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 Haygood, Alan R. Light, Eric W. Schmidt

Research output: Contribution to journalArticle

12 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)4867-4869
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number17
DOIs
StatePublished - Sep 1 2013

Fingerprint

Gordonia Bacterium
Norepinephrine Plasma Membrane Transport Proteins
Conus Snail
Snails
Venoms
Spinal Ganglia
Metabolites
Action Potentials
Cones
Assays
Bacteria
Neurons
Fractionation
Ducts
Association reactions
acyloin
kurasoin B

Keywords

  • Natural product
  • Neuroassay
  • Symbiont

ASJC Scopus subject areas

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

Cite this

Lin, Z., Marett, L., Hughen, R. W., Flores, M., Forteza, I., Ammon, M. A., ... 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

Neuroactive diol and acyloin metabolites from cone snail-associated bacteria. / Lin, Zhenjian; Marett, Lenny; Hughen, Ronald W.; Flores, Malem; Forteza, Imelda; Ammon, Mary Anne; Concepcion, Gisela P.; Espino, Samuel; Olivera, Baldomero M.; Rosenberg, Gary; Haygood, Margo; Light, Alan R.; Schmidt, Eric W.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 17, 01.09.2013, p. 4867-4869.

Research output: Contribution to journalArticle

Lin, Z, Marett, L, Hughen, RW, Flores, M, Forteza, I, Ammon, MA, Concepcion, GP, Espino, S, Olivera, BM, Rosenberg, G, Haygood, M, Light, AR & Schmidt, EW 2013, 'Neuroactive diol and acyloin metabolites from cone snail-associated bacteria', Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 17, pp. 4867-4869. https://doi.org/10.1016/j.bmcl.2013.06.088
Lin, Zhenjian ; Marett, Lenny ; Hughen, Ronald W. ; Flores, Malem ; Forteza, Imelda ; Ammon, Mary Anne ; Concepcion, Gisela P. ; Espino, Samuel ; Olivera, Baldomero M. ; Rosenberg, Gary ; Haygood, Margo ; Light, Alan R. ; Schmidt, Eric W. / Neuroactive diol and acyloin metabolites from cone snail-associated bacteria. In: Bioorganic and Medicinal Chemistry Letters. 2013 ; Vol. 23, No. 17. pp. 4867-4869.
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