两株海藻内生真菌次生代谢产物及其生物活性研究
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摘要
海洋微生物拥有丰富多样的次生代谢途径,其中海洋生物内生真菌次生代谢产物研究日益受到天然产物化学界的重视。本论文以菌丝体生物量、发酵产物重量、抗菌与细胞毒活性、薄层色谱分析结果以及高效液相色谱分析结果等为评价依据对采自青岛沿海的13株海藻内生真菌在四种液体培养基上的静置发酵产物进行了综合评价,并从中选择了黑曲霉Aspergillus niger EN-13(分离自褐藻囊藻Colpomenia sinuosa)和杂色曲霉A. versicolor EN-7(分离自褐藻鼠尾藻Sargassum thunbergii)两株真菌进行了30升规模发酵(分别采用GPYM培养基和PDB培养)和化学成分的研究,对分离得到的大部分化合物进行了初步的生物活性筛选。
发酵提取物采用常规的硅胶柱层析、反相硅胶柱层析,凝胶Sephadex LH-20柱层析、制备薄层层析、半制备高效液相色谱以及重结晶等分离手段,得到单体化合物。利用各种现代波谱技术(IR、UV、EI-MS、FAB-MS、HR-ESI-MS、1H-NMR、13C-NMR、DEPT、1H-1H COSY、HSQC、HMBC等)并结合化学方法从两种菌株发酵提取物中鉴定了55个化合物的结构。其中从菌株A. niger EN-13分离鉴定了31个化合物,发现9个新化合物,包括2个鞘酯类化合物(AN-1~2)、3个萘并-γ-吡喃酮类化合物(AN-3~5)、3个苯乙基取代的α-吡喃酮类化合物(AN-17, AN-19~20)和1个甾体Diels-Alder加成产物(AN-21),另有1个新的天然环二肽(AN-27)被分离鉴定;从菌株A. versicolor EN-7分离鉴定了24个化合物,发现2个新化合物,为蒽醌AV-12与AV-17,另外,从前一菌株(A. niger EN-13)中鉴定的2个新鞘酯类化合物(AN-1~2)在A. versicolor EN-7中也被再次分离到。
对大部分单体化合物进行了抗菌活性、DPPH自由基清除活性和细胞毒活性测试。结果显示新化合物AN-1、AN-5和AN-20具有弱或中等强度的抑制白色念珠菌生长的活性,AN-4、AN-5、AN-21显示了弱或中等强度的抑制黑曲霉生长的活性,AV-12、AV-17显示了弱的抑制大肠杆菌生长的活性。在DPPH自由基清除活性筛选中,AN-5显示了中等强度的活性,其EC50为109.3μM,与阳性对照BHT相近(EC50为81.8μM)。其它部分已知化合物在抗菌和DPPH自由基清除活性的筛选中也显示了弱或中等强度的活性。在针对人肝癌细胞株SMMC-7721和人肺腺癌细胞株A549的体外细胞毒活性筛选中,所测样品均未显示显著活性。
Marine microorganisms possess highly diverse metabolism pathways. Among them, the research on the secondary metabolites of marine endophytic fungi have drawn the interest of more and more natural product chemists. In this dissertation, on the basis of mycelia’biomass, weight of fermentation extracts, antimicrobial and cytotoxic activities, the results of TLC and HPLC analysis, the static fermentation extracts of 13 endophytic fungal strains (isolated from seaweeds collected along Qingdao coastline) on 4 kinds of liquid cultural mediums, were comprehensively evaluated. And two strains Aspergillus niger EN-1 (isolated from the brown algae Colpomenia sinuosa) and A. versicolor EN-7 (isolated from the brown algae Sargassum thunbergii) were selected as aimed strains to be fermented on 30 liters of GPYM and PDB cultural medium respectively for further investigation of chemical constituents. Most of the isolated compounds were preliminary screened on their bioactivities.
The compounds were isolated from the fermentation extracts by repeated column chromatography (CC) on silica gel, RP-18, and Sephadex LH-20, as well as by preparative thin layer chromatography (PTLC), semi-preparative HPLC and recrystallization. The structures of these compounds were elucidated by means of spectroscopic methods including IR, UV, EI-MS, FAB-MS, HR-ESI-MS, 1D-NMR (1H-NMR, 13C-NMR, DEPT) and 2D-NMR (1H-1H COSY, HSQC, HMBC) as well as chemical method. Totally, 55 compounds were structurally elucidated. From the extracts of A. niger EN-13, 31 compounds were isolated and structurally elucidated. Among them, Nine were found to be new compounds, including two new sphingolipids (AN-1~2), three new naphtho-γ-pyrones (AN-3~5), three new phenethyl-α-pyrone derivatives (AN-17, AN-19~20), and a new steroidal Diels-Alder adduct (AN-21). Additionally, a new naturally reported cyclodipeptide (AN-27) were also elucidated. From the extracts of fungus A. versicolor EN-7, 24 compounds were isolated and structurally elucidated. Among them, two were found to be new compounds as new anthraquinones (AV-12, AV-17). In addition, the two new sphingolipids (AN-1~2) from fungus A. niger EN-13 were reisolated from fungus A. versicolor EN-7.
Most of the pure compounds were screened for their antimicrobial, DPPH scavenging and cytotoxic activities. It was revealed that the new compounds AN-1, AN-5 and AN-20 exhibited moderate or weak inhibitory activity against Candida albicans, compound AN-4, AN-5 and AN-21 exhibited moderate or weak inhibitory activity against Aspergillus niger, compound AV-12 and AV-17 showed weak inhibitory activity against Escherichia coli. In the DPPH scavenging assay, compound AN-5 showed moderate free radical scavenging activities with an EC50 of 109.3μM, compared with the 81.8μM for positive control BHT. Part of the isolated known compounds also exhibited moderate or weak activity in the antimicrobial and DPPH scavenging assay. None of the tested compounds showed remarkable activity in the in vitro cytotoxic assay against tumor cell lines SMMC-7721 and A-549.
发酵提取物采用常规的硅胶柱层析、反相硅胶柱层析,凝胶Sephadex LH-20柱层析、制备薄层层析、半制备高效液相色谱以及重结晶等分离手段,得到单体化合物。利用各种现代波谱技术(IR、UV、EI-MS、FAB-MS、HR-ESI-MS、1H-NMR、13C-NMR、DEPT、1H-1H COSY、HSQC、HMBC等)并结合化学方法从两种菌株发酵提取物中鉴定了55个化合物的结构。其中从菌株A. niger EN-13分离鉴定了31个化合物,发现9个新化合物,包括2个鞘酯类化合物(AN-1~2)、3个萘并-γ-吡喃酮类化合物(AN-3~5)、3个苯乙基取代的α-吡喃酮类化合物(AN-17, AN-19~20)和1个甾体Diels-Alder加成产物(AN-21),另有1个新的天然环二肽(AN-27)被分离鉴定;从菌株A. versicolor EN-7分离鉴定了24个化合物,发现2个新化合物,为蒽醌AV-12与AV-17,另外,从前一菌株(A. niger EN-13)中鉴定的2个新鞘酯类化合物(AN-1~2)在A. versicolor EN-7中也被再次分离到。
对大部分单体化合物进行了抗菌活性、DPPH自由基清除活性和细胞毒活性测试。结果显示新化合物AN-1、AN-5和AN-20具有弱或中等强度的抑制白色念珠菌生长的活性,AN-4、AN-5、AN-21显示了弱或中等强度的抑制黑曲霉生长的活性,AV-12、AV-17显示了弱的抑制大肠杆菌生长的活性。在DPPH自由基清除活性筛选中,AN-5显示了中等强度的活性,其EC50为109.3μM,与阳性对照BHT相近(EC50为81.8μM)。其它部分已知化合物在抗菌和DPPH自由基清除活性的筛选中也显示了弱或中等强度的活性。在针对人肝癌细胞株SMMC-7721和人肺腺癌细胞株A549的体外细胞毒活性筛选中,所测样品均未显示显著活性。
Marine microorganisms possess highly diverse metabolism pathways. Among them, the research on the secondary metabolites of marine endophytic fungi have drawn the interest of more and more natural product chemists. In this dissertation, on the basis of mycelia’biomass, weight of fermentation extracts, antimicrobial and cytotoxic activities, the results of TLC and HPLC analysis, the static fermentation extracts of 13 endophytic fungal strains (isolated from seaweeds collected along Qingdao coastline) on 4 kinds of liquid cultural mediums, were comprehensively evaluated. And two strains Aspergillus niger EN-1 (isolated from the brown algae Colpomenia sinuosa) and A. versicolor EN-7 (isolated from the brown algae Sargassum thunbergii) were selected as aimed strains to be fermented on 30 liters of GPYM and PDB cultural medium respectively for further investigation of chemical constituents. Most of the isolated compounds were preliminary screened on their bioactivities.
The compounds were isolated from the fermentation extracts by repeated column chromatography (CC) on silica gel, RP-18, and Sephadex LH-20, as well as by preparative thin layer chromatography (PTLC), semi-preparative HPLC and recrystallization. The structures of these compounds were elucidated by means of spectroscopic methods including IR, UV, EI-MS, FAB-MS, HR-ESI-MS, 1D-NMR (1H-NMR, 13C-NMR, DEPT) and 2D-NMR (1H-1H COSY, HSQC, HMBC) as well as chemical method. Totally, 55 compounds were structurally elucidated. From the extracts of A. niger EN-13, 31 compounds were isolated and structurally elucidated. Among them, Nine were found to be new compounds, including two new sphingolipids (AN-1~2), three new naphtho-γ-pyrones (AN-3~5), three new phenethyl-α-pyrone derivatives (AN-17, AN-19~20), and a new steroidal Diels-Alder adduct (AN-21). Additionally, a new naturally reported cyclodipeptide (AN-27) were also elucidated. From the extracts of fungus A. versicolor EN-7, 24 compounds were isolated and structurally elucidated. Among them, two were found to be new compounds as new anthraquinones (AV-12, AV-17). In addition, the two new sphingolipids (AN-1~2) from fungus A. niger EN-13 were reisolated from fungus A. versicolor EN-7.
Most of the pure compounds were screened for their antimicrobial, DPPH scavenging and cytotoxic activities. It was revealed that the new compounds AN-1, AN-5 and AN-20 exhibited moderate or weak inhibitory activity against Candida albicans, compound AN-4, AN-5 and AN-21 exhibited moderate or weak inhibitory activity against Aspergillus niger, compound AV-12 and AV-17 showed weak inhibitory activity against Escherichia coli. In the DPPH scavenging assay, compound AN-5 showed moderate free radical scavenging activities with an EC50 of 109.3μM, compared with the 81.8μM for positive control BHT. Part of the isolated known compounds also exhibited moderate or weak activity in the antimicrobial and DPPH scavenging assay. None of the tested compounds showed remarkable activity in the in vitro cytotoxic assay against tumor cell lines SMMC-7721 and A-549.
引文
1. Abdel-Lateff A, Klemke C, K?nig GM, Wright AD. Two new xanthone derivatives from the algicolous marine fungus Wardomyces anomalus. J. Nat. Prod., 2003, 66(5):706–708
2. Abdel-Lateff A, K?nig GM, Fisch KM, H?ller U, Jones PG, Wright AD. New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp. J. Nat. Prod., 2002, 65(11):1605–1611
3. Abdel-Mallek AY, El-Maraghy SSM, Hasan HAH. Mycotoxin-producing potential of some Aspergillus, Penicillium and Fusarium isolates found on corn grains and sunflower seeds in Egypt. J. Isl. Acad. Sci., 1993, 6(3):189–192
4. Abraham EP, Loder PB. Cephalosporin C, in Cephalosporins and Penicillins: Chemistry and Biology, ed. E. H. Flynn, New York : Academic Press, 1972
5. Abrell LM, Borgeson B, Crews P. Chloro-polyketides from the cultured fungus (Aspergillus) separated from a marine sponge. Tetrahedron Lett., 1996, 37(14):2331–2334
6. Akihisa T, Kithsiri Wijeratne EM, Tokuda H, Enjo F, Toriumi M, Kimura Y, Koike K, Nikaido T, Tezuka Y, Nishino H. Eupha-7,9(11),24-trien-3beta-ol ("antiquol C") and other triterpenes from Euphorbia antiquorum latex and their inhibitory effects on Epstein-Barr virus activation. J. Nat. Prod., 2002, 65(2):158–162
7. Akiyama K, Teraguchi Y, Hamasaki Y, Mori M, Tatsumi K, Ohnishi K, Hayashi H. New dimeric naphthopyrones from Aspergillus niger. J. Nat. Prod., 2003, 66(1):136–139
8. Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffmann C, Rothcock J, Lopez M, Joshua H, Harris E, Patchett A, Monaghan R, Currie S, Stapley E, Albers-Schonberg G, Hensens O, Hirshfield J, Hoogsteen K, Liesch J, Springer J. Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl- coenzyme A reductase and a cholesterol-lowering agent. Proc. Natl. Acad. Sci. U.S.A., 1980, 77(7):3957–3961
9. Al-Burtamani SKS, Fatope MO, Marwah RG, Onifade AK, Al-Saidi SH. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J. Ethnopharmacol., 2005, 96(1–2):107–112
10. Amagata T, Minoura K, Numata A. Cytotoxic metabolites produced by a fungal strain from a Sargassum alga. J. Antibiot.,1998, 51(4):432–434
11. Barbosa FG, Oliveira MCF, Braz-Filho R, Silveira ER. Anthraquinones and naphthopyrones from Senna rugosa. Biochem. Syst. Ecol., 2004, 32(3):363–365
12. Barrow CJ, Cai P, Snyder JK, Sedlock DM, Sun HH, Cooper R. WIN 64821, a new competitive antagonist to substance P, isolated from an Aspergillus species: structure determination and solution conformation. J. Org. Chem., 1993, 58(22):6016–6021
13. Barton DHR, Bruun T. New sterol from a strain of Aspergillus niger. J. Chem. Soc., 1951, 2728–2733
14. Bell AA, Stipanovic RD, Puhalla JE. Pentaketide metabolites of verticillium dahliae: Identification of (+)-scytalone as a natural precursor to melanin. Tetrahedron, 1976, 32(12):1353–1356
15. Belofsky GN, Jensen PR, Renner MK, Fenical W. New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron, 1998, 54(9):1715–1724
16. Bondarenko-Gheorghiu LG, Lorenc LB, Mihailovic MLJ. Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. J. Serb. Chem. Soc., 2000, 65(3):147–156
17. Bouras N, Mathieu F, Coppel Y, Lebrihi A. Aurasperone F-a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C–433. Nat. Prod. Res., 2005, 19(7):653–659
18. Brodesser S, Sawatzki P, Kolter T. Bioorganic chemistry of ceramide. Eur. J. Org. Chem. 2003, 2021–2034
19. Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM. Yanuthones: Novel Metabolites from a Marine Isolate of Aspergillus niger. J. Org.Chem., 2000, 65(21):7195–7200
20. Bugni TS, Ireland CM. Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Nat. Prod. Rep., 2004, 21(1):143–63
21. 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
22. Campos FR, Barison A, Daolio C, Ferreira AG, Rodrigues-Fo E. Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus. Magn. Reson. Chem., 2005, 43(11):962–965
23. Catalfomo P, Block JH, Constantine GH, Kirk PW. Choline sulfate (ester) in marine higher fungi. Mar. Chem., 1972,1(2):157–162
24. Chen C, Imamura N, Nishijima M, Adachi K, Sakai M, Sano H. Halymecins, new antimicroalgal substances produced by fungi isolated from marine algae. J. Antibiot.,1996, 49(10):998–1005
25. Chen JH, Cui GY, Liu JY, Tan RX. Pinelloside, an antimicrobial cerebroside from Pinellia ternata. Phytochemistry, 2003, 64(4):903–906
26. Chen X, Wu YL, Chen D. Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl. TetrahedronLett., 2002, 43(19):3529–3532
27. Chexal KK, Holker JSE, Simpson TJ, Young K. The biosynthesis of fungal metabolites. Part V. Structure of variecoxanthones A, B, and C, metabolites of Aspergillus variecolor; conversion of variecoxanthone A into (±)-de-C-prenylepishamixanthone. J. Chem. Soc., Perkin Trans. 1, 1975, 6:543–548
28. Clark RL, Johnston BF, Suckling CJ, Mackay SP. A modelling study of a non-concerted hydrolytic cycloaddition reaction by the catalytic antibody H11. Bioorg. Med. Chem., 2006, 14(8):2674–2683
29. Coelho RG, Vilegas W, Devienne KF, Raddi MSG. A new cytotoxic naphthopyrone dimer from Paepalanthus bromelioides. Fitoterapia, 2000, 71(5):497–500
30. Cueto M, Jensen PR, Fenical W. Aspergilloxide, A novel sesterterpene epoxide from marine–derived fungus of the genus Aspergillus. Org. Lett., 2002, 4(9):1583–1585
31. Cueto M, Jensen PR, Kauman C, Fenical W, Lobkovsky E, Clardy J. Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. J. Nat. Prod., 2001, 64(11):1444–1446
32. Cueto M, MacMillan JB, Jensen PR, Fenical W. Tropolactones A–D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus. Phytochemistry, 2006, 67(16):1826–1831
33. Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H. Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus. J. Antibiot., 1995, 48(11):1382–1384
34. Cuomo V, Palomba I, Perretti A, Guerriero A, D'Ambrosio M, Pietra F. Antimicrobial activities from marine fungi. J. Mar. Biotechnol., 1995, 2(3): 199-204
35. Dreyfuss M, Harri E, Hotmann H, Kobel H, Pache W, Tscherter H. Cyclosporin A and C. Eur. J. Appl. Microbiol. Biotechnol., 1976, 3:125–133
36. Du L, Zhu TJ, Fang YC, Liu HB, Gu QQ, Zhu WM. Aspergiolide A, a novel anthraquinone derivative with naphtho[1,2,3-de]chromene-2,7-dione skeleton isolated from a marine-derived fungus Aspergillus glaucus. Tetrahedron, 2007, 63(5):1085–1088
37. Duan XJ, Zhang WW, Li XM, Wang BG. Evaluation of antioxidant property of extract and fractions obtained from a red alga, Polysiphonia urceolata. Food Chem., 2006, 95(1):37–43
38. Ehrlich KC, Delucca II AJ, Ciegler A. Naphtho-γ-pyrone production by Aspergillus niger isolated from stored cottonseed. Appl. Environ. Microbiol., 1984, 48(1):1–4
39. Epstein WW, Lear GV. Metabolites of Fomes officinalis1a. J. Org. Chem., 1966, 31(10):3434–3435
40. Ernst-Russell MA, Chai CLL, Wardlaw JH, Elix JA. Euplectin and coneuplectin, new naphthopyrones from the lichen Flavoparmelia euplecta. J. Nat. Prod., 2000, 63(1):129–131
41. Fleming A.Br. On the antibacterial action of cultures of a Penicillium, with special reference to their use in the isolation of B influenzae. J. Exp. Pathol., 1929, 10:226–236
42. Galmarini OL, Mastronardi IO, Priestap HA. Two novel metabolites of Aspergillus fonsecaeus. Experientia, 1974, 30:586
43. Galmarini OL, Stodola FH. Fonsecin, a pigment from an Aspergillus fonsecaeus Mutant. J. Org. Chem., 1965, 30(1):112–115
44. Gao JM, Hu J, Dong ZJ, Liu JK. A new ceramide from the basidiomycete Russula cyanoxantha. Lipids, 2001b, 36(2):175–180
45. Gao JM, Hu J, Dong ZJ, Liu JK. New glycosphingolipid containing an unusual sphingoid base from the basidiomycete Polyporus ellisii. Lipids, 2001a, 36(5):521–527
46. Genshiro K, Yonosuke I, Keisuk T. Fruiting of Schizophyllum commune induced by certain ceramides and cerebrosides from Penicillium funiculosum. Agric. Biol. Chem., 1994, 59:144–147
47. Ghosal S, Biswas K, Chakrabarti DK. Toxic naphtho-γ-pyrones from Aspergillus niger. J. Agric. Food. Chem., 1979, 27(6):1347–1351
48. Goodman GA, Goodman LS, Rall TW, Murad F. (eds.) Macmillan. 7th ed. New York. 1985, 1298–1299
49. Green LR, Sinackevich NV. Use of L-Glu-L-Trp or other dipeptide in the treatment of HIV infection. PCT Int. Appl., 1999, 32
50. Hiort J, Maksimenka K, Reichert M, Perovic-Ottstadt S, Lin WH, Wray V, Steube K, Schaumann K, Weber H, Proksch P, Ebel R, Muller WEG, Bringmann G. New natural products from the sponge-derived fungus Aspergillus niger. J. Nat. Prod., 2004, 67(9): 1532–1543
51. Holler U, K?nig G, Wright AD. 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., 1999, 1999(11):2949–2955
52. Hyodo S, Fujita K, Kasuya O, Takahashi I, Uzawa J, Koshino H. Structures of phospholipase A2 inhibitors, ergophilones A and B. Tetrahedron, 1995, 51(24):6717–6724
53. Iwamoto C, Minoura K, Hagishita S, Nomoto K, Numata A. Penostatins F-I, novel cytotoxic metabolites from a Penicillium species separated from an Enteromorpha marine alga. J. Chem. Soc., Perkin Trans. 1, 1998, (3):449–456
54. Iwamoto C, Minoura K, Oka T, Ohta T, Hagishita S, Numata A. Absolute stereostructuresof novel cytotoxic metabolites, penostatins A–E, from a Penicillium species separated from an Enteromorpha alga. Tetrahedron, 1999, 55(50):14353–14368
55. 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
56. Jenkins KM, Renner MK, Jensen PR, Fenical W. Exumolides A and B: antimicroalgal cyclic depsipeptides produced by a marine fungus of the genus Scytalidium. Tetrahedron Lett.,1998b, 39(17):2463–2466
57. Jenkins KM, Toske SG, Jensen PR, Fenical W. Solanapyrones E-G, antialgal metabolites produced by a marine fungus. Phytochemistry, 1998c, 49(8):2299–2304
58. Jenkins, KM. Chemical investigations of marine filamentous and zoosporic fungi and studies in marine microbial chemical ecology . Dissertation of University of California, San Diego. 1998a
59. Jiang T, Li T, Li J, Fu HZ, Pei YH, Lin WH. Cerebroside analogues from marine-derived fungus Aspergillus flavipes. J. Asian. Nat. Prod. Res., 2004, 6(4):249–257
60. Jiang Z, Barret MO, Boyd KG, Adams DR, Boyd ASF, Burgess JG. JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species. Phytochemistry, 2002, 60(1):33–38
61. Kakeya H, Takahashi I, Okada G, Isono K, Osada H. Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, produced by a marine fungus. J Antibiot., 1995, 48(7):733–735
62. Katayama K, Kobayashi T, Oikawa H, Honma M, Ichihara A. Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction. Biochim. Biophys. Acta., 1998, 1384(2):387–395
63. Kawagishi H, Katsumi R, Sazawa T, Mizuno T, Hagiwara T, Nakamura T. Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry, 1988, 27(9):2777–2779
64. Keusgen M, Yu CM, Curtis JM, Brewer D, Ayer SW. A cerebroside from the marine fungus Microsphaeropsis olivacea (Bonord.) h?nn. Biochem. Syst. Ecol., 1996, 24(5):465–468
65. Kimura Y, Sawada A, Kuramata M, Kusano M, Fujioka S, Kawano T, Shimada A. Brevicompanine C, cyclo-(D-Ile-L-Trp), and cyclo-(D-Leu-L-Trp), plant growth regulators from Penicillium brevicompactum. J. Nat. Prod., 2005, 68(2):237–239
66. 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
67. Kingston DGI, Chen PN, Vercellotti JR. Metabolites of Aspergillus versicolor: 6,8-di-O-methylnidurufin, griseofulvin, dechlorogriseofluvin, and 3,8-dihydroxy-6-methoxy-1-methylxanthone. Phytochemistry, 1976, 15(6):1037–1039
68. Klemke C, Kehraus S, Wright AD, K?nig GM. New secondary metabolites from the marine endophytic fungus Apiospora montagnei. J. Nat. Prod., 2004, 67(6):1058–1063
69. Komatsu K, Shigemori H, Shiro M, Kobayashi J. Revised Stereochemistry and Biosynthesis of Seragakinone A. Tetrahedrion, 2000, 56(45):8841–8844
70. Krohn K, Dai J, Fl?rke U, Aust HJ, Dr?ger S, Schulz B. Botryane metabolites from the fungus Geniculosporium sp. isolated from the marine red alga Polysiphonia. J. Nat. Prod., 2005, 68(3):400–405
71. Kupka J, Anke T, Steglich W, Zechlin L. Antibiotics from basidiomycetes. XI. The biological activity of siccayne, isolated from the marine fungus Halocyphina villosa J. & E. Kohlmeyer. J. Antibiot., 1981, 34(3):298–304
72. Lee D, Choi J, Yang M, Lee W, Kim D, Choi H, Son B. Natural Product Sciences, 1999, 5, 93–96
73. Lee SM, Li XF, Jiang HL, Cheng JG, Seong S, Choi HD, Son BW. Terreusinone, a novel UV-A protecting dipyrroloquinone from the marine algicolous fungus Aspergillus terreus. Tetrahedron Lett., 2003, 44(42):7707–7710
74. Lin WH, Brauers G, Ebel R, Wray V, Sudarsono BA, Proksch P. Novel chromone derivatives from the fungus Aspergillus versicolor isolated from the marine sponge Xestospongia exigua. J. Nat. Prod., 2003, 66(1):57–61
75. Lin WH, Fu HZ, Li J, Proksch P. Novel chromone derivatives from marine fungus Aspergillus versicolor isolated from the sponge Xestospongia exigua. Chin. Chem. Lett., 2001b, 12(3):235–238
76. Lin WH, Li J, Fu HZ, Proksch P. Four novel hydropyranoindeno-derivatives from marine fungus Aspergillus versicolor. Chin. Chem. Lett., 2001a, 12(5):435–438
77. Lorenz P, Jensen PR, Fenical W. Mactanamide, A new fungistatic diketopiperazine produced by a marine Aspergillus sp. Nat. Prod. Lett.,1998,12(1):55–60
78. Lo SK, Baharin BS, Tan CP, Lai OM. Diacylglycerols from palm oil deodorizer distillate. Part 2-physical and chemical characterization. Food Sci. Technol. Int., 2004, 10(3):157–161
79. Malmstrom J, Ryager A, Anthoni U, Nielsen PH. Unguisin C, a GABA–containing cyclic peptide from the fungus Emericella unguis. Phytochemistry, 2002, 60(8):869–872
80. Malmstrom J. Unguisins A and B: new cyclic peptides from the marine-derived fungus Emericella unguis. J. Nat. Prod., 1999, 62(5):787–789
81. Marcel SF, Lie KJ, Mustafa J. High-resolution nuclear magnetic resonance spectroscopy —Applications to fatty acids and triacylglycerols. Lipids, 1997, 32(10):1019–1034
82. Maskey RP, Grun-Wollny I, Laatsch H. Isolation, structure elucidation and biological activity of 8-O-methylaverufin and 1,8-O-dimethylaverantin as new antifungal agents from Penicillium chrysogenum. J. Antibiot., 2003, 56(5):459–463
83. Mielcarek M, Barciszewska MZ, Salanski P, Stobiecki M, Jurczak J, Barciszewski J. Native transfer RNA catalyzes Diels-Alder reaction. Biochem. Biophys. Res. Comm., 2002, 294(1):145–148
84. Mori K, Uenishi K. Synthesis of sphingosine relatives. Part 17. Synthesis of (2S, 2'R, 3R, 3'E, 4E, 8E)-1-O-(β-D-glucopyranosyl)-N-(2'- hydroxy-3'-octadecenoyl)-9-methyl-4, 8-sphingadienine (Pen II), the major cerebroside isolated from Penicillium funiculosum as the fruiting-inducer against Schizophyllum commune. Liebigs Annalen der Chemie, 1996, 1–6
85. Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J. Absolute stereochemistry of citrinadins A and B from marine-derived fungus. J. Org. Chem., 2005, 70(23):9430–9435
86. Mukhtar N, Iqbal K, Anis I, Malik A. Sphingolipids from Conyza canadensis. Phytochemistry, 2002, 61(8):1005–1008
87. Nakatsuka S, Miyazaki H, Goto T. Total synthesis of (±)-neoechinulin A, an indole alkaloid containing oxidized diketopiperazine. Tetrahedron Lett., 1980, 21(29):2817–2820
88. Nielsen J, Nielsen PH, Frisvad JC. Fungal depside, guisinol, from a marine derived strain of Emericella unguis. Phytochemistry, 1998, 50(2):263–265
89. Numata A, Takahashi C, Ito Y, Minoura K, Yamada T, Matsuda C, Nomoto K. 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, 1996, (3):239–246
90. Numata A, Takahashi C, Ito Y, Takada T, Kawai K, Usami Y, Matsumura E, Imachi M, Ito T, Hasegawa T. Communesins, cytotoxic metabolites of a fungus isolated from a marine alga. Tetrahedron Lett., 1993, 34(14):2355–2358
91. Numata A, Takahashi C, Matsushita T, Miyamoto T, Kawai K, Usami Y, Matsumura E, Inoue M, Ohishi H, Shingu T. Fumiquinazolines, novel metabolites of a fungus isolated from a saltfish. Tetrahedron Lett., 1992, 33(12):1621–1624
92. Oikawa H, Tokiwano T. Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products. Nat. Prod. Rep., 2004, 21(3):321–352
93. Okutani K. Gliotoxin produced by a strain of Aspergillus isolated from marine mud. Bull. Jap. Soc. Fish., 1977, 43:995–1000
94. Ose T, Watanabe K, Mie T, Honma M, Watanabe H, Yao M, Oikawa H, Tanaka I. Insightinto a natural Diels-Alder reaction from the structure of macrophomate synthase. Nature, 2003, 422:185–189
95. Osterhage C, Kaminsky R, K?nig GM, Wright AD. Ascosalipyrrolidinone A, an antimicrobial alkaloid, from the obligate marine fungus Ascochyta salicorniae. J. Org. Chem., 2000, 65(20):6412–6417
96. Osterhage C, K?nig GM, Holler U, Wright AD. Rare sesquiterpenes from the algicolous fungus Drechslera dematioidea. J. Nat.Prod., 2002, 65(3):306–313
97. Osterhage C. Isolation, structure determination and biological activity assessment of secondary metabolites from marine-derived fungi. Dissertation of Technischen Universit?t Carolo-Wilhelmina. 2001
98. Ouyang MA, Liu R, Kuo YH. A new cerebroside, Asperiamide A, from the marine fungus Asperillus sp. J. Asian. Nat. Prod. Res., 2005, 7(5):761–765
99. Ovenden SP, Sberna G, Tait RM, Wildman HG, Patel R, Li B, Steffy K, Nguyen N, Meurer-Grimes BM. A diketopiperazine dimer from a marine-derived isolate of Aspergillus niger. J. Nat. Prod., 2004, 67(12):2093–2095
100. Peters L, Konig GM, Terlau H, Wright AD. Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea. J. Nat. Prod., 2002, 65(11):1633–1637
101. Priestap HA. 13C NMR spectroscopy of naphtho-γ-pyrones. Magn. Reson. Chem., 1986, 24:875–878
102. Priestap HA. New naphthopyrones from Aspergillus fonsecaeus. Tetrahedron, 1984, 40(18):3617–3624
103. Ray FE, Sawicki E, Borum OH. Diels-Alder reactions of maleimide. J. Am. Chem. Soc., 1952, 74(5):1247–1249
104. Rehm HJ. Industrielle Mikrobiologie. 2nd ed. Berlin: Springer-Verlag, 1980.
105. Sabri A, Jacques P, Weekers F, Bare G, Hiligsmann S, Moussaif M, Thonart P. Effect of temperature on growth of psychrophilic and psychrotrophic members of Rhodotorula aurantiaca. Appl. Biochem. Biotechnol., 2000, 84(1–9):391–400
106. Sakurai M, Kohno J, Yamamoto K, Okuda T, Nishio M, Kawano K, Ohnuki T. TMC-256A1 and C1, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var niger TC 1629. J. Antibiot., 2002, 55(8):685–692
107. Schulte KE, Rücker G., Fachmann H. Ergosta-4,6,8(14),22-tetraenon-(3) als inhaltsstoff des l?rchenschwammes. Tetrahedron Lett., 1968, 9(46):4763–4764
108. Seelig B, Jaschke A. A small catalytic RNA motif with Diels-Alderase activity. Chem. Biol., 1999, 6(3):167–176
109. Seto H, Cary LW, Tanabe M. Utilization of 13C-13C coupling in structural and biosyntheticstudies V. The 13C ft nmr spectrum of sterigmatocystin. Tetrahedron Lett., 1974, 15(51–52):4491–4494
110. Shigemori H, Komatsu K, Mikamia Y, Kobayashi J. Seragakinone A, a new pentacyclic metabolite from a marine-derived fungus. Tetrahedron, 1999, 55(52):14925–14930
111. Shin J, Fenical W. Isolation of gliovictin from the marine deuteromycete Asteromyces cruciatus. Phytochemistry, 1987, 26(12):3347
112. Son BW, Choi JS, Kim JC, Nam KW, Kim DS, Chung HY, Kang JS, Choi HD. Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus. J. Nat. Prod., 2002, 65(5):794–795
113. Son BW, Jensen PR, Kauman CA, Fenical W. New cytotoxic epidithiodioxopiperazines related to Verticillin A from a marine isolate of the fungus Penicillium. Nat. Prod. Lett., 1999, 13(3):213–222
114. Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX. Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiol. Lett., 2004, 241(1):67–72
115. Steyn PS, Vleggaar R, Wessels PL, Cole RJ, Scott DB. Structure and carbon-13 nuclear magnetic resonance assignments of versiconal acetate, versiconol acetate, and versiconol, metabolites from cultures of Aspergillus parasiticus treated with dichlorvos. J. Chem. Soc., Perkin Trans. 1, 1979, 451–459
116. Stocking EM, Sanz-Cervera JF, Unkefer CJ, Williams RM. Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework. Tetrahedron, 2001, 57(25):5303–5320
117. Stocking EM, Williams RM. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew. Chem. Int. Ed. Engl., 2003, 42(27):3078–3115
118. Strobel GA. Endophytes as sources of bioactive products. Microbes. Infect., 2003, 5(6):535–44
119. 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 Trans. 1, 1995c, (18):2345–2353
120. Takahashi C, Minoura K, Yamada K, Numata A, Kushida K, Shingu T, Hagishita S, Nakai H, Sato T, Harada H. Potent cytotoxic metabolites from a Leptosphaeria species. Structure determination and conformational analysis. Tetrahedron, 1995b, 51(12):3483–3498
121. Takahashi C, Numata A, Ito Y, Matsumura E, Araki H, Iwaki H, Kushida K. Leptosins, antitumour metabolites of a fungus isolated from a marine alga. J. Chem. Soc., Perkin Trans. 1, 1994a, (13):1859–1864
122. Takahashi C, Numata A, Matsumura E, Minoura K, Eto H, Shingu T, Ito T, Hasegawa T. Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures. J. Antibiot., 1994b, 47(11):1242–1249
123. Takahashi C, Numata A, Yamada T, Minoura K, Enomoto S, Konishi K, Nakai M, Matsuda C, Nomoto K. Penostatins, novel cytotoxic metabolites from a Penicillium species separated from a green alga. Tetrahedron Lett., 1996, 37(5):655–658
124. Takahashi C, Takai Y, Kimura Y, Numata A, Shigematsu N, Tanaka H. Cytotoxic metabolites from a fungal adherent of a marine alga. Phytochemistry, 1995a, 38(1):155–158
125. Tan RX, Chen JH. The cerebrosides. Nat. Prod. Rep., 2003, 20(5):509–534
126. Tan RX, Zou WX. Endophytes: a rich source of functional metabolites. Nat. Prod. Rep., 2001, 18(4):448–459
127. Tanaka H, Wang PL, Yamada O, Tamura T. Yellow pigments of Aspergillus niger and A. awamori. Part I. Isolation of aurasperone A and related pigments. Agric. Biol. Chem., 1966, 30(2):107–113
128. Townsend CA. Progress toward a biosynthetic rationale of the aflatoxin pathway. Pure & Appl. Chem., 1986, 58(2):227–238
129. Tsuda M, Kasai Y, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum. Organic Lett., 2004, 6(18):3087–3089
130. Tsuda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Shiro M, Hirai M, Ohizumie Y, Kobayashia J. Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii. Tetrahedron, 2003, 59(18):3227–3230
131. Tsukamoto S, Hirota H, Imachi M, Fujimuro M, Onuki H, Ohta T, Yokosawa H. Himeic acid A: a new ubiquitin-activating enzyme inhibitor isolated from a marine-derived fungus, Aspergillus sp. Bioorg. Med. Chem. Lett., 2005, 15(1):191–194
132. Tsukamoto S, Miura S, Yamashita Y, Ohta T. Aspermytin A: a new neurotrophic polyketide isolated from a marine-derived fungus of the genus Aspergillus. Bioorg. Med. Chem. Lett., 2004, 14(2):417–420
133. Ui H, Shiomi K, Yamaguchi Y, Masuma R, Nagamitsu T, Takano D, Sunazuka T, Namikoshi M, Omura S. Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554. J. Antibiot., 2001, 54(3): 234–238
134. Valisolalao J, Luu B, Ourisson G. Steroids cytotoxiques de Polyporus versicolor. Tetrahedron, 1983, 39(17):2779–2785
135. Varoglu M, Corbett TH, Valeriote FA, Crews P. Asperazine, a selective cytotoxic alkaloidfrom a sponge-derived culture of Aspergillus niger. J. Org. Chem., 1997, 62(21): 7078–7079
136. Varoglu M, Crews P. Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger. J. Nat. Prod., 2000, 63(1):41–43
137. Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J. Nat. Prod., 2006, 69(11):1622–1625
138. Yamada T, Iwamoto C, Yamagaki N, Yamanouchi T, Minoura K, Yamori T, Uehara Y, Andoh T, Umemura K, Numata A. Leptosins M–N1, cytotoxic metabolites from a Leptosphaeria species separated from a marine alga. Structure determination and biological activities. Tetrahedron, 2002, 58(3):479–487
139. Yang RY, Li CY, Lin YC, Peng GT, She ZG, Zhou SN. Lactones from a brown alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities. Bioorg. Med. Chem. Lett., 2006, 16(16):4205–4208
140. Yue JM, Chen SN, Lin ZW, Sun HD. Sterols from the fungus Lactarium volemus. Phytochemistry, 2001, 56(8):801–806
141. 高坤, 贾忠建. 齿叶橐吾中甾醇类化合物结构研究. 兰州大学学报(自然科学版), 1997, 33(4):77–80
142. 郭志峰, 康现江, 蔺智强, 李彦芹, 安秋荣, 黄增瑞, 刘龙. 日本沼虾卵巢发育过程中脂肪酸变化的研究. 分析化学, 2003, 31(4):433–436
143. 林永成, 周世宁. 海洋微生物及其次生代谢产物. 第一版. 北京:化学工业出版社, 2003. 23–27
144. 刘大有, 王晓颖, 夏忠庭, 王旭. 两头尖化学成分研究. 长春中医学院学报, 2003, 19(3):71
145. 马悦欣, 孙田, 王海燕, 王岩, 朱莹. 大连海区潮间带海藻附生真菌的抗微生物活性. 大连水产学院学报, 2004, 19(1):6–9
146. 齐祖同. 中国真菌志—中国真菌志第 5 卷曲霉属及其相关有性型. 第一版. 北京:科学出版社, 1997, 1–3
147. 史大永, 韩丽君, 孙杰, 王瑛, 杨永春, 石建功, 范晓. 海藻基根硬毛藻的化学成分研究. 中国中药杂志, 2005, 30(5):347–350
148. 王新,郑天凌,胡忠,苏建强. 海洋微生物毒素研究进展. 海洋科学, 2006, 30(7):76–81
149. 谢芬, 郭顺星. 真菌来源鞘脂的结构及其活性研究进展. 中国药学杂志, 2002, 37(7):481–484
150. 许向前, 洪文荣, 陈代杰. 黑麦麦角菌产生麦角甾醇的研究. 中国抗生素杂志, 2006,31(6):379–381
151. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京: 科学出版社, 1999a, 860–867
152. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京: 科学出版社, 1999e, 794–795
153. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999b, 798
154. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999c, 794
155. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999d, 805
156. 朱峰 , 林永成 , 周世宁 , Vrijmoedd LLP. 从红树林内源真菌 2526# 分离到的sterigmatocystin. 应用化学, 2003, 20(3):272–274
157. 朱峰, 林永成, 周世宁. 南海海洋真菌 2526#中蒽醌类代谢产物的研究. 有机化学, 2004, 24(9):1114–1117
2. Abdel-Lateff A, K?nig GM, Fisch KM, H?ller U, Jones PG, Wright AD. New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp. J. Nat. Prod., 2002, 65(11):1605–1611
3. Abdel-Mallek AY, El-Maraghy SSM, Hasan HAH. Mycotoxin-producing potential of some Aspergillus, Penicillium and Fusarium isolates found on corn grains and sunflower seeds in Egypt. J. Isl. Acad. Sci., 1993, 6(3):189–192
4. Abraham EP, Loder PB. Cephalosporin C, in Cephalosporins and Penicillins: Chemistry and Biology, ed. E. H. Flynn, New York : Academic Press, 1972
5. Abrell LM, Borgeson B, Crews P. Chloro-polyketides from the cultured fungus (Aspergillus) separated from a marine sponge. Tetrahedron Lett., 1996, 37(14):2331–2334
6. Akihisa T, Kithsiri Wijeratne EM, Tokuda H, Enjo F, Toriumi M, Kimura Y, Koike K, Nikaido T, Tezuka Y, Nishino H. Eupha-7,9(11),24-trien-3beta-ol ("antiquol C") and other triterpenes from Euphorbia antiquorum latex and their inhibitory effects on Epstein-Barr virus activation. J. Nat. Prod., 2002, 65(2):158–162
7. Akiyama K, Teraguchi Y, Hamasaki Y, Mori M, Tatsumi K, Ohnishi K, Hayashi H. New dimeric naphthopyrones from Aspergillus niger. J. Nat. Prod., 2003, 66(1):136–139
8. Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffmann C, Rothcock J, Lopez M, Joshua H, Harris E, Patchett A, Monaghan R, Currie S, Stapley E, Albers-Schonberg G, Hensens O, Hirshfield J, Hoogsteen K, Liesch J, Springer J. Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl- coenzyme A reductase and a cholesterol-lowering agent. Proc. Natl. Acad. Sci. U.S.A., 1980, 77(7):3957–3961
9. Al-Burtamani SKS, Fatope MO, Marwah RG, Onifade AK, Al-Saidi SH. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J. Ethnopharmacol., 2005, 96(1–2):107–112
10. Amagata T, Minoura K, Numata A. Cytotoxic metabolites produced by a fungal strain from a Sargassum alga. J. Antibiot.,1998, 51(4):432–434
11. Barbosa FG, Oliveira MCF, Braz-Filho R, Silveira ER. Anthraquinones and naphthopyrones from Senna rugosa. Biochem. Syst. Ecol., 2004, 32(3):363–365
12. Barrow CJ, Cai P, Snyder JK, Sedlock DM, Sun HH, Cooper R. WIN 64821, a new competitive antagonist to substance P, isolated from an Aspergillus species: structure determination and solution conformation. J. Org. Chem., 1993, 58(22):6016–6021
13. Barton DHR, Bruun T. New sterol from a strain of Aspergillus niger. J. Chem. Soc., 1951, 2728–2733
14. Bell AA, Stipanovic RD, Puhalla JE. Pentaketide metabolites of verticillium dahliae: Identification of (+)-scytalone as a natural precursor to melanin. Tetrahedron, 1976, 32(12):1353–1356
15. Belofsky GN, Jensen PR, Renner MK, Fenical W. New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor. Tetrahedron, 1998, 54(9):1715–1724
16. Bondarenko-Gheorghiu LG, Lorenc LB, Mihailovic MLJ. Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. J. Serb. Chem. Soc., 2000, 65(3):147–156
17. Bouras N, Mathieu F, Coppel Y, Lebrihi A. Aurasperone F-a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C–433. Nat. Prod. Res., 2005, 19(7):653–659
18. Brodesser S, Sawatzki P, Kolter T. Bioorganic chemistry of ceramide. Eur. J. Org. Chem. 2003, 2021–2034
19. Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM. Yanuthones: Novel Metabolites from a Marine Isolate of Aspergillus niger. J. Org.Chem., 2000, 65(21):7195–7200
20. Bugni TS, Ireland CM. Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Nat. Prod. Rep., 2004, 21(1):143–63
21. 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
22. Campos FR, Barison A, Daolio C, Ferreira AG, Rodrigues-Fo E. Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus. Magn. Reson. Chem., 2005, 43(11):962–965
23. Catalfomo P, Block JH, Constantine GH, Kirk PW. Choline sulfate (ester) in marine higher fungi. Mar. Chem., 1972,1(2):157–162
24. Chen C, Imamura N, Nishijima M, Adachi K, Sakai M, Sano H. Halymecins, new antimicroalgal substances produced by fungi isolated from marine algae. J. Antibiot.,1996, 49(10):998–1005
25. Chen JH, Cui GY, Liu JY, Tan RX. Pinelloside, an antimicrobial cerebroside from Pinellia ternata. Phytochemistry, 2003, 64(4):903–906
26. Chen X, Wu YL, Chen D. Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl. TetrahedronLett., 2002, 43(19):3529–3532
27. Chexal KK, Holker JSE, Simpson TJ, Young K. The biosynthesis of fungal metabolites. Part V. Structure of variecoxanthones A, B, and C, metabolites of Aspergillus variecolor; conversion of variecoxanthone A into (±)-de-C-prenylepishamixanthone. J. Chem. Soc., Perkin Trans. 1, 1975, 6:543–548
28. Clark RL, Johnston BF, Suckling CJ, Mackay SP. A modelling study of a non-concerted hydrolytic cycloaddition reaction by the catalytic antibody H11. Bioorg. Med. Chem., 2006, 14(8):2674–2683
29. Coelho RG, Vilegas W, Devienne KF, Raddi MSG. A new cytotoxic naphthopyrone dimer from Paepalanthus bromelioides. Fitoterapia, 2000, 71(5):497–500
30. Cueto M, Jensen PR, Fenical W. Aspergilloxide, A novel sesterterpene epoxide from marine–derived fungus of the genus Aspergillus. Org. Lett., 2002, 4(9):1583–1585
31. Cueto M, Jensen PR, Kauman C, Fenical W, Lobkovsky E, Clardy J. Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. J. Nat. Prod., 2001, 64(11):1444–1446
32. Cueto M, MacMillan JB, Jensen PR, Fenical W. Tropolactones A–D, four meroterpenoids from a marine-derived fungus of the genus Aspergillus. Phytochemistry, 2006, 67(16):1826–1831
33. Cui CB, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H. Tryprostatins A and B, novel mammalian cell cycle inhibitors produced by Aspergillus fumigatus. J. Antibiot., 1995, 48(11):1382–1384
34. Cuomo V, Palomba I, Perretti A, Guerriero A, D'Ambrosio M, Pietra F. Antimicrobial activities from marine fungi. J. Mar. Biotechnol., 1995, 2(3): 199-204
35. Dreyfuss M, Harri E, Hotmann H, Kobel H, Pache W, Tscherter H. Cyclosporin A and C. Eur. J. Appl. Microbiol. Biotechnol., 1976, 3:125–133
36. Du L, Zhu TJ, Fang YC, Liu HB, Gu QQ, Zhu WM. Aspergiolide A, a novel anthraquinone derivative with naphtho[1,2,3-de]chromene-2,7-dione skeleton isolated from a marine-derived fungus Aspergillus glaucus. Tetrahedron, 2007, 63(5):1085–1088
37. Duan XJ, Zhang WW, Li XM, Wang BG. Evaluation of antioxidant property of extract and fractions obtained from a red alga, Polysiphonia urceolata. Food Chem., 2006, 95(1):37–43
38. Ehrlich KC, Delucca II AJ, Ciegler A. Naphtho-γ-pyrone production by Aspergillus niger isolated from stored cottonseed. Appl. Environ. Microbiol., 1984, 48(1):1–4
39. Epstein WW, Lear GV. Metabolites of Fomes officinalis1a. J. Org. Chem., 1966, 31(10):3434–3435
40. Ernst-Russell MA, Chai CLL, Wardlaw JH, Elix JA. Euplectin and coneuplectin, new naphthopyrones from the lichen Flavoparmelia euplecta. J. Nat. Prod., 2000, 63(1):129–131
41. Fleming A.Br. On the antibacterial action of cultures of a Penicillium, with special reference to their use in the isolation of B influenzae. J. Exp. Pathol., 1929, 10:226–236
42. Galmarini OL, Mastronardi IO, Priestap HA. Two novel metabolites of Aspergillus fonsecaeus. Experientia, 1974, 30:586
43. Galmarini OL, Stodola FH. Fonsecin, a pigment from an Aspergillus fonsecaeus Mutant. J. Org. Chem., 1965, 30(1):112–115
44. Gao JM, Hu J, Dong ZJ, Liu JK. A new ceramide from the basidiomycete Russula cyanoxantha. Lipids, 2001b, 36(2):175–180
45. Gao JM, Hu J, Dong ZJ, Liu JK. New glycosphingolipid containing an unusual sphingoid base from the basidiomycete Polyporus ellisii. Lipids, 2001a, 36(5):521–527
46. Genshiro K, Yonosuke I, Keisuk T. Fruiting of Schizophyllum commune induced by certain ceramides and cerebrosides from Penicillium funiculosum. Agric. Biol. Chem., 1994, 59:144–147
47. Ghosal S, Biswas K, Chakrabarti DK. Toxic naphtho-γ-pyrones from Aspergillus niger. J. Agric. Food. Chem., 1979, 27(6):1347–1351
48. Goodman GA, Goodman LS, Rall TW, Murad F. (eds.) Macmillan. 7th ed. New York. 1985, 1298–1299
49. Green LR, Sinackevich NV. Use of L-Glu-L-Trp or other dipeptide in the treatment of HIV infection. PCT Int. Appl., 1999, 32
50. Hiort J, Maksimenka K, Reichert M, Perovic-Ottstadt S, Lin WH, Wray V, Steube K, Schaumann K, Weber H, Proksch P, Ebel R, Muller WEG, Bringmann G. New natural products from the sponge-derived fungus Aspergillus niger. J. Nat. Prod., 2004, 67(9): 1532–1543
51. Holler U, K?nig G, Wright AD. 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., 1999, 1999(11):2949–2955
52. Hyodo S, Fujita K, Kasuya O, Takahashi I, Uzawa J, Koshino H. Structures of phospholipase A2 inhibitors, ergophilones A and B. Tetrahedron, 1995, 51(24):6717–6724
53. Iwamoto C, Minoura K, Hagishita S, Nomoto K, Numata A. Penostatins F-I, novel cytotoxic metabolites from a Penicillium species separated from an Enteromorpha marine alga. J. Chem. Soc., Perkin Trans. 1, 1998, (3):449–456
54. Iwamoto C, Minoura K, Oka T, Ohta T, Hagishita S, Numata A. Absolute stereostructuresof novel cytotoxic metabolites, penostatins A–E, from a Penicillium species separated from an Enteromorpha alga. Tetrahedron, 1999, 55(50):14353–14368
55. 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
56. Jenkins KM, Renner MK, Jensen PR, Fenical W. Exumolides A and B: antimicroalgal cyclic depsipeptides produced by a marine fungus of the genus Scytalidium. Tetrahedron Lett.,1998b, 39(17):2463–2466
57. Jenkins KM, Toske SG, Jensen PR, Fenical W. Solanapyrones E-G, antialgal metabolites produced by a marine fungus. Phytochemistry, 1998c, 49(8):2299–2304
58. Jenkins, KM. Chemical investigations of marine filamentous and zoosporic fungi and studies in marine microbial chemical ecology . Dissertation of University of California, San Diego. 1998a
59. Jiang T, Li T, Li J, Fu HZ, Pei YH, Lin WH. Cerebroside analogues from marine-derived fungus Aspergillus flavipes. J. Asian. Nat. Prod. Res., 2004, 6(4):249–257
60. Jiang Z, Barret MO, Boyd KG, Adams DR, Boyd ASF, Burgess JG. JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species. Phytochemistry, 2002, 60(1):33–38
61. Kakeya H, Takahashi I, Okada G, Isono K, Osada H. Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, produced by a marine fungus. J Antibiot., 1995, 48(7):733–735
62. Katayama K, Kobayashi T, Oikawa H, Honma M, Ichihara A. Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction. Biochim. Biophys. Acta., 1998, 1384(2):387–395
63. Kawagishi H, Katsumi R, Sazawa T, Mizuno T, Hagiwara T, Nakamura T. Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry, 1988, 27(9):2777–2779
64. Keusgen M, Yu CM, Curtis JM, Brewer D, Ayer SW. A cerebroside from the marine fungus Microsphaeropsis olivacea (Bonord.) h?nn. Biochem. Syst. Ecol., 1996, 24(5):465–468
65. Kimura Y, Sawada A, Kuramata M, Kusano M, Fujioka S, Kawano T, Shimada A. Brevicompanine C, cyclo-(D-Ile-L-Trp), and cyclo-(D-Leu-L-Trp), plant growth regulators from Penicillium brevicompactum. J. Nat. Prod., 2005, 68(2):237–239
66. 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
67. Kingston DGI, Chen PN, Vercellotti JR. Metabolites of Aspergillus versicolor: 6,8-di-O-methylnidurufin, griseofulvin, dechlorogriseofluvin, and 3,8-dihydroxy-6-methoxy-1-methylxanthone. Phytochemistry, 1976, 15(6):1037–1039
68. Klemke C, Kehraus S, Wright AD, K?nig GM. New secondary metabolites from the marine endophytic fungus Apiospora montagnei. J. Nat. Prod., 2004, 67(6):1058–1063
69. Komatsu K, Shigemori H, Shiro M, Kobayashi J. Revised Stereochemistry and Biosynthesis of Seragakinone A. Tetrahedrion, 2000, 56(45):8841–8844
70. Krohn K, Dai J, Fl?rke U, Aust HJ, Dr?ger S, Schulz B. Botryane metabolites from the fungus Geniculosporium sp. isolated from the marine red alga Polysiphonia. J. Nat. Prod., 2005, 68(3):400–405
71. Kupka J, Anke T, Steglich W, Zechlin L. Antibiotics from basidiomycetes. XI. The biological activity of siccayne, isolated from the marine fungus Halocyphina villosa J. & E. Kohlmeyer. J. Antibiot., 1981, 34(3):298–304
72. Lee D, Choi J, Yang M, Lee W, Kim D, Choi H, Son B. Natural Product Sciences, 1999, 5, 93–96
73. Lee SM, Li XF, Jiang HL, Cheng JG, Seong S, Choi HD, Son BW. Terreusinone, a novel UV-A protecting dipyrroloquinone from the marine algicolous fungus Aspergillus terreus. Tetrahedron Lett., 2003, 44(42):7707–7710
74. Lin WH, Brauers G, Ebel R, Wray V, Sudarsono BA, Proksch P. Novel chromone derivatives from the fungus Aspergillus versicolor isolated from the marine sponge Xestospongia exigua. J. Nat. Prod., 2003, 66(1):57–61
75. Lin WH, Fu HZ, Li J, Proksch P. Novel chromone derivatives from marine fungus Aspergillus versicolor isolated from the sponge Xestospongia exigua. Chin. Chem. Lett., 2001b, 12(3):235–238
76. Lin WH, Li J, Fu HZ, Proksch P. Four novel hydropyranoindeno-derivatives from marine fungus Aspergillus versicolor. Chin. Chem. Lett., 2001a, 12(5):435–438
77. Lorenz P, Jensen PR, Fenical W. Mactanamide, A new fungistatic diketopiperazine produced by a marine Aspergillus sp. Nat. Prod. Lett.,1998,12(1):55–60
78. Lo SK, Baharin BS, Tan CP, Lai OM. Diacylglycerols from palm oil deodorizer distillate. Part 2-physical and chemical characterization. Food Sci. Technol. Int., 2004, 10(3):157–161
79. Malmstrom J, Ryager A, Anthoni U, Nielsen PH. Unguisin C, a GABA–containing cyclic peptide from the fungus Emericella unguis. Phytochemistry, 2002, 60(8):869–872
80. Malmstrom J. Unguisins A and B: new cyclic peptides from the marine-derived fungus Emericella unguis. J. Nat. Prod., 1999, 62(5):787–789
81. Marcel SF, Lie KJ, Mustafa J. High-resolution nuclear magnetic resonance spectroscopy —Applications to fatty acids and triacylglycerols. Lipids, 1997, 32(10):1019–1034
82. Maskey RP, Grun-Wollny I, Laatsch H. Isolation, structure elucidation and biological activity of 8-O-methylaverufin and 1,8-O-dimethylaverantin as new antifungal agents from Penicillium chrysogenum. J. Antibiot., 2003, 56(5):459–463
83. Mielcarek M, Barciszewska MZ, Salanski P, Stobiecki M, Jurczak J, Barciszewski J. Native transfer RNA catalyzes Diels-Alder reaction. Biochem. Biophys. Res. Comm., 2002, 294(1):145–148
84. Mori K, Uenishi K. Synthesis of sphingosine relatives. Part 17. Synthesis of (2S, 2'R, 3R, 3'E, 4E, 8E)-1-O-(β-D-glucopyranosyl)-N-(2'- hydroxy-3'-octadecenoyl)-9-methyl-4, 8-sphingadienine (Pen II), the major cerebroside isolated from Penicillium funiculosum as the fruiting-inducer against Schizophyllum commune. Liebigs Annalen der Chemie, 1996, 1–6
85. Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J. Absolute stereochemistry of citrinadins A and B from marine-derived fungus. J. Org. Chem., 2005, 70(23):9430–9435
86. Mukhtar N, Iqbal K, Anis I, Malik A. Sphingolipids from Conyza canadensis. Phytochemistry, 2002, 61(8):1005–1008
87. Nakatsuka S, Miyazaki H, Goto T. Total synthesis of (±)-neoechinulin A, an indole alkaloid containing oxidized diketopiperazine. Tetrahedron Lett., 1980, 21(29):2817–2820
88. Nielsen J, Nielsen PH, Frisvad JC. Fungal depside, guisinol, from a marine derived strain of Emericella unguis. Phytochemistry, 1998, 50(2):263–265
89. Numata A, Takahashi C, Ito Y, Minoura K, Yamada T, Matsuda C, Nomoto K. 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, 1996, (3):239–246
90. Numata A, Takahashi C, Ito Y, Takada T, Kawai K, Usami Y, Matsumura E, Imachi M, Ito T, Hasegawa T. Communesins, cytotoxic metabolites of a fungus isolated from a marine alga. Tetrahedron Lett., 1993, 34(14):2355–2358
91. Numata A, Takahashi C, Matsushita T, Miyamoto T, Kawai K, Usami Y, Matsumura E, Inoue M, Ohishi H, Shingu T. Fumiquinazolines, novel metabolites of a fungus isolated from a saltfish. Tetrahedron Lett., 1992, 33(12):1621–1624
92. Oikawa H, Tokiwano T. Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products. Nat. Prod. Rep., 2004, 21(3):321–352
93. Okutani K. Gliotoxin produced by a strain of Aspergillus isolated from marine mud. Bull. Jap. Soc. Fish., 1977, 43:995–1000
94. Ose T, Watanabe K, Mie T, Honma M, Watanabe H, Yao M, Oikawa H, Tanaka I. Insightinto a natural Diels-Alder reaction from the structure of macrophomate synthase. Nature, 2003, 422:185–189
95. Osterhage C, Kaminsky R, K?nig GM, Wright AD. Ascosalipyrrolidinone A, an antimicrobial alkaloid, from the obligate marine fungus Ascochyta salicorniae. J. Org. Chem., 2000, 65(20):6412–6417
96. Osterhage C, K?nig GM, Holler U, Wright AD. Rare sesquiterpenes from the algicolous fungus Drechslera dematioidea. J. Nat.Prod., 2002, 65(3):306–313
97. Osterhage C. Isolation, structure determination and biological activity assessment of secondary metabolites from marine-derived fungi. Dissertation of Technischen Universit?t Carolo-Wilhelmina. 2001
98. Ouyang MA, Liu R, Kuo YH. A new cerebroside, Asperiamide A, from the marine fungus Asperillus sp. J. Asian. Nat. Prod. Res., 2005, 7(5):761–765
99. Ovenden SP, Sberna G, Tait RM, Wildman HG, Patel R, Li B, Steffy K, Nguyen N, Meurer-Grimes BM. A diketopiperazine dimer from a marine-derived isolate of Aspergillus niger. J. Nat. Prod., 2004, 67(12):2093–2095
100. Peters L, Konig GM, Terlau H, Wright AD. Four new bromotryptamine derivatives from the marine bryozoan Flustra foliacea. J. Nat. Prod., 2002, 65(11):1633–1637
101. Priestap HA. 13C NMR spectroscopy of naphtho-γ-pyrones. Magn. Reson. Chem., 1986, 24:875–878
102. Priestap HA. New naphthopyrones from Aspergillus fonsecaeus. Tetrahedron, 1984, 40(18):3617–3624
103. Ray FE, Sawicki E, Borum OH. Diels-Alder reactions of maleimide. J. Am. Chem. Soc., 1952, 74(5):1247–1249
104. Rehm HJ. Industrielle Mikrobiologie. 2nd ed. Berlin: Springer-Verlag, 1980.
105. Sabri A, Jacques P, Weekers F, Bare G, Hiligsmann S, Moussaif M, Thonart P. Effect of temperature on growth of psychrophilic and psychrotrophic members of Rhodotorula aurantiaca. Appl. Biochem. Biotechnol., 2000, 84(1–9):391–400
106. Sakurai M, Kohno J, Yamamoto K, Okuda T, Nishio M, Kawano K, Ohnuki T. TMC-256A1 and C1, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var niger TC 1629. J. Antibiot., 2002, 55(8):685–692
107. Schulte KE, Rücker G., Fachmann H. Ergosta-4,6,8(14),22-tetraenon-(3) als inhaltsstoff des l?rchenschwammes. Tetrahedron Lett., 1968, 9(46):4763–4764
108. Seelig B, Jaschke A. A small catalytic RNA motif with Diels-Alderase activity. Chem. Biol., 1999, 6(3):167–176
109. Seto H, Cary LW, Tanabe M. Utilization of 13C-13C coupling in structural and biosyntheticstudies V. The 13C ft nmr spectrum of sterigmatocystin. Tetrahedron Lett., 1974, 15(51–52):4491–4494
110. Shigemori H, Komatsu K, Mikamia Y, Kobayashi J. Seragakinone A, a new pentacyclic metabolite from a marine-derived fungus. Tetrahedron, 1999, 55(52):14925–14930
111. Shin J, Fenical W. Isolation of gliovictin from the marine deuteromycete Asteromyces cruciatus. Phytochemistry, 1987, 26(12):3347
112. Son BW, Choi JS, Kim JC, Nam KW, Kim DS, Chung HY, Kang JS, Choi HD. Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus. J. Nat. Prod., 2002, 65(5):794–795
113. Son BW, Jensen PR, Kauman CA, Fenical W. New cytotoxic epidithiodioxopiperazines related to Verticillin A from a marine isolate of the fungus Penicillium. Nat. Prod. Lett., 1999, 13(3):213–222
114. Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX. Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiol. Lett., 2004, 241(1):67–72
115. Steyn PS, Vleggaar R, Wessels PL, Cole RJ, Scott DB. Structure and carbon-13 nuclear magnetic resonance assignments of versiconal acetate, versiconol acetate, and versiconol, metabolites from cultures of Aspergillus parasiticus treated with dichlorvos. J. Chem. Soc., Perkin Trans. 1, 1979, 451–459
116. Stocking EM, Sanz-Cervera JF, Unkefer CJ, Williams RM. Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework. Tetrahedron, 2001, 57(25):5303–5320
117. Stocking EM, Williams RM. Chemistry and biology of biosynthetic Diels-Alder reactions. Angew. Chem. Int. Ed. Engl., 2003, 42(27):3078–3115
118. Strobel GA. Endophytes as sources of bioactive products. Microbes. Infect., 2003, 5(6):535–44
119. 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 Trans. 1, 1995c, (18):2345–2353
120. Takahashi C, Minoura K, Yamada K, Numata A, Kushida K, Shingu T, Hagishita S, Nakai H, Sato T, Harada H. Potent cytotoxic metabolites from a Leptosphaeria species. Structure determination and conformational analysis. Tetrahedron, 1995b, 51(12):3483–3498
121. Takahashi C, Numata A, Ito Y, Matsumura E, Araki H, Iwaki H, Kushida K. Leptosins, antitumour metabolites of a fungus isolated from a marine alga. J. Chem. Soc., Perkin Trans. 1, 1994a, (13):1859–1864
122. Takahashi C, Numata A, Matsumura E, Minoura K, Eto H, Shingu T, Ito T, Hasegawa T. Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures. J. Antibiot., 1994b, 47(11):1242–1249
123. Takahashi C, Numata A, Yamada T, Minoura K, Enomoto S, Konishi K, Nakai M, Matsuda C, Nomoto K. Penostatins, novel cytotoxic metabolites from a Penicillium species separated from a green alga. Tetrahedron Lett., 1996, 37(5):655–658
124. Takahashi C, Takai Y, Kimura Y, Numata A, Shigematsu N, Tanaka H. Cytotoxic metabolites from a fungal adherent of a marine alga. Phytochemistry, 1995a, 38(1):155–158
125. Tan RX, Chen JH. The cerebrosides. Nat. Prod. Rep., 2003, 20(5):509–534
126. Tan RX, Zou WX. Endophytes: a rich source of functional metabolites. Nat. Prod. Rep., 2001, 18(4):448–459
127. Tanaka H, Wang PL, Yamada O, Tamura T. Yellow pigments of Aspergillus niger and A. awamori. Part I. Isolation of aurasperone A and related pigments. Agric. Biol. Chem., 1966, 30(2):107–113
128. Townsend CA. Progress toward a biosynthetic rationale of the aflatoxin pathway. Pure & Appl. Chem., 1986, 58(2):227–238
129. Tsuda M, Kasai Y, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum. Organic Lett., 2004, 6(18):3087–3089
130. Tsuda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Shiro M, Hirai M, Ohizumie Y, Kobayashia J. Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii. Tetrahedron, 2003, 59(18):3227–3230
131. Tsukamoto S, Hirota H, Imachi M, Fujimuro M, Onuki H, Ohta T, Yokosawa H. Himeic acid A: a new ubiquitin-activating enzyme inhibitor isolated from a marine-derived fungus, Aspergillus sp. Bioorg. Med. Chem. Lett., 2005, 15(1):191–194
132. Tsukamoto S, Miura S, Yamashita Y, Ohta T. Aspermytin A: a new neurotrophic polyketide isolated from a marine-derived fungus of the genus Aspergillus. Bioorg. Med. Chem. Lett., 2004, 14(2):417–420
133. Ui H, Shiomi K, Yamaguchi Y, Masuma R, Nagamitsu T, Takano D, Sunazuka T, Namikoshi M, Omura S. Nafuredin, a novel inhibitor of NADH-fumarate reductase, produced by Aspergillus niger FT-0554. J. Antibiot., 2001, 54(3): 234–238
134. Valisolalao J, Luu B, Ourisson G. Steroids cytotoxiques de Polyporus versicolor. Tetrahedron, 1983, 39(17):2779–2785
135. Varoglu M, Corbett TH, Valeriote FA, Crews P. Asperazine, a selective cytotoxic alkaloidfrom a sponge-derived culture of Aspergillus niger. J. Org. Chem., 1997, 62(21): 7078–7079
136. Varoglu M, Crews P. Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger. J. Nat. Prod., 2000, 63(1):41–43
137. Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J. Nat. Prod., 2006, 69(11):1622–1625
138. Yamada T, Iwamoto C, Yamagaki N, Yamanouchi T, Minoura K, Yamori T, Uehara Y, Andoh T, Umemura K, Numata A. Leptosins M–N1, cytotoxic metabolites from a Leptosphaeria species separated from a marine alga. Structure determination and biological activities. Tetrahedron, 2002, 58(3):479–487
139. Yang RY, Li CY, Lin YC, Peng GT, She ZG, Zhou SN. Lactones from a brown alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities. Bioorg. Med. Chem. Lett., 2006, 16(16):4205–4208
140. Yue JM, Chen SN, Lin ZW, Sun HD. Sterols from the fungus Lactarium volemus. Phytochemistry, 2001, 56(8):801–806
141. 高坤, 贾忠建. 齿叶橐吾中甾醇类化合物结构研究. 兰州大学学报(自然科学版), 1997, 33(4):77–80
142. 郭志峰, 康现江, 蔺智强, 李彦芹, 安秋荣, 黄增瑞, 刘龙. 日本沼虾卵巢发育过程中脂肪酸变化的研究. 分析化学, 2003, 31(4):433–436
143. 林永成, 周世宁. 海洋微生物及其次生代谢产物. 第一版. 北京:化学工业出版社, 2003. 23–27
144. 刘大有, 王晓颖, 夏忠庭, 王旭. 两头尖化学成分研究. 长春中医学院学报, 2003, 19(3):71
145. 马悦欣, 孙田, 王海燕, 王岩, 朱莹. 大连海区潮间带海藻附生真菌的抗微生物活性. 大连水产学院学报, 2004, 19(1):6–9
146. 齐祖同. 中国真菌志—中国真菌志第 5 卷曲霉属及其相关有性型. 第一版. 北京:科学出版社, 1997, 1–3
147. 史大永, 韩丽君, 孙杰, 王瑛, 杨永春, 石建功, 范晓. 海藻基根硬毛藻的化学成分研究. 中国中药杂志, 2005, 30(5):347–350
148. 王新,郑天凌,胡忠,苏建强. 海洋微生物毒素研究进展. 海洋科学, 2006, 30(7):76–81
149. 谢芬, 郭顺星. 真菌来源鞘脂的结构及其活性研究进展. 中国药学杂志, 2002, 37(7):481–484
150. 许向前, 洪文荣, 陈代杰. 黑麦麦角菌产生麦角甾醇的研究. 中国抗生素杂志, 2006,31(6):379–381
151. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京: 科学出版社, 1999a, 860–867
152. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京: 科学出版社, 1999e, 794–795
153. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999b, 798
154. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999c, 794
155. 于德泉, 杨峻山. 分析化学手册 第七分册:核磁共振波谱分析, 第二版. 北京:化学工业出版社, 1999d, 805
156. 朱峰 , 林永成 , 周世宁 , Vrijmoedd LLP. 从红树林内源真菌 2526# 分离到的sterigmatocystin. 应用化学, 2003, 20(3):272–274
157. 朱峰, 林永成, 周世宁. 南海海洋真菌 2526#中蒽醌类代谢产物的研究. 有机化学, 2004, 24(9):1114–1117