n-Nonacosadienes from the marine haptophytes Emiliania huxleyi and Gephyrocapsa oceanica

Hideto Nakamura; Ken Sawada; Hiroya Araie; Iwane Suzuki; Yoshihiro Shiraiwa

doi:10.1016/j.phytochem.2014.12.023

n-Nonacosadienes from the marine haptophytes Emiliania huxleyi and Gephyrocapsa oceanica

Phytochemistry. 2015 Mar:111:107-13. doi: 10.1016/j.phytochem.2014.12.023. Epub 2015 Jan 13.

Authors

Hideto Nakamura¹, Ken Sawada², Hiroya Araie³, Iwane Suzuki³, Yoshihiro Shiraiwa³

Affiliations

¹ Department of Natural History Sciences, Faculty of Science, Hokkaido University, N10W8, Kita-ku, Sapporo 060-0810, Japan; CREST, Japan Science and Technology Agency (JST), N10W8, Kita-ku, Sapporo 060-0810, Japan. Electronic address: hideton@mail.sci.hokudai.ac.jp.
² Department of Natural History Sciences, Faculty of Science, Hokkaido University, N10W8, Kita-ku, Sapporo 060-0810, Japan; CREST, Japan Science and Technology Agency (JST), N10W8, Kita-ku, Sapporo 060-0810, Japan.
³ Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8572, Japan; CREST, Japan Science and Technology Agency (JST), 1-1-1 Tennodai, Tsukuba 305-8572, Japan.

PMID: 25595675
DOI: 10.1016/j.phytochem.2014.12.023

Abstract

The hydrocarbons in cultures of marine haptophytes Emiliania huxleyi NIES837 and Gephyrocapsa oceanica NIES1315 were analyzed, and nonacosadienes and hentriacontadienes were detected as the major compounds in both strains. C29 and C31 monoenes and di-, tri- and tetra-unsaturated C33 alkenes were also detected as minor compounds but not C37 and C38 alkenes. The positions of the double bonds in the C29 and C31 alkenes were determined by mass spectrometry of their dimethyl disulfide (DMDS) adducts. Among the four C29 alkenes identified, the most abundant isomer was 2,20-nonacosadiene, and the other three compounds were 1,20-nonacosadiene, 3,20-nonacosadiene and 9-nonacosene, respectively. Hitherto, 2,20-nonacosadiene and 3,20-nonacosadiene were unknown to be natural products. The double bond at the n-9 (ω9) position in these C29 alkenes is hypothesized to be derived from precursors of unsaturated fatty acids possessing an n-9 double bond, such as (9Z)-9-octadecenoic acid. Nonacosadienes have the potential for being used as distinct haptophyte biomarkers.

Keywords: Biomarker; Emiliania huxleyi; Gephyrocapsa oceanica; Haptophyte; Long chain alkene; Noelaerhabdaceae; Nonacosadiene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemistry
Alkadienes / isolation & purification*
Gas Chromatography-Mass Spectrometry
Haptophyta / chemistry*
Marine Biology
Molecular Structure
Oleic Acid / chemistry
Oleic Acids
Stereoisomerism

Substances

Alkadienes
Oleic Acids
Oleic Acid
elaidic acid