In order to find non-toxic antifouling natural products from marine microorganisms, the chemical constituents of two marine derived fungi Penicillium sp. and Aspergillus sydowii have been investigated under bio-guided fractionation. A new indolyl diketopiperazine compound, penilloid A (1), together with 15 known ones were isolated from these two strains. The structure of 1 was elucidated on the basis of NMR and mass spectra. Some alkaloids showed significant antifouling and antibacterial activities. The results indicate that indole alkaloids could be a potential antifouling agent resource.
(a) DobretsovS., DahmsH.U., QianP.Y. (2006) A review: Inhibition of biofouling by marine microorganisms and their metabolites. Biofouling, 22, 43–54; (b) Wahl M. (1989). Marine epibiosis. 1. Fouling and antifouling: some basic aspects. Marine Ecology Progress Series, 58, 175-189.
3.
(a) ChambersL.D., StokesK.R., WalshF.C., WoodR.J.K. (2006) Modern approaches to marine antifouling coatings. Surface and Coatings Technology, 201, 3642–3652; (b) Yebra DM, Kiil S, Dam-Johansen K. (2004) Antifouling technology – past, present and future steps towards efficient and environmentally friendly antifouling coatings. Progress in Organic Coatings, 50, 75-104.
4.
BhaduryP., WrightP.C. (2004) Exploitation of marine algae: biogenic compounds for potential antifouling applications. Planta, 219, 561–578.
5.
(a) AlzieuC. (2000) Impact of tributyltin on marine invertebrates. Ecotoxicology, 9, 71–76; (b) Dahlstrom M, Martensson L, Jonsson P, Amebrant T, Elwing H. (2002) Surface active adrenoreceptor compounds prevent the settlement of cyprid larvae of Balanus improvisus. Biofouling, 16, 191-198; (c) Fusetani D. (2004) Biofouling and antifouling. Natural Products Reports, 21, 94-104; (d) Fusetani D. (2011) Antifouling marine natural products. Natural Products Reports, 28, 400-410; (e) He F, Liu Z, Yang J, Fu P, Peng J, Zhu WM, Qi SH. (2012) A novel antifouling alkaloid from halotolerant fungus Penicillium sp. OUCMDZ-776. Tetrahedron Letters, 53, 2280-2283.
6.
(a) QiS.H., MiaoL., GaoC.H., XuY., ZhangS., QianP.Y. (2010) New steroids and a new alkaloid from the Gorgonian Isis minorbrachyblasta: structures, cytotoxicity, and antilarval activity. Helvetica Chimica Acta, 93, 511–516; (b) Qi SH, Xu Y, Xiong HR, Qian PY, Zhang S. (2009) Antifouling and antibacterial compounds from a marine fungus Cladosporium sp. F14. World Journal of Microbial Biotechnology, 25, 399-406.
7.
(a) QiS.H., ZhangS., QianP.Y., XiaoZ.H., LiM.Y. (2006) Ten new antifouling briarane diterpenoids from the South China Sea gorgonian Junceella juncea.Tetrahedron, 62, 9123–9130; (b) Scott PM, Polonsky J, Merrien MA. (1979) Configuration of the 3, 12 double bond of roquefortine. Journal of Agriculture and Food Chemistry, 27, 201-202; (c) Nozawa K, Nakajima S. (1979) Isolation of radicicol from Penicillium luteo-aurantum, and meleagrin, a new metabolite, from Penicillium meleagrinum. Journal of Natural Products, 42, 374-377.
8.
(a) VinokurovaN.G., BoichenkoL.V., ArinbasarovM.U. (2003) Production of alkaloids by fungi of the genus Penicillium grown on wheat grain. Applied Biochemistry and Microbiolology, 39, 403–406; (b) Konda Y, Onda M, Hirano A, Omura S. (1980) Oxaline and neoxaline. Chemical and Pharmaceutical Bulletin, 28, 2987-2993; (c) Scott PM, Kennedy BPC. (1976) Analysis of blue cheese for roquefortine and other alkaloids from Penicillium roqueforti. Journal of Agriculture and Food Chemistry, 24, 865-868; (d) Schiavi BM, Richard DJ, Joullie MM. (2002) Total synthesis of isoroquefortine C. Journal of Organic Chemistry, 67, 620-624; (e) Nielsen KF, Sumarah MW, Frisvad JC, Miller JD. (2006) Production of metabolites from the Penicillium roqueforti complex. Journal of Agriculture and Food Chemistry, 54, 3756-3763.
9.
TakahashiC., MatsushitaT., DoiM., MinouraK., ShinguT., KumedaY., NumataA. (1995) Fumiquinazolines A–G, novel metabolites of a fungus separated from a Pseudolabrus marine fish. Journal of the Chemical Society, Perkin Transactions I, 2345–2352.
10.
CuiC.B., KakeyaH., OsadaH. (1997) Novel mammalian cell cycle inhibitor, cyclotryprostatins A–D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase. Tetrahedron, 53, 59–72.
11.
AbrahamW.R., ArfmannH.A. (1990) 12, 13-Dihydroxyfumitremorgin C from Aspergillus fumigatus.Phytochemistry, 29, 1025–1026.
12.
(a) BirchA.J., RussellR.A. (1972) Studies in relation to biosynthesis-XLIV: structural elucidations of brevianamides–B,-C,-D and–F. Tetrahedron, 28, 2999–3008; (b) Shang GN, Hehre WJ, Ohlinger WS, Beavers MP, Joullie MM. (2008) The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C. Journal of American Chemical Society, 130, 6281-6287.
13.
(a) HeF., SunY.L., LiuK.S., ZhangX.Y., QianP.Y., WangY.F., QiS.H. (2012) Indole alkaloids from marine-derived fungi Aspergillus sp. SCSIO 00305. Journal of Antibiotics, 65, 109–111; (b) Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2011) Marine natural products. Natural Product Reports, 28, 196-268; (c) Penez N, Culioli G, Perez T, Briand JF, Thomas OP, Blache Y. (2011) Antifouling properties of simple indole and purine alkaloids from the Mediterranean Gorgonian Paramuricea clavata. Journal of Natural Products, 74, 2304-2308.
14.
(a) HednerE., SjogrenM., HodzicS., AnderssonR., GoranssonU., JonssonP.R., BohlinL. (2008) Antifouling activity of a dibrominated cyclopeptide from the marine sponge Geodia barretti.Journal of Natural Products, 71, 330–333; (b) Sjogren M, Goransson U, Johnson AL, Dahlstrom M, Andersson R, Bergman J, Jonsson PR, Bohlin L. (2004) Antifouling activity of brominated cyclopeptides from the marine sponge Geodia barrette. Journal of Natural Products, 67, 368-372; (c) Hirota M, Matsuno T, Fujiwara T, Sugiyama H, Mineshita S. (2000) Enhanced cytotoxicity in a Z-phtoisomer of a benzopyran derivative of propolis. Journal of Natural Products, 63, 366-370.
15.
ThiyagarajanV., HarderT., QianP.Y. (2003) Combined effects of temperature and salinity on larval development and attachment of the subtidal barnacle Balanus trigonus Darwin. Journal of Experimental Marine Biology and Ecology, 287, 223–226.
16.
BryanP.J., KreiderJ.L., QianP.Y. (1998) Settlement of the serpulid polychaete Hydroides elegans (Haswell) on the arborescent bryozoan Bugula neritina (L.): evidence of a chemically mediated relationship. Journal of Experimental Marine Biology and Ecology, 220, 171–190.
17.
QiS.H., ZhangS., YangL.H., QianP.Y. (2008) Antifouling and antibacterial compounds from gorgonians Subergorgia suberosa and Scripearia gracillis.Natural Products Research, 22, 154–166.
18.
AcarJ.F. (1980) The disc susceptibility test. In Antibiotics in laboratory medicine.LorianV. (Ed.). Williams and Wilkins, Baltimore, pp 24–54.
19.
LauS.C.K., MakK.K., ChenW.F., QianP.Y. (2002) Bioactivity of bacterial strains isolated from marine biofilms in Hong Kong waters for the induction of larval settlement in the marine polychaete Hydroides elegans.Marine Ecology Progress Series, 226, 301–310.
Supplementary Material
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
