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

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Standard

Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures : HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study. / Kesting, Julie Regitze; Olsen, Lars; Stærk, Dan; Tejesvi, Mysore V; Kini, Kukkundoor R; Prakash, Harishchandra S; Jaroszewski, Jerzy W.

I: Journal of Natural Products, Bind 74, Nr. 10, 26.09.2011, s. 2206-2215.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Harvard

Kesting, JR, Olsen, L, Stærk, D, Tejesvi, MV, Kini, KR, Prakash, HS & Jaroszewski, JW 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, bind 74, nr. 10, s. 2206-2215. https://doi.org/10.1021/np2005665

APA

Kesting, J. R., Olsen, L., Stærk, D., Tejesvi, M. V., Kini, K. R., Prakash, H. S., & Jaroszewski, J. W. (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. https://doi.org/10.1021/np2005665

Vancouver

Kesting JR, Olsen L, Stærk D, Tejesvi MV, Kini KR, Prakash HS o.a. 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. 2011 sep 26;74(10):2206-2215. https://doi.org/10.1021/np2005665

Author

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

Bibtex

@article{11a78d92c5a0442a832c7cc9d9c07fa0,
title = "Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures: HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study",
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.",
keywords = "Former Faculty of Pharmaceutical Sciences, Former LIFE faculty",
author = "Kesting, {Julie Regitze} and Lars Olsen and Dan St{\ae}rk and Tejesvi, {Mysore V} and Kini, {Kukkundoor R} and Prakash, {Harishchandra S} and Jaroszewski, {Jerzy W.}",
year = "2011",
month = sep,
day = "26",
doi = "10.1021/np2005665",
language = "English",
volume = "74",
pages = "2206--2215",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "10",

}

RIS

TY - JOUR

T1 - Production of unusual dispiro metabolites in Pestalotiopsis virgatula endophyte cultures

T2 - HPLC-SPE-NMR, electronic circular dichroism, and time-dependent density-functional computation study

AU - Kesting, Julie Regitze

AU - Olsen, Lars

AU - Stærk, Dan

AU - Tejesvi, Mysore V

AU - Kini, Kukkundoor R

AU - Prakash, Harishchandra S

AU - Jaroszewski, Jerzy W.

PY - 2011/9/26

Y1 - 2011/9/26

N2 - 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.

AB - 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.

KW - Former Faculty of Pharmaceutical Sciences

KW - Former LIFE faculty

U2 - 10.1021/np2005665

DO - 10.1021/np2005665

M3 - Journal article

C2 - 21942847

VL - 74

SP - 2206

EP - 2215

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 10

ER -

ID: 34528049