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Oxylipins from marine invertebrates

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Marine Natural Products — Diversity and Biosynthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 167))

Abstract

Marine invertebrates are a surprisingly rich source of oxidized fatty acid-derived substances known as oxylipins. They occur in many phyla of marine invertebrates, including Porifera, Coelenterata, Crustacea, Mollusca, Echinodermata, and Urochordata. Many of the oxylipins obtained from these life forms are structurally unique and have no direct parallel to oxylipins from other sources. Consequently, the biosynthetic pathways responsible for their formation are also unique. Even those oxylipins of comparable structure to those occurring terrestrially are produced by novel biosynthetic pathways in marine organisms. Hence, biosynthetic studies of marine oxylipins are providing fundamental new insights into the scope and nature of oxylipin chemistry and metabolism. Further, study of the ecological and potentially useful pharmacological properties of these unique substances continues to provide new opportunities in medicine and biology.

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Abbreviations

AA:

eicosa-5Z,8Z,11Z,14Z-tetraenoic acid = arachidonic acid

ATP:

adenosine triphosphate

CD:

circular dichroism

COSY:

correlation spectroscopy

diHETE:

dihydroxyeicosatetraenoic acid

DMP:

4,6-dimethylpyrimidyl

EPA:

eicosa-5Z,8Z,11Z,14Z,17Z-pentaenoic acid

FAB:

fast atom bombardment

FMRF:

Phe-Met-Arg-Phe

FT-IR:

Fourier transform infrared spectroscopy

GC:

gas chromatography

HEPE:

hydroxyeicosapentaenoic acid

HETE:

hydroxyeicosatetraenoic acid

HPETE:

hydroperoxyeicosatetraenoic acid

HPLC:

high performance liquid chromatography

5-HT:

5-hydroxytryptamine

Hz:

Hertz

IC50 :

concentration required for 50 percent inhibition

IR:

infrared spectroscopy

KETE:

ketoeicosatetraenoic acid

LPO:

lipoxygenase

LSC:

liquid scintillation counting

LTB4 :

leukotriene B4

MC:

(—)-menthoxycarbonyl

MHFA:

monohydroxy fatty acids

MS:

mass spectrometry

NDGA:

nordihydroguaiaretic acid

NMDA:

N-methyl-d-aspartate

NMR:

nuclear magnetic resonance spectroscopy

ORD:

optical rotatory dispersion

PC:

preclavulone

PG:

prostaglandin

ppb:

parts per billion

R f :

retention factor

RIA:

radioimmunoassay

T/C:

(treatment/control) × 100

THFA:

trihydroxy fatty acid

TLC:

thin layer chromatography

TMS:

trimethylsilyl

UV:

ultraviolet

W:

watt

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Authors and Affiliations

  1. College of Pharmacy, Oregon State University, 97331, Corvallis, Oregon

    William H. Gerwick, Dale G. Nagle & Philip J. Proteau

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  1. William H. Gerwick
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  2. Dale G. Nagle
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  3. Philip J. Proteau
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Paul J. Scheuer

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© 1993 Springer-Verlag

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Gerwick, W.H., Nagle, D.G., Proteau, P.J. (1993). Oxylipins from marine invertebrates. In: Scheuer, P.J. (eds) Marine Natural Products — Diversity and Biosynthesis. Topics in Current Chemistry, vol 167. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0034372

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  • DOI: https://doi.org/10.1007/BFb0034372

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  • Print ISBN: 978-3-540-56513-0

  • Online ISBN: 978-3-540-47576-7

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