The Sterols of Marine Invertebrates: Composition, Biosynthesis, and Metabolites

Goad, L. John

doi:10.1016/b978-0-12-624002-3.50009-7

Cited by 105 publications

(50 citation statements)

References 378 publications

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“…Desmosterol may also be of some importance in providing cholesterol, since it is an intermediate in cholesterol synthesis. Gastropods can synthesize cholesterol de novo (32), but it is a very slow process, as evidenced by the low cholesterol levels in these pteropods (11.6% cholesterol in C. limacina, Table 2). Cholesterol was present in only six of 14 diatom species studied by Barrett et al (33).…”

Section: Discussionmentioning

confidence: 99%

Lipids and buoyancy in Southern Ocean pteropods

Phleger

Nichols

Virtue

1997

Lipids

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The lipids of Clione limacina, a Southern Ocean pteropod (order Gymnosomata), contain 28% diacylglyceryl ether (DAGE) (as percentage of total lipid) whereas the pteropod Limacina helicina (order Thecosomata) lacks DAGE. The alkyl glyceryl ether diols (1-O-alkyl glycerols, GE) of Clione DAGE are dominated by 16:0 (60%) and 15:0 (21%), in contrast with deep-sea shark liver DAGE, which is dominated by 18:1 GE. The fatty acid profiles of Clione and Limacina are similar (28-32% polyunsaturated, 26-34% monounsaturated) as are the sterols, which include 24-methylenecholesterol, transdehydrocholesterol, cholesterol, and desmosterol. This finding probably reflects the fact that Limacina is the major food source for Clione. Spongiobranchaea australis, another Southern Ocean pteropod (order Gymnosomata), has 0.9-1.7% DAGE, but has less lipid (3.3-4.8 mg/g lipid, wet weight) than Clione (50.8 mg/g lipid, wet weight). We propose a buoyancy role for DAGE in Clione since Limacina has bubbles for flotation which Clione lack; DAGE provides 23% more uplift than triacylglycerol at a concentration of 1.025 g/mL seawater.

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Section: Discussionmentioning

confidence: 99%

Lipids and buoyancy in Southern Ocean pteropods

Phleger

Nichols

Virtue

1997

Lipids

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“…Classes of organisms capable of de novo cholesterol biosynthesis determined by radiolabeled acetate or mevalonate incorporation are shaded [70]. Groups partially shaded have produced conflicting data regarding de novo cholesterol biosynthesis [44, 45, 70-72].…”

Section: Figurementioning

confidence: 99%

Identification, modeling and ligand affinity of early deuterostome CYP51s, and functional characterization of recombinant zebrafish sterol 14α-demethylase

Morrison

Goldstone

Lamb

et al. 2014

Biochimica et Biophysica Acta (BBA) - General Subjects

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Background Sterol 14α-demethylase (cytochrome P450 51, CYP51, P45014DM) is a microsomal enzyme that in eukaryotes catalyzes formation of sterols essential for cell membrane function and as precursors in biosynthesis of steroid hormones. Functional properties of CYP51s are unknown in non-mammalian deuterostomes. Methods PCR-cloning and sequencing and computational analyses (homology modeling and docking) addressed CYP51 in zebrafish Danio rerio, the reef fish sergeant major Abudefduf saxatilis, and the sea urchin Strongylocentrotus purpuratus. Following N-terminal amino acid modification, zebrafish CYP51 was expressed in Escherichia coli, and lanosterol 14α-demethylase activity and azole inhibition of CYP51 activity were characterized using GC/MS. Results Molecular phylogeny positioned S. purpuratus CYP51 at the base of the deuterostome clade. In zebrafish, CYP51 is expressed in all organs examined, most strongly in intestine. The recombinant protein bound lanosterol and catalyzed 14α-demethylase activity, at 3.2 nmol/min/nmol CYP51. The binding of azoles to zebrafish CYP51 gave KS (dissociation constant) values of 0.26 μM for ketoconazole and 0.64 μM for propiconazole. Displacement of carbon monoxide also indicated zebrafish CYP51 has greater affinity for ketoconazole. Docking to homology models showed that lanosterol docks in fish and sea urchin CYP51s with an orientation essentially the same as in mammalian CYP51. Docking of ketoconazole indicates it would inhibit fish and sea urchin CYP51s. Conclusions Biochemical and computational analyses are consistent with lanosterol being a substrate for early deuterostome CYP51s. General Significance The results expand the phylogenetic view of animal CYP51, with evolutionary, environmental and therapeutic implications.

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“…The occurrence of Cholesterol äs the predominant sterol of most red algae is unique to the plant kingdom and undoubtedly phylogenetically important (Goad and Goodwin 1972). A number of other C 27 -sterols are commonly encountered along with some rare and unusual phytosterols sometimes present in high concentrations (Goad 1978). Two C 2 7 sterols frequently detected in red algae are desmosterol and 22-dehydrocholesterol (Goad and Goodwin 1972, Ferezou et al 1974, Meumerefal.…”

Section: Introductionmentioning

confidence: 98%

“…There have consequently been numerous investigation s since these early studies with considerable contributions from Japan, Great Britain, and Canada. The literature on this subject has been extensively reviewed by Austin (1970), Premuzic (1971), Goad and Goodwin (1972), Scheuer (1973), Baker and Murphy (1976), and Goad (1976Goad ( , 1978.…”

Section: Introductionmentioning

confidence: 98%

Sterol Distribution in Red Algae from the Waters of Eastern Long Island

Goldberg¹,

Hubby²,

Cobb³

et al. 1982

Botanica Marina

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Seven species of red algae from the waters of eastern Long Island, New York were analyzed for their sterol content. The species studied were: Agardhiella tenera, Ahnfeltia plicata, Chondrus crispus, Corallina officinalis^Cystoclonium purpureum var. cirrhosum, Gracilaria foliifera, und Palmaria palmata. The major sterols found belong to C 27 compounds. Cholesterol was the predominant sterol in all species with the possible exception of Palmaria palmata. The presence of cholest-7-en-3/3-ol is reported for the first time in the Order Gigartinales. Considerable variations in the total sterol contents among these species were observed, ranging from l mg/kg for Palmaria palmata to 117 mg/kg for Agardhiella tenera. Comparison of the total sterol content of Palmaria palmata with previous analyses (50 to 190 mg/kg) from waters off eastern Canada indicate that significant regional differences in the sterol content of a given species can occur.

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The Sterols of Marine Invertebrates: Composition, Biosynthesis, and Metabolites

Cited by 105 publications

References 378 publications

Lipids and buoyancy in Southern Ocean pteropods

Lipids and buoyancy in Southern Ocean pteropods

Identification, modeling and ligand affinity of early deuterostome CYP51s, and functional characterization of recombinant zebrafish sterol 14α-demethylase

Sterol Distribution in Red Algae from the Waters of Eastern Long Island

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