Abstract
Cancer is one of the major diseases, which require the improved drugs with fewer side effects. Until now, several marine natural products have been accessed for the anticancer property and few of them are in clinical trials too. Marine fungi are taxonomically diverse, largely productive, biologically active, and chemically unique offering a great scope for discovery of new anticancer drugs. The natural products isolated from the marine fungi are possibly inhibiting the processes such as inflammation, cell differentiation and survival, and metastasis of various signal transduction pathways and their by reducing the risk of cancer. In this chapter, we have discussed about the anticancer, anti-inflammatory and cytotoxic activities of marine derived fungi.
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References
Heron M (2007) Deaths: Leading causes for 2004. Natl Vital. Stat Rep 56:1–96
Heron M (2009) Deaths: Leading causes for 2005. Natl Vital. Stat Rep 58:1–97
David V, Jaime RA, Cristina T et al. (2010) Studies on quinones. Part 46. Synthesis and in vitro antitumor evaluation of aminopyrimidoisoquinolinequinones. Eur J Med Chem 45:5234–5242
Thomas TRA, Kavlekar DP, LokaBharathi PA (2010) Marine drugs from sponge-microbe association—a review. Mar Drugs 8:1417–1468
Wang L, Li D, Xu S et al. (2012) The conversion of oridonin to spirolactone-type or enmein-type diterpenoid, synthesis and biological. evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents. Eur J Med Chem 52:242–250
Schwartsmann G, Da Rocha AB, Mattei J, Lopes R (2003) Marine-derived anticancer agents in clinical trials. Expert Opin Inv Drug 12:1367–1383
D’Incalci M, Simone M, Tavecchio M, Damia G, Garbi A, Erba E (2004) New drugs from the sea. J Chemother 16:86–89
O’Hanlon LH (2006) Scientists are searching the seas for cancer drugs. J Natl Cancer Inst 98:662–663
Banerjee S, Wang Z, Mohammad M, Sarkar FH (2008) Mohammad R.M. Efficacy of selected natural products as therapeutic agents against cancer. J Nat Prod 71:492–496
Faulkner DJ (2000a) Highlights of marine natural products chemistry (1972–1999). Nat Prod Rep 17:1–6
Faulkner DJ (2000b) Marine pharmacology. Antonie van Leeuwenhoek 77:135–145
Bhadury P, Wright PC (2004) Exploitation of marine algae: biogenic compounds for potential antifouling applications. Planta 219:561–578
Donia M, Hamann MT (2003) Marine natural products and their potential applications as anti-infective agents. Lancet Infect Dis 3:338–348
Mayer AM, Hamann MT (2004) Marine pharmacology in 2000: marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Mar Biotechnol 6:37–52
Mehta AS, Gu B, Conyers B et al. (2004) alpha-Galactosylceramide and novel synthetic glycolipids directly induce the innate host defense pathway and have direct activity against hepatitis B and C viruses. Antimicrob Agents Chemother 48:2085–2090
Rowley DC, Hansen MS, Rhodes D et al. (2002) Thalassiolins A–C: new marine-derived inhibitors of HIV cDNA integrase. Bioorg Med Chem 10:3619–3625
Bhadury P, Mohammad BT, Wright PC (2006) The current status of natural roducts from marine fungi and their potential as anti-infective agents. J Ind Microbiol Biotechnol 33: 325–337
Fenical W, Jensen PR (1993) Marine microorganisms: a new biomedical resource. In: Attaway DH, Zaborsky OR (eds) Marine biotechnology, vol 1. Plenum Press, New York, pp 419–457
Gallo ML, Seldes AM, Cabrera GM (2004) Antibiotic longchain and a, b-unsaturated aldehydes from the culture of the marine fungus Cladosporium sp. Biochem Syst Ecol 32:545–551
Abdel-Lateff A, Klemke C, Konig GM, Wright AD (2003b) Two new xanthone derivatives from the algicolous marine fungus Wardomyces anomalus. J Nat Prod 66:706–708
Daferner M, Anke T, Sterner O (2002) Zopfiellamides A and B, antimicrobial pyrrolidinone derivatives from the marine fungus Zopfiella latipes. Tetrahedron 58:7781–7784
Davidson BS (1995) New dimensions in natural products research: cultured marine microorganisms. Curr Opin Biotechnol 6:284–291
Fenical W (1997) New pharmaceuticals from marine organisms. Trends Biotechnol 15:339–341
Gautschi JT, Amagata T, Amagata A, Valeriote FA, Mooberry SL, Crews P (2004) Expanding the strategies in natural product studies of marine-derived fungi: a chemical investigation of Penicillium obtained from deep water sediment. J Nat Prod 67:362–367
Isaka M, Suyarnsestakorn C, Tanticharoen M, Kongsaeree P, Thebtaranonth Y (2002) Aigialomycins A–E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus. J Org Chem 67:1561–1566
Li X, Choi HD, Kang JS, Lee CO, Son BW (2003) New polyoxygenated farnesylcyclohexenones, deacetoxyyanuthone A and its hydro derivative from the marine-derived fungus Penicillium sp. J Nat Prod 66:1499–1500
Bugni TS, Ireland CM (2004) Marine derived fungi: a chemically and biologically diverse group of microorganisms. Nat Prod Rep 21:143–163
Lee M, Murphy G (2004) Matrix metalloproteinases at a glance. J Cell Sci 117:4015–4016
Gill S, Parks W (2008) Metalloproteinases and their inhibitors: regulators of wound healing. Int J Biochem Cell Biol 40:1334–1347
Egeblad M, Werb Z (2002) New functions for the matrix metalloproteinase in cancer progression. Nat Rev Cancer 2:161–174
Overall CM, Lopez-Otin C (2002) Strategies for MMP inhibition in cancer: innovations for the posttrial era. Nat Rev Cancer 2:657–672
Zhang C, Kim SK (2012) Antimetastasis effect of anthraquinones from marine fungus, Microsporum sp.. In: Kim SK (ed) Advances in food and nutrition research, vol 65. Academic, Waltham, pp 415–421
Champoux JJ (2001) DNA topoisomerases: structure, function, and mechanism. Ann Rev Biochem 70:369–413
Wang JC (1996) DNA topoisomerases. Annu Rev Biochem 65:635–92
Wang JC (1998) Moving one DNA double helix through another by a type II DNA topoisomerase: the story of a simple molecular machine. Q Rev Biophys 31:107–44
Pommier Y, Pourquier P, Fan Y, Strumberg D (1998) Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzymes. Biochem Biophys Acta 1400:83–105
Chen AY, Liu LF (1994) DNA topoisomerases: essential enzymes and lethal targets. Annu Rev Pharmacol Toxicol 34:191–218
Bhatnagar I, Kim SK (2010) Marine Antitumor Drugs: Status, Shortfalls and Strategies. Mar Drugs 8:2702–2720
Yanagihara M, Sasaki-Takahashi N, Sugahara T et al. (2005) Leptosins isolated from marine fungus Leptoshaeria species inhibit DNA topoisomerases I and/or II and induce apoptosis by inactivation of Akt/protein kinase B. Cancer Sci 96:816–824
Hong R (2011) Secalonic acid D as a novel DNA topoisomerase I inhibitor from marine lichen-derived fungus Gliocladium sp. T31. Pharm Biol 49(8):796–799
Koivunen J, Aaltonena V, Peltonen J (2006) Protein kinase C (PKC) family in cancer progression. Cancer Letters 235:1–10
Gorin MA, Pan Q (2009) Protein kinase Cε: an oncogene and emerging tumor biomarker. Mol Cancer 8:9. doi:10.1186/1476-4598-8-9
Abdel-Lateff A (2008) Chaetominedione, a new tyrosine kinase inhibitor isolated from the algicolous marine fungus Chaetomium sp. Tetrahedron Letters 49:6398–6400
Holler U, Konig G, Wright AD (1999) A new tyrosine kinase inhibitor from a marine isolate of ulocladium botrytis and new metabolites from the marine fungi Asteromyces cruciatus and Varicosporina ramulosa. Eur J Org Chem 11:2949–2955
Brauers G, Edrada RA, Ebel R et al. (2000) Anthraquinones and betaenone derivatives from the sponge associated fungus Microsphaeropsis species: Novel inhibitors of protein kinase. J Nat Prod 63:739–745
Kang L, Cai M, Yu C et al. (2011) Improved production of the anticancer compound 1403C by glucose pulse feeding of marine Halorosellinia sp. (No. 1403) in submerged culture. Bioresource Technology 102:10750–10753
Reed JC (2002) Apoptosis-based therapies. Nat Rev Drug Discov 1:111–121
Sellers WR, Fisher DE (1999) Apoptosis and cancer drug targeting. J Clin Invest 104:1655–1661
Stenner-Liewen F, Reed JC (2003) Apoptosis and cancer: basic mechanisms and therapeutic opportunities in the postgenomic era. Cancer Res 63:263–628
Nagle DG, Zhou Y-D, Mora FD et al. (2004) Mechanism targeted discovery of antitumor marine natural products. Curr Med Chem 11(13):1725–1756
Zhang J.-Y, Tao L.-Y, Liang Y.-J et al. (2010) Anthracenedione derivatives as anticancer agents isolated from secondary metabolites of the mangrove endophytic fungi. Mar Drugs 8:1469–1481
Asami Y, Jang JH, Soung NK et al. (2012) Protuboxepin A, a marine fungal metabolite, inducing metaphase arrest and chromosomal misalignment in tumor cells. Bioorg Med Chem 20:3799–3806
Namikoshi M, Kobayashi H, Yoshimoto T et al. (2000) Isolation and characterization of bioactive metabolites from marine-derived filamentous fungi collected from tropical and sub-tropical coral reefs Chem Pharm Bull 48:1452–1457
Zhang Z, Miao L, Lv C et al. (2013) Wentilactone B induces G2/M phase arrest and apoptosis via the Ras/Raf/MAPK signaling pathway in human hepatoma SMMC-7721 cells. Cell Death Dis 4:e657
Wang J, Zhao B, Zhang W et al. (2010) Mycoepoxydiene, a fungal polyketide, induces cell cycle arrest at the G2/M phase and apoptosis in HeLa cells. Bioorg Med Chem Lett 20: 7054–7058
Tsukamoto S, Hirota H, Imachi M et al. (2005) Himeic acid A: a new ubiquitin-activating enzyme inhibitor isolated from a marine-derived fungus, Aspergillus sp. Bioorg Med Chem Lett 15:191–194
McDonald LA, Abbanat DR, Barbieri LR et al. (1999) Spiroxins, DNA cleaving antitumor antibiotics from a marine-derived fungus. Tetrahedron Lett 40:2489–2492
Tang B, He W-L, Zheng C et al. (2012) Marine fungal metabolite 1386A alters the microRNA profile in MCF-7 breast cancer cells. Mol Med Rep 5:610–618
Wijesekara I, Zhang C, Taa QV et al. (2014) Physcion from marine-derived fungus Microsporum sp. induces apoptosis in human cervical carcinoma HeLa cells. Microbiol Res. 169:255–261
Balkwill F, Mantovani A (2001) Inflammation and cancer: back to Virchow? Lancet 357:539–545
Philip M, Rowley DA, Schreiber H (2004) Inflammation as a tumor promoter in cancer induction. Semin Cancer Biol 14:433–439
Coussens LM, Werb Z (2002) Inflammation and cancer. Nature 420:860–867
Okada F (2002) Inflammation and free radicals in tumor development and progression. Redox Rep 7:357–368
Yang C.-R, Hsieh S.-L, Ho F.-M et al. (2005) Decoy receptor 3 increases monocyte adhesion to endothelial cells via NF-nB-dependent up-regulation of intercellular adhesion molecule-1, VCAM-1, and IL-8 expression. J Immunol 174:1647–1656
Dou H, Song Y, Liu X et al. (2011) Chaetoglobosin fex from the marine-derived endophytic fungus inhibits induction of inflammatory mediators via toll-like receptor 4 signaling in macrophages. Biol Pharm Bull 34(12):1864–1873
Song Y, Dou H, Gong W et al. (2013) Bis-N-norgliovictin, a small-molecule compound from marine fungus, inhibits LPS-induced inflammation in macrophages and improves survival in sepsis. Eur J Pharmacol 705:49–60
Lee DS, Jeong GS, Li B et al. (2011) Asperlin from the marine-derived fungus Aspergillus sp. SF-5044 exerts anti-inflammatory effects through heme oxygenase-1 expression in murine macrophages. J Pharmacol Sci 116:283–295
Neumann K, Kehraus S, Gutschow M et al. (2009) Cytotoxic and HLE-inhibitory tetramic acid derivatives from marine-derived fungi. Nat Prod Comms 4:347–354
Pontius A, Krick A, Kehraus S et al. (2008) Antiprotozoal activities of heterocyclic-substituted xanthones from the marine-derived fungus Chaetomium sp. J Nat Prod 71:1579–1584
Krick A, Kehraus S, Gerhauser C et al. (2007) Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from novel heterodimeric chromanone with cancer chemopreventive potential. Chem Eur J 14:9860–9863
Numata A, Amagata T, Minoura K, Ito T (1997) T. Gymnastatins, Novel cytotoxic metabolites produced by a fungal strain from a sponge. Tetrahedron Lett 38:5675–5678
Amagata T, Doi M, Ohta T et al. (1998a) Absolute stereostructures of novel cytotoxic metabolites, Gymnastatins A-E, from a Gymnascella species separated from a Halichondria sponge. J Chem Soc Perkin Trans 1:3585–3599
Amagata T, Minoura K, Numata A (1998b) Gymnasterones, novel cytotoxic metabolites produced by a fungal strain from a sponge. Tetrahedron Lett 39:3773–3774
Amagata T, Doi M, Tohgo M (1999) Dankasterone, a new class of cytotoxic steroid produced by a Gymnascella species from a marine sponge. Chem Commun 14:1321–1322
Varoglu M, Crews P J. (2000) Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger. J Nat Prod 63:41–43
Usami Y, Ikura T, Amagata T, Numata A (2000) First total syntheses and configurational assignments of cytotoxic trichodenones A-C. Tetrahedron: Asymmetry 11:3711–3725
Takahashi C, Numata A, Ito Y et al. (1994a) Leptosins, antitumour metabolites of a fungus isolated from a marine alga. J Chem Soc Perkin Trans 1:1859–1864
Takahashi C, Numata A, Matsumura E et al. (1994b) Leptosins I and J, cytotoxic substances produced by a Leptosphaeria species physico-chemical properties and structures. J Antibiot 47:1242–1249
Takahashi C, Takai Y, Kimura Y, et al. (1995a) Cytotoxic metabolitesfrom fungal adherent of a marine alga. Phytochemistry 38:155–158
Takahashi C, Minoura K, Yamada K et al. (1995b) Po-tent cytotoxic from a Leptosphaeria species structure de-termination and conformational analysis. Tetrahedron 51:3483–3498
Yamada T, Iwamoto C, Yamagaki N et al. (2002) Leptosins M-N, cytotoxic metabolites from a leptospaeria species separated from a marine alga. structure determination and biological activities. Tetrahedron 58:479–487
Amagata T, Minoura K, Numata A, (1998) Cytotoxic metabolites produced by a fungal strain from a Sargassum alga. J Antibiot 51:432–434
Belofsky GN, Jensen PR, Renner MK, et al. (1998) New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron, 54:1715–1724
Numata A, Takahashi C, Ito Y et al. (1993) Communesins, cytotoxic metabolites of a fungus isolated from a marine alga. Tetrahedron Lett 34:2355–2358
Iwamoto C, Yamada T, Ito Y et al. (2001) Cytotoxic cytochalasans from a Penicillium species separated from a marine alga. Tetrahedron 57:2997–3004
Numata A, Takahashi C, Ito Y et al. (1996) Penochalasins, a novel class of cytotoxic cytochalasans from a Penicillium species separated from a marine alga: structure determination and solution conformation. J Chem Soc Perkin Trans 1:239–245
Iwamoto C, Minoura K, Hagishita S et al. (1998) Penostatins f–I, novel cytotoxic metabolites from a Penicillium species separated from an Enteromorpha marine alga. J Chem Soc Perkin Trans 1:449–456
Iwamoto C, Minoura K, Oka T et al. (1999) Absolute stereo structures of novel cytotoxic metabolites, penostatins A-E, from a Penicillium species separated from an Enteromorpha alga. Tetrahedron 55:14353–14368
Takahashi C, Numata A, Yamada T et al. (1996) Penostatins, novel cytotoxic metabolites from a Penicillium species separated from a green alga. Tetrahedron Lett 37:655–658
Son BW, Jensen PR, Kauffman CA et al. (1999) New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium. Nat Prod Lett 13:213–222
Renner MK, Jensen PR, Fenical. W (1998) neomangicols: structures and absolute stercochemistries of unpreccedented halogenated sesterterpenes from a marine fungus of the genus Fusarium. J Org Chem 63:8346–8354
Renner MK, Jensen PR, Fenical W (2000) Mangicols: structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. J Org Chem 65:4843–4852
Lu Z, Zhu H, Fu P, Wang Y et al. (2010) Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum. J Nat Prod 73:911–914
Chen H, Zhu X, Zhong L.-L et al. (2012) Synthesis and antitumor activities of derivatives of the marine mangrove fungal metabolite deoxybostrycin. Mar Drugs 10:2715–2728
Namikoshi M, Akano K, Meguro S et al. (2001) A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in palau. J Nat Prod 64:396–398
Laurent D, Guella G, Roquebert MF et al. (2000) Cytotoxins, mycotoxins and drugs from a new deuteromycete, Acremonium neocaledoniae, from the southwestern lagoon of New Caledonia. Planta Med 66:63–66
Toske SG, Jensen PR, Kauffman CA et al. (1998) Aspergillamides A and B: modified cytotoxic tripeptides produced by a marine fungus of the genus Aspergillus. Tetrahedron 54:13459–13466
Belofsky GN, Jensen PR, Fenical W (1999) Sansalvamide: a new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium. Tetrahedron Lett 40:2913–2916
Cueto M, Jensen PR, Fenical W (2000) N-Methylsansalvamide, a cytotoxic cyclic depsipeptide from a marine fungus of the genus Fusarium. Phytochemistry 55:223–226
Shigemori H, Wakuri S, Yazawa K et al. (1991) Fellutamide-A and fellutamide-B, cytotoxic peptides from a marine fish-possessing fungus Penicillium fellutanum. Tetrahedron 47:8529–8534
Muroga Y, Yamada T, Numata A et al. (2010) 11- and 4´-epimers of chaetomugilin A, novel cytostatic metabolites from marine fish-derived fungus Chaetomium globosum. Helvetica Chimica Acta 93:542–549
Thomas E (2010) Cancer therapy with natural products and medicinal plants. Planta Med 76:1035–1036
Hiort J, Maksimenka K, Reichert M et al. (2004) New natural products from the sponge-derived fungus Aspergillus niger. J Nat Prod 67:1532–1543
Lee YM, Dang HT, Hong J et al. (2010) A cytotoxic lipopeptide from the sponge-derived fungus Aspergillus versicolor. B Kor Chem Soc 31:205–208
Yu Z, Lang G, Kajahn I et al. (2008) Scopularides A and B, cyclodepsipeptides from a marine sponge-derived fungus, Scopulariopsis brevicaulis. J Nat Prod 71:1052–1054
Mohamed IE, Gross H, Pontius A et al. (2009) Epoxyphomalin A and B, prenylated polyketides with potent cytotoxicity from the marine-derived fungus Phoma sp. Org Lett 11:5014–5017
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This work was supported by the High-Tech Research and Development Program of China (2013AA092901).
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Karuppiah, V., Zhang, F., Li, Z. (2015). Natural Products with Anticancer Activity from Marine Fungi. In: Kim, SK. (eds) Handbook of Anticancer Drugs from Marine Origin. Springer, Cham. https://doi.org/10.1007/978-3-319-07145-9_13
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