Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus

Louise C. Forster; Gregory K. Pierens; Andrew M. White; Karen L. Cheney; Pradeep Dewapriya; Robert J. Capon; Mary J. Garson

doi:10.1021/acsomega.7b00641

Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus

Louise C. Forster, Gregory K. Pierens, Andrew M. White, Karen L. Cheney, Pradeep Dewapriya, Robert J. Capon, Mary J. Garson^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2672-2677
Number of pages	6
Journal	ACS Omega
Volume	2
Issue number	6
DOIs	https://doi.org/10.1021/acsomega.7b00641
Publication status	Published - 30 Jun 2017
Externally published	Yes

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title = "Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus",

abstract = "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.",

author = "Forster, {Louise C.} and Pierens, {Gregory K.} and White, {Andrew M.} and Cheney, {Karen L.} and Pradeep Dewapriya and Capon, {Robert J.} and Garson, {Mary J.}",

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AU - Forster, Louise C.

AU - Pierens, Gregory K.

AU - White, Andrew M.

AU - Cheney, Karen L.

AU - Dewapriya, Pradeep

AU - Capon, Robert J.

AU - Garson, Mary J.

PY - 2017/6/30

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N2 - 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.

AB - 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.

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Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus

Abstract

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