Sterols with unusual nuclear unsaturation from three cultured marine dinoflagellates
TL;DR: Several new 4α-methyl sterols with unusual unsaturation in the Δ 8(14) or Δ 14 -positions, such as 4α,24 S -dimethyl-5α-cholest-8 (14)-en-3β-ol, 4αmethyl-24ξ-ethyl-methyl-5 α-choline-8(14)-EN-3 β-ol and 14-dehydrodinosterol, have been isolated from extracts of the cultured marine dinoflagellates Amphidinium carterae
About: This article is published in Phytochemistry.The article was published on 1981-01-01. It has received 88 citations till now. The article focuses on the topics: Amphidinium carterae & Dinophyceae.
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TL;DR: It is indicated that inferences drawn from sterol distributions regarding sources of organic matter must be made with caution and should be supported using other lipid data, and that in ancient sediments and crude oils a high proportion of C 29 steranes need not indicate that most of the organic matter was derived from vascular plants.
1,713 citations
TL;DR: The relationship between the lipid composition of organisms in the water column of an eutrophic lake and the lipid compositions of underlying sediments, previously examined for n-alkanols and steroids, is now reported for hydrocarbons, ketones and carboxylic acids.
763 citations
TL;DR: This review describes the variety of sterol structures found in microalgae, yeasts, fungi, protozoans and microheterotrophs, and possible application areas for sterols derived from mass culture of micro algae and other microorganisms are highlighted.
Abstract: Sterols are vital components of all eukaryotic cells. This review describes the variety of sterol structures found in microalgae, yeasts, fungi, protozoans and microheterotrophs. Reports of the occurrence of sterols in prokaryotic cells are critically assessed. Methylotrophic bacteria contain unusual 4-methylsterols, but reports of 4-desmethyl sterols in cyanobacteria and other bacteria are limited and many of these seem dubious. Possible application areas for sterols derived from mass culture of microalgae and other microorganisms are highlighted.
743 citations
Cites background from "Sterols with unusual nuclear unsatu..."
...The most abundant sterol is usually dinosterol (4a,23,24-trimethyl-5a-cholest-22E-en-3b-ol) (Withers 1987; Mansour et al. 1999 and references therein), although it is not found in all species (e.g. Kokke et al. 1981)....
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TL;DR: In this article, the use of a number of commonly utilized organic geochemical and isotopic proxies and their potential for environmental reconstruction in Quaternary lacustrine deposits is discussed.
348 citations
Cites background from "Sterols with unusual nuclear unsatu..."
...However, it should be noted that dinosterol it is not found in all dinoflagellate species (Kokke et al., 1981) and in...
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TL;DR: In this article, the authors studied the lipid components of the dinoflagellate Peridinlum lomnickii Woloszynska collected from the waters of Priest Pot, a eutrophic lake in the English Lake District.
Abstract: Biological marker compounds provide useful tools for evaluating the depositional environments of Recent and ancient sediments and petroleums1, largely through established relationships between the organic matter of sediments and source organisms1,2. Such relationships are best tested and explored by investigating the lipid components of natural populations of autochthonous biota that can be clearly recognized as contributors to underlying bottom sediments. In this context we have studied the lipids of the freshwater dinoflagellate Peridinlum lomnickii Woloszynska (order Peridiniales, class Dinophyceae) collected from the waters of Priest Pot3, a eutrophic lake in the English Lake District. Its distributions of both 4α-methylsterols and 4α-methylstanones closely resemble those of the underlying bottom sediments, demonstrating that dinoflagellates are important contributors of these sedimentary compounds. The 4-methylsteroidal hydrocarbons found in ancient sediments and petroleums4–6 are presumably diagenetic products of such 4α-methylsteroids and therefore reflect dino flagellate inputs to the original depositional environments. Furthermore, the prominence of 5α(H)-cholestan-3β-ol in P. lomnickii suggests that dinoflagellates may be the long sought, direct biological source of sedimentary 5α(H)-stanols.
276 citations
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TL;DR: In this paper, the chemical shifts of the 18-and 19-hydrogen atoms of 265 steroids of known structure have been recorded for 0-1M solutions in deuterochloroform and the positions of the signals of the 17-and 18-hydrogens atoms have been measured.
Abstract: The proton NMR spectra of 265 steroids of known structure have been recorded for 0,1M solutions in deuterochloroform and the positions of the signals of the 18-and 19-hydrogen atoms have been measured. The additional chemical shifts due to various substituents at many different positions of the steroid skeleton are compiled in a table. With its help most chemical shifts of the 18- and 19-hydrogen atoms of these and unknown steroids may be computed with an accuracy of ± 0,015 ppm. An example show how to calculate the chemical shifts. The physical basis of teh influences due to substituents and double bond, as well as the reasons for the generally small deviations from the calculated chemical shifts, are reviewed and illustrated. The additional chemical shifts due to identical funcitonal groups in equivalent positions, i. e. in approximately the same steric relation to one of the tertiary methyl groups, are collected in a table. Possible reason for teh variation of these additional chemical shifts within sets of identical functional functional groups in equivalent positions are discussed. The table furnishes interesting insights into the conformation of certain steroids and shows the average values and deviations one has to reckon with if the chemical shifts on methyl groups in non-steroidal compounds due to functional groups in corresponding positions to those in steroids are to be computed.
466 citations
TL;DR: The 4,4-dimethyl and 4alpha-methyl sterols of the bacterium Methylococcus capsulatus were identified as 4, 4-dim methyl- and 4 alpha-methyl-5alpha-cholest-8(14)-en-3beta-ol and 4,2-Dimethyl- and 5alpha- methyl-5 alpha- cholesta-8 (14),24-dien-3 beta-ol.
Abstract: The 4,4-dimethyl and 4alpha-methyl sterols of the bacterium Methylococcus capsulatus were identified as 4,4-dimethyl- and 4alpha-methyl-5alpha-cholest-8(14)-en-3beta-ol and 4,4-dimethyl- and 4alpha-methyl-5alpha-cholesta-8(14),24-dien-3beta-ol. Sterol biosynthesis is blocked at the level of 4alpha-methyl delta8(14)-sterols.
160 citations
TL;DR: Neither silicate nor its competitive inhibitor germanate affects generation time or cell yield indicating silicon is not required, and of a variety of buffers tested, Tris is the best.
Abstract: SUMMARY
Two media have been devised: an enriched seawater medium for culture of dinoflagellates and a defined medium for rapid growth of the dinoflagellate Cachonina niei. A wide range in salinity (10.23–42.38 g/liter NaCl) is tolerated by C. niei. Below 0.6 g/liter MgSO4, 0.19 g/liter KCl, and 0.22 g/liter CaCl2, the generation time greatly increases. Increase in MgSO4 to 7.22 g/liter, KCl to 1.12 g/liter or CaCl2 to 2.22 g/liter has little effect on generation time. The temperature optimum is 19–23 C. Saturating light intensity for growth is 1000 ft-c and for photosynthesis (determined manometrically) is slightly less than 2000 ft-c. Cachonina niei requires B12 and thiamin. Neither silicate nor its competitive inhibitor germanate affects generation time or cell yield indicating silicon is not required. Of a variety of buffers tested, Tris is the best. Optimal growth occurs at pHs of 7.5–8.3. Glycerol is inhibitory and does not support dark growth.
127 citations
120 citations