Identification of 24-n-propylidenecholesterol in a member of the Foraminifera

Jonathan Grabenstatter; Sabine Méhay; Anna McIntyre-Wressnig; José Luis Giner; Virginia P. Edgcomb; David J. Beaudoin; Joan M. Bernhard; Roger E. Summons

doi:10.1016/j.orggeochem.2013.08.010

Identification of 24-n-propylidenecholesterol in a member of the Foraminifera

Jonathan Grabenstatter
, Sabine Méhay
, Anna McIntyre-Wressnig
, José Luis Giner
, Virginia P. Edgcomb
, David J. Beaudoin
, Joan M. Bernhard
, Roger E. Summons

Chemistry

College of Environmental Science & Forestry

Massachusetts Institute of Technology
Reservoir Laboratory
Woods Hole Oceanographic Institution

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

26 Scopus citations

Abstract

We report a study of the sterols produced by the thecate allogromid foraminiferan, Allogromia laticollaris, grown in culture. Gas chromatographic retention time, together with mass spectrometric fragmentation patterns of trimethysilyl and acetate derivatives enabled us to assign a suite of C₂₇-C₃₀ sterols. Two C₃₀ sterols were identified as (24E)-n-propylidenecholesterol and its 24Z isomer by direct comparison with an authentic standard. The C₃₀ sterols were not detected in the two algae, Isochrysis galbana and Dunaliella tertiolecta, used as a food source for the A. laticollaris, consistent with previous analysis of these organisms. The assignment of (24E)-n-propylidenecholesterol was confirmed using 600MHz ¹H nuclear magnetic resonance (NMR) spectroscopy. The result has relevance as to how we might interpret fossil sterane distributions.

Original language	English
Pages (from-to)	145-151
Number of pages	7
Journal	Organic Geochemistry
Volume	63
DOIs	https://doi.org/10.1016/j.orggeochem.2013.08.010
State	Published - Oct 2013

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10.1016/j.orggeochem.2013.08.010

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title = "Identification of 24-n-propylidenecholesterol in a member of the Foraminifera",

abstract = "We report a study of the sterols produced by the thecate allogromid foraminiferan, Allogromia laticollaris, grown in culture. Gas chromatographic retention time, together with mass spectrometric fragmentation patterns of trimethysilyl and acetate derivatives enabled us to assign a suite of C27-C30 sterols. Two C30 sterols were identified as (24E)-n-propylidenecholesterol and its 24Z isomer by direct comparison with an authentic standard. The C30 sterols were not detected in the two algae, Isochrysis galbana and Dunaliella tertiolecta, used as a food source for the A. laticollaris, consistent with previous analysis of these organisms. The assignment of (24E)-n-propylidenecholesterol was confirmed using 600MHz 1H nuclear magnetic resonance (NMR) spectroscopy. The result has relevance as to how we might interpret fossil sterane distributions.",

author = "Jonathan Grabenstatter and Sabine M{\'e}hay and Anna McIntyre-Wressnig and Giner, \{Jos{\'e} Luis\} and Edgcomb, \{Virginia P.\} and Beaudoin, \{David J.\} and Bernhard, \{Joan M.\} and Summons, \{Roger E.\}",

year = "2013",

month = oct,

doi = "10.1016/j.orggeochem.2013.08.010",

language = "English",

volume = "63",

pages = "145--151",

journal = "Organic Geochemistry",

issn = "0146-6380",

publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Identification of 24-n-propylidenecholesterol in a member of the Foraminifera

AU - Grabenstatter, Jonathan

AU - Méhay, Sabine

AU - McIntyre-Wressnig, Anna

AU - Giner, José Luis

AU - Edgcomb, Virginia P.

AU - Beaudoin, David J.

AU - Bernhard, Joan M.

AU - Summons, Roger E.

PY - 2013/10

Y1 - 2013/10

N2 - We report a study of the sterols produced by the thecate allogromid foraminiferan, Allogromia laticollaris, grown in culture. Gas chromatographic retention time, together with mass spectrometric fragmentation patterns of trimethysilyl and acetate derivatives enabled us to assign a suite of C27-C30 sterols. Two C30 sterols were identified as (24E)-n-propylidenecholesterol and its 24Z isomer by direct comparison with an authentic standard. The C30 sterols were not detected in the two algae, Isochrysis galbana and Dunaliella tertiolecta, used as a food source for the A. laticollaris, consistent with previous analysis of these organisms. The assignment of (24E)-n-propylidenecholesterol was confirmed using 600MHz 1H nuclear magnetic resonance (NMR) spectroscopy. The result has relevance as to how we might interpret fossil sterane distributions.

AB - We report a study of the sterols produced by the thecate allogromid foraminiferan, Allogromia laticollaris, grown in culture. Gas chromatographic retention time, together with mass spectrometric fragmentation patterns of trimethysilyl and acetate derivatives enabled us to assign a suite of C27-C30 sterols. Two C30 sterols were identified as (24E)-n-propylidenecholesterol and its 24Z isomer by direct comparison with an authentic standard. The C30 sterols were not detected in the two algae, Isochrysis galbana and Dunaliella tertiolecta, used as a food source for the A. laticollaris, consistent with previous analysis of these organisms. The assignment of (24E)-n-propylidenecholesterol was confirmed using 600MHz 1H nuclear magnetic resonance (NMR) spectroscopy. The result has relevance as to how we might interpret fossil sterane distributions.

UR - https://www.scopus.com/pages/publications/84884170150

U2 - 10.1016/j.orggeochem.2013.08.010

DO - 10.1016/j.orggeochem.2013.08.010

M3 - Article

SN - 0146-6380

VL - 63

SP - 145

EP - 151

JO - Organic Geochemistry

JF - Organic Geochemistry

ER -

Identification of 24-n-propylidenecholesterol in a member of the Foraminifera

Abstract

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