Neuroactive diol and acyloin metabolites from cone snail-associated bacteria

Zhenjian Lin; Lenny Marett; Ronald W. Hughen; Malem Flores; Imelda Forteza; Mary Anne Ammon; Gisela P. Concepcion; Samuel Espino; Baldomero M. Olivera; Gary Rosenberg; Margo G. Haygood; Alan R. Light; Eric W. Schmidt

doi:10.1016/j.bmcl.2013.06.088

Neuroactive diol and acyloin metabolites from cone snail-associated bacteria

Zhenjian Lin, Lenny Marett, Ronald W. Hughen, Malem Flores, Imelda Forteza, Mary Anne Ammon, Gisela P. Concepcion, Samuel Espino, Baldomero M. Olivera, Gary Rosenberg, Margo G. Haygood, Alan R. Light, Eric W. Schmidt

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

19 Scopus citations

Abstract

The bacterium Gordonia sp. 647 W.R.1a.05 was cultivated from the venom duct of the cone snail, Conus circumcisus. The Gordonia sp. organic extract modulated the action potential of mouse dorsal root ganglion neurons. Assay-guided fractionation led to the identification of the new compound circumcin A (1) and 11 known analogs (2-12). Two of these compounds, kurasoin B (7) and soraphinol A (8), were active in a human norepinephrine transporter assay with K_i values of 2575 and 867 nM, respectively. No neuroactivity had previously been reported for compounds in this structural class. Gordonia species have been reproducibly isolated from four different cone snail species, indicating a consistent association between these organisms.

Original language	English (US)
Pages (from-to)	4867-4869
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2013.06.088
State	Published - Sep 1 2013
Externally published	Yes

Keywords

Natural product
Neuroassay
Symbiont

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2013.06.088

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Lin, Z., Marett, L., Hughen, R. W., Flores, M., Forteza, I., Ammon, M. A., Concepcion, G. P., Espino, S., Olivera, B. M., Rosenberg, G., Haygood, M. G., Light, A. R., & Schmidt, E. W. (2013). Neuroactive diol and acyloin metabolites from cone snail-associated bacteria. Bioorganic and Medicinal Chemistry Letters, 23(17), 4867-4869. https://doi.org/10.1016/j.bmcl.2013.06.088

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title = "Neuroactive diol and acyloin metabolites from cone snail-associated bacteria",

abstract = "The bacterium Gordonia sp. 647 W.R.1a.05 was cultivated from the venom duct of the cone snail, Conus circumcisus. The Gordonia sp. organic extract modulated the action potential of mouse dorsal root ganglion neurons. Assay-guided fractionation led to the identification of the new compound circumcin A (1) and 11 known analogs (2-12). Two of these compounds, kurasoin B (7) and soraphinol A (8), were active in a human norepinephrine transporter assay with Ki values of 2575 and 867 nM, respectively. No neuroactivity had previously been reported for compounds in this structural class. Gordonia species have been reproducibly isolated from four different cone snail species, indicating a consistent association between these organisms.",

keywords = "Natural product, Neuroassay, Symbiont",

author = "Zhenjian Lin and Lenny Marett and Hughen, {Ronald W.} and Malem Flores and Imelda Forteza and Ammon, {Mary Anne} and Concepcion, {Gisela P.} and Samuel Espino and Olivera, {Baldomero M.} and Gary Rosenberg and Haygood, {Margo G.} and Light, {Alan R.} and Schmidt, {Eric W.}",

note = "Funding Information: This work was funded by ICBG grant U01TW008163 from Fogarty (NIH). We thank the government of the Philippines and the community of Mactan Island for permission to conduct this study. Binding assay data was generously provided by the National Institute of Mental Health{\textquoteright}s Psychoactive Drug Screening Program, Contract # HHSN-271-2008-00025-C (NIMH PDSP). The NIMH PDSP is directed by B.L. Roth MD, Ph.D. at the University of North Carolina at Chapel Hill and Project Officer J. Driscol at NIMH, Bethesda MD, USA. ",

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doi = "10.1016/j.bmcl.2013.06.088",

language = "English (US)",

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AU - Lin, Zhenjian

AU - Marett, Lenny

AU - Hughen, Ronald W.

AU - Flores, Malem

AU - Forteza, Imelda

AU - Ammon, Mary Anne

AU - Concepcion, Gisela P.

AU - Espino, Samuel

AU - Olivera, Baldomero M.

AU - Rosenberg, Gary

AU - Haygood, Margo G.

AU - Light, Alan R.

AU - Schmidt, Eric W.

N1 - Funding Information: This work was funded by ICBG grant U01TW008163 from Fogarty (NIH). We thank the government of the Philippines and the community of Mactan Island for permission to conduct this study. Binding assay data was generously provided by the National Institute of Mental Health’s Psychoactive Drug Screening Program, Contract # HHSN-271-2008-00025-C (NIMH PDSP). The NIMH PDSP is directed by B.L. Roth MD, Ph.D. at the University of North Carolina at Chapel Hill and Project Officer J. Driscol at NIMH, Bethesda MD, USA.

PY - 2013/9/1

Y1 - 2013/9/1

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AB - The bacterium Gordonia sp. 647 W.R.1a.05 was cultivated from the venom duct of the cone snail, Conus circumcisus. The Gordonia sp. organic extract modulated the action potential of mouse dorsal root ganglion neurons. Assay-guided fractionation led to the identification of the new compound circumcin A (1) and 11 known analogs (2-12). Two of these compounds, kurasoin B (7) and soraphinol A (8), were active in a human norepinephrine transporter assay with Ki values of 2575 and 867 nM, respectively. No neuroactivity had previously been reported for compounds in this structural class. Gordonia species have been reproducibly isolated from four different cone snail species, indicating a consistent association between these organisms.

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ER -

Neuroactive diol and acyloin metabolites from cone snail-associated bacteria

Abstract

Keywords

ASJC Scopus subject areas

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