Metabolites from the endophytic mitosporic Dothideomycete sp. LRUB20

Phytochemistry

Volumn 70, Issue 1, 2009, Pages 121-127

  Chomcheon, Porntep ^a,b   Wiyakrutta, Suthep ^c   Sriubolmas, Nongluksna ^b   Ngamrojanavanich, Nattaya ^b   Mahidol, Chulabhorn ^a,d   Ruchirawat, Somsak ^a,d   Kittakoop, Prasat ^a  

^a Toxicology and Management of Chemicals   (Thailand)

^b CHULALONGKORN UNIVERSITY   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

^d MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Bioactive compounds; Building blocks; Cytotoxic activity; Dothideomycete sp.; Endophytic fungi; Muconic acid; Pyrone; White biotechnology

Indexed keywords

ANTINEOPLASTIC AGENT; PYRONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DEUTEROMYCETES; HUMAN; METABOLISM; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; HUMANS; MITOSPORIC FUNGI; MOLECULAR STRUCTURE; PYRONES;

FUNGI;

EID: 59049083596     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.10.007     Document Type: Article

References (50)

1. Barba B., Diaz J.G., and Herz W. Anthraquinones and other constituents of two Senna species. Phytochemistry 31 (1992) 4374-4375
2. Boonen G., and Haberlein H. Influence of genuine kavapyrone enantiomers on the GABA-A binding site. Planta Med. 64 (1998) 504-506
3. Carmichael J., DeGraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 47 (1987) 936-942
4. Choi S.G., Kim J., Sung N.D., Son K.H., Cheon H.G., Kim K.R., and Kwon B.M. Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb. Nat. Prod. Res. 21 (2007) 487-493
5. Chomcheon P., Sriubolmas N., Wiyakrutta S., Ngamrojanavanich N., Chaichit N., Mahidol C., Ruchirawat S., and Kittakoop P. Cyclopentenones, scaffolds for organic synthesis produced by the endophytic fungus, mitosporic Dothideomycete sp. LRUB20. J. Nat. Prod. 69 (2006) 1351-1353
6. Chomcheon P., Wiyakrutta S., Sriubolmas N., Ngamrojanavanich N., Isarangkul D., and Kittakoop P. 3-Nitropropionic acid (3-NPA), a potent antimycobacterial agent from endophytic fungi: Is 3-NPA in some plants produced by endophytes?. J. Nat. Prod. 68 (2005) 1103-1105
7. Dale J.A., and Mosher H.S. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 95 (1973) 512-519
8. Doyle A., and Griffiths J.B. Mammalian Cell Culture: Essential Techniques (1997), John Wiley and Sons
9. Draths K.M., and Frost J.W. Environmentally compatible synthesis of adipic acid from D-glucose. J. Am. Chem. Soc. 116 (1994) 399-400
10. Elvidge J.A., Linstead R.P., Peter S., and Orkin B.A. The third isomeric (cis-trans)-muconic acid. J. Chem. Soc. (1950) 2235-2241
11. Eriksson O. Notes on ascomycete systematics. Myconet 5 (2000) 1-35
12. Feng Y., Blunt J.W., Cole A.L., and Munro M.H. The isolation of two new chromone derivatives from the New Zealand fungus Tolypocladium extinguens. J. Nat. Prod. 65 (2002) 1681-1682
13. Folmer F., Harrison W.T., Tabudravu J.N., Jaspars M., Aalbersberg W., Feussner K., Wright A.D., Dicato M., and Diederich M. NF-kappaB-inhibiting naphthopyrones from the Fijian echinoderm Comanthus parvicirrus. J. Nat. Prod. 71 (2008) 106-111
14. Fujimoto H., Satoh Y., Nakayama M., Takayama T., and Yamazaki M. Isolation of some immunosuppressive components from an ascomycete, Gelasinospora multiforis. Chem. Pharm. Bull. 43 (1995) 547-552
15. Gunatilaka A.A.L. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J. Nat. Prod. 69 (2006) 509-526
16. Hargreaves J., Park J.O., Ghisalberti E.L., Sivasithamparam K., Skelton B.W., and White A.H. New chlorinated diphenyl ethers from an Aspergillus species. J. Nat. Prod. 65 (2002) 7-10
17. Hipkin C.R., Simpson D.J., Wainwright S.J., and Salem M.A. Nitrification by plants that also fix nitrogen. Nature 430 (2004) 98-101
18. Huneck S. 6-Hydroxymethyleugenitin, ein neues chromon aus Roccella fuciformis. Phytochemistry 11 (1972) 1489-1490
19. 1H NMR glycosylation and alkylation shifts. Phytochemistry 28 (1989) 3459-3463
20. Lumbsch H.T., and Huhndorf S.M. Outline of Ascomycota - 2007. Myconet 13 (2007) 1-58
21. Maury J., Asadollahi M.A., Moller K., Clark A., and Nielsen J. Microbial isoprenoid production: an example of green chemistry through metabolic engineering. Adv. Biochem. Eng. Biotechnol. 100 (2005) 19-51
22. Melikian A.A., Qu Q., Shore R., Li G., Li H., Jin X., Cohen B., Chen L., Li Y., Yin S., Mu R., Zhang X., and Wang Y. Personal exposure to different levels of benzene and its relationships to the urinary metabolites S-phenylmercapturic acid and trans, trans-muconic acid. J. Chromatogr. B 778 (2002) 211-221
23. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
24. Navasumrit P., Arayasiri M., Hiang O.M., Leechawengwongs M., Promvijit J., Choonvisase S., Chantchaemsai S., Nakngam N., Mahidol C., and Ruchirawat M. Potential health effects of exposure to carcinogenic compounds in incense smoke in temple workers. Chem. Biol. Interact. 173 (2008) 19-31
25. Navasumrit P., Chanvaivit S., Intarasunanont P., Arayasiri M., Lauhareungpanya N., Parnlob V., Settachan D., and Ruchirawat M. Environmental and occupational exposure to benzene in Thailand. Chem. Biol. Interact. 153-154 (2005) 75-83
26. Niu W., Draths K.M., and Frost J.W. Benzene-free synthesis of adipic acid. Biotechnol. Prog. 18 (2002) 201-211
27. Pedras M.S., and Chumala P.B. Phomapyrones from blackleg causing phytopathogenic fungi: isolation, structure determination, biosyntheses and biological activity. Phytochemistry 66 (2005) 81-87
28. Pongcharoen W., Rukachaisirikul V., Phongpaichit S., Kuhn T., Pelzing M., Sakayaroj J., and Taylor W.C. Metabolites from the endophytic fungus Xylaria sp. PSU-D14. Phytochemistry 69 (2008) 1900-1902
29. Rukachaisirikul V., Sommart U., Phongpaichit S., Sakayaroj J., and Kirtikara K. Metabolites from the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry 69 (2008) 783-787
30. Schulz B., Boyle C., Draeger S., Rommert A.K., and Krohn K. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycological Res. 106 (2002) 996-1004
31. Schwarz M., Kopcke B., Weber R.W., Sterner O., and Anke H. 3-hydroxypropionic acid as a nematicidal principle in endophytic fungi. Phytochemistry 65 (2004) 2239-2245
32. Shen Y.C., Prakash C.V., and Kuo Y.H. Three new furan derivatives and a new fatty acid from a Taiwanese marine sponge Plakortis simplex. J. Nat. Prod. 64 (2001) 324-327
33. Shimada A., Shiokawa C., Kusano M., Fujioka S., and Kimura Y. Hydroxysulochrin, a tea pollen growth inhibitor from the fungus Aureobasidium sp. Biosci. Biotechnol. Biochem. 67 (2003) 442-444
34. Stermitz F.R., Schroeder H.A., and Geigert J. Asterric acid from Scytalidium. Phytochemistry 12 (1973) 1173
35. Stone J.K., Polishook J.D., and White J.F. Endophytic fungi. In: Mueller G.M., Bills G.F., and Foster M.S. (Eds). Biodiversity of Fungi: Inventory and Monitoring Methods (2004), Elsevier Academic Press, China 241-270
36. Stottmeister U., Aurich A., Wilde H., Andersch J., Schmidt S., and Sicker D. White biotechnology for green chemistry: fermentative 2-oxocarboxylic acids as novel building blocks for subsequent chemical syntheses. J. Ind. Microbiol. Biotechnol. 32 (2005) 651-664
37. Strobel G. Harnessing endophytes for industrial microbiology. Curr. Opin. Microbiol. 9 (2006) 240-244
38. Strobel G., Yang X., Sears J., Kramer R., Sidhu R.S., and Hess W.M. Taxol from Pestalotiopsis microspora, an endophytic fungus of Taxus wallachiana. Microbiology 142 (1996) 435-440
39. Tan R.X., and Zou W.X. Endophytes: a rich source of functional metabolites. Nat. Prod. Rep. 18 (2001) 448-459
40. Thomas J.M., Raja R., Johnson B.F., O'Connell T.J., Sankar G., and Khimyak T. Bimetallic nanocatalysts for the conversion of muconic acid to adipic acid. Chem. Commun. (2003) 1126-1127
41. Tominaga H., Ishiyama M., Ohseto F., Sasamoto K., Hamamoto T., Suzuki K., and Watanabe M. A water-soluble tetrazolium salt useful for colorimetric cell viability assay. Anal. Commun. 36 (1999) 47-50
42. Tsai S.C., Tsai L.D., and Li Y.K. An isolated Candida albicans TL3 capable of degrading phenol at large concentration. Biosci. Biotechnol. Biochem. 69 (2005) 2358-2367
43. Tubaki K. Studies on Japanese hyphomycetes. J. Hattori Bot. Lab. 20 (1958) 142-244
44. Webster J. Conidia of Acrospermum compressum and A. Gramineum. Trans. Br. Mycol. Soc. 39 (1956) 361-366
45. Wijeratne E.M.K., Paranagama P.A., and Gunatilaka A.A.L. Five new isocoumarins from Sonoran desert plant-associated fungal strains Paraphaeosphaeria quadriseptata and Chaetomium chiversii. Tetrahedron 62 (2006) 8439-8446
46. Wiyakrutta S., Sriubolmas N., Panphut W., Thongon N., Danwisetkanjana K., Ruangrungsi N., and Meevootisom V. Endophytic fungi with anti-microbial, anti-cancer and anti-malarial activities isolated from Thai medicinal plants. World J. Microbiol. Biotechnol. 20 (2004) 265-272
47. Xiao Y., Zhang J.J., Liu H., and Zhou N.Y. Molecular characterization of a novel ortho-nitrophenol catabolic gene cluster in Alcaligenes sp. strain NyZ215. J. Bacteriol. 189 (2007) 6587-6593
48. Yardley-Jones A., Anderson D., and Parke D.V. The toxicity of benzene and its metabolism and molecular pathology in human risk assessment. Br. J. Ind. Med. 48 (1991) 437-444
49. Yoshikawa N., Ohta K., Mizuno S., and Ohkishi H. Production of cis, cis-muconic acid from benzoic acid. Bioprocess Technol. 16 (1993) 131-147
50. Zhan J., Gunaherath G.M., Wijeratne E.M., and Gunatilaka A.A. Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis. Phytochemistry 68 (2007) 368-372