Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis

Molecules

Volumn 19, Issue 5, 2014, Pages 6597-6608

  Chapla, Vanessa Mara ^a   Zeraik, Maria Luiza ^a   Ximenes, Valdecir F ^a   Zanardi, Lisinéia Maria ^a   Lopes, Márcia N ^a   Cavalheiro, Alberto José ^a   Silva, Dulce Helena S ^a   Young, Maria Cláudia M ^b   Da Fonseca, Luiz Marcos ^a   Bolzani, Vanderlan S ^a   Araújo, Angela Regina ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b Instituto de Pesquisas Ambientais do Estado de São Paulo   (Brazil)

Author keywords

Bioactivities; Endophytic fungi; Phomopsis sp.; Secondary metabolites; Senna spectabilis

Indexed keywords

ALTERNARIOL; ALTERNARIOL MONOMETHYL ETHER; ANTIFUNGAL AGENT; ANTIOXIDANT; CHOLINESTERASE INHIBITOR; CYTOCHALASIN; CYTOCHALASIN H; CYTOCHALASIN J; CYTOSPOROLIDE C; LACTONE; MYCOTOXIN; NONSTEROID ANTIINFLAMMATORY AGENT; REACTIVE OXYGEN METABOLITE; SESQUITERPENE;

ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; ENDOPHYTE; HUMAN; METABOLISM; MICROBIOLOGY; NEUTROPHIL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROCEDURES; SECONDARY METABOLISM; SENNA;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIFUNGAL AGENTS; ANTIOXIDANTS; ASCOMYCOTA; CHOLINESTERASE INHIBITORS; CYTOCHALASINS; DRUG EVALUATION, PRECLINICAL; ENDOPHYTES; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYCOTOXINS; NEUTROPHILS; REACTIVE OXYGEN SPECIES; SECONDARY METABOLISM; SENNA PLANT; SESQUITERPENES;

EID: 84901398769     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19056597     Document Type: Article

References (41)

1. Aly H.A.; Debbab A.; Proksch P. Fungal endophytes: Unique plant inhabitants with great promises. Appl. Microbiol. Biotechnol. 2011, 90, 1829-1845.
2. Gunatilaka A.A.L. Natural Products from plant-Associated microorganisms: Distribution, structutal diversity, bioactivity, and implications of their occurrence. J. Nat. Prod. 2006, 69, 509-526.
3. Jalgaonwala R.E.; Mohite B.V.; Mahajan R.T. A review: Natural products from plant associated endophytic fungi. J. Microbiol. Biotech. Res. 2011, 1, 21-32.
4. Magnani R.F.; de Souza G.D.; Rodrigues-Filho E. Analysis of alternariol and alternariol monomethyl ether on flavedo and albedo tissues of tangerines (Citrus reticulata) with symptoms of Alternaria brown spot. J. Agric. Food Chem. 2007, 55, 4980-4986.
5. Watanabe I.; Kakishima M.; Adachi Y.; Nakajima H. Potencial mycotoxin productivity of Alternaria alternata isolated from garden trees. Mycotoxins 2007, 57, 3-9.
6. Bolzani V.S.; Trevisan L.M.V.; Young M.C.M. Caffeic acid esters and triterpenes of Alibertia macrophyla. Phytochemistry 1991, 30, 2089-2091.
7. Young M.C.M.; Braga M.R.; Dietrich S.M.C.; Gottlieb H.E.; Trevisan L.M.V.; Bolzani V.S. Fungitoxic non-glycosidic iridoids from Alibertia macrophylla. Phytochemistry 1992, 31, 3433-3435.
8. Silva V.C.; Faria A.O.; Bolzani V.S.; Lopes M.N. A new ent-kaurane diterpene from stems of Alibertia macrophylla K. Schum. (Rubiaceae). Helv. Chim. Acta 2007, 90, 1781-1785.
9. Junior C.V.; Pivatto M.; Rezende A.; Hamerski L.; Silva D.H.S.; Bolzani V.S. (-)-7-Hydroxycassine: A new 2, 6-dialkylpiperidin-3-ol alkaloid and other constituents isolated from flowers and fruits of Senna spectabilis (Fabaceae). J. Braz. Chem. Soc. 2013, 24, 230-235.
10. Izawa Y.; Hirose T.; Shimizu T.; Koyama K.; Natori S. Six new 10-phenyl-[11]cytochalasans, cytochalasins N-S from Phompsis sp. Tetrahedron 1989, 45, 2323-2335.
11. Tao Y.; Zeng X.; Mou C.; Li J.; Cai X.; She Z.; Zhou S.; Lin Y. 1H and 13C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08). Magn. Reson. Chem. 2008, 46, 501-505.
12. Ondeyka J.; Hensens O.D.; Zink D.; Ball R.; Lingham R.B.; Bills G.; Dombrowski A.; Goetz M. L-696, 474, a novel cytochalasin as an inhibitor of HIV-1-protease. II. Isolation and structure. J. Antibiot. 1992, 45, 679-685.
13. Bradburn N.; Coker R.D.; Blunden G.; Turner C.H.; Crabb T.A. 5'-Epiltenuene and neoaltenuene, dibenzo-A-pyrones from Alternaria alternata cultured on rice. Phytochemistry 1994, 35, 665-669.
14. Jiao P.; Gloer J.B.; Campbell J.; Shearer C.A. Altenuene derivatives from an unidentified freshwater fungus in the family Tubeufiaceae. J. Nat. Prod. 2006, 69, 612-615.
15. Gu W. Bioactive metabolites from Alternaria brassicicola ML-P08, an endophytic fungus residing in Malus halliana. World J. Microbiol. Biotechnol. 2009, 25, 1677-1683.
16. Aly A.H.; Edrada-ebel R.; Indriani I.D.; Wray V.; Muller W.E.G.; Totzke F.; Zirrgiebel U.; Schachtele C.; Kubbutat M.H.G.; Lin W.H.; et al. Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection on its host plant Polygonum senegalense. J. Nat. Prod. 2008, 71, 972-980.
17. Tan N.; Tao Y.; Pan J.; Wang S.; Xu F.; She Z.; Lin Y.; Jones E.B.G. Isolation, structure elucidation, and mutagenicity of four alternariol derivatives produced by the mangrove endophytic fungus No. 2240. Chem. Nat. Comp. 2008, 43, 296-300.
18. Xu J.; Kjer J.; Sendker J.; Wray V.; Guan H.; Edrada R.; Muller V.E.G.; Bayer M.; Lin W.; Wu J.; et al. Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophoramucronata. Bioorg. Med. Chem. 2009, 17, 7362-7367.
19. Brady S.F.; Wagenaar M.M.; Singh M.P.; Janso F.E.; Cardy J. The cytosporones, new octaketide antibiotics isolated from an endophytic fungus. Organic Letters 2000, 25, 4043-4046.
20. Pfeiffer E.; Schebb N.H.; Podlech J.; Metzler M. Novel oxidative in vitro metabolites of the mycotoxins alternariol and alternariol methyl ether. Mol. Nutr. Food Res. 2007, 51, 307-316.
21. Almeida A.C.; Marques O.C.; Arslanian C.; Condino-Neto A.; Ximenes V.F. 4-Fluoro-2-methoxyphenol, na apocynin analog with enhaced inhibitory effect on leukocyte oxidant production and phagocytosis. Eur. J. Pharmacol. 2011, 660, 445-453.
22. Jan A.T.; Kamli M.R.; Murtaza I.; Singh J.B.; Ali A.; Haq Q.M.R. Dietary flavonoid quercetin and associated health benefits -An overview. Food Rev. Int. 2010, 26, 302-317.
23. Ford D.A. Lipid oxidation by hypochlorous acid: Chlorinated lipids in atherosclerosis and myocardial ischemia. Clin. Lipidol. 2010, 5, 835-852.
24. Summers F.A.; Morgan P.E.; Davies M.J.; Hawkins C.L. Identification of plasma proteins that are susceptible to thiol oxidation by hypochlorous acid and N-chloramines. Chem. Res. Toxicol. 2008, 21, 1832-1840.
25. Klebanoff S.J. Myeloperoxiase: Friend and foe. J. Leukocyte Biol. 2005, 77, 598-625.
26. Xu S.; Ge H.M.; Song Y.C.; Shen Y.; Ding H.; Tan R.X. Cytotoxic cytochalasin metabolites of endophytic Endothia gyrosa. Chem. Biodivers. 2009, 6, 739-745.
27. Lin Z.; Zhang G.; Zhu T.; Liu R.; Wei H.; Gu Q. Bioactive cytochalasins from Aspergillus flavipes, an endophytic fungus associated with the mangrove plant Acanthus ilicifolius. Helv. Chim. Acta 2009, 92, 1538-1544.
28. Ostry V. Alternaria mycotoxins: An overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs. World Mycot. J. 2008, 1, 175-188.
29. Kettle A.J. Detection of 3-chlorotyrosine in proteins exposed to neutrophil oxidants. Meth. Enzymol. 1999, 300, 111-120.
30. Beers R.J.; Sizer I.W. A spectrophotometric method for measuring the breakdown of hydrogen peroxide by catalase. J. Biol. Chem. 1952, 195, 133-140.
31. Silva G.H.; Teles H.L.; Zanardi L.M.; Young M.C.M.; Eberlin M.N.; Haddad R.; Pfenning L.H.; Costa-Neto C.; Castro-Gamboa I.; Bolzani V.S.; et al. Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis (Leguminosae). Phytochemistry 2006, 67, 1964-1969.
32. English D.; Andersen B.R. Single-step separation of red blood cells, granulocytes and mononuclear leukocytes on discontinuous density gradients of Ficoll-Hypaque. J. Immunol. Methods 1974, 5, 249-252.
33. Kitagawa R.R.; Raddi M.S.G.; Khalil N.M.; Vilegas W.; Fonseca L.M. Effect of the isocoumarin paepalantine on the luminol and lucigenin amplified chemiluminescence of rat neutrophils. Biol. Pharm. Bull. 2003, 26, 905-908.
34. Malle E.; Furtmuller P.G.; Sattler W.; Obinger C. Myeloperoxidase: A target for new drug development? Br. J. Pharmacol. 2007, 152, 838-854.
35. Zeraik M.L; Ximenes V.F.; Regasini L.O.; Dutra L.A.; Silva D.H.; Fonseca L.M.; Coelho D.; Machado S.A.; Bolzani V.S. 4'-Aminochalcones as novel inhibitors of the chlorinating activity of myeloperoxidase. Curr. Med. Chem. 2012, 19, 5405-5413.
36. Ximenes V.F.; Kanegae M.P.; Rissato S.R.; Galhiane M.S. The oxidation of apocynin catalyzed by myeloperoxidase: Proposal for NADPH oxidase inhibition. Arch. Biochem. Biophys. 2007, 457, 134-141.
37. Tan A.S.; Berridge M.V. Superoxide produced by active neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: A simple colorimetric assay for measuring respiratory burst activation and for screening anti-inflammatory agents. J. Immunol. Methods 2000, 238, 59-68.
38. Brand-Williams W.; Cuvelier M.E.; Berset C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. Technol. 1995, 28, 25-30.
39. Zeraik M.L.; Yariwake J.H.; Wauters J.N.; Tits M.; Angenot L. Analysis of passion fruit rinds (Passiflora edulis): Isoorientin quantification by HPTLC and evaluation of antioxidant (radical scavenging) capacity. Quim. Nova 2012, 35, 541-545.
40. Rahalison L.; Hamburger M.; Hostettmann K.; Monod M.; Frenk E. A bioautographic agar overlay method for the detection of antifungal compounds from higher plants. Phytochem. Anal. 1991, 2, 199-203.
41. Marston A.; Kissling J.; Hostettmann K. A rapid TCL bioautographic method for the detection of acetylcholinesterase and butyrylcholinesterase inhibitors in plants. Phytochem. Anal. 2002, 13, 51-54.