iso-Petromyroxols: Novel Dihydroxylated Tetrahydrofuran Enantiomers from Sea Lamprey (Petromyzon marinus)

Ke Li; Cory O. Brant; Ugo Bussy; Harshita Pinnamaneni; Hinal Patel; Thomas R. Hoye; Weiming Li

doi:10.3390/molecules20035215

Molecules (Mar 2015)

iso-Petromyroxols: Novel Dihydroxylated Tetrahydrofuran Enantiomers from Sea Lamprey (Petromyzon marinus)

Ke Li,
Cory O. Brant,
Ugo Bussy,
Harshita Pinnamaneni,
Hinal Patel,
Thomas R. Hoye,
Weiming Li

Affiliations

Ke Li: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
Cory O. Brant: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
Ugo Bussy: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
Harshita Pinnamaneni: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
Hinal Patel: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
Thomas R. Hoye: Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, MN 55455, USA
Weiming Li: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA

DOI: https://doi.org/10.3390/molecules20035215
Journal volume & issue: Vol. 20, no. 3
pp. 5215 – 5222

Abstract

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An enantiomeric pair of new fatty acid-derived hydroxylated tetrahydrofurans, here named iso-petromyroxols, were isolated from sea lamprey larvae-conditioned water. The relative configuration of iso-petromyroxol was elucidated with 1D and 2D NMR spectroscopic analyses. The ratio of enantiomers (er) in the natural sample was measured by chiral-HPLC-MS/MS to be ca. 3:1 of (–)- to (+)-antipodes.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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