Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula

Bingnan Han; Kerry L. McPhail; Harald Gross; Douglas E. Goeger; Susan L. Mooberry; William H. Gerwick

doi:10.1016/j.tet.2005.09.036

Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula

Bingnan Han, Kerry L. McPhail, Harald Gross, Douglas E. Goeger, Susan L. Mooberry, William H. Gerwick

Department of Pharmacology

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

72 Scopus citations

Abstract

Five new lyngbyabellin analogs along with a known compound, dolabellin, have been isolated from the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea. The structures of lyngbyabellins E-I were elucidated through extensive spectroscopic analysis, including HR-FABMS and 1D and 2D NMR experiments. The absolute configurations of lyngbyabellin E and H were ascertained by chiral HPLC and GC/MS analysis of degradation products, in combination with NMR experiments. All five lyngbyabellins showed cytotoxicity to NCI-H460 human lung tumor and neuro-2a mouse neuroblastoma cell lines with LC₅₀ values between 0.2 and 4.8 μM.

Original language	English (US)
Pages (from-to)	11723-11729
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2005.09.036
State	Published - Dec 5 2005

Keywords

Actin-disruption
Cytotoxin
Dolabellin
Lipopeptide
Lyngbya majuscula
Lyngbyabellin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula",

abstract = "Five new lyngbyabellin analogs along with a known compound, dolabellin, have been isolated from the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea. The structures of lyngbyabellins E-I were elucidated through extensive spectroscopic analysis, including HR-FABMS and 1D and 2D NMR experiments. The absolute configurations of lyngbyabellin E and H were ascertained by chiral HPLC and GC/MS analysis of degradation products, in combination with NMR experiments. All five lyngbyabellins showed cytotoxicity to NCI-H460 human lung tumor and neuro-2a mouse neuroblastoma cell lines with LC50 values between 0.2 and 4.8 μM.",

keywords = "Actin-disruption, Cytotoxin, Dolabellin, Lipopeptide, Lyngbya majuscula, Lyngbyabellin",

author = "Bingnan Han and McPhail, {Kerry L.} and Harald Gross and Goeger, {Douglas E.} and Mooberry, {Susan L.} and Gerwick, {William H.}",

note = "Funding Information: We gratefully acknowledge the government of Papua New Guinea for permission and L. Matainaho, University of Papua New Guinea for assistance in making these collections, the NMR facility of the Department of Chemistry at Oregon State University, and the OSU mass spectrometry facility, which is supported in part by the National Institute of Environmental Health Sciences (P30 ES00210). Financial support for work at OSU came from the National Institutes of Health (GM 63554 and CA52955) and at SFBR from the William Randolph Hearst Foundation. ",

year = "2005",

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doi = "10.1016/j.tet.2005.09.036",

language = "English (US)",

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AU - Goeger, Douglas E.

AU - Mooberry, Susan L.

AU - Gerwick, William H.

N1 - Funding Information: We gratefully acknowledge the government of Papua New Guinea for permission and L. Matainaho, University of Papua New Guinea for assistance in making these collections, the NMR facility of the Department of Chemistry at Oregon State University, and the OSU mass spectrometry facility, which is supported in part by the National Institute of Environmental Health Sciences (P30 ES00210). Financial support for work at OSU came from the National Institutes of Health (GM 63554 and CA52955) and at SFBR from the William Randolph Hearst Foundation.

PY - 2005/12/5

Y1 - 2005/12/5

N2 - Five new lyngbyabellin analogs along with a known compound, dolabellin, have been isolated from the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea. The structures of lyngbyabellins E-I were elucidated through extensive spectroscopic analysis, including HR-FABMS and 1D and 2D NMR experiments. The absolute configurations of lyngbyabellin E and H were ascertained by chiral HPLC and GC/MS analysis of degradation products, in combination with NMR experiments. All five lyngbyabellins showed cytotoxicity to NCI-H460 human lung tumor and neuro-2a mouse neuroblastoma cell lines with LC50 values between 0.2 and 4.8 μM.

AB - Five new lyngbyabellin analogs along with a known compound, dolabellin, have been isolated from the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea. The structures of lyngbyabellins E-I were elucidated through extensive spectroscopic analysis, including HR-FABMS and 1D and 2D NMR experiments. The absolute configurations of lyngbyabellin E and H were ascertained by chiral HPLC and GC/MS analysis of degradation products, in combination with NMR experiments. All five lyngbyabellins showed cytotoxicity to NCI-H460 human lung tumor and neuro-2a mouse neuroblastoma cell lines with LC50 values between 0.2 and 4.8 μM.

KW - Actin-disruption

KW - Cytotoxin

KW - Dolabellin

KW - Lipopeptide

KW - Lyngbya majuscula

KW - Lyngbyabellin

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Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula

Abstract

Keywords

ASJC Scopus subject areas

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