Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities

Springer Science and Business Media LLC - Tập 19 Số 6 - Trang 7169-7188
Shiqiong Lu1, Jin Tian2, Weibo Sun3, Jiajia Meng4, Xiaohan Wang5, Xiaoxiang Fu6, Ali Wang7, Daowan Lai8, Liu Yang9, Ligang Zhou10
1MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China
2MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
3MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
4MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
5MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
6MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
7MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
8MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].
9Institute of Agro-products Processing Science and Technology, Chinese Academy of Agricultural Sciences, Beijing 100193, China
10MOA Key Laboratory of Plant Pathology, Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China. [email protected].

Tóm tắt

Bis-naphtho-γ-pyrones are an important group of aromatic polyketides derived from fungi. They have a variety of biological activities including cytotoxic, antitumor, antimicrobial, tyrosine kinase and HIV-1 integrase inhibition properties, demonstrating their potential applications in medicine and agriculture. At least 59 bis-naphtho-γ-pyrones from fungi have been reported in the past few decades. This mini-review aims to briefly summarize their occurrence, biosynthesis, and structure, as well as their biological activities. Some considerations regarding to synthesis, production, and medicinal and agricultural applications of bis-naphtho-γ-pyrones are also discussed.

Từ khóa


Tài liệu tham khảo

Nielsen, 2009, Review of secondary metabolites and mycotoxins from the Aspergillus niger group, Anal. Bioanal. Chem., 395, 1225, 10.1007/s00216-009-3081-5

Koyama, 1988, Cytotoxicity and antitumor activities of fungal bis(naphtho-γ-pyrone) derivatives, J. Pharmacobiodyn., 11, 630, 10.1248/bpb1978.11.630

Singh, 2003, Four novel bis-(naphtho-γ-pyrones) isolated from Fusarium species as inhibitors of HIV-1 integrase, Bioorg. Med. Chem. Lett., 13, 713, 10.1016/S0960-894X(02)01057-0

Sakai, 2008, Selective inhibition of Acyl-CoA:Cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species, J. Antibiot., 61, 568, 10.1038/ja.2008.76

Steyn, 1980, Structural elucidation of the nigerones, four new naphthopyrones from cultures of Aspergillus niger, J. Chem. Soc. Perkin Trans. 1, 1980, 2474

Koyama, 1987, Absolute configurations of chaetochromin A and related bis(naphtho-γ-pyrone) mold metabolites, Chem. Pharm. Bull., 35, 4049, 10.1248/cpb.35.4049

Zhang, 2008, Isolation, structure elucidation, and antimycobacterial properties of dimeric naphtho-γ-pyrones from the marine-derived fungus Aspergillus carbonarius, Chem. Biodivers., 5, 93, 10.1002/cbdv.200890017

Li, 2013, Naphtho-γ-pyrones from endophyte Aspergillus niger occurring in the liverwort Heteroscyphus tener (Steph.) Schiffn, Chem. Biodivers., 10, 1193, 10.1002/cbdv.201300042

Koyama, 1990, Supplemental observations on atropisomerism of fungal bis(naphtho-γ-pyrone)s, Chem. Pharm. Bull., 38, 2259, 10.1248/cpb.38.2259

Koyama, 1987, Chaetochromins B, C and D, bis(naphtho-γ-pyrone) derivatives from Chaetomium gracile, Chem. Pharm. Bull., 35, 578, 10.1248/cpb.35.578

Paranagama, 2007, Uncovering biosynthetic potential of plant-associated fungi: Effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii, J. Nat. Prod., 70, 1939, 10.1021/np070504b

Xu, 2014, Isochaetochromin A2, a new bis(naphthodihydropyran-4-one) with antimicrobial and immunological activities from fungus Chaetomium microcephalum, Arch. Pharm. Res., 37, 575, 10.1007/s12272-013-0206-3

Sekita, 1980, Chaetochromin, a bis(naphthodihydropyran-4-one) mycotoxin from Chaetomium thielavioideum: Application of 13C-1H long-range coupling to the structure elucidation, Chem. Pharm. Bull., 28, 2428, 10.1248/cpb.28.2428

Ugaki, 2012, New isochaetochromin, an inhibitor of triacylalycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: I. Taxonomy, fermentation, isolation and biological properties, J. Antibiot., 65, 15, 10.1038/ja.2011.105

Ugaki, 2012, New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: II. Structure elucidation, J. Antibiot., 65, 21, 10.1038/ja.2011.106

Kong, 2013, Aromatic polyketides from a sponge-derived fungus Metarhizium anisopliae mxh-99 and their antitubercular activities, Arch. Pharm. Res., 36, 739, 10.1007/s12272-013-0077-7

Haskins, 1969, Cephalosporium species (PRL 2070) and the production of cephalochromin, Can. J. Microbiol., 15, 435, 10.1139/m69-076

Hsiao, 2014, Cephalochromin induces G0/G1 cell cycle arrest and apoptosis in A549 human non-small-cell lung cancer cells by inflicting mitochondrial disruption, J. Nat. Prod., 77, 758, 10.1021/np400517g

Carey, 1975, Metabolites of Pyrenomycetes. V. identification of an antibiotic from two species of Nectria, as cephalochromin, Lloydia, 38, 448

Kock, 2009, Pseudoanguillosporin A and B: Two new isochromans isolated from the endophytic fungus Pseudoanguillospora sp., Eur. J. Org. Chem., 2009, 1427, 10.1002/ejoc.200801083

Matsumoto, 1975, Cephalochromin, dihydroisoustilaginoidin A, and isoustilaginoidin A from Verticillium sp. K-113, J. Antibiot., 28, 602, 10.7164/antibiotics.28.602

Hegde, 1993, Sch 45752—An inhibitor of calmodulin-sensitive cyclic nucleotide phosphodiesterase activities, J. Antibiot., 46, 207, 10.7164/antibiotics.46.207

Ohkawa, 2010, Antiangiogenic metabolites from a marine-derived fungus, Hypocrea vinosa, J. Nat. Prod., 73, 579, 10.1021/np900698p

Shibata, 1963, Metabolic products of fungi. XXII. On ustilaginoidins. 2. The structure of ustilaginoidin A, Chem. Pharm. Bull., 11, 1179, 10.1248/cpb.11.1179

Shibata, 1963, Metabolic products of fungi. XXIII. Ustilaginoidins. 3. The structure of ustilaginoidins B and C, Chem. Pharm. Bull., 11, 1576, 10.1248/cpb.11.1576

Koyama, 1988, Further characterization of seven bis(naphtho-γ-pyrone) congeners of ustilaginoidins, coloring matters of Claviceps virens (Ustilaginoidea virens), Chem. Pharm. Bull., 36, 146, 10.1248/cpb.36.146

Shaaban, 2012, Seven naphtho-γ-pyrones from the marine derived fungus Alternaria alternata: Structure elucidation and biological properties, Org. Med. Chem. Lett., 2, 6, 10.1186/2191-2858-2-6

Tanaka, 1966, Yellow pigments of Aspergillus niger and Aspergillus awamori. Part I. Isolation of aurasperone A and related pigments, Agric. Biol. Chem., 30, 107

Priestap, 1984, New naphthopyrones from Aspergillus fonsecaeus, Tetrahedron, 40, 3617, 10.1016/S0040-4020(01)88792-5

Akiyama, 2003, New dimeric naphthopyrones from Aspergillus niger, J. Nat. Prod., 66, 136, 10.1021/np020174p

Song, 2004, Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths, FEMS Microbiol. Lett., 241, 67, 10.1016/j.femsle.2004.10.005

Campos, 2005, Complete 1H- and 13C-NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus, Magn. Reson. Chem., 43, 962, 10.1002/mrc.1654

Chiang, 2011, Characterization of a polyketide synthase in Aspergillus niger whose product is a precursor for both dihydroxynaphthalene (DHN) melanin and naphtho-γ-pyrone, Fungal Genet. Biol., 48, 430, 10.1016/j.fgb.2010.12.001

Xiao, J., Zhang, Q., Gao, Y.-Q., Shi, X.-W., and Gao, J.-M. (2014). Antifungal and antibacterial metabolites from an endophytic Aspergillus sp. associated with Melia azedarach. Nat. Prod. Res., 28.

Meng, 2013, Chemical constituents from the endophytic fungus Aspergillus sp. DCS31 of Daphniphyllum longeracemosum, Nat. Prod. Res. Dev., 25, 190

Zhan, 2007, Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis, Phytochemistry, 68, 368, 10.1016/j.phytochem.2006.09.038

Wang, 1966, Yellow pigments of Aspergillus niger and Aperigillus awamori. Part II. Chemical structure of aurasperone A, Agric. Biol. Chem., 30, 683

Ehrlich, 1984, Naphtho-γ-pyrone production by Aspergillus niger isolated from stored cottonseed, Appl. Environ. Microbiol., 48, 1, 10.1128/aem.48.1.1-4.1984

Tanaka, 1972, Structure of aurasperone C, Agric. Biol. Chem., 36, 2511, 10.1080/00021369.1972.10860562

Bouras, 2005, Aurasperone F—A new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C-433, Nat. Prod. Res., 19, 653, 10.1080/14786410412331286955

Frisvad, 2005, Aspergillus vadensis, a new species of the group of black Aspergilli, Antonie Van Leeuwenkoek, 87, 195, 10.1007/s10482-004-3194-y

Ghosal, 1979, Toxic naphtho-γ-pyrones from Aspergillus niger, J. Agric. Food. Chem., 27, 1347, 10.1021/jf60226a018

Bouras, 2007, Occurrence of naphtho-gamma-pyrones- and ochratoxin A—Producing fungi in French grapes and characterization of new naphtho-gamma-pyrone polyketide (aurasperone G) isolated from Aspergillus niger C-433, J. Agric. Food Chem., 55, 8920, 10.1021/jf071406z

Ye, 2005, Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFB-E002, J. Nat. Prod., 68, 1106, 10.1021/np050059p

Zhang, 2007, Nigerasperones A-C, new monomeric and dimeric naphtho-γ-pyrones from marine alga-derived endophytic fungus Aspergillus niger EN-13, J. Antibiot., 60, 204, 10.1038/ja.2007.24

Huang, 2010, Three dimeric naphtho-γ-pyrones from the mangrove endophytic fungus Aspergillus tubingensis isolated from Pongamia pinnata, Planta Med., 76, 1888, 10.1055/s-0030-1249955

Huang, 2011, Cytotoxic naphtho-γ-pyrones from the mangrove endophytic fungus Aspergillus tubingensis (GX1–5E), Helv. Chim. Acta, 94, 1732, 10.1002/hlca.201100050

Geiser, 2007, The current status of species recognition and identification in Aspergillus, Stud. Mycol., 59, 1, 10.3114/sim.2007.59.01

Perrone, 2007, Biodiversity of Aspergillus species in some important agricultural products, Stud. Mycol., 59, 53, 10.3114/sim.2007.59.07

Samson, 2009, What is a species in Aspergillus?, Med. Mycol., 47, S13, 10.1080/13693780802354011

Koyama, 1989, Biosynthesis of chaetochromin A, a bis(naphtho-γ-pyrone), in Chaetomium spp., Chem. Pharm. Bull., 37, 2022, 10.1248/cpb.37.2022

Sakurai, 2002, TMC-256A1 and C1, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var. niger TC 1629, J. Antibiot., 55, 685, 10.7164/antibiotics.55.685

Asai, 2012, Aromatic polyketide production in Cordyceps indigotica, an entomopathogenic fungus, induced by exposure to a histone deacetylase inhibitor, Org. Lett., 14, 2006, 10.1021/ol3005062

Tsuchiya, 1987, Effect of chaetochromin A, chaetochromin D and ustilaginoidin A, bisnaphtho-γ-pyrone derivatives, on the mouse embryo limb bud and midbrain cells in culture, Cong. Anom., 27, 245, 10.1111/j.1741-4520.1987.tb00707.x

Kawai, 1991, The impairing effect of chaetochromin A and related mycotoxins on mitochondrial respiration, Proc. Jpn. Assoc. Mycotoxicol., 33, 31, 10.2520/myco1975.1991.31

Campbell, 2001, Bacterial fatty acid biosynthesis: Targets for antibacterial drug discovery, Annu. Rev. Microbiol., 55, 305, 10.1146/annurev.micro.55.1.305

Zheng, 2007, Cephalochromin, a FabI-directed antibacterial of microbial origin, Biochem. Biophys. Res. Commun., 362, 1107, 10.1016/j.bbrc.2007.08.144

Cardellina, 2012, Fungal bis-naphthopyrones as inhibitors of botulinum neurotoxin serotype A, ACS Med. Chem. Lett., 3, 387, 10.1021/ml200312s

Ikeda, 1990, Aspergillus species strain M39 produces two naphtho-γ-pyrones that reverse drug resistance in human KB cells, Int. J. Cancer, 45, 508, 10.1002/ijc.2910450323

Ito, 1987, Teratogenicity of oral chaetochromin, a polyphenolic mycotoxin produced by Chaetomium spp., to mice embryo, Bull. Environ. Contam. Toxicol., 39, 299, 10.1007/BF01689421

Mori, 1993, The impairing effects of chaetochromin D on mitochondrial respiration and structure, Mycotoxin Res., 9, 85, 10.1007/BF03192239

Ishii, 2005, Inhibitory effects of fungal bis(naphtho-γ-pyrone) derivatives on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-γ, Biol. Pharm. Bull., 28, 786, 10.1248/bpb.28.786

Zhao, 2011, Plant-derived bioactive compounds produced by endophytic fungi, Mini Rev. Med. Chem., 11, 159, 10.2174/138955711794519492

Gutierrez, 2012, Compounds derived from endophytes: A review of phytochemistry and pharmacology, Curr. Med. Chem., 19, 2992, 10.2174/092986712800672111

Debbab, 2013, Mangrove derived fungal endophytes—A chemical and biological perception, Fungal Divers., 61, 1, 10.1007/s13225-013-0243-8

Lee, 2013, Marine-derived Aspergillus species as a source of bioactive secondary metabolites, Mar. Biotechnol., 15, 499, 10.1007/s10126-013-9506-3

Morishita, 1967, Metabolic products of fungi. XXVII. Synthesis of racemic unstilaginoidin A and its related compounds, Chem. Pharm. Bull., 15, 1772, 10.1248/cpb.15.1772

DiVirgilio, 2007, Asymmetric total synthesis of nigerone, Org. Lett., 9, 385, 10.1021/ol062468y

Kozlowski, 2007, Asymmetric total synthesis of nigerone and ent-nigerone: Enantioselective oxidative biaryl coupling highly hindered naphthols, Adv. Synth. Catal., 349, 583, 10.1002/adsc.200600570

Marin, 2013, Potential effects of environmental conditions on the efficiency of the antifungal tebuconazole controlling Fusarium verticillioides and Fusarium proliferatum growth rate and fumonisin biosynthesis, Int. J. Food Microbiol., 165, 251, 10.1016/j.ijfoodmicro.2013.05.022

Jorgensen, 2011, The molecular and genetic basis of conidial pigmentation in Aspergillus niger, Fungal Genet. Biol., 48, 544, 10.1016/j.fgb.2011.01.005

Melborn, B.J., and Greene, J.C. (2012). Mycotoxins: Properties, Applications and Hazards, Nova Science Publishers.