Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination
Tóm tắt
The chemical constituents and biological activities of the terrestrial Aspergillus flavipes MM2 isolated from Egyptian rice hulls are reported. Seven bioactive compounds were obtained, of which one sterol: ergosterol (1), four butyrolactones: butyrolactone I (2), aspulvinone H (3), butyrolactone-V (6) and 4,4'-diydroxypulvinone (7), along with 6-methylsalicylic acid (4) and the cyclopentenone analogue; terrien (5). Structures of the isolated compounds were deduced by intensive studies of their 1D & 2D NMR, MS data and comparison with related structures. The strain extract and the isolated compounds (1-7) were biologically studied against number of microbial strains, and brine shrimp for cytotoxicity. In this article, the taxonomical characterization of A. flavipes MM2 along with its upscale fermentation, isolation and structural assignment of the obtained bioactive metabolites, and evaluate their antimicrobial and cytotoxic activities were described.
Tài liệu tham khảo
Faulkner DJ: Marine bacterial metabolites. Edited by: Proksch P, Muller WEG. Frontiers in marine biotechnology. Horizon Bioscience; 2006:225–288.
Laatsch H: A data base for rapid structural determination of microbial natural products and annual updates. Chemical Concepts, Weinheim, Germany; 2010.
Larsen TO, Smedsgaard J, Nielsen KF, Hansen ME, Frisvad JC: Phenotypic taxonomy and metabolite profiling in microbial drug discovery. Nat Prod Rep 2005, 22: 672–695. 10.1039/b404943h
Hassan AEHA: Novel natural products from endophytic fungi of Egyptian medicinal plants--chemical and biological characterization. Dissertation, Düsseldorf, Germany; 2007.
Butler MS: The role of natural product chemistry in drug discovery. J Nat Prod 2004, 67: 2141–2153. 10.1021/np040106y
Rasmussen TB, Skinderso ME, Bjarnsholt T, Phipps RK, Christensen KB, Andersen JB, Koch B, Larsen TO, Hentzer M, Hoiby N, Givskov M: Identity and effects of quorum-sensing inhibitors produced by Penicillium species. Microbiology 2005, 151: 1325–1340. 10.1099/mic.0.27715-0
Li JY, Strobel GA: Jesterone and hydroxyjesterone antioomycete cyclohexenenone epoxides from the endophytic fungus: Pestalotiopsis jesteri. Phytochemistry 2001, 57: 261–265. 10.1016/S0031-9422(01)00021-8
Brady SF, Clardy J: CR377, a new pentaketide antifungal agent isolated from an endophytic fungus. J Nat Prod 2000, 63: 1447–1448. 10.1021/np990568p
Singh SB, Zink DL, Guan Z, Collado J, Pelaez F, Felock PJ, Hazuda DJ: Isolation, structure and HIV-1 integrase inhibitory activity of xanthoviridicatin E and F two novel fungal metabolites produced by Penicillium chrysogenum . Helv Chim Acta 2003, 86: 3380–3385. 10.1002/hlca.200390281
Zhang HW, Song YC, Tan RX: Biology and chemistry of endophytes. Nat Prod Rep 2006, 23: 753–771. 10.1039/b609472b
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: 67–72. 10.1016/j.femsle.2004.10.005
Lubertozzi D, Keasling JD: Developing Aspergillus as a host for heterologous expression. Biotechnol Adv 2009, 27: 53–75. 10.1016/j.biotechadv.2008.09.001
Zhang Z: A new species of Aspergillus. Int J Biol 2009, 1: 78–80.
Raper KB, Fennel DI: The genus Aspergillus . Williams and Wilkins Baltimore. USA 1965.
Liebermann C: Ueber das oxychinoterpen, Berichte. 1885, 18: 1803–1807.
Mourao F, Umeo SH, Takemura OS, Linde GA, Colauto NB: Antioxidant activity of Agaricus brasiliensis basidiocarps on different maturation phases. Braz J Microbiol 2011, 42: 197–202. 10.1590/S1517-83822011000100024
Dissanayake DP, Abeytunga DTU, Vasudewa NS, Ratnasooriya WD: Inhibition of lipid peroxidation by extracts of Pleurotus ostreatus . Pharmacogn Mag 2009, 5: 266–271.
Chen A, Chen H, Shao Y, Fan M: Active components and free radical scavenging activity of fermented mycelia and broth of Paecilomyces tenuipes . Shipin Kexue 2009, 30: 25–28.
Han X, Lin Z, Tao H, Liu P, Wang Y, Zhu W: Cytotoxic metabolites from symbiotic fungus Penicillium sp. HK13–8 with Rhizophora stylosa. Zhongguo Haiyang Yaowu 2009, 28: 11–16.
Bao HY, Bau T, Li Y, Kim YH: Antitumor components from Naematoloma fasciculare . J Microbiol Biotechnol 2009, 19: 1135–1138.
Nitta K, Fujita N, Yoshimura T, Arai K, Yamamoto U: Metabolic products of Aspergillus terreus . IX: biosynthesis of butyrolactone derivatives isolated from strain IFO 8835 and 4100. Chem Pharm Bull 1983, 31: 1528–1533. 10.1248/cpb.31.1528
Zain ME, Awaad AS, Al-Jaber NA, Maitland DJ: New phenolic compounds with antifungal activity from Aspergillus terreus isolated from desert soil. J Saudi Chem Soc 2008, 12: 107–113.
Nuclear P, Sommit D, Boonyuen N, Pudhom K: Butenolide and furandione from an endophytic Aspergillus terreus . Chem Pharm Bull 2010, 58: 1221–1223. 10.1248/cpb.58.1221
Rao KV, Sadhukhan AK, Veerender M, Ravikumar V, Mohan EVS: Butyrolactones from Aspergillus terreus . Chem Pharm Bull 2000, 48: 559–562. 10.1248/cpb.48.559
Parvatkar RR, Souza CD, Tripathi A, Naik CG: Aspernolides Α and Β, butenolides from a marine-derived fungus. Aspergillus terreus. Phytochemistry 2009, 70: 128–132.
Kitagawa M, Okabe T, Ogino H, Matsumoto H, Suzuki-Takahashi I: Butyrolactone I, a selective inhibitor of cdk2 and cdc2 kinase. Oncogene 1993, 8: 2425–2432.
Someya A, Tanaka N, Okuyama A: Inhibition of cell cycle oscillation of DNA replication by a selective inhibitor of the cdc2 kinase family, butyrolactone I, in Xenopus egg extracts. Biochem Biophys Res Commun 1994, 198: 536–545. 10.1006/bbrc.1994.1079
Kitagawa M, Higashi H, Takahashi IS, Okabe T, Ogino H: A cyclin-dependent kinase inhibitor, butyrolactone I, inhibits phosphorylation of RB protein and cell cycle progression. Oncogene 1994, 9: 2549–2457.
Nishio K, Ishida T, Arioka H, Kurokawa H, Fukuoka K: Antitumor effects of butyrolactone I, a selective cdc2 kinase inhibitor, on human lung cancer cell lines. Anticancer Res 1996,16(6B):3387–3395.
Suzuki M, Hosaka Y, Matsushima H, Goto T, Kitamura T, Kawabe K: Butyrolactone I induces cyclin B1 and causes G2/M arrest and skipping of mitosis in human prostate cell lines. Cancer Lett 1999, 138: 121–130. 10.1016/S0304-3835(98)00381-4
Ojima N, Takahashi I, Ogura K, Shuichi SS: New metabolites from Aspergillus terreus related to the biosynthesis of aspulvinones. Tetrahedron Lett 1976, 13: 1013–1014.
Venkatasubbaiah P, Van Dyke CG, Chilton WS: Phytotoxic metabolites of phoma sorghina , a new foliar pathogen of pokeweed. Mycologia 1992, 84: 715–723. 10.2307/3760381
Shao C, Guo Z, Peng H, Peng G, Huang Z: A new isoprenyl phenyl ether compound from mangrove fungus. Chem Nat Comp 2007, 43: 377–380. 10.1007/s10600-007-0142-x
Yamasaki S, Nobusada M, Sasaki T, Shimada A: 6-Methylsalicylic acid, an antifungal substance, produced by an unidentified fungus, No 3. Kyushu Kyoritsu Daigaku Kogakubu Kenkyu Hokoku 1999, 23: 67–71.
Sievertsson H, Nilsson JLG: Analgesic properties of methylsalicylic acids. Acta Pharm Suecica 1970, 7: 289–292.
Thomas GJ: Herbicidal activity of 6-methylanthranilic acid and analogs. J Agric Food Chem 1984, 32: 747–749. 10.1021/jf00124a011
Kubo I, Muroi H, Kubo A: Naturally occurring antiacne agents. J Nat Prod 1994, 57: 9–17. 10.1021/np50103a002
Nielsen KF, Smedsgaard J: Fungal metabolite screening: database of 474 mycotoxins and fungal metabolites for dereplication by standardised liquid chromatography-UV-mass spectrometry methodology. J Chromatog A 2003, 1002: 111–136. 10.1016/S0021-9673(03)00490-4
Harper JK, Mulgrew AE, Li JY, Barich DH, Strobel GA, Grant DM: Characterization of stereochemistry and molecular conformation using solid-state NMR tensors. J Am Chem Soc 2001, 123: 9837–9842. 10.1021/ja010997l
Park SH, Kim DS, Kim WG, Ryoo IJ, Lee DH, Huh CH, Youn SW, Yoo ID, Park KC: Terrein: a new melanogenesis inhibitor and its mechanism. Cell Mol Life Sci 2004, 61: 2878–2885. 10.1007/s00018-004-4341-3
Hosoe T, Moriyama H, Wakana D, Itabashi T, Kawai K: Inhibitory effects of dihydroterrein and terrein isolated from Aspergillus novofumigatus on platelet aggregation. Mycotoxins 2009, 59: 75–82. 10.2520/myco.59.75
Kim DS, Lee HK, Park SH, Lee S, Ryoo IJ: Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest. Exp Dermatol 2008, 17: 312–317. 10.1111/j.1600-0625.2007.00646.x
Macedo JFC, Porto ALM, Marzaioli AJ: Terreinol: a novel metabolite from Aspergillus terreus : structure and C labeling. Tetrahedron Lett 2004, 45: 53–55. 10.1016/j.tetlet.2003.10.128
Lin T, Lu C, She Y: Secondary metabolites of Aspergillus sp. F1, a commensal fungal strain of Trewia nudiflora. Nat Prod Res 2009, 23: 77–85.
Haritakun R, Rachtawee P, Chanthaket R, Boonyuen N, Isaka M: Butyrolactones from the fungus Aspergillus terreus BCC 4651. Chem Pharm Bull 2010, 58: 1545–1548. 10.1248/cpb.58.1545
Ojima N, Takenaka S, Seto S: Structures of pulvinone derivatives from Aspergillus terreus . Phytochemistry 1975, 14: 573–576. 10.1016/0031-9422(75)85131-4
Burkholder P, Burkholder IM, Almodovar LR: Antibiotic activity of some marine algae of Puerto Rico. Botanica Marina 1960, 2: 149–156. 10.1515/botm.1960.2.1-2.149
Sajid I, Fondja YCB, Shaaban KA, Hasnain S, Laatsch H: Antifungal and antibacterial activities of indigenous Streptomyces isolates from saline farmlands: prescreening, ribotyping and metabolic diversity. World J Microbiol Biotechnol 2009, 25: 601–610. 10.1007/s11274-008-9928-7