Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures: HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study
Language: 
English
Short Title: 
Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures
Abstract: 

The endophytic fungus Pestalotiopsis virgatula, derived from the plant Terminalia chebula and previously found to produce a large excess of a single metabolite when grown in the minimal M1D medium, was induced to produce a variety of unusual metabolites by growing in potato dextrose broth medium. Analysis of the fermentation medium extract was performed using an HPLC-PDA-MS-SPE-NMR hyphenated system, which led to the identification of a total of eight metabolites (1-8), six of which are new. Most of the metabolites are structurally related and are derivatives of benzo[c]oxepin, rare among natural products. This includes dispiro derivatives 7 and 8 (pestalospiranes A and B), having a novel 1,9,11,18-tetraoxadispiro[6.2.6.2]octadecane skeleton. Relative and absolute configurations of the latter were determined by a combination of NOESY spectroscopy and electronic circular dichroism spectroscopy supported by time-dependent density-functional theory calculations (B3LYP/TZVP level). This work demonstrates that a largely complete structure elucidation of numerous metabolites present in a raw fermentation medium extract can be performed by the HPLC-SPE-NMR technique using only a small amount of the extract, even with unstable metabolites that are difficult to isolate by traditional methods.

Author(s): 
Kesting, Julie R.
Olsen, Lars
Staerk, Dan
Tejesvi, Mysore V.
Kini, Kukkundoor R.
Prakash, Harishchandra S.
Jaroszewski, Jerzy W.
Item Type: 
Journal Article
Publication Title: 
Journal of Natural Products
Journal Abbreviation: 
J. Nat. Prod.
Publication Date: 
10/28/2011
Publication Year: 
2011
Pages: 
2206-2215
Volume: 
74
Issue: 
10
ISSN: 
1520-6025
DOI: 
10.1021/np2005665
Library Catalog: 
PubMed
Extra: 
PMID: 21942847

Turabian/Chicago Citation

Julie R. Kesting, Lars Olsen, Dan Staerk, Mysore V. Tejesvi, Kukkundoor R. Kini, Harishchandra S. Prakash and Jerzy W. Jaroszewski. 10/28/2011. "Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures: HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study." Journal of Natural Products 74: 10: 2206-2215. 10.1021/np2005665.

Wikipedia Citation

<ref> {{Cite journal | doi = 10.1021/np2005665 | issn = 1520-6025 | volume = 74 | pages = 2206-2215 | last = Kesting | first = Julie R. | coauthors = Olsen, Lars, Staerk, Dan, Tejesvi, Mysore V., Kini, Kukkundoor R., Prakash, Harishchandra S., Jaroszewski, Jerzy W. | title = Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures: HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study | journal = Journal of Natural Products | date = 10/28/2011 | pmid = | pmc = }} </ref>