Isolation and structure of three new ceramides from the starfish Acanthaster planci

Masanori Inagaki, Ryuichi Isobe, Yasuhiro Kawano, Tomofumi Miyamoto, Tetsuya Komori, Ryuichi Higuchi

Research output: Contribution to journalArticle

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Abstract

Three new phytosphingosine-type ceramides, AC-1-6, AC-1-10 and AC-1-11, were isolated from the ceramide molecular species AC-1, obtained from the less polar fraction of the CHCl3/MeOH extract of the starfish Acanthaster planci. The structures of these ceramides were determined on the basis of chemical and spectroscopic evidence as (2S,2′ R,3S,4R,9Z)-2-(2-hydroxyhexadecanoylamino)-9-docosene-1,3,4-triol (AC-1-6), (2S,2′ R,3S,4R,)-2-(2-hydroxytricosanoylamino)hexadecane-1,3,4-triol (AC-1-10) and (2S,2′ R,3S,4R,)-2(2-hydroxytetracosanoylamino)hexadecane-1,3,4-triol (AC-1-11). Positive ion FABMS/MS of each ceramide gave important information for their structure elucidation. Mass spectrometry of the dimethyl disulfide derivatives of ceramide was also useful for the determination of the double bond position in the long-chain base.

Original languageEnglish
Pages (from-to)129-131
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number1
Publication statusPublished - Jan 1 1998

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Ceramides
isolation
alternating current
triols
phytosphingosine
Mass spectrometry
disulfides
Positive ions
positive ions
Derivatives
mass spectroscopy
n-hexadecane

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Isolation and structure of three new ceramides from the starfish Acanthaster planci. / Inagaki, Masanori; Isobe, Ryuichi; Kawano, Yasuhiro; Miyamoto, Tomofumi; Komori, Tetsuya; Higuchi, Ryuichi.

In: European Journal of Organic Chemistry, No. 1, 01.01.1998, p. 129-131.

Research output: Contribution to journalArticle

Inagaki, Masanori ; Isobe, Ryuichi ; Kawano, Yasuhiro ; Miyamoto, Tomofumi ; Komori, Tetsuya ; Higuchi, Ryuichi. / Isolation and structure of three new ceramides from the starfish Acanthaster planci. In: European Journal of Organic Chemistry. 1998 ; No. 1. pp. 129-131.
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