Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus

[Image: see text] Epoxygoniolide-1 (1), possessing spiroepoxide lactone, enal, and masked dialdehyde functionalities, has been characterized from the conspicuously patterned mollusc Goniobranchus splendidus. Its relative configuration was investigated by spectroscopic analyses, molecular modeling, a...

Descripción completa

Detalles Bibliográficos
Autores principales: Forster, Louise C., Pierens, Gregory K., White, Andrew M., Cheney, Karen L., Dewapriya, Pradeep, Capon, Robert J., Garson, Mary J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044697/
https://www.ncbi.nlm.nih.gov/pubmed/30023672
http://dx.doi.org/10.1021/acsomega.7b00641
_version_ 1783339523849060352
author Forster, Louise C.
Pierens, Gregory K.
White, Andrew M.
Cheney, Karen L.
Dewapriya, Pradeep
Capon, Robert J.
Garson, Mary J.
author_facet Forster, Louise C.
Pierens, Gregory K.
White, Andrew M.
Cheney, Karen L.
Dewapriya, Pradeep
Capon, Robert J.
Garson, Mary J.
author_sort Forster, Louise C.
collection PubMed
description [Image: see text] Epoxygoniolide-1 (1), possessing spiroepoxide lactone, enal, and masked dialdehyde functionalities, has been characterized from the conspicuously patterned mollusc Goniobranchus splendidus. Its relative configuration was investigated by spectroscopic analyses, molecular modeling, and density functional theory calculations. The biosynthesis of 1 may involve rearrangement of a diterpene framework, providing a precursor to cometabolite gonioline (2), followed by C–C bond cleavage (via Grob or P450 mechanism). Moderate cytotoxicity to NCIH-460, SW60, or HepG2 cancer cells was observed for norditerpene 1.
format Online
Article
Text
id pubmed-6044697
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60446972018-07-16 Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus Forster, Louise C. Pierens, Gregory K. White, Andrew M. Cheney, Karen L. Dewapriya, Pradeep Capon, Robert J. Garson, Mary J. ACS Omega [Image: see text] Epoxygoniolide-1 (1), possessing spiroepoxide lactone, enal, and masked dialdehyde functionalities, has been characterized from the conspicuously patterned mollusc Goniobranchus splendidus. Its relative configuration was investigated by spectroscopic analyses, molecular modeling, and density functional theory calculations. The biosynthesis of 1 may involve rearrangement of a diterpene framework, providing a precursor to cometabolite gonioline (2), followed by C–C bond cleavage (via Grob or P450 mechanism). Moderate cytotoxicity to NCIH-460, SW60, or HepG2 cancer cells was observed for norditerpene 1. American Chemical Society 2017-06-15 /pmc/articles/PMC6044697/ /pubmed/30023672 http://dx.doi.org/10.1021/acsomega.7b00641 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Forster, Louise C.
Pierens, Gregory K.
White, Andrew M.
Cheney, Karen L.
Dewapriya, Pradeep
Capon, Robert J.
Garson, Mary J.
Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title_full Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title_fullStr Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title_full_unstemmed Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title_short Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
title_sort cytotoxic spiroepoxide lactone and its putative biosynthetic precursor from goniobranchus splendidus
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044697/
https://www.ncbi.nlm.nih.gov/pubmed/30023672
http://dx.doi.org/10.1021/acsomega.7b00641
work_keys_str_mv AT forsterlouisec cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT pierensgregoryk cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT whiteandrewm cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT cheneykarenl cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT dewapriyapradeep cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT caponrobertj cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus
AT garsonmaryj cytotoxicspiroepoxidelactoneanditsputativebiosyntheticprecursorfromgoniobranchussplendidus

Ejemplares similares