NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata

Bao Ning Su; Muriel Cuendet; Dejan Nikolic; Hördur Kristinsson; Kristín Ingólfsdóttir; Richard B. Van Breemen; Harry H.S. Fong; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1002/mrc.1181

NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata

Bao Ning Su, Muriel Cuendet, Dejan Nikolic, Hördur Kristinsson, Kristín Ingólfsdóttir, Richard B. Van Breemen, Harry H.S. Fong, John M. Pezzuto, A. Douglas Kinghorn

Faculty of Pharmaceutical Sciences

University of Iceland

Research output: Contribution to journal › Article › peer-review

Abstract

A lichen depsidone derivative, fumarprotocetraric acid, was obtained as the major constituent of Cladonia furcata (Huds.) Schrad. collected in Iceland. In the ¹H NMR spectrum (in DMSO-d₆) of this compound, the trans double bond proton signals of the fumaryl unit appeared as overlapping singlets. To confirm the presence of a trans double bond in the molecule, fumarprotocetraric acid was treated with triethylamine. The ¹H NMR spectrum of the resultant triethylamine salt displayed a pair of clear doublets with coupling constants of 15.7 Hz, which are characteristic of a trans double bond. Unambiguous ¹H and ¹³C NMR spectral data for both fumarprotocetraric acid and its triethylamine salt were assigned for the first time based on the interpretation of their 2D NMR (HMQC, HMBC and NOESY) spectra.

Original language	English
Pages (from-to)	391-394
Number of pages	4
Journal	Magnetic Resonance in Chemistry
Volume	41
Issue number	5
DOIs	https://doi.org/10.1002/mrc.1181
Publication status	Published - 1 May 2003

Other keywords

2D NMR
C NMR
Cladonia furcata
Depsidone derivative
Fumarprotocetraric acid
H NMR
Lichen
NMR
Triethylamine salt
trans double bond

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@article{f2e30b8e704f4715a7ae05d679ee32e0,

title = "NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata",

abstract = "A lichen depsidone derivative, fumarprotocetraric acid, was obtained as the major constituent of Cladonia furcata (Huds.) Schrad. collected in Iceland. In the 1H NMR spectrum (in DMSO-d6) of this compound, the trans double bond proton signals of the fumaryl unit appeared as overlapping singlets. To confirm the presence of a trans double bond in the molecule, fumarprotocetraric acid was treated with triethylamine. The 1H NMR spectrum of the resultant triethylamine salt displayed a pair of clear doublets with coupling constants of 15.7 Hz, which are characteristic of a trans double bond. Unambiguous 1H and 13C NMR spectral data for both fumarprotocetraric acid and its triethylamine salt were assigned for the first time based on the interpretation of their 2D NMR (HMQC, HMBC and NOESY) spectra.",

keywords = "2D NMR, C NMR, Cladonia furcata, Depsidone derivative, Fumarprotocetraric acid, H NMR, Lichen, NMR, Triethylamine salt, trans double bond",

author = "Su, \{Bao Ning\} and Muriel Cuendet and Dejan Nikolic and H{\"o}rdur Kristinsson and Krist{\'i}n Ing{\'o}lfsd{\'o}ttir and \{Van Breemen\}, \{Richard B.\} and Fong, \{Harry H.S.\} and Pezzuto, \{John M.\} and Kinghorn, \{A. Douglas\}",

year = "2003",

month = may,

day = "1",

doi = "10.1002/mrc.1181",

language = "English",

volume = "41",

pages = "391--394",

journal = "Magnetic Resonance in Chemistry",

issn = "0749-1581",

publisher = "John Wiley and Sons Ltd",

number = "5",

}

TY - JOUR

T1 - NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata

AU - Su, Bao Ning

AU - Cuendet, Muriel

AU - Nikolic, Dejan

AU - Kristinsson, Hördur

AU - Ingólfsdóttir, Kristín

AU - Van Breemen, Richard B.

AU - Fong, Harry H.S.

AU - Pezzuto, John M.

AU - Kinghorn, A. Douglas

PY - 2003/5/1

Y1 - 2003/5/1

N2 - A lichen depsidone derivative, fumarprotocetraric acid, was obtained as the major constituent of Cladonia furcata (Huds.) Schrad. collected in Iceland. In the 1H NMR spectrum (in DMSO-d6) of this compound, the trans double bond proton signals of the fumaryl unit appeared as overlapping singlets. To confirm the presence of a trans double bond in the molecule, fumarprotocetraric acid was treated with triethylamine. The 1H NMR spectrum of the resultant triethylamine salt displayed a pair of clear doublets with coupling constants of 15.7 Hz, which are characteristic of a trans double bond. Unambiguous 1H and 13C NMR spectral data for both fumarprotocetraric acid and its triethylamine salt were assigned for the first time based on the interpretation of their 2D NMR (HMQC, HMBC and NOESY) spectra.

AB - A lichen depsidone derivative, fumarprotocetraric acid, was obtained as the major constituent of Cladonia furcata (Huds.) Schrad. collected in Iceland. In the 1H NMR spectrum (in DMSO-d6) of this compound, the trans double bond proton signals of the fumaryl unit appeared as overlapping singlets. To confirm the presence of a trans double bond in the molecule, fumarprotocetraric acid was treated with triethylamine. The 1H NMR spectrum of the resultant triethylamine salt displayed a pair of clear doublets with coupling constants of 15.7 Hz, which are characteristic of a trans double bond. Unambiguous 1H and 13C NMR spectral data for both fumarprotocetraric acid and its triethylamine salt were assigned for the first time based on the interpretation of their 2D NMR (HMQC, HMBC and NOESY) spectra.

KW - 2D NMR

KW - C NMR

KW - Cladonia furcata

KW - Depsidone derivative

KW - Fumarprotocetraric acid

KW - H NMR

KW - Lichen

KW - NMR

KW - Triethylamine salt

KW - trans double bond

UR - https://www.scopus.com/pages/publications/0038036860

U2 - 10.1002/mrc.1181

DO - 10.1002/mrc.1181

M3 - Article

SN - 0749-1581

VL - 41

SP - 391

EP - 394

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 5

ER -

NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata

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