In vitro inhibition of 5-lipoxygenase by protolichesterinic acid from Cetraria islandica

K. Ingolfsdottir; W. Breu; S. Huneck; G. A. Gudjonsdottir; B. Müller-Jakic; H. Wagner

doi:10.1016/S0944-7113(11)80063-2

In vitro inhibition of 5-lipoxygenase by protolichesterinic acid from Cetraria islandica

K. Ingolfsdottir, W. Breu, S. Huneck, G. A. Gudjonsdottir, B. Müller-Jakic, H. Wagner

Faculty of Pharmaceutical Sciences

University of Iceland

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

Abstract

The aliphatic α-methylene-γ-lactone (+)-protolichesterinic acid (1), isolated from Cetraria islandica, has been shown to exhibit inhibitory effects on the enzyme 5-lipoxygenase in an in vitro assay in which porcine leucocytes are used as a source of the enzyme system. The isomeric compounds (+)-lichesterinic acid (2) and (−)-lichesterinic acid (4), prepared from (+)-protolichesterinic- and (−)-allo-protolichesterinic acids, respectively, exhibited anti-5-lipoxygenase activity of the same order of magnitude. (+)-Methyl lichesterinate (3) was, however, inactive. It was shown that despite its lipophilic nature, protolichesterinic acid is extractable into an aqueous medium, the concentration being dependent on the length of extraction.

Original language	English
Pages (from-to)	187-191
Number of pages	5
Journal	Phytomedicine
Volume	1
Issue number	3
DOIs	https://doi.org/10.1016/S0944-7113(11)80063-2
Publication status	Published - 1994

Bibliographical note

Funding Information: The authors wish to thank Dr. O. Seligmann (Institute of Pharmaceutical Biology,University of Munich) for recording IH NMR spectra and Dr. Sigridur Jonsdottir (Science Institute, University of Iceland) for recording BC NMR spectra. The work was supported in part by the Icelandic Council of Science and The University of Iceland Research Fund.

Other keywords

5-lipoxygenase
Cetraria islandica
Iceland Moss
leukotriene synthesis
lichen
lichesterinic acid
protolichesterinic acid

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10.1016/S0944-7113(11)80063-2

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@article{c7e60b64965b4edf90b89a950ec6b258,

title = "In vitro inhibition of 5-lipoxygenase by protolichesterinic acid from Cetraria islandica",

abstract = "The aliphatic α-methylene-γ-lactone (+)-protolichesterinic acid (1), isolated from Cetraria islandica, has been shown to exhibit inhibitory effects on the enzyme 5-lipoxygenase in an in vitro assay in which porcine leucocytes are used as a source of the enzyme system. The isomeric compounds (+)-lichesterinic acid (2) and (−)-lichesterinic acid (4), prepared from (+)-protolichesterinic- and (−)-allo-protolichesterinic acids, respectively, exhibited anti-5-lipoxygenase activity of the same order of magnitude. (+)-Methyl lichesterinate (3) was, however, inactive. It was shown that despite its lipophilic nature, protolichesterinic acid is extractable into an aqueous medium, the concentration being dependent on the length of extraction.",

keywords = "5-lipoxygenase, Cetraria islandica, Iceland Moss, leukotriene synthesis, lichen, lichesterinic acid, protolichesterinic acid",

author = "K. Ingolfsdottir and W. Breu and S. Huneck and Gudjonsdottir, \{G. A.\} and B. M{\"u}ller-Jakic and H. Wagner",

note = "Funding Information: The authors wish to thank Dr. O. Seligmann (Institute of Pharmaceutical Biology,University of Munich) for recording IH NMR spectra and Dr. Sigridur Jonsdottir (Science Institute, University of Iceland) for recording BC NMR spectra. The work was supported in part by the Icelandic Council of Science and The University of Iceland Research Fund.",

year = "1994",

doi = "10.1016/S0944-7113(11)80063-2",

language = "English",

volume = "1",

pages = "187--191",

journal = "Phytomedicine",

issn = "0944-7113",

publisher = "Elsevier GmbH",

number = "3",

}

TY - JOUR

T1 - In vitro inhibition of 5-lipoxygenase by protolichesterinic acid from Cetraria islandica

AU - Ingolfsdottir, K.

AU - Breu, W.

AU - Huneck, S.

AU - Gudjonsdottir, G. A.

AU - Müller-Jakic, B.

AU - Wagner, H.

N1 - Funding Information: The authors wish to thank Dr. O. Seligmann (Institute of Pharmaceutical Biology,University of Munich) for recording IH NMR spectra and Dr. Sigridur Jonsdottir (Science Institute, University of Iceland) for recording BC NMR spectra. The work was supported in part by the Icelandic Council of Science and The University of Iceland Research Fund.

PY - 1994

Y1 - 1994

N2 - The aliphatic α-methylene-γ-lactone (+)-protolichesterinic acid (1), isolated from Cetraria islandica, has been shown to exhibit inhibitory effects on the enzyme 5-lipoxygenase in an in vitro assay in which porcine leucocytes are used as a source of the enzyme system. The isomeric compounds (+)-lichesterinic acid (2) and (−)-lichesterinic acid (4), prepared from (+)-protolichesterinic- and (−)-allo-protolichesterinic acids, respectively, exhibited anti-5-lipoxygenase activity of the same order of magnitude. (+)-Methyl lichesterinate (3) was, however, inactive. It was shown that despite its lipophilic nature, protolichesterinic acid is extractable into an aqueous medium, the concentration being dependent on the length of extraction.

AB - The aliphatic α-methylene-γ-lactone (+)-protolichesterinic acid (1), isolated from Cetraria islandica, has been shown to exhibit inhibitory effects on the enzyme 5-lipoxygenase in an in vitro assay in which porcine leucocytes are used as a source of the enzyme system. The isomeric compounds (+)-lichesterinic acid (2) and (−)-lichesterinic acid (4), prepared from (+)-protolichesterinic- and (−)-allo-protolichesterinic acids, respectively, exhibited anti-5-lipoxygenase activity of the same order of magnitude. (+)-Methyl lichesterinate (3) was, however, inactive. It was shown that despite its lipophilic nature, protolichesterinic acid is extractable into an aqueous medium, the concentration being dependent on the length of extraction.

KW - 5-lipoxygenase

KW - Cetraria islandica

KW - Iceland Moss

KW - leukotriene synthesis

KW - lichen

KW - lichesterinic acid

KW - protolichesterinic acid

UR - https://www.scopus.com/pages/publications/0028251510

U2 - 10.1016/S0944-7113(11)80063-2

DO - 10.1016/S0944-7113(11)80063-2

M3 - Article

SN - 0944-7113

VL - 1

SP - 187

EP - 191

JO - Phytomedicine

JF - Phytomedicine

IS - 3

ER -

In vitro inhibition of 5-lipoxygenase by protolichesterinic acid from Cetraria islandica

Abstract

Bibliographical note

Other keywords

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