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1.
Stephanie M. Barrett John K. Volkman Graeme A. Dunstan Jeannie-Marie LeRoi 《Journal of phycology》1995,31(3):360-369
The sterol compositions of 14 species of marine diatoms were determined by gas chromatography and gas chromatography-mass spectrometry. A variety of sterol profiles were found. The sterols 24-methylcholesta-5,22E-dien-3β-ol, cholest-5-en-3β-ol, and 24-methylcholesta-5,24(28)-dien-3β-ol, previously described as the most common sterols found in diatoms, were major sterols in only a few of the species. In light of this and other recent data, it is clear that these three sterols are not typical constituents of many diatom species. Most of the centric species examined had 24-methylcholesta-5,24(28)-dien-3β-ol and 24-methylcholest-5-en-3β-ol as two of their major sterols. The exception was Rhizosolenia setigera, which possessed cholesta-5,24-dien-3β-ol as its single major sterol. In contrast to the centric species, the pennate diatoms examined did not have any particular sterols common to most species. Minor levels ofΔ7-sterols, rarely found in large amounts in diatoms, were found in four species. C29sterols were found in many species; seven contained 24-ethylcholest-5-en-3β-ol and three contained 24-ethylcholesta-5,22E-dien-3β-ol, reinforcing previous suggestions that C29 sterols are not restricted to higher plants and macroalgae. 24-Ethylcholesta-5,22E-dien-3β-ol may prove to be useful for taxonomy of the genus Amphora and the order Thalassiophysales. A major sterol of Fragilaria pinnata was the uncommon algal sterol 23,24-dimethylcholesta-5,22E-dien-3β-ol. Cholesta-5,24-dien-3β-ol was the only sterol found in the culture of Nitzschia closterium. This differed from previous reports of 24-methylcholesta-5,22E-dien-3β-ol as the single major sterol in N. closterium. Two C28 sterols possessing an unusual side chain were found in Thalassi-onema nitzschioides, a C28:2 sterol (16%) and a C28:1 sterol in lower abundance (2.5%), which may be 23-methylcholesta-5,22E-dien-3β-ol and 23-methyl-5α-cholest-22E-en-3β-ol, respectively. The species Cylindrotheca fusiformis, T. nitzschioides, and Skeletonema sp. may be useful as direct sources of cholesterol in mariculture feeds due to their moderate to high content of this sterol. 相似文献
2.
Carmenza Duque Jorge Rojas Sven Zea Alejandro J. Roccatagliata Marta S. Maier Alicia M. Seldes 《Biochemical Systematics and Ecology》1997,25(8):775-778
Sterol compositions of the cold water ophiuroids Ophioplocus januarii and Ophionotus victoriae and of the tropical ophiuroids Ophiocoma echinata and Ophiocoma wendtii are reported. The four sterol mixtures contain Δ5 mono- and di-unsaturated common 3β-hydroxy-sterols. Ophioplocus januarii and O. victoriae contain 24-methylcholesta-5,24(28)-dien-3β-ol and 24ζ-ethylcholesta-5,24(28)-dien-3β-ol in higher abundance than in O. echinata. These sterols were not found in O. wendtii. An interesting finding is the presence of Δ5,24(28)-24-n-propylidenecholesterol in 7.6% in Ophionotus victoriae. 相似文献
3.
Sterols from free sterol and steryl ester fractions from Heterodera zeae and from total lipids of Zea mays roots were analyzed by gas-liquid chromatography (GLC) and by GLC-mass spectrometry. The major free sterols of H. zeae were 24-ethylcholesterol (54.4% of total free sterol), 24-ethylcholesta-5,22-dien-3β-ol (13.3%), 24-methylcholesterol (12.5%), and cholesterol (7.2%). The same four sterols comprised 34.6%, 7.2%, 30.3%, and 18.6%, respectively, of the esterified sterols of H. zeae. Corn root sterols included 46.6% 24-ethylcholesta-5,22-dien-3β-ol, 16.7% methylcholesterol, 16.4% cycloartenol, 12.7% 24-ethylcholesterol, and 0.5% cholesterol. The sterol 24-composition of H. zeae differed greatly from that of the only other cyst nematode previously investigated, Globodera solanacearum. 相似文献
4.
《Comparative biochemistry and physiology. B, Comparative biochemistry》1983,74(1):167-171
- 1.1. Sulphated and etherified sterols were isolated from the far eastern holothurian Stichopus japonicus S. The sterol composition of both fractions was determined using gas-liquid chromatography and mass-spectroscopic methods. The structures of individual sterols were proved on the basis of mass-spectrometry and 1H-NMR-spectroscopy data.
- 2.2. The structures of 29 sterols were established.
- 3.3. Sterols (22E, 24R)-23,24-dimethyl-5α-cholest-22-en-3β-ol, 23,24-dimethyl-cholesta-5,22-dien-3β-ol, 24-methyl-cholesta-5,24(28)-dien-3β-ol, (24Z)-24-ethyl-cholesta-5,24(28)-dien-3β-ol, 24-nor-cholesta-5,22-dien-3β-ol, 24-ethyl-cholesta-5,25-dien-3β-ol were described for holothurians for the first time.
- 4.4. Δ5-sterols were shown to be the main components of the sulphated alcohol fractions (67.61%), while the saturated and Δ7-sterols were there in less quantities (14.72 and 9.52%, respectively).
- 5.5. The etherified sterols were represented, mainly, by saturated and Δ7-sterols (37.82% and 33.95%, respectively). Δ5-sterols were 19%.
- 6.6. The sensitivity of liposomal membranes, containing steroid metabolites of the holothurian St. japonicus (Δ7-, sulphated and glycosilated sterols) to the action of endotoxin-stichoposide A, was studied.
5.
《Harmful algae》2017
Sterols, a group of stable lipid compounds, are often used as biomarkers in marine biogeochemical studies to indicate sources of organic matter. In this study, sterols in 13 species of major bloom-forming algae in China, which belong to Dinophyceae, Bacillariophyceae, Ulvophyceae, and Pelagophyceae, were analyzed with gas chromatography-mass spectrometry (GC–MS) to test their feasibility in representing different types of harmful algal blooms (HABs). It was found that (24Z)-stigmasta-5,24-dien-3β-ol (28-isofucosterol) was a major sterol component in green-tide forming macroalga Ulva prolifera. In bloom-forming dinoflagellates Alexandrium spp., Prorocentrum micans and Scrippsiella trochoidea, (22E)-4α,23-dimethyl-5α-ergost-22-en-3β-ol (dinosterol) was detected in addition to cholest-5-en-3β-ol (cholesterol), (22E)-ergosta-5,22-dien-3β-ol, (22E)-stigmasta-5,22-dien-3β-ol and other minor sterol components. In brown-tide forming pelagophyte Aureococcus anophagefferens, (24E)-24-propylcholesta-5,24-dien-3β-ol ((24E)-24-propylidenecholesterol) and (24Z)-24-propylcholesta-5,24-dien-3β-ol ((24Z)-24-propylidenecholesterol) were detected together with cholesterol, (22E)-stigmasta-5,22-dien-3β-ol, stigmast-5-en-3β-ol and campest-5-en-3β-ol. Among the selected bloom-forming diatoms, Chaetoceros sp. and Pseudo-nitzschia spp. only produced cholesterol, while Cylindrotheca closterium produced solely (22E)-ergosta-5,22-dien-3β-ol. Sterol content in four bloom-forming algal species correlates well with their biomass or abundance. It's proposed that 28-isofucosterol could serve as a promising biomarker for green algae in green-tide studies. Dinosterol and (24Z)-24-propylidenecholesterol can be used as potential biomarkers to represent bloom-forming dinoflagellates and pelagophytes, while (22E)-ergosta-5,22-dien-3β-ol is not a good indicator for diatoms. 相似文献
6.
Nancy W. Withers Robert C. Tuttle George G. Holz David H. Beach L.John Goad Trevor W. Goodwin 《Phytochemistry》1978,17(11):1987-1989
The heterotrophic dinoflagellate Crypthecodinium cohnii contained the 4α-methyl sterols, dinosterol, dehydrodinosterol (4α,23,24-trimethylcholesta-5,22-dien-3β-ol) and the tentatively identified 4α,24-dimethyl-cholestan-3β-ol and 4α,24-dimethylcholest-5-en-3β-ol. The major 4-demethyl sterol was cholesta-5,7-dien-3β-ol which was accompanied by a smaller amount of cholesterol and traces of several other C27,C28 and C29 sterols. In addition, a 3-oxo-steroid fraction was isolated and the major component identified as dinosterone (4α,23,24-trimethylcholest-22-en-3-one). The possible biosynthetic relationships of these compounds are discussed. 相似文献
7.
The sterols of Zea mays shoots were isolated and characterized by TLC, HPLC, GC/MS and 1H NMR techniques. In all, 22 4-demethyl sterols were identified and they included trace amounts of the Δ23-, Δ24- and Δ25-sterols, 24-methylcholesta-5,E-23-dien-3β-ol, 24-methylcholesta-5,Z-23-dien-3β-ol, 24-methylcholesta-5,25-dien-3β-ol, 24-ethylcholesta-5,25-dien-3β-ol and 24-ethylcholesta-5,24-dien-3β-ol. In the 4,4-dimethyl sterol fraction, cycloartenol and 24-methylenecycloartanol were the major sterol components but small amounts of the Δ23-compound, cyclosadol, and the Δ25-compound, cyclolaudenol, were recognized. These various Δ23- and Δ25-sterols may have some importance in alternative biosynthetic routes to the major sterols, particularly the 24β-methylcholest-5-en-3β-ol component of the C28-sterols. Radioactivity from both [2-14C]MVA and [methyl-14C]methionine was incorporated by Z. mays shoots into the sterol mixture. Although 24-methylene and 24-ethylidene sterols were relatively highly labelled, the various Δ23- and Δ25-sterols contained much lower levels of radioactivity, which is possibly indicative of their participation in alternative sterol biosynthetic routes. (24R)-24-Ethylcholest-5-en-3β-ol (sitosterol) had a significantly higher specific activity than the 24-methylcholest-5-en-3β-ol indicating that the former is synthesized at a faster rate. 相似文献
8.
Two rare C30-sterols, (24E)-24-n-propylidenecholest-5-en-3β-ol and 24-n-propylcholest-5-en-3β-ol, and (24S)-24-ethylcholesta-5,22-dien- 3β-ol (stigmasterol) are the major sterols of Nematochrysopsis roscoffensis, a Chrysophyte of the Sarcinochrysidales order. This unique sterol composition is different from the sterol contents of other Chrysophytes and justifies the peculiar position of the Sarcinochrysidales, which are by some characteristics morphologically and biologically related to the Phaeophyceae. The presence of (24S)-24-methylcholesta-5,22-dien-3β-ol (24-epibrassicasterol) as a major sterol in Chrysotila lamellosa is in accordance with the few previous results obtained from other Prymnesiophyceae, although the presence of the other major sterol, (24R)-24-ethylcholesta-5,22-dien-3β-ol (poriferasterol) has never been reported in these algae. 相似文献
9.
Patrick Moreau Marie-Andrée Hartmann Anne-Marie Perret Bénédicte Sturbois-Balcerzak Claude Cassagne 《Plant physiology》1998,117(3):931-937
To investigate the intracellular transport of sterols in etiolated leek (Allium porrum L.) seedlings, in vivo pulse-chase experiments with [1-14C]acetate were performed. Then, endoplasmic reticulum-, Golgi-, and plasma membrane (PM)-enriched fractions were prepared and analyzed for the radioactivity incorporated into free sterols. In leek seedlings sterols are present as a mixture in which (24R)-24-ethylcholest-5-en-3β-ol is by far the major compound (around 60%). The other sterols are represented by cholest-5-en-3β-ol, 24-methyl-cholest-5-en-3β-ol, (24S)-24-ethylcholesta-5,22E-dien-3β-ol, and stigmasta-5,24(241)Z-dien-3β-ol. These compounds are shown to reside mainly in the PM. Our results clearly indicate that free sterols are actively transported from the endoplasmic reticulum to the PM during the first 60 min of chase, with kinetics very similar to that of phosphatidylserine. Such a transport was found to be decreased at low temperature (12°C) and following treatment with monensin and brefeldin A. These data are consistent with a membrane-mediated process for the intracellular transport of sterols to the PM, which likely involves the Golgi apparatus. 相似文献
10.
Norio Awata Masuo Morisaki Yoshinori Fujimoto Nobuo Ikekawa 《Journal of insect physiology》1976,22(3):403-408
Steroidal allenes, stigmasta-5,24(28),28-trien-3β-ol (allene-I) and cholesta-5,23,24-trien-3β-ol (allene-II), were tested for their inhibitory effects on growth, development, and steroid metabolism in the silkworm, Bombyx mori. The allenic analogue (I) of stigmasta-5,24(28)-dien-3β-ol (2) was found to be a specific inhibitor for the conversion of stigmast-5-en-3β-ol (1) to stigmasta-5, 24(28)-dien-3β-ol (2) and/or stigmasta-5,24(28)-dien-3β-ol (2) to 24,28-epoxy-stigmast-5-en-3β-ol (3) This inhibitor held the larvae in the second instar for more than 20 days without developing to the third instar, when administered alone or with the dietary sterols of stigmast-5-en-3β-ol (1) or stigmasta-5,24(28)-dien-3β-ol (2). The second allene (II) with a similar structure to cholesta-5,24-dien-3β-ol (4) was also found to be an inhibitor for insect growth and development, but it appeared not to be acting via inhibition of sterol dealkylation. 相似文献
11.
A method is described for the chemical synthesis of stigmasta-5,24-dien-3β-ol-[26-14C] and (24S)-24-ethylcholesta-5,25-dien-3β-ol-[26-14C] (clerosterol). 28-Isofucosterol-[7-3H2] fed to developing barley seedlings (Hordeum vulgare) was incorporated into sitosterol and stigmasterol confirming the utilisation of a 24-ethylidene sterol intermediate in 24α-ethyl sterol production in this plant. Also, the use of mevalonic acid-[2-14C(4R)-4-3H1] verified the loss of the C-25 hydrogen of 28-isofucosterol during its conversion into sitosterol and stigmasterol in agreement with the previously postulated isomerisation of the 24-ethylidene sterol to a Δ24(25)-sterol prior to reduction. However, feeding stigmasta-5,24-dien-3β-ol [26-14C] to barley seedlings gave very low incorporation into sitosterol. Attempts to trap radioactivity from mevalonic-[2-14C(4R)-4-3H1] in stigmasta-5,24-dien-3β-ol when this unlabelled sterol was administered to barley seedlings gave only a very small incorporation although both 28-isofucosterol and sitosterol were labelled. 相似文献
12.
《Comparative biochemistry and physiology. B, Comparative biochemistry》1983,74(3):569-573
- 1.1. The bivalve molluscs Cerastoderma edula, Chlamys opercularis, Ensis soliqua, Modiolus modiolus, Mya arenaria, Mytilus edulis and Pecten maximus contained mixtures of C26-, C27-, C28- and C29-sterols. Cholesterol, 24-methylcholesta-5,22-dien-3β-ol and 24-methylene-cholesterol were the major sterols.
- 2.2. The sterols of Cerastoderma edula, Mya arenaria and Mytilus edulis contained 6–16% of cholesta-5,24-dien-3β-ol.
- 3.3. All the molluscs contained Δ5,7-sterols in amounts ranging from 2 to 21% of the total sterols.
- 4.4. Cholesta-5,7-dien-3β-ol and 24-methylcholesta-5,7,22-trien-3β-ol were identified in Mytilus edulis. 25-Norcholesta-5,7,22-trien-3β-ol was detected in Modiolus modiolus.
13.
The fatty acid, sterol and chlorophyll pigment compositions of the marine dinoflagellates Gymnodinium wilczeki and Prorocentrum cordatum are reported. The fatty acids of both algae show a typical dinoflagellate distribution pattern with a predominance of C18, C20 and C22 unsaturated components. The acid 18:5ω3 is present at high concentration in these two dinoflagellates. G. wilczeki contains a high proportion (93.4%) of 4-methyl-5α-stanols including 4,23,24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol), dinostanol and 4,23,24-trimethyl-5α-cholest-7-en-3β-ol reported for the first time in dinoflagellates. The role of this sterol in the biosynthesis of 5α-stanols in dinoflagellates is discussed. P. cordatum contains high concentrations of a number of δ 24(28)-sterols with dinosterol, 24-methylcholesta-5,24(28)-dien-3β-ol, 23,24-dimethylcholesta-5,22E-dien-3β-ol, 4,24-dimethyl-5α-cholest-24(28)-en-3β-ol and a sterol identified as either 4,23,24-trimethyl- or 4-methyl-24-ethyl-5α-cholest-24(28)-en-3β-ol present as the five major components. The role of marine dinoflagellates in the input of both 4-methyl- and 4-desmethyl-5α-stanols to marine sediments is discussed. 相似文献
14.
Sterols extracted from Xanthoria parietina with organic solvents and released by saponification of the residual lichen tissue were analysed by GC-MS. The main components of the solvent-extractable sterols were two C28 trienes and those of the more tightly bound sterols were ergost-5-en-3β-ol and two C29 compounds. The structures of the C28 compounds were shown to be ergosta-5,7,22-trien-3β-ol, Ia (ergosterol) and the previously unreported ergosta-5,8,22-trien-3β-ol, IIa, for which the name lichesterol is proposed. The main C29 sterol was identified as (24R)-24-ethylcholesta-5,22-dien-3β-ol (poriferasterol). 相似文献
15.
《Phytochemistry》1987,26(3):731-733
The sterols from eight species in seven genera of the Cactaceae are 24-alkyl-Δ5-sterols. In all eight species, Echinopsis tubiflora, Pereskia aculeata, Hylocereus undatus, Notocactus scopa, Epiphyllum sp., Schlumbergera bridgesii, Opuntia comonduensis and O. humifusa, the dominant sterol is sitosterol (24α-ethylcholest-5-en-3β-ol) at 66–87% of the total sterol composition with the 24ξ-methylcholest-5-en-3β-ol present at 8–33%. Stigmasterol (24α-ethylcholesta-5,22E-dien-3β-ol) is present at 2–8% of the total sterol in P. aculeata, H. undatus, N. scopa and Epiphyllum sp. whereas cholesterol (cholest-5-en-3β-ol) is present in six species at levels of <0.1–5.0%. Avenasterol (24-ethylcholesta-7,24(28)Z-dien-3/gb-ol) and sitostanol (24α-ethyl-5α-cholestan-3β-ol) are each present in two species. 相似文献
16.
When Chlorella sorokiniana was cultured in the presence of 1 mg/1 triparanol succinate, there was a 42% reduction in total sterol concentration. Algal biomass was reduced by approximately the same amount. In addition to the cycloartenol, cyclolaudenol, 24-methyl-pollinastanol, ergosta-5, 7-dien-3β-ol, and ergosterol that occur in control culture, pollinastanol, 14α-methyl-5α-ergost-8-en-3β-ol, 5α-ergosta-8, 14, 22-trien-3β-ol, 5α-ergosta-8(14), 22-dien-3β-ol, 5α-ergosta-8(9), 22-dien-3β-ol, 5α-ergosta-8, 14-dien-3β-ol, 5α-ergost-8(9)-3n-3β-ol, 5α-ergost-8(14)-en-3β-ol, 5α-ergosta-7, 22-dien-3β-ol, and 5α-ergost-7-en-3β-ol were isolated and identified from triparanol succinate-treated cells. A biosynthetic pathway for sterol biosynthesis in this organism is postulated based on all the sterols that were isolated and identified in triparanol-treated cultures of C. sorokiniana. Cyclolaudenol appears to be the product of the first alkylation at C-24 in this organism rather than the more common 24-methylene cycloartanol. Since 24-methylene sterols are needed for the second alkylation reaction, this would explain the absence of C-29 sterols in C. sorokiniana. Four of the sterols identified in C. sorokiniana are reported for the first time in a living organism. They are: 24-methyl pollinastanol, 5α-ergosta-8, 14, 22-trien-3β-ol, 5α-ergosta-8(14), 22-dien-3β-ol and 5α-ergost-8(14)-en-3β-ol. 相似文献
17.
The free sterol mixture of the sponge Psammaplysilla purpurea was shown to contain aplysterol as the major constituent. In addition to other sterols such as 5,7-cholestadien-3β-ol, cholesterol, 5α-cholestan-3β-ol, 24ε-methylcholesta-5,22-dien-3β-ol, 24ε-methylcholesterol, 24ε-ethylcholesta-5,22-dien-3β-ol and 24,28-dehydroaplysterol, a new minor sterol was isolated and shown by spectral analysis as well as partial synthesis to be 3β-hydroxy-26,27-bisnorcholest-5-en-24-one. The sterol mixture contains no other short side chain or 24-keto sterols except for small amounts of 3β-hydroxypregn-5-en-20-one and 3β-hydroxy-5α-pregnan-20-one. 相似文献
18.
A mixture of C27, C28 and C29 sterols was isolated from the lichen Pseudevernia furfuracea and characterized by means of GLC and MS. Mono-, di- and tri-unsaturated sterols were identified as well as a small amount of fully saturated sterols (stanols). Only a part of the total sterols present in the lichen tissue was easily extractable with organic solvents. Another portion was only obtained after saponification of the lichen residue remaining after extraction with organic solvents. The composition of these two fractions difrered considerably, the former contained predominantly 5a,8a-epidioxy-5a-ergosta-6,22-dien-3β-ol (ergosterol peroxide) and 24-ethylcholesta-5,22-dien-3β-ol while in the latter 24-ethylcholesta-5,22-dien- 3β-ol and C28 triene sterols were the main components. 相似文献
19.
In 3- and 14-day-old seedlings and in the leaves of Calendula officinalis the following sterols were identified: cholestanol, campestanol, stigmastanol, cholest-7-en-3-β-ol, 24-methylcholest-7-en-3β-ol, stigmast-7-en-3β-ol, cholesterol, campesterol, sitosterol, 24-methylcholesta-5,22-dien-3β-ol, 24-methylenecholesterol, stigmasterol and clerosterol. Sitosterol was predominant in young and stigmasterol in old tissues. Young tissues contained relatively more campesterol but in old tissues a C28Δ5,22 diene was present suggesting transformation of campesterol to its Δ5,22 analog, similar to that of sitosterol to stigmasterol. All the identified sterols were present as free compounds and also in the steryl esters, glucosides, acylated glucosides and water-soluble complexes. The variations in the amounts of these fractions in the embryo axes and cotyledons of 3- and 14-day-old seedlings and the distribution of individual sterols among the fractions are discussed. 相似文献
20.
Jeffrey D. Leblond Lindsey C. Elkins Kyra Sabir 《The Journal of eukaryotic microbiology》2023,70(1):e12942
The dinoflagellates Amphidinium carterae and Amphidinium corpulentum have been previously characterized as having Δ8(14)-nuclear unsaturated 4α-methyl-5α-cholest-8(14)-en-3β-ol (C28:1) and 4α-methyl-5α-ergosta-8(14),24(28)-dien-3β-ol (amphisterol; C29:2) as predominant sterols, where they comprise approximately 80% of the total sterol composition. These two sterols have hence been considered as possible major sterol biomarkers for the genus. Here, we have examined the sterols of four recently identified species of Amphidinium (Amphidinium fijiense, Amphidinium magnum, Amphidinium theodori, and Amphidinium tomasii) that are closely related to Amphidinium operculatum as part of what is termed the Operculatum Clade to show that each species has its sterol composition dominated by the common dinoflagellate sterol cholesterol (cholest-5-en-3β-ol; C27:1), which is found in many other dinoflagellate genera, rather than Δ8(14) sterols. While the Δ8(14) sterols 4α-methyl-5α-cholest-8(14)-en-3β-ol and 4α,23,24-trimethyl-5α-cholest-8(14),22E-dien-3β-ol (C30:2) were present as minor sterols along with another common dinoflagellate sterol, 4α,23,24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol; C30:1), in some of these four species, amphisterol was not conclusively observed. From a chemotaxonomic perspective, while this does reinforce the genus Amphidinium's ability to produce Δ8(14) sterols, albeit here as minor sterols, these results demonstrate that caution should be used when considering Δ8(14) sterols, especially amphisterol, as Amphidinium-specific biomarkers within these species where cholesterol is the predominant sterol. 相似文献