Occurrence of 23, 24-Dimethylcholesta-5, 22-dien-3β-ol in a Soft Coral, Sarcophyta elegans

昭夫, 金沢; 新一, 手島; 哲夫, 安藤; 茂夫, 富田

doi:10.2331/suisan.40.729

Cited by 32 publications

(8 citation statements)

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“…The occurrence of 23,24-dimethylcholesta-5,22E-dien-3fl-ol is not widespread among algal groups, but it has been found in a few members of the Dinophyceae (Goad and Withers 1982, Nichols et al 1984, Robinson et al 1984 and Prymnesiophyceae (Volkman et al 1981, Marlowe et al 1984 and in a unicellular marine alga, FCRG 51, of uncertain taxonomy (Nichols et al 1983). It has also been found in a soft coral, Sarcophyta elegans (Kanazawa et al 1974), and a diatomaceous ooze (Wardroper and Maxwell 1978).…”

Section: Resultsmentioning

confidence: 93%

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹

Barrett

Volkman

Dunstan

et al. 1995

Journal of Phycology

181

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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.

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Section: Resultsmentioning

confidence: 93%

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹

Barrett

Volkman

Dunstan

et al. 1995

Journal of Phycology

181

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“…This sterol has been identified in a soft coral (Kanazawa et al 1974), a mollusc (Ando et al 1979) and in several marine sediments (Wardroper et al 1978;Lee, Gagosian & Farrington, 1980). Small amounts are present in the marine diatom Biddulphia sinensis but this represents the only other report of its occurrence in algae.…”

Section: Sterolsmentioning

confidence: 95%

Sterol and fatty acid composition of four marine haptophycean algae

et al. 1981

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The lipids of four marine coccolithophorids (class Haptophyceae), Emiliania huxleyi, Hymenomonas carterae, Isochrysis galbana and Crystallolithus hyalinus, were examined by capillary gas chromatography-mass spectrometry. Fatty acids ranged from Ci 4 to C 2 2 and were predominantly of even chain length. The major acids were polyunsaturated C 18 acids, 22:6 and either 14:0 or 16:0. C M fatty acids were of low abundance. Significant amounts of octadecapentaenoic acid (18:5), previously thought to be unique to dinoflagellates, were identified in three of the algae. A small amount of a di-unsaturated C 36 w-alkenoic acid was identified in E. huxleyi, which is the first report of such a long-chain fatty acid in any alga. Traces of wax esters, which are reportedly uncommon inalgae, were found in three of the species. The sterol distributions were very simple, with two or three compounds accounting for > 99 % of the total sterols. In each case, the major component was 24-methylcholesta-5,22E-dien-3/?-ol. H. carterae and C. hyalinus also contained 24-ethylcholesta-5,22E-dien-3/?-ol and significant amounts of cholest-5-en-3/?-ol were found in E. huxleyi and /. galbana. An unusual sterol, 23,24-dimethylcholesta-5,22 E-dien-3/S-ol, was identified in H. carterae. These sterols were mostly non-esterified although small amounts of sterol esters were identified in E. huxleyi. The lipid composition of E. huxleyi is distinctive in that it contains, in addition to the C 36 fatty acid, novel C 37 -C 39 unsaturated ketones and C 31 -C 3S alkenes. Of the other coccolithophorids only /. galbana contained small quantities of one of the C 3l alkenes.

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“…For instance 23,24-dimethylcholesta-5,22-dien-3ß-ol (38) has recently been obtained by Japanese workers from Sarcophyton elegans. 34 Di-and polyhydroxysterols are quite frequently encountered in soft corals, 25-hydroxy-24~-methyl cholesterol (39) Two triols, 24E-methylc~olestane-3ß,5a,6ß-triol (41) and 24-methylenecholestane-3ß,5a,6ß-triol (42), each accompanied by its 6-monoacetate, were isolated from Sinularia dissecta, collected at Leti Island. Their structures have been established mainly by chemical correlation.37 These compounds are closely related to 24E-methylcholestane-3ß,5a,6ß,25-tetrol25-monoacetate (43), previously obtained from Sarcophyton elegans (collected in the Seychelles Islands) and whose structure was demonstrated by chemical and spectral arguments.…”

Section: Sterolsmentioning

confidence: 99%

Some Recent Developments in the Chemistry of Alcyonaceans

Tursch

1976

Pure and Applied Chemistry

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Abstract-Sesquiterpenes, diterpenes and sterols found in Alcyonaceans are briefty reviewed. Tbeir biogenetical origin, their distribution and their biological significance are discussed.Coral reefs are scattered in tropical shallow waters and their bulky, tleshy colonies yield !arge proportians of covering about 190,000,000 km 2 • It has been estimated that extractable organic matter. Indeed, alcyonaceans seem to the area of the reefs themselves .is comparable to that of be the largest single contributors to the biomass of many all cultivated land on earth. 1 .2 The. primary productivity of Indo-Pacific reefs, a view supported by recent careful reef the reefs varies from 1500 to 3500 g of carbon/m 2 /yr: this transect studies. 6 is a hundred times more than th'at of the surrounding seasIn addition to their ponderal importance, Octocorallia and eight times more than tt{at of the most productive are remarkable by their ability to ward off algal and regions of temperate seas. 3 ·~ A striking characteristic of microbial growth and to prevent the settlement of the reefs is their diven1tty: they contain many more larvae. 7 ' 8 Alcyonaceans are submitted only to negligible species than any other marine biotope. Coral reefs thus grazing by large predators and all crude soft coral extracts constitute a potentially yery important natural asset. They tested so far were indeed highly unpalatable to a variety are still practically untapped to this day but it can be of reef fishes. The existence of such a set of diversified safely predicted that they will be systematically exploited · ·,and effective chemical defenses having been surmised in years to come. )t can only be hoped that massive 'many years ago, it is not surprising that Octocorals have exploitation will be delayed until reliable conservation been one of the first marine groups to be the target of rules are worked.out through progress in reef ecology, a systematical-chen:,ical scrutiny. very complex field which is still in jts prime infancy.Gorgonians, being'\J.iitliiii e-asy reach·of-well-establisbed ~ The reef environment ideally fulfills the needs of the chemicallaboratories, were naturally studied first. Within marine natural products chemist. A maximum diversity of a few years they yielded a rieb crop of novel and species provides the opportunity for practically unlimited interesting compounds 9 including sterols, 10 prostaglanchemical prospection. Furthermore, since reefs are dins,u butenolides/ 2 sesquiterpenoid hydrocarbons, 13 necessarily located in clear, shallow waters, collecting can cembranolide 9 ' 14 and other 15 diterpenoids. Since a very generally be effected without the need of very sophisti-large number of gorgonian species still remain to be cated equipment. These conditions certainly favour the investigated one can assume that theseimpressive results, pursuit of classical activities such as detection and study in great part due to the group of the University of of potentially useful physiologically active compounds or Oklahoma, are yet a hors d...

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Occurrence of 23, 24-Dimethylcholesta-5, 22-dien-3β-ol in a Soft Coral, Sarcophyta elegans

Cited by 32 publications

References 1 publication

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹

Sterol and fatty acid composition of four marine haptophycean algae

Some Recent Developments in the Chemistry of Alcyonaceans

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Occurrence of 23, 24-Dimethylcholesta-5, 22-dien-3β-ol in a Soft Coral, Sarcophyta elegans

Cited by 32 publications

References 1 publication

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)1

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)1

Sterol and fatty acid composition of four marine haptophycean algae

Some Recent Developments in the Chemistry of Alcyonaceans

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Product

Resources

About

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹

STEROLS OF 14 SPECIES OF MARINE DIATOMS (BACILLARIOPHYTA)¹