Preedanon, S.; Sakayaroj, J. Sesquiterpene and xanthone derivatives from the sea fan-derived fungus Aspergillus sydowii PSU-F154. J. Nat. Prod., 2011, 74(7), 1663-1667.
[http://dx.doi.org/10.1021/np200374j] [PMID: 21718031]
[154]
Tsuda, Y.; Kaneda, M.; Tada, A.; Nitta, K.; Yamamoto, Y.; Iitaka, Y. Aspterric acid, a new sesquiterpenoid of the carotane group, a metabolite from Aspergillus terreus IFO-6123. X-Ray crystal and molecular structure of its p-bromobenzoate. J. Chem. Soc. Chem. Commun., 1978, 1978(4), 160-161.
[http://dx.doi.org/10.1039/c39780000160]
[155]
Van der Pyl, D.; Inokoshi, J.; Shiomi, K.; Yang, H.; Takeshima, H.; Omura, S. Inhibition of farnesyl-protein transferase by gliotoxin and acetylgliotoxin. J. Antibiot. (Tokyo), 1992, 45(11), 1802-1805.
[http://dx.doi.org/10.7164/antibiotics.45.1802] [PMID: 1281813]
[156]
Wagenaar, M.M.; Clardy, J. Dicerandrols, new antibiotic and cytotoxic dimers produced by the fungus Phomopsis longicolla isolated from an endangered mint. J. Nat. Prod., 2001, 64(8), 1006-1009.
[http://dx.doi.org/10.1021/np010020u] [PMID: 11520215]
[157]
Wang, F.Z.; Huang, Z.; Shi, X.F.; Chen, Y.C.; Zhang, W.M.; Tian, X.P.; Li, J.; Zhang, S. Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457. Bioorg. Med. Chem. Lett., 2012, 22(23), 7265-7267.
[http://dx.doi.org/10.1016/j.bmcl.2012.08.115] [PMID: 23079524]
[158]
Wang, J.; Lu, Z.; Liu, P.; Wang, Y.; Li, J.; Hong, K.; Zhu, W. Cytotoxic polyphenols from the fungus Penicillium expansum 091 006 endogenous with the mangrove plant Excoecaria agallocha. Planta Med., 2012, 78(17), 1861-1866.
[http://dx.doi.org/10.1055/s-0032-1315395] [PMID: 23059631]
[159]
Wang, L.; Li, M.; Tang, J.; Li, X. Eremophilane sesquiterpenes from a deep marine-derived fungus, Aspergillus sp. SCSIOW2, cultivated in the presence of epigenetic modifying agents. Molecules, 2016, 21(4), 473.
[http://dx.doi.org/10.3390/molecules21040473] [PMID: 27096861]
[160]
Wang, W.L.; Lu, Z.Y.; Tao, H.W.; Zhu, T.J.; Fang, Y.C.; Gu, Q.Q.; Zhu, W.M. Isoechinulin-type alkaloids, variecolorins A-L, from halotolerant Aspergillus variecolor. J. Nat. Prod., 2007, 70(10), 1558-1564.
[http://dx.doi.org/10.1021/np070208z] [PMID: 17896816]
[161]
Wang, W.; Liao, Y.; Chen, R.; Hou, Y.; Ke, W.; Zhang, B.; Gao, M.; Shao, Z.; Chen, J.; Li, F. Chlorinated azaphilone pigments with antimicrobial and cytotoxic activities isolated from the deep sea derived fungus Chaetomium sp. NA-S01-R1. Mar. Drugs, 2018, 16(2), 1-11.
[http://dx.doi.org/10.3390/md16020061] [PMID: 29438326]
[162]
Wang, Y.; Qi, S.; Zhan, Y.; Zhang, N.; Wu, A.A.; Gui, F.; Guo, K.; Yang, Y.; Cao, S.; Hu, Z.; Zheng, Z.; Song, S.; Xu, Q.; Shen, Y.; Deng, X. Aspertetranones A–D, putative meroterpenoids from the marine algal-associated fungus Aspergillus sp. ZL0-1b14. J. Nat. Prod., 2015, 78(10), 2405-2410.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00487] [PMID: 26378981]
[163]
Wei, M.Y.; Wang, C.Y.; Liu, Q.A.; Shao, C.L.; She, Z.G.; Lin, Y.C. Five sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from a gorgonian Dichotella gemmacea. Mar. Drugs, 2010, 8(4), 941-949.
[http://dx.doi.org/10.3390/md8040941] [PMID: 20479961]
[164]
Whyte, A.C.; Gloer, J.B.; Wicklow, D.T.; Dowdw, P.F. Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum. J. Nat. Prod., 1996, 59(11), 1093-1095.
[http://dx.doi.org/10.1021/np960607m] [PMID: 8946752]
[165]
Witt, A.; Bergman, J. Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C. J. Org. Chem., 2001, 66(8), 2784-2788.
[http://dx.doi.org/10.1021/jo001696h] [PMID: 11304202]
[166]
Wu, B.; Chen, G.; Liu, Z.G.; Pei, Y. Two new alkaloids from a marine-derived fungus Neosartorya fischeri. Rec. Nat. Prod., 2015, 9, 271-275.
[167]
Wu, B.; Wiese, J.; Wenzel-Storjohann, A.; Malien, S.; Schmaljohann, R.; Imhoff, J.F. Engyodontochones, antibiotic polyketides from the marine fungus Engyodontium album strain LF069. Chemistry, 2016, 22(22), 7452-7462.
[http://dx.doi.org/10.1002/chem.201600430] [PMID: 27098103]
[168]
Wu, G.; Lin, A.; Gu, Q.; Zhu, T.; Li, D. Four new chloro-eremophilane sesquiterpenes from an Antarctic deep-sea derived fungus, Penicillium sp. PR19N-1. Mar. Drugs, 2013, 11(4), 1399-1408.
[http://dx.doi.org/10.3390/md11041399] [PMID: 23612371]
[169]
Wu, G.; Ma, H.; Zhu, T.; Li, J.; Gu, Q.; Li, D. Penilactones A and B, two novel polyketides from Antarctic deep-sea derived fungus Penicillium crustosum PRB-2. Tetrahedron, 2012, 68(47), 9745-9749.
[http://dx.doi.org/10.1016/j.tet.2012.09.038]
[170]
Xia, M.W.; Cui, C.B.; Li, C.W.; Wu, C.J.; Peng, J.X.; Li, D.H. Rare chromones from a fungal mutant of the marine-derived Penicillium purpurogenum G59. Mar. Drugs, 2015, 13(8), 5219-5236.
[http://dx.doi.org/10.3390/md13085219] [PMID: 26295241]
[171]
Xing, C.P.; Xie, C.L.; Xia, J.M.; Liu, Q.M.; Lin, W.X.; Ye, D.Z.; Liu, G.M.; Yang, X.W. Penigrisacids A-D, Four new sesquiterpenes from the deep-sea-derived Penicillium griseofulvum. Mar. Drugs, 2019, 17(9), 1-8.
[http://dx.doi.org/10.3390/md17090507] [PMID: 31470535]
[172]
Xu, D.; Pang, X.J.; Zhao, T.; Xu, L.L.; Yang, X.L. New alkenylated tetrahydropyran derivatives from the marine sediment-derived fungus Westerdykella dispersa and their bioactivities. Fitoterapia, 2017, 122, 45-51.
[http://dx.doi.org/10.1016/j.fitote.2017.08.010] [PMID: 28842357]
[173]
Xu, L.L.; Zhang, C.C.; Zhu, X.Y.; Cao, F.; Zhu, H.J. Bioactive phenyl ether derivatives from the marine-derived fungus Aspergillus carneus. Nat. Prod. Res., 2017, 31(16), 1875-1879. b
[http://dx.doi.org/10.1080/14786419.2016.126384810] [PMID: 27917659357]
[174]
Xu, D.; Zhang, X.; Shi, X.; Xian, P.J.; Hong, L.; Tao, Y.D.; Yang, X.L. Two new cytochalasans from the marine sediment-derived fungus Westerdykella dispersa and their antibacterial activities. Phytochem. Lett., 2019, 32, 52-55.
[http://dx.doi.org/10.1016/j.phytol.2019.05.002]
[175]
Xu, X.; He, F.; Zhang, X.; Bao, J.; Qi, S. New mycotoxins from marine-derived fungus Aspergillus sp. SCSGAF0093. Food Chem. Toxicol., 2013, 53, 46-51.
[http://dx.doi.org/10.1016/j.fct.2012.11.037] [PMID: 23220611]
[176]
Xu, Y.; Zhang, M.; Liu, Q.A.; Hu, L.D.; Li, W.; Zhu, H.J.; Cao, F. New verrucosidin derivatives from the marine-derived fungus Penicillium sp. XL-01. Nat. Prod. Commun., 2018, 13(10), 1329-1332.
[http://dx.doi.org/10.1177/1934578X1801301024]
[177]
Xu, X.; Yang, H.; Xu, H.; Yin, L.; Chen, Z.; Shen, H. Diphenyl ethers from a marine-derived isolate of Aspergillus sp. CUGB-F046. Nat. Prod. Res., 2018, 32(7), 821-825.
[http://dx.doi.org/10.1080/14786419.2017.1363754] [PMID: 28826261]
[178]
Xu, Y.; Lu, C.; Zheng, Z. A new 3, 4-dihydroisocoumarin isolated from Botryosphaeria sp. F00741. Chem. Nat. Compd., 2012, 48(2), 205-207.
[http://dx.doi.org/10.1007/s10600-012-0205-5]
[179]
Yamada, T.; Doi, M.; Shigeta, H.; Muroga, Y.; Hosoe, S.; Numata, A.; Tanaka, R. Absolute stereostructures of cytotoxic metabolites, chaetomugilins A–C, produced by a Chaetomium species separated from a marine fish. Tetrahedron Lett., 2008, 49(26), 4192-4195.
[http://dx.doi.org/10.1016/j.tetlet.2008.04.060]
[180]
Yamazaki, M.; Fujimoto, H.; Kawasaki, T. Chemistry of tremorogenic metabolites. I. Fumitremorgin A from Aspergillus fumigatus. Chem. Pharm. Bull. (Tokyo), 1980, 28(1), 245-254.
[http://dx.doi.org/10.1248/cpb.28.245] [PMID: 6988091]
[181]
Yang, Y.; Yang, F.; Zhao, L.; Duang, R.; Chen, G.; Li, X.; Li, Q.; Qin, S.; Ding, Z. A new polyoxygenated farnesylcyclohexenone from Fungus Penicillium sp. Nat. Prod. Res., 2016, 30(1), 65-68.
[http://dx.doi.org/10.1080/14786419.2015.1034712] [PMID: 25906789]
[182]
Yao, Q.; Wang, J.; Zhang, X.; Nong, X.; Xu, X.; Qi, S. Cytotoxic polyketides from the deep-sea-derived fungus Engyodontium album DFFSCS021. Mar. Drugs, 2014, 12(12), 5902-5915.
[http://dx.doi.org/10.3390/md12125902] [PMID: 25501793]
[183]
Yoshida, S.; Kito, K.; Ooi, T.; Kanoh, K.; Shizuri, Y.; Kusumi, T. Four pimarane diterpenes from marine fungus: Chloroform incorporated in crystal lattice for absolute configuration analysis by X-ray. Chem. Lett., 2007, 36(11), 1386-1387.
[http://dx.doi.org/10.1246/cl.2007.1386]
[184]
Yu, G.H.; Wu, G.W.; Zhu, T.J.; Gu, Q.Q.; Li, D.H. Cladosins F and G, two new hybrid polyketides from the deep-sea-derived Cladosporium sphaerospermum 2005-01-E3. J. Asian Nat. Prod. Res., 2015, 17(2), 120-124.
[http://dx.doi.org/10.1080/10286020.2014.940330] [PMID: 25081023]
[185]
Yu, K.; Ren, B.; Wei, J.; Chen, C.; Sun, J.; Song, F.; Dai, H.; Zhang, L. Verrucisidinol and verrucosidinol acetate, two pyrone-type polyketides isolated from a marine derived fungus, Penicillium aurantiogriseum. Mar. Drugs, 2010, 8(11), 2744-2754.
[http://dx.doi.org/10.3390/md8112744] [PMID: 21139842]
[186]
Yue, J.M.; Chen, S.N.; Lin, Z.W.; Sun, H.D. Sterols from the fungus Lactarium volemus. Phytochemistry, 2001, 56(8), 801-806.
[http://dx.doi.org/10.1016/S0031-9422(00)00490-8] [PMID: 11324907]
[187]
Yurchenko, A. A.; Smetanina, O. F.; Kalinovsky, A. I.; Kirichuk, N. N.; Pivkin, M. V.; Ivanets, E. V.; Afiyatullov, S. S. New metabolites from a marine sediment-derived fungus, Aspergillus carneus. Nat. Prod. Communicat., 2015, 10(7)1934578X1501000728
[188]
Yurchenko, A.N.; Smetanina, O.F.; Kalinovsky, A.I.; Pivkin, M.V.; Dmitrenok, P.S.; Kuznetsova, T.A. A new meroterpenoid from the marine fungus Aspergillus versicolor (Vuill.). Tirab. Russ. Chem. Bull., 2010, 59(4), 852-856.
[http://dx.doi.org/10.1007/s11172-010-0173-5]
[189]
Yurchenko, A.N.; Smetanina, O.F.; Kalinovsky, A.I.; Pushilin, M.A.; Glazunov, V.P.; Khudyakova, Y.V.; Kirichuk, N.N.; Ermakova, S.P.; Dyshlovoy, S.A.; Yurchenko, E.A.; Afiyatullov, S.Sh. Oxirapentyns F-K from the marine-sediment-derived fungus Isaria felina KMM 4639. J. Nat. Prod., 2014, 77(6), 1321-1328.
[http://dx.doi.org/10.1021/np500014m] [PMID: 24911656]
[190]
Yurchenko, A.N.; Trinh, P.T.H.; Girich Ivanets, E.V.; Smetanina, O.F.; Rasin, A.B.; Popov, R.S.; Dyshlovoy, S.A.; von Amsberg, G.; Menchinskaya, E.S.; Thanh Van, T.T.; Afiyatullov, S.S. Biologically active metabolites from the marine sediment-derived fungus Aspergillus flocculosus. Mar. Drugs, 2019, 17(10), 1-12.
[http://dx.doi.org/10.3390/md17100579] [PMID: 31614563]
[191]
Zhang, Y.; Wang, S.; Li, X.M.; Cui, C.M.; Feng, C.; Wang, B.G. New sphingolipids with a previously unreported 9-methyl-C20-sphingosine moiety from a marine algous endophytic fungus Aspergillus niger EN-13. Lipids, 2007, 42(8), 759-764.
[http://dx.doi.org/10.1007/s11745-007-3079-8] [PMID: 17605063]
[192]
Zhao, L.L.; Zhang, H.P. Isolation of secondary metabolites of 9F series marine fungi and their bioactivities against Pyricularia oryzae. Nat. Prod. Res. Develop., 2005, 17(6), 677.
[193]
Zhao, W.Y.; Zhu, T.J.; Han, X.X.; Fan, G.T.; Liu, H.B.; Zhu, W.M.; Qun Gu, Q. Q. A new gliotoxin analogue from a marine-derived fungus Aspergillus fumigatus Fres. Nat. Prod. Res., 2009, 23(3), 203-207.
[http://dx.doi.org/10.1080/14786410600906970] [PMID: 19235019]
[194]
Zhong, W.M.; Wang, J.F.; Shi, X.F.; Wei, X.Y.; Chen, Y.C.; Zeng, Q.; Xiang, Y.; Chen, X.Y.; Tian, X.P.; Xiao, Z.H.; Zhang, W.M.; Wang, F.Z.; Zhang, S. Eurotiumins A–E, five new alkaloids from the marine-derived fungus Eurotium sp. SCSIO F452. Mar. Drugs, 2018, 16(4), 1-12.
[http://dx.doi.org/10.3390/md16040136] [PMID: 29690501]
[195]
Zhou, L.N.; Zhu, T.J.; Cai, S.X.; Gu, Q.Q.; Li, D.H. Three new indole-containing diketopiperazine alkaloids from a deep-ocean sediment derived fungus Penicillium griseofulvum. Helv. Chim. Acta, 2010, 93(9), 1758-1763.
[http://dx.doi.org/10.1002/hlca.200900443]
[196]
Zhuravleva, O.I.; Afiyatullov, S.Sh.; Vishchuk, O.S.; Denisenko, V.A.; Slinkina, N.N.; Smetanina, O.F. Decumbenone C, a new cytotoxic decaline derivative from the marine fungus Aspergillus sulphureus KMM 4640. Arch. Pharm. Res., 2012, 35(10), 1757-1762.
[http://dx.doi.org/10.1007/s12272-012-1007-9] [PMID: 23139126]
[197]
Zuo, Z.; Ma, D. Enantioselective total syntheses of communesins A and B. Angew. Chem. Int. Ed. Engl., 2011, 50(50), 12008-12011.
[http://dx.doi.org/10.1002/anie.201106205] [PMID: 22006672]