Antifouling indole alkaloids from two marine derived fungi

Natural Product Communications

Volumn 8, Issue 3, 2013, Pages 329-332

  He, Fei ^a   Han, Zhuang ^a   Peng, Jiang ^a   Qian, Pei Yuan ^b   Qi, Shu Hua ^a  

^a SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Antifouling; Aspergillus sydowii; Indole alkaloid; Penicillium sp.

Indexed keywords

11ALPHA METHOXYROQUEFORTINE C; 3 (1H IMIDAZOLE 4 YIMETHYLENE) 6 (1H INDL 3 YLMETHYL) 2,5 PIPERAZINEDIOL; ACETONE; ANTIFOULING AGENT; ANTIINFECTIVE AGENT; ASPERGILLUS SYDOWII EXTRACT; CYCLO-L-TRYPTOPHYL-L-PROLINE; CYCLOTRYPROSTATINS B; CYCLOTRYPTOPHYLPROLINE; DIHYDROXYFUMITREMORGIN C; FUMIQUINAZOLINE A; FUMIQUINAZOLINE D; FUMIQUINAZOLINE E; FUMIQUINAZOLINE F; FUMIQUINAZOLINE G; FUNGAL EXTRACT; GLANDICOLINE B; INDOLE ALKALOID; ISOROQUEFORTINE C; MELEAGRIN; NEOXALINE; PENICILLIN DERIVATIVE; PENILLOID A; ROQUEFORTINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASPERGILLUS SYDOWII; BALANUS AMPHITRITE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONCENTRATION RESPONSE; CONTROLLED STUDY; DERIVATIZATION; FERMENTATION; FRACTIONATION; FUNGAL STRAIN; FUNGUS; LARVA; LC 50; MARINE SPECIES; MEDIAN EFFECTIVE CONCENTRATION; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PENICILLIUM; PSEUDOALTEROMONAS; PSEUDOALTEROMONAS PISCIDA; STRUCTURE ANALYSIS;

EID: 84875795886     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1300800313     Document Type: Article

References (38)

1. (a) Xu Y, He HP, Schulz S, Liu X, Fusetani N, Xiong HR, Qian PY. (2010) Potent antifouling compounds produced by marine Streptomyces. Bioresource Technology, 101, 1331-1336;
2. (b) Callow ME, Callow JE. (2002) Marine biofouling: a sticky problem. Biologist (London), 49, 10-14.
3. (a) Dobretsov S, Dahms HU, Qian PY. (2006) A review: Inhibition of biofouling by marine microorganisms and their metabolites. Biofouling, 22, 43-54;
4. (b) Wahl M. (1989). Marine epibiosis. 1. Fouling and antifouling: some basic aspects. Marine Ecology Progress Series, 58, 175-189.
5. (a) Chambers LD, Stokes KR, Walsh FC, Wood RJK. (2006) Modern approaches to marine antifouling coatings. Surface and Coatings Technology, 201, 3642-3652;
6. (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.
7. Bhadury P, Wright PC. (2004) Exploitation of marine algae: biogenic compounds for potential antifouling applications. Planta, 219, 561-578.
8. (a) Alzieu C. (2000) Impact of tributyltin on marine invertebrates. Ecotoxicology, 9, 71-76;
9. (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;
10. (c) Fusetani D. (2004) Biofouling and antifouling. Natural Products Reports, 21, 94-104;
11. (d) Fusetani D. (2011) Antifouling marine natural products. Natural Products Reports, 28, 400-410;
12. (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.
13. (a) Qi SH, Miao L, Gao CH, Xu Y, Zhang S, Qian PY. (2010) New steroids and a new alkaloid from the Gorgonian Isis minorbrachyblasta: structures, cytotoxicity, and antilarval activity. Helvetica Chimica Acta, 93, 511-516;
14. (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.
15. (a) Qi SH, Zhang S, Qian PY, Xiao ZH, Li MY. (2006) Ten new antifouling briarane diterpenoids from the South China Sea gorgonian Junceella juncea. Tetrahedron, 62, 9123-9130;
16. (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;
17. (c) Nozawa K, Nakajima S. (1979) Isolation of radicicol from Penicillium luteoaurantum, and meleagrin, a new metabolite, from Penicillium meleagrinum. Journal of Natural Products, 42, 374-377.
18. (a) Vinokurova NG, Boichenko LV, Arinbasarov MU. (2003) Production of alkaloids by fungi of the genus Penicillium grown on wheat grain. Applied Biochemistry and Microbiolology, 39, 403-406;
19. (b) Konda Y, Onda M, Hirano A, Omura S. (1980) Oxaline and neoxaline. Chemical and Pharmaceutical Bulletin, 28, 2987-2993;
20. (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;
21. (d) Schiavi BM, Richard DJ, Joullie MM. (2002) Total synthesis of isoroquefortine C. Journal of Organic Chemistry, 67, 620-624;
22. (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.
23. Takahashi C, Matsushita T, Doi M, Minoura K, Shingu T, Kumeda Y, Numata A. (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.
24. Cui CB, Kakeya H, Osada H. (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.
25. Abraham WR, Arfmann HA. (1990) 12, 13-Dihydroxyfumitremorgin C from Aspergillus fumigatus. Phytochemistry, 29, 1025-1026.
26. (a) Birch AJ, Russell RA. (1972) Studies in relation to biosynthesis-XLIV: structural elucidations of brevianamides-B,-C,-D and-F. Tetrahedron, 28, 2999-3008;
27. (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.
28. (a) He F, Sun YL, Liu KS, Zhang XY, Qian, PY, Wang, YF, Qi, SH. (2012) Indole alkaloids from marine-derived fungi Aspergillus sp. SCSIO 00305. Journal of Antibiotics, 65, 109-111;
29. (b) Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2011) Marine natural products. Natural Product Reports, 28, 196-268;
30. (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.
31. (a) Hedner E, Sjogren M, Hodzic S, Andersson R, Goransson U, Jonsson PR, Bohlin L. (2008) Antifouling activity of a dibrominated cyclopeptide from the marine sponge Geodia barretti. Journal of Natural Products, 71, 330-333;
32. (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;
33. (c) Hirota M, Matsuno T, Fujiwara T, Sugiyama H, Mineshita S. (2000) Enhanced cytotoxicity in a Zphtoisomer of a benzopyran derivative of propolis. Journal of Natural Products, 63, 366-370.
34. Thiyagarajan V, Harder T, Qian PY. (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.
35. Bryan PJ, Kreider JL, Qian PY. (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.
36. Qi SH, Zhang S, Yang LH, Qian PY. (2008) Antifouling and antibacterial compounds from gorgonians Subergorgia suberosa and Scripearia gracillis. Natural Products Research, 22, 154-166.
37. Acar JF. (1980) The disc susceptibility test. In Antibiotics in laboratory medicine. Lorian V. (Ed.). Williams and Wilkins, Baltimore, pp 24-54.
38. Lau SCK, Mak KK, Chen WF, Qian PY. (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.