Subscribe to RSS
DOI: 10.1055/s-0029-1185951
HPLC‐SPE‐NMR Identification of a Novel Metabolite Containing the Benzo[c]oxepin Skeleton from the Endophytic Fungus Pestalotiopsis virgatula Culture
Publication History
received May 1, 2009
revised June 13, 2009
accepted June 17, 2009
Publication Date:
16 July 2009 (online)
Abstract
HPLC‐SPE‐NMR analysis of a crude extract of fermentation broth of cultured Pestalotiopsis virgatula isolate TC-320 from Terminalia chebula Retz. (Combretaceae) disclosed the presence of a simple but unprecedented low-molecular-weight metabolite, 9-hydroxybenzo[c]oxepin-3[1H]-one, subsequently isolated by a targeted purification procedure.
Key words
endophytes - Pestalotiopsis virgatula - Amphisphaeriaceae - HPLC‐SPE‐NMR - NMR hyphenation
References
- 1 Zhang H W, Song Y C, Tan R X. Biology and chemistry of endophytes. Nat Prod Rep. 2006; 23 753-771
- 2 Gunatilaka A AL. Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod. 2006; 69 509-526
- 3 Strobel G A. Endophytes as sources of bioactive products. Microbes Infect. 2003; 5 535-544
- 4 Schulz B, Boyle C, Draeger S, Römmert A K, Krohn K. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res. 2002; 106 996-1004
- 5 Stierle A, Strobel G, Stierle D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Science. 1993; 260 214-216
- 6 Jaroszewski J W. Hyphenated NMR methods in natural products research, Part 2: HPLC‐SPE‐NMR and other new trends in NMR hyphenation. Planta Med. 2005; 71 795-802
- 7 Clarkson C, Stærk D, Hansen S H, Jaroszewski J W. Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC‐DAD‐SPE‐NMR to identification of constituents of Kanahia laniflora. Anal Chem. 2005; 77 3547-3553
- 8 Clarkson C, Madikane E V, Hansen S H, Smith P J, Jaroszewski J W. HPLC‐SPE‐NMR characterization of sesquiterpenes in an antimycobacterial fraction from Warburgia salutaris. Planta Med. 2007; 73 578-584
- 9 Lee S S, Lai Y C, Chen C K, Tseng L H, Wang C Y. Characterization of isoquinoline alkaloids from Neolitsea sericea var. aurata by HPLC‐SPE‐NMR. J Nat Prod. 2007; 70 637-642
- 10 Sprogøe K, Staerk D, Jäger A K, Adsersen A, Hansen S H, Witt M, Landbo A K, Meyer A S, Jaroszewski J W. Targeted natural product isolation guided by HPLC‐SPE‐NMR: constituents of Hubertia species. J Nat Prod. 2007; 70 1472-1477
- 11 Agarwal A K, Chauhan S. A new species of the genus Pestalotiopsis from Indian soil. Indian Phytopathol. 1988; 41 625-627
- 12 Zhang J, Xu T, Ge Q. Notes on Pestalotiopsis from Southern China. Mycotaxon. 2003; 85 91-99
- 13 Tejesvi M V, Kini K R, Prakash H S, Subbiah V, Shetty H S. Genetic diversity and antifungal activity of species of Pestalotiopsis isolated as endophytes from medicinal plants. Fungal Div. 2007; 24 37-54
- 14 Ding G, Zheng Z, Liu S, Zhang H, Guo L, Che Y. Photinides A–F, cytotoxic benzofuranone-derived γ-lactones from the plant endophytic fungus Pestalotiopsis photiniae. J Nat Prod. 2009; 72 942-945
- 15 Ding G, Li Y, Fu S, Liu S, Wei J, Che Y. Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp. J Nat Prod. 2009; 72 182-186
- 16 Xu J, Kjer J, Sendker J, Wray V, Guan H, Edrada R, Lin W, Wu J, Proksch P. Chromones from the endophytic fungus Pestalotiopsis sp. isolated from the chinese mangrove plant Rhizophora mucronata. J Nat Prod. 2009; 72 662-665
- 17 Liu L, Liu S, Chen X, Guo L, Che Y. Pestalofones A–E, bioactive cyclohexanone derivatives from the plant endophytic fungus Pestalotiopsis fici. Bioorg Med Chem. 2009; 17 606-613
- 18 Ding G, Liu S, Guo L, Zhou Y, Che Y. Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan. J Nat Prod. 2008; 71 615-618
- 19 Li E, Tian R, Liu S, Chen X, Guo L, Che Y. Pestalotheols A–D, bioactive metabolites from the plant endophytic fungus Pestalotiopsis theae. J Nat Prod. 2008; 71 664-668
- 20 Gangadevi V, Muthumary J. Taxol production by Pestalotiopsis terminaliae, an endophytic fungus of Terminalia arjuna (arjun tree). Biotechnol Appl Biochem. 2009; 52 9-15
- 21 Tejesvi M V, Mahesh B, Nalini M S, Prakash H S, Kini K R, Subbiah V, Shetty H S. Fungal endophyte assemblages from ethnopharmaceutically important medicinal trees. Can J Microbiol. 2006; 52 427-435
- 22 Tejesvi M V, Kini K R, Prakash H S, Subbiah V, Shetty H S. Antioxidant, antihypertensive, and antibacterial properties of endophytic Pestalotiopsis species from medicinal plants. Can J Microbiol. 2008; 54 769-780
- 23 Bouillant M L, Favre-Bonvin J, Salin N, Bernillon J. Sordariol and related compounds, hexaketides in the fungus Sordaria macrospora. Phytochemistry. 1988; 27 1517-1519
- 24 Bouillant M L, Bernillon J, Favre-Bonvin J, Salin N. New hexaketides related to sordariol in Sordaria macrospora. Z Naturforsch. 1989; 44c 719-723
- 25 Höller U, Gloer J B, Wicklow D T. Biologically active polyketide metabolites from an undetermined fungicolus hyphomycete resembling Cladosporium. J Nat Prod. 2002; 65 876-882
- 26 Fujimoto H, Asai T, Kim Y P, Ishibashi M. Nine constituents including six xanthone-related compounds isolated from two Ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity. Chem Pharm Bull. 2006; 54 550-553
- 27 Pinkerton F, Strobel G. Serinol as an activator of toxin production in attenuated cultures of Helminthosporium sacchari. Proc Natl Acad Sci USA. 1976; 73 4007-4011
Prof. Jerzy W. Jaroszewski
Department of Medicinal Chemistry
Faculty of Pharmaceutical Sciences
University of Copenhagen
Universitetsparken 2
2100 Copenhagen
Denmark
Phone: + 45 35 33 63 72
Fax: + 45 35 33 60 41
Email: jj@farma.ku.dk