Marine sterols from some gorgonians

The sterol composition from three animals of the cnidariań class Anthozoa is reported. Cholesterol was the predominant sterol in three species from the family Gorgoniidae. The cyclopropane-containing sterol, gorgosterol, when present, was the second most plentiful component.     

Marine sterols. VI(1). Sterols of the scallop, Patinopecten yessoensis.

The sterols of the scallop, Patinopecten yessoensis Jay, was found to contain over 20 components. The major components were delta5-sterols, and lesser amount of ring-saturated sterols were also present. Biogenetically unusual C26 sterols (24-norcholesta-5,22-dien-3beta-ol and 24-norcholest-22-en-3beta-ol) and 24(28)-cis-24-propylidenecholest-5-en-3beta-ol (29-methylisofucosterol), 22-trans-27-nor-(24S)-24-methylcholesta-5,22-dien-3beta-ol (occelasterol), and a new sterol, 22-trans-27-nor-(24S)-24-methylcholest-22-en-3beta-ol (patinosterol), were isolated and their structures were confirmed. Occurrence of 22-trans-(24S)-24-methylcholesta-5,22-dien-3beta-ol (24-epibrassicasterol) was confirmed. 22-cis-Cholesta-5,22-dien-3beta-ol was not found.     

Marine sterols. V. sterols of some tunicata. The occurrence of saturated ring sterols in these filter-feeding organisms

The sterols present in one oceanic and two coastal tunicates have been determined by combined gas chromatography-mass spectrometry techniques.Very complex sterol profiles were found in a Pyrosoma sp. and Ascidia mentula O. F. Müller, with 25 and 27 sterols, respectively, in which a high proportion of the sterols were identified as saturated ring compounds. The analyses established the presence of related pairs of 5α-stanols and Δ5-sterols with identical sidechains, whereas Δ7-sterols were almost absent in these extracts. A number of the 5α-stanols found are very uncommon in the marine environment and the presence of new C31 and C32 sterols with long sidechains indicated in the Ascidia mentula extracts is notable.Extracts of the coastal species, Ciona intestinalis L., were much simpler and contained only 13 sterols, some of which were saturated ring compounds.     

Sterols from some sponges

The sterol composition of four sponges was determined by a combination of gas chromatography and mass spectrometry. Cliona viridis and Chondrosia reniformis contained mainly C₂₇-C₂₉Δ⁵ mono- and di-unsaturated sterols. Halichondria bowerbanki and Hymeniacidon sanguinea contained stanols and Δ⁵-sterols. Cholestanol was the major component of the sterol mixtures.     

On the sterols of some ascidians.

The lipid content of sea squirts is low, namely less than a half percent of the fresh weight. Lipids consist of about seventy percent of saponifiable lipids and of about twenty percent of non-saponifiable lipids. Both types of these lipids, including sterols, can be synthesized from acetate by these animals. Small amounts of C30 sterols were observed only in Microcosmus sulcatus and Halocynthia papillosa, the species with a low content of C27 sterols and a high content of C28 sterols. In addition these species contained considerable higher amounts of sterols with a double bond at the C22 position than Ciona intestinalis and Styela plicata did.     

Sterols of some chilean algae

The distribution of sterols in 14 Chilean Rhodophyceae and in Lessonia sp. (Phaeophyceae) has been examined. Cholesterol is present in all the red algae examined. Golidium filicinum contains, in addition desmosterol and 24-methylene-cholesterol. Cholest-7-en-3-β-ol was found in Cryptonemia angustate and Neoagardhiella gaudichaudii. Fucosterol and 24-methylenecholesterol were found in Lessonia sp.     

Sterols of some red algae

The sterol composition of 17 red algae has been determined. Only C-27 sterols have been found in substantial amounts; details of the structural elucidation of liagosterol (cholesta-5,23-diene-3β,25-diol) are given. The possible taxonomic significance of the sterol distribution is briefly discussed.     

Marine sterols X. Minor constituents of the sterols of the soft coral Sarcophyton glaucum

The sterol mixture of the southern Japan soft coral $\text{Sarcophyton glaucum}$ was found to contain a variety of minor components overlooked in a previous study. Five 4α-methylsterols ($\text{1}$ to $\text{5}$) and three 4-demethyl-sterols ($\text{6}$ to $\text{8}$) were isolated and their structures were confirmed.     

Free sterols from the holothurians Synapta maculata, Cladolabes bifurcatus and Cucumaria sp

Free sterol fractions from the holothurians (sea cucumbers) Synapta maculata, Cladolabes bifurcatus and Cucumaria sp. have been isolated and studied by HPLC, GLC, GLC-MS and NMR methods. Forty seven sterols were identified, including several rare ones. In contrast with previously studied holothurians, the presence of a minor amount of Delta7 sterols was indicated in the sterols of S. maculata. This animal contains predominantly Delta(9(11))sterols as well as an abnormally high concentration of Delta5 sterols. In C. bifurcatus and Cucumaria sp., 14alpha-methyl and 4alpha,14alpha-dimethyl-Delta(9(11))sterols were found to be the main sterol constituents. Peculiarities of sterol distribution and the relationship between sterol compositions and taxonomic positions, ecology and toxicity of the corresponding sea cucumbers were discussed.     

Palmitoyl diol S- and O-phosphoroamidates of some sterols.

The hexamethylphosphorus triamide activated by the addition of iodine at the optimum molar ratio 1.05:0.05 was used as a phosphorylating reagent to synthesize 1-palmitoyloxyethyl-2-O-, 1-palmitoyloxypropyl-3-O- and 1-palmitoyloxybutyl-4-O-(N,N-dimethylamido)thiophosphate and -phosphate derivatives of beta-sitosterol, cholesterol and stigmasterol in a one-pot procedure with overall yields of 80-87%. 1-Palmitoyloxypropyl-3-O-(cholesteryl-3-O)-(N,N-dimethylamido++ +) phosphite was used as a model synthon for the preparation of transamidated morpholido-thiophosphate and -phosphate analogues with final yields of 82-86%.     

Sterols of scallop. Part II. Structure of unknown sterols by combination gas-liquid chromatography and mass spectrometry.

Four sterols, isolated from the scallop Pacopecten magellanicus have been identified as 24-nor-5alpha-cholest-22-en-3beta-ol; 24-norcholest-5-en-3beta-ol; 5alpha-cholest-22-en-3beta-ol; and (E) -24-propylidenecholest-5-en-3beta-ol. These bring to seventeen the total number of sterols identified in this marine mollusc. A fifth newly detected sterol, closely similar in its mass spectrometric properties is 22-cis and trans-cholesta-5, 22-dien-3beta-ol, was clearly distinguished from these by its shorter retention time by GLC.     

Sterols from some black sea ulvaceae

The free and esterified sterol composition of Ulva rigida and Enteromorpha linza (Ulvaceae) from the Black Sea was investigated. The main sterol component of Ulva rigida was identified as fucosterol. The influence of the season and water pollution on the sterol composition was investigated. The origin of the C₂₆,- and C₂₅-sterols and of saringasterol in these seaweeds is discussed.     

Sterols of the Toxic Marine Dinoflagellate,Pyrodinium bahamense

Pyrodinium bahamense is a dinoflagellate of concern in subtropical and tropical coastal environments. To date, there is only a single published study on its fatty acids, but no published data on its sterol composition. Sterols, which are membrane‐reinforcing lipids in eukaryotes, display a great diversity of structures in dinoflagellates, with some serving as chemotaxonomic markers. We have examined the sterol compositions of two isolates of P. bahamense from Indian River Lagoon and Tampa Bay, Florida, and have found both to produce three sterols: cholesterol, dinosterol, and 4α‐methylgorgostanol. All three sterols are found in closely related, armored taxa.     

Marine sterols. VII. Synthesis of patinosterol,a minor constituent of sterols of the scallop, Patinopecten yessoensis

The structure of patinosterol, a minor sterol from the scallop, Patinopecten yessoensis, was established as 22-trans-27-nor- (24S)-24-methyl-5α-cholest-22-en-3β-ol by synthesis through Wittig reaction.