Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

Andrew M. White; Gregory K. Pierens; Louise C. Forster; Anne E. Winters; Karen L. Cheney; Mary J. Garson

doi:10.1021/acs.jnatprod.5b00866

Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

Andrew M. White, Gregory K. Pierens, Louise C. Forster, Anne E. Winters, Karen L. Cheney, Mary J. Garson^*

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.

Original language	English
Pages (from-to)	477-483
Number of pages	7
Journal	Journal of Natural Products
Volume	79
Issue number	3
DOIs	https://doi.org/10.1021/acs.jnatprod.5b00866
Publication status	Published - 25 Mar 2016
Externally published	Yes

Access to Document

10.1021/acs.jnatprod.5b00866

Cite this

@article{b417b2bc64684aa18a7b88dd5dcb9dbe,

title = "Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks",

abstract = "Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.",

author = "White, {Andrew M.} and Pierens, {Gregory K.} and Forster, {Louise C.} and Winters, {Anne E.} and Cheney, {Karen L.} and Garson, {Mary J.}",

note = "Publisher Copyright: {\textcopyright} 2015 The American Chemical Society and American Society of Pharmacognosy.",

year = "2016",

month = mar,

day = "25",

doi = "10.1021/acs.jnatprod.5b00866",

language = "English",

volume = "79",

pages = "477--483",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

AU - White, Andrew M.

AU - Pierens, Gregory K.

AU - Forster, Louise C.

AU - Winters, Anne E.

AU - Cheney, Karen L.

AU - Garson, Mary J.

PY - 2016/3/25

Y1 - 2016/3/25

N2 - Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.

AB - Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.

UR - http://www.scopus.com/inward/record.url?scp=84962476655&partnerID=8YFLogxK

U2 - 10.1021/acs.jnatprod.5b00866

DO - 10.1021/acs.jnatprod.5b00866

M3 - Article

C2 - 26698272

AN - SCOPUS:84962476655

SN - 0163-3864

VL - 79

SP - 477

EP - 483

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 3

ER -

Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

Abstract

Access to Document

Other files and links

Fingerprint

Cite this