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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

General Review Article

Chemical and Bioactive Marine Natural Products of Coral-Derived Microorganisms (2015-2017)

Author(s): Xue-Mei Hou, Yang Hai, Yu-Cheng Gu, Chang-Yun Wang* and Chang-Lun Shao*

Volume 26, Issue 38, 2019

Page: [6930 - 6941] Pages: 12

DOI: 10.2174/0929867326666190626153819

Price: $65

Abstract

Coral-derived microorganisms are known for their inherent ability to produce novel products of pharmaceutical importance. Nearly 260 marine natural products (MNPs) have been isolated from coral-derived microorganisms till 2014. In the last three years, 118 MNPs have been isolated from coral-associated microorganisms including 46 new compounds, two with a novel skeleton, and four new natural products. Most of them exhibited in vitro or in vivo activities against tumor cell lines, parasites, pathogenic bacteria, fungi and virus. We reviewed the natural products reported from 2015 to 2017 that have a wide range of bioactivities against different biological targets.

Keywords: Coral-derived microorganism, marine natural product, bioactivity, drug potential, parasite, pathogenic bacteria.

[1]
Abdelmohsen, U.R.; Balasubramanian, S.; Oelschlaeger, T.A.; Grkovic, T.; Pham, N.B.; Quinn, R.J.; Hentschel, U. Potential of marine natural products against drug-resistant fungal, viral, and parasitic infections. Lancet Infect. Dis., 2017, 17(2), e30-e41.
[http://dx.doi.org/10.1016/S1473-3099(16)30323-1] [PMID: 27979695]
[2]
Blunt, J.W.; Carroll, A.R.; Copp, B.R.; Davis, R.A.; Keyzers, R.A.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep., 2018, 35(1), 8-53.
[http://dx.doi.org/10.1039/C7NP00052A] [PMID: 29335692]
[3]
Hou, X.M.; Xu, R.F.; Gu, Y.C.; Wang, C.Y.; Shao, C.L. Biological and chemical diversity of coral-derived microorganisms. Curr. Med. Chem., 2015, 22(32), 3707-3762.
[http://dx.doi.org/10.2174/0929867322666151006093755] [PMID: 26438250]
[4]
Kellogg, C.A.; Ross, S.W.; Brooke, S.D. Bacterial community diversity of the deep-sea octocoral Paramuricea placomus. PeerJ, 2016, 4e2529
[http://dx.doi.org/10.7717/peerj.2529] [PMID: 27703865]
[5]
Pham, T.M.; Wiese, J.; Wenzel-Storjohann, A.; Imhoff, J.F. Diversity and antimicrobial potential of bacterial isolates associated with the soft coral Alcyonium digitatum from the Baltic Sea. Antonie van Leeuwenhoek, 2016, 109(1), 105-119.
[http://dx.doi.org/10.1007/s10482-015-0613-1] [PMID: 26558794]
[6]
Zhang, Y.Y.; Ling, J.; Yang, Q.S.; Wang, Y.S.; Sun, C.C.; Sun, H.Y.; Feng, J.B.; Jiang, Y.F.; Zhang, Y.Z.; Wu, M.L.; Dong, J.D. The diversity of coral associated bacteria and the environmental factors affect their community variation. Ecotoxicology, 2015, 24(7-8), 1467-1477.
[http://dx.doi.org/10.1007/s10646-015-1454-4] [PMID: 25833806]
[7]
Mahmoud, H.M.; Kalendar, A.A. Coral-associated actinobacteria: diversity, abundance, and biotechnological potentials. Front. Microbiol., 2016, 7, 204.
[http://dx.doi.org/10.3389/fmicb.2016.00204] [PMID: 26973601]
[8]
Hayashi, A.; Crombie, A.; Lacey, E.; Richardson, A.J.; Vuong, D.; Piggott, A.M.; Hallegraeff, G. Aspergillus sydowii marine fungal bloom in Australian coastal waters, its metabolites and potential impact on Symbiodinium dinoflagellates. Mar. Drugs, 2016, 14(3), 59.
[http://dx.doi.org/10.3390/md14030059] [PMID: 26999164]
[9]
Putria, D.A.; Radjasa, O.K.; Pringgenies, D. Effectiveness of marine fungal symbiont isolated from soft coral Sinularia sp. from Panjang Island as antifungal. Procedia Environ. Sci., 2015, 23, 351-357.
[http://dx.doi.org/10.1016/j.proenv.2015.01.051]
[10]
Shirur, K.P.; Jackson, C.R.; Goulet, T.L. Lesion recovery and the bacterial microbiome in two Caribbean gorgonian corals. Mar. Biol., 2016, 163, 238.
[http://dx.doi.org/10.1007/s00227-016-3008-6]
[11]
Salerno, J.L.; Bowen, B.W.; Rappé, M.S. Biogeography of planktonic and coral-associated microorganisms across the Hawaiian Archipelago. FEMS Microbiol. Ecol., 2016, 92(8)fiw109
[http://dx.doi.org/10.1093/femsec/fiw109] [PMID: 27222221]
[12]
Kuek, F.W.I.; Lim, L.F.; Ngu, L.H.; Mujahid, A.; Lim, P.T.; Leaw, C.P.; Müller, M. The potential roles of bacterial communities in coral defence: a case study at Talang-Talang reef. Ocean Sci. J., 2015, 50, 269-282.
[http://dx.doi.org/10.1007/s12601-015-0024-2]
[13]
Lema, K.A.; Clode, P.L.; Kilburn, M.R.; Thornton, R.; Willis, B.L.; Bourne, D.G. Imaging the uptake of nitrogen-fixing bacteria into larvae of the coral Acropora millepora. ISME J., 2016, 10(7), 1804-1808.
[http://dx.doi.org/10.1038/ismej.2015.229] [PMID: 26696324]
[14]
Shao, C.L.; Xu, R.F.; Wei, M.Y.; She, Z.G.; Wang, C.Y. Structure and absolute configuration of fumiquinazoline L, an alkaloid from a gorgonian-derived Scopulariopsis sp. fungus. J. Nat. Prod., 2013, 76(4), 779-782.
[http://dx.doi.org/10.1021/np4002042] [PMID: 23586849]
[15]
Shao, C.L.; Chao, R.; Xu, R.F.; Cao, F.; Wei, M.Y. Scopuquinolone A, a new terpenoids dihydroquinolone alkaloid from a gorgonian coral-derived Scopulariopsis sp. fungus. Chin. J. Mar. Drugs., 2016, 35, 1-5.
[16]
Shao, C.L.; Xu, R.F.; Wang, C.Y.; Qian, P.Y.; Wang, K.L.; Wei, M.Y. Potent antifouling marine dihydroquinolin-2(1H)-one-containing alkaloids from the gorgonian coral-derived fungus Scopulariopsis sp. Mar. Biotechnol. (NY), 2015, 17(4), 408-415.
[http://dx.doi.org/10.1007/s10126-015-9628-x] [PMID: 25833409]
[17]
Elnaggar, M.S.; Ebada, S.S.; Ashour, M.L.; Ebrahim, W.; Müller, W.E.G.; Mándi, A.; Kurtán, T.; Singab, A.; Lin, W.H.; Liu, Z.; Proksch, P. Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. Tetrahedron, 2016, 72(19), 2411-2419.
[http://dx.doi.org/10.1016/j.tet.2016.03.073]
[18]
Elnaggar, M.S.; Ebada, S.S.; Ashour, M.L.; Ebrahim, W.; Singab, A.; Lin, W.; Liu, Z.; Proksch, P. Two new triterpenoids and a new naphthoquinone derivative isolated from a hard coral-derived fungus Scopulariopsis sp. Fitoterapia, 2017, 116, 126-130.
[http://dx.doi.org/10.1016/j.fitote.2016.12.003] [PMID: 27932272]
[19]
Jia, Y.L. Wei, M.Y.; Chen, H.Y.; Guan, F.F.; Wang, C.Y.; Shao, C.L. (+)-and (−)-Pestaloxazine A, a pair of antiviral enantiomeric alkaloid dimers with a symmetric spiro[oxazinane-piperazinedione] skeleton from Pestalotiopsis sp. Org. Lett., 2015, 17(17), 4216-4219.
[http://dx.doi.org/10.1021/acs.orglett.5b01995] [PMID: 26291636]
[20]
Wang, K.T.; Xu, M.Y.; Liu, W.; Li, H.J.; Xu, J.; Yang, D.P.; Lan, W.J.; Wang, L.Y. Two additional new compounds from the marine-derived fungus Pseudallescheria ellipsoidea F42-3. Molecules, 2016, 21(4), 442.
[http://dx.doi.org/10.3390/molecules21040442] [PMID: 27043524]
[21]
Lan, W.J.; Wang, K.T.; Xu, M.Y.; Zhang, J.J.; Lam, C.K.; Zhong, G.H.; Xu, J.; Yang, D.P.; Li, H.J.; Wang, L.Y. Secondary metabolites with chemical diversity from the marine-derived fungus Pseudallescheria boydii F19-1 and their cytotoxic activity. RSC Advances, 2016, 6(80), 76206-76213.
[http://dx.doi.org/10.1039/C6RA06661E]
[22]
Huang, L.H.; Chen, Y.X.; Yu, J.C.; Yuan, J.; Li, H.J.; Ma, W.Z.; Watanapokasin, R.; Hu, K.C.; Niaz, S.I.; Yang, D.P.; Lan, W.J. Secondary metabolites from the marine-derived fungus Dichotomomyces sp. L-8 and their cytotoxic activity. Molecules, 2017, 22(3), 444.
[http://dx.doi.org/10.3390/molecules22030444] [PMID: 28287456]
[23]
Liu, B.X.; Guo, Q.; Peng, G.T.; He, X.X.; Chen, X.J.; Lei, L.F.; Deng, Y.; Jun, Su. X.; Zhang, C.X.; Su, X.J. New cyclic tetrapeptide from the coral-derived endophytic bacteria Brevibacterium sp. L-4 collected from the South China Sea. Nat. Prod. Res., 2016, 30(1), 7-12.
[http://dx.doi.org/10.1080/14786419.2015.1026340] [PMID: 26214049]
[24]
Yu, Z.; Lang, G.; Kajahn, I.; Schmaljohann, R.; Imhoff, J.F. Scopularides A and B, cyclodepsipeptides from a marine sponge-derived fungus, Scopulariopsis brevicaulis. J. Nat. Prod., 2008, 71(6), 1052-1054.
[http://dx.doi.org/10.1021/np070580e] [PMID: 18412398]
[25]
Kramer, A.; Labes, A.; Imhoff, J.F. Phylogenetic relationship and secondary metabolite production of marine fungi producing the cyclodepsipeptides scopularide A and B. Mar. Biotechnol. (NY), 2016, 18(4), 466-474.
[http://dx.doi.org/10.1007/s10126-016-9707-7] [PMID: 27209381]
[26]
Xing, Q.; Gan, L.S.; Mou, X.F.; Wang, W.; Wang, C.Y.; Wei, M.Y.; Shao, C.L. Isolation, resolution and biological evaluation of pestalachlorides E and F containing both point and axial chirality. RSC Advances, 2016, 6(27), 22653-22658.
[http://dx.doi.org/10.1039/C6RA00374E]
[27]
Xing, Q.; Li, D.; Guo, Z.Y.; Wang, C.Y.; Shao, C.L. Pestarhamnoses A-C, rhamnosylated phenol derivatives from the soft coral-derived fungus Pestalotiopsis sp. Chem. Nat. Compd., 2015, 51(6), 1080-1084.
[http://dx.doi.org/10.1007/s10600-015-1497-z]
[28]
Jia, Y.L.; Guan, F.F.; Ma, J.; Wang, C.Y.; Shao, C.L. Pestalotiolide A, a new antiviral phthalide derivative from a soft coral-derived fungus Pestalotiopsis sp. Nat. Prod. Sci., 2015, 21(4), 227-230.
[http://dx.doi.org/10.20307/nps.2015.21.4.227]
[29]
Sun, Y.Z.; Kurtán, T.; Mándi, A.; Tang, H.; Chou, Y.; Soong, K.; Su, L.; Sun, P.; Zhuang, C.L.; Zhang, W. Immunomodulatory polyketides from a Phoma-like fungus isolated from a soft coral. J. Nat. Prod., 2017, 80(11), 2930-2940.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00463] [PMID: 29048894]
[30]
Zheng, C.J.; Shao, C.L.; Guo, Z.Y.; Chen, J.F.; Deng, D.S.; Yang, K.L.; Chen, Y.Y.; Fu, X.M.; She, Z.G.; Lin, Y.C.; Wang, C.Y. Bioactive hydroanthraquinones and anthraquinone dimers from a soft coral-derived Alternaria sp. fungus. J. Nat. Prod., 2012, 75(2), 189-197.
[http://dx.doi.org/10.1021/np200766d] [PMID: 22276679]
[31]
Zheng, C.J.; Shao, C.L.; Wu, L.Y.; Chen, M.; Wang, K.L.; Zhao, D.L.; Sun, X.P.; Chen, G.Y.; Wang, C.Y. Bioactive phenylalanine derivatives and cytochalasins from the soft coral-derived fungus, Aspergillus elegans. Mar. Drugs, 2013, 11(6), 2054-2068.
[http://dx.doi.org/10.3390/md11062054] [PMID: 23752358]
[32]
Zheng, C.J.; Shao, C.L.; Chen, M.; Niu, Z.G.; Zhao, D.L.; Wang, C.Y. Merosesquiterpenoids and ten-membered macrolides from a soft coral-derived Lophiostoma sp. fungus. Chem. Biodivers., 2015, 12(9), 1407-1414.
[http://dx.doi.org/10.1002/cbdv.201400331] [PMID: 26363884]
[33]
Zheng, C.J.; Fu, X.M.; Zhang, X.L.; Kong, W.W.; Wang, C.Y. Bioactive perylene derivatives from a soft coral-derived fungus Alternaria sp. (ZJ-2008017). Chem. Nat. Compd., 2015, 51(4), 766-768.
[http://dx.doi.org/10.1007/s10600-015-1406-5]
[34]
Tsuda, M.; Mugishima, T.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Kobayashi, J. Modiolides A and B, two new 10-membered macrolides from a marine-derived fungus. J. Nat. Prod., 2003, 66(3), 412-415.
[http://dx.doi.org/10.1021/np0203943] [PMID: 12662103]
[35]
Hawas, U.W.; El-Desouky, S.; Abou El-Kassem, L.; Elkhatee, W. Alternariol derivatives from Alternaria alternate, an endophytic fungus residing in Red Sea soft coral, inhibit HCV NS3/4A protease. Appl. Biochem. Microbiol., 2015, 51(5), 579-584.
[http://dx.doi.org/10.1134/S0003683815050099]
[36]
Hamed, A.; Abdel-Razek, A.S.; Frese, M.; Wibberg, D.; El-Haddad, A.F.; Tarek, M.A.; Ibrahim, T.M.A.; Kalinowski, J.; Sewald, N.; Shaaban, M. New oxaphenalene derivative from marine-derived Streptomyces Griseorubens sp. ASMR4. Z. Naturforsch., 2017, 72(1), 53-62.
[http://dx.doi.org/10.1515/znb-2016-0145]
[37]
Burkhardt, H.J.; Forgacs, J. O-methylsterigmatocystin, a new metabolite from Aspergillus flavus, link ex fries. Tetrahedron, 1968, 24(2), 717-720.
[http://dx.doi.org/10.1016/0040-4020(68)88020-2]
[38]
Bradner, W.T.; Bush, J.A.; Myllymaki, R.W.; Nettleton, D.E., Jr; O’Herron, F.A. Fermentation, isolation, and antitumor activity of sterigmatocystins. Antimicrob. Agents Chemother., 1975, 8(2), 159-163.
[http://dx.doi.org/10.1128/AAC.8.2.159] [PMID: 1180542]
[39]
Wei, M.Y.; Wang, C.F.; Wang, K.L.; Qian, P.Y.; Wang, C.Y.; Shao, C.L. Preparation, structure, and potent antifouling activity of sclerotioramine derivatives. Mar. Biotechnol. (NY), 2017, 19(4), 372-378.
[http://dx.doi.org/10.1007/s10126-017-9760-x] [PMID: 28688034]
[40]
Wolff, K.A.; Nguyen, H.T.; Cartabuke, R.H.; Singh, A.; Ogwang, S.; Nguyen, L. Protein kinase G is required for intrinsic antibiotic resistance in mycobacteria. Antimicrob. Agents Chemother., 2009, 53(8), 3515-3519.
[http://dx.doi.org/10.1128/AAC.00012-09] [PMID: 19528288]
[41]
Chen, D.; Ma, S.; He, L.; Yuan, P.; She, Z.; Lu, Y. Sclerotiorin inhibits protein kinase G from Mycobacterium tuberculosis and impairs mycobacterial growth in macrophages. Tuberculosis (Edinb.), 2017, 103, 37-43.
[http://dx.doi.org/10.1016/j.tube.2017.01.001] [PMID: 28237032]
[42]
Shao, C.L.; Wu, H.X.; Wang, C.Y.; Liu, Q.A.; Xu, Y.; Wei, M.Y.; Qian, P.Y.; Gu, Y.C.; Zheng, C.J.; She, Z.G.; Lin, Y.C. Potent antifouling resorcylic acid lactones from the gorgonian-derived fungus Cochliobolus lunatus. J. Nat. Prod., 2011, 74(4), 629-633.
[http://dx.doi.org/10.1021/np100641b] [PMID: 21348465]
[43]
Zhang, X.Q.; Spadafora, C.; Pineda, L.M.; Ng, M.G.; Sun, J.H.; Wang, W.; Wang, C.Y.; Gu, Y.C.; Shao, C.L. Discovery, semisynthesis, antiparasitic and cytotoxic evaluation of 14-membered resorcylic acid lactones and their derivatives Sci. Rep.-UK,, 2017, 7(1), 11822.
[http://dx.doi.org/10.1038/s41598-017-12336-0] [PMID: 28924201]
[44]
Liao, H.X.; Sun, D.W.; Zheng, C.J.; Wang, C.Y. A new hexahydrobenzopyran derivative from the gorgonian-derived fungus Eutypella sp. Nat. Prod. Res., 2017, 31(14), 1640-1646.
[http://dx.doi.org/10.1080/14786419.2017.1285301] [PMID: 28278631]
[45]
Shi, T.; Qi, J.; Shao, C.L.; Zhao, D.L.; Hou, X.M.; Wang, C.Y. Bioactive diphenyl ethers and isocoumarin derivatives from a gorgonian-derived fungus Phoma sp. (TA07-1). Mar. Drugs, 2017, 15(6), 146.
[http://dx.doi.org/10.3390/md15060146] [PMID: 28587090]
[46]
Zhu, M.; Gao, H.; Wu, C.; Zhu, T.; Che, Q.; Gu, Q.; Guo, P.; Li, D. Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp. TZP29. Bioorg. Med. Chem. Lett., 2015, 25(17), 3606-3609.
[http://dx.doi.org/10.1016/j.bmcl.2015.06.072] [PMID: 26169125]
[47]
Braña, A.F.; Sarmiento-Vizcaíno, A.; Osset, M.; Pérez-Victoria, I.; Martín, J.; de Pedro, N.; de la Cruz, M.; Díaz, C.; Vicente, F.; Reyes, F.; García, L.A.; Blanco, G. Lobophorin K, a new natural product with cytotoxic activity produced by Streptomyces sp. M-207 associated with the deep-sea coral Lophelia pertusa. Mar. Drugs, 2017, 15(5), 144.
[http://dx.doi.org/10.3390/md15050144] [PMID: 28534807]
[48]
Raina, J.B.; Tapiolas, D.; Motti, C.A.; Foret, S.; Seemann, T.; Tebben, J.; Willis, B.L.; Bourne, D.G. Isolation of an antimicrobial compound produced by bacteria associated with reef-building corals. PeerJ, 2016, 4e2275
[http://dx.doi.org/10.7717/peerj.2275] [PMID: 27602265]
[49]
Raina, J.B.; Tapiolas, D.M.; Forêt, S.; Lutz, A.; Abrego, D.; Ceh, J.; Seneca, F.O.; Clode, P.L.; Bourne, D.G.; Willis, B.L.; Motti, C.A. DMSP biosynthesis by an animal and its role in coral thermal stress response. Nature, 2013, 502(7473), 677-680.
[http://dx.doi.org/10.1038/nature12677] [PMID: 24153189]
[50]
Yu, M.L.; Guan, F.F.; Cao, F.; Jia, Y.L.; Wang, C.Y. A new antiviral pregnane from a gorgonian-derived Cladosporium sp. fungus. Nat. Prod. Res., 2018, 32(11), 1260-1266.
[http://dx.doi.org/10.1080/14786419.2017.1342086] [PMID: 28641456]

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