New sesquiterpenoid isonitriles from three species of phyllidid nudibranchs

Desmond C.M. Sim; I. Wayan Mudianta; Andrew M. White; Ni Wayan Martiningsih; Jasmine J.M. Loh; Karen L. Cheney; Mary J. Garson

doi:10.1016/j.fitote.2017.10.003

New sesquiterpenoid isonitriles from three species of phyllidid nudibranchs

Desmond C.M. Sim, I. Wayan Mudianta, Andrew M. White, Ni Wayan Martiningsih, Jasmine J.M. Loh, Karen L. Cheney, Mary J. Garson^*

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

Chemical investigation of the two nudibranch species Phyllidiella pustulosa and Phyllidia ocellata collected in Queensland, Australia, provided new stereoisomers of 4-isocyano-9-amorphene (1) and of 10-isocyano-4-amorphene (2), respectively. A specimen of Phyllidia picta collected from Bali, Indonesia, contained the axane sesquiterpenoids pictaisonitrile-1 (3) and pictaisonitrile-2 (4). The planar structures were elucidated using 1D and 2D NMR spectroscopy, while relative configurations were established using NOESY correlations, coupling constant data, and comparison with literature data.

Original language	English
Pages (from-to)	69-73
Number of pages	5
Journal	Fitoterapia
Volume	126
DOIs	https://doi.org/10.1016/j.fitote.2017.10.003
Publication status	Published - Apr 2018
Externally published	Yes

Access to Document

10.1016/j.fitote.2017.10.003

Cite this

@article{885104a9e93740dcbda7cf19ba6eadc9,

title = "New sesquiterpenoid isonitriles from three species of phyllidid nudibranchs",

abstract = "Chemical investigation of the two nudibranch species Phyllidiella pustulosa and Phyllidia ocellata collected in Queensland, Australia, provided new stereoisomers of 4-isocyano-9-amorphene (1) and of 10-isocyano-4-amorphene (2), respectively. A specimen of Phyllidia picta collected from Bali, Indonesia, contained the axane sesquiterpenoids pictaisonitrile-1 (3) and pictaisonitrile-2 (4). The planar structures were elucidated using 1D and 2D NMR spectroscopy, while relative configurations were established using NOESY correlations, coupling constant data, and comparison with literature data.",

keywords = "Isocyanide, NMR, Phyllidia, Phyllidiella, Sesquiterpene",

author = "Sim, {Desmond C.M.} and {Wayan Mudianta}, I. and White, {Andrew M.} and Martiningsih, {Ni Wayan} and Loh, {Jasmine J.M.} and Cheney, {Karen L.} and Garson, {Mary J.}",

note = "Publisher Copyright: {\textcopyright} 2017",

year = "2018",

month = apr,

doi = "10.1016/j.fitote.2017.10.003",

language = "English",

volume = "126",

pages = "69--73",

journal = "Fitoterapia",

issn = "0367-326X",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - New sesquiterpenoid isonitriles from three species of phyllidid nudibranchs

AU - Sim, Desmond C.M.

AU - Wayan Mudianta, I.

AU - White, Andrew M.

AU - Martiningsih, Ni Wayan

AU - Loh, Jasmine J.M.

AU - Cheney, Karen L.

AU - Garson, Mary J.

PY - 2018/4

Y1 - 2018/4

N2 - Chemical investigation of the two nudibranch species Phyllidiella pustulosa and Phyllidia ocellata collected in Queensland, Australia, provided new stereoisomers of 4-isocyano-9-amorphene (1) and of 10-isocyano-4-amorphene (2), respectively. A specimen of Phyllidia picta collected from Bali, Indonesia, contained the axane sesquiterpenoids pictaisonitrile-1 (3) and pictaisonitrile-2 (4). The planar structures were elucidated using 1D and 2D NMR spectroscopy, while relative configurations were established using NOESY correlations, coupling constant data, and comparison with literature data.

AB - Chemical investigation of the two nudibranch species Phyllidiella pustulosa and Phyllidia ocellata collected in Queensland, Australia, provided new stereoisomers of 4-isocyano-9-amorphene (1) and of 10-isocyano-4-amorphene (2), respectively. A specimen of Phyllidia picta collected from Bali, Indonesia, contained the axane sesquiterpenoids pictaisonitrile-1 (3) and pictaisonitrile-2 (4). The planar structures were elucidated using 1D and 2D NMR spectroscopy, while relative configurations were established using NOESY correlations, coupling constant data, and comparison with literature data.

KW - Isocyanide

KW - NMR

KW - Phyllidia

KW - Phyllidiella

KW - Sesquiterpene

UR - http://www.scopus.com/inward/record.url?scp=85036498725&partnerID=8YFLogxK

U2 - 10.1016/j.fitote.2017.10.003

DO - 10.1016/j.fitote.2017.10.003

M3 - Article

C2 - 29031559

AN - SCOPUS:85036498725

SN - 0367-326X

VL - 126

SP - 69

EP - 73

JO - Fitoterapia

JF - Fitoterapia

ER -

New sesquiterpenoid isonitriles from three species of phyllidid nudibranchs

Abstract

Access to Document

Other files and links

Fingerprint

Cite this