CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. XXVI.<sup>1</sup> STEROLS FROM SPONGES OF THE FAMILY SUBERITIDAE<sup>2</sup>

Bergmann, Werner; McTIGUE, Frank H.; Low, Eva M.; Stokes, William M.; Feeney, Robert J.

doi:10.1021/jo01147a016

Cited by 13 publications

(10 citation statements)

References 6 publications

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“…Sterols of Tzeteki. The presence of cholestanol and lesser amounts of other saturated compounds in this sponge, as well as a sterol believed to possess unsaturation only in the side chain, was reported by Bergmann et al [7] almost 30 years ago. Our reexamination confirms these findings in that 7 Sa-stanols comprise more than 90% of the sterol mixture, 5a-cholestanol (le) being the predominant one (59%).…”

Section: Discussionsupporting

confidence: 57%

“…-The sponge Terpios zeteki (de Laubenfels, 1936) is classified in the order Hadromerida and in the family Suberitidae of the class Desmospongia. Little work has been reported on the sterols of sponges belonging to this family since the pioneering studies of Bergmann [7]. He found that cholestanol and other nuclear saturated sterols predominate in 5 other species of this family.…”

Section: Discussionmentioning

confidence: 99%

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5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

Delseth

Tolela

Djerassi

et al. 1979

Helvetica Chimica Acta

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SummaryThe steroidal components of 2 marine sponges, Terpios zeteki (from Hawaii) and Dysidea herbacea (from Australia) were fractionated through a combination of chromatographic methods, including reversed phase HPLC., and were analyzed by a combination of physical methods, including high resolution GC.-MS. and 360 MHz 'H-NMR. T. zeteki contains 6 conventional 5a-stanols which comprise 91% of the sterol mixture, and traces (0.5%) of a new C26 sterol, 5a-24-norcholestan-3/3-01. Minor amounts of conventional d5-sterols (6.5%) and of a single d4-3-ketosteroid (1.5%) were also present. In contrast, the Australian sponge (D. herbacea) contains 3 d5,7-sterols which comprise 1.5% of the sterol mixture, and one new C29 sterol, (24 Z)-stigmasta-5,7,24 (28)-trien-38-01, as the major component (75%). In addition, minor amounts of conventional 5a-stanols (0.5%), d5-sterols (5%) and 5a-d7-sterols (18%) were present in this complex sterol mixture. The possible dietary or endosymbiotic origins of these sterols are discussed.

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Section: Discussionsupporting

confidence: 57%

Section: Discussionmentioning

confidence: 99%

5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

Delseth

Tolela

Djerassi

et al. 1979

Helvetica Chimica Acta

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“…Cholesta-5,22-dien-3ß-ol (22-dehydrocholesterol) (13) (25), 271 (50), 255 (100), 253 (13), 241 (11), 229 (14), 213 (33), 207 (10), 199 (21), 187 (18), 173 (20) (42), 368 (53), 353 (38), 326 (13), 302 (13), 301 (59), 276 (23), 275 (61), 255 (31), 247 (15), 231 (18), 213 (47),199 (16), 187 (17), 178 (18), 173 (17), 163 (29), 161 (40), 159 (36), 145 (41), 133 (37), 119 (32), 105 (61), 95 (17), 91 (57), 81 (47), 79 (38), 69 (26), 67 (23), 57 (37), 55 (41), 43 (76), 41 (44). (9), 255 (62), 241 (5), 228 (6), 213 (19), 199 (9), 185 (8), 173 (17), 161 159 (35), 147 (28), 145 (31), 143 (16), 139 (13), 135 (11), 133 (34), 131 (22), 129 (90), 123 (9), 121…”

Section: Spectroscopic Data Of Steroidsunclassified

“…, 357 (89), 343 (6), 329 (5), 303 275 (10), 255 (20), 213 (13), 199 (6), 189 (5), 185 (5), 177 (5), 175 (8), 173 (14), 171 (5), 163 (11), 161 (17), 159 (25), 157 (10), 149 (9), 147 (19), 145 (28), 143 (18), 135 (14), 133 (23), 131 (20), 129 (100), 121 (26), 119 (29), 117 (9), 109 (15), 107 (27), 105 (26), 97 (8), 95 (31), 93 (21), 91 (20), 85 (12), 83 (9), 81 (28), 79 (15), 75 (35), 73 (52), 71 (15), 69 (21), 67 (15), 57 (28), 55 (24), 43 (40), 41…”

Section: Spectroscopic Data Of Steroidsunclassified

In vitro anti-proliferative activities of the sterols and fatty acids isolated from the Persian Gulf sponge; Axinella sinoxea

et al. 2019

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Purpose Marine sponges are rich sources of anticancer metabolites. Axinella sinoxea is a less studied sponge, found in the Larak Island's waters, of the Persian Gulf. In the present study, we have explored the cytotoxic properties and chemical constituents of A. sinoxea. Methods Repeated silica gel flash column chromatography of methanol extract of the Axinella sinoxea sponge, yielded fatty acid and sterol fractions. These fractions were analyzed by GC-MS and their anti-proliferative activities were evaluated by MTT assay against three human cancer cell lines including MOLT-4, MCF-7 and HT-29 as well as NIH/3 T3 fibroblast cells. The sterol-rich fractions were pooled and purified by HPLC and its sub fractions' cytotoxic activities were evaluated by MTT assay against MOLT-4 and NIH/3 T3 cells. ResultsThe GC-MS spectral analysis of a fraction eluted with hexane: diethyl ether (90: 10), resulted in the identification of twelve fatty acids, including five linear chain saturated fatty acids; tetrdecanoic acid (1), pentadecanoic acid (3), hexadecanoic acid (5), heptadecanoic acid (7), and octadecanoic acid (10); one branched chain isoprenoid fatty acid, 4,8,12trimethyltridecanoic acid (2); four monoenoic fatty acids; 9-hexadecenoic acid (4), 7-methyl-6-hexadecanoic acid (6), 9octadecenoic acid (8) and 11-octadecenoic acid (9) and two polyunsaturated fatty acids; 5,8,11,14-eicosatetraenoic acid (11) and 4,7,10,13,16,19-docosahexaenoic acid (12). Spectral analysis of a non-polar fraction eluted with hexane: diethyl ether (85: 15), resulted in the identification of eight steroids including: cholesta-5,22-dien-3β-ol (13), cholest-5-en-3β-ol (14), ergosta-5,22-dien-3β-ol (15), ergost-5-en-3β-ol (16), stigmasta-5,22-dien-3β-ol (17), γ-sitosterol (18), 33-norgorgosta-5,24(28)-dien-3βol (19) and stigmasta-5,24(28)-dien-3β-ol (20). Fatty acids-containing fraction was active against HT-29 cell line with IC 50 26.52 ± 8.19 μg/mL, while the steroids-rich fraction was active against the three above mentioned cell lines with IC 50 values of 1.20 ± 0.24, 4.12 ± 0.40 and 2.47 ± 0.31 μg/mL, respectively. All of the above-mentioned fractions and sub-fractions were inactive (IC 50 s > 50 μg/mL) when assayed against normal fibroblast cells. Conclusion The present study suggests A. sinoxea as a potential natural source of cancer chemotherapeutics.

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“…Terpios zeteki was one of the first marine sponges to be investigated by Bergmann and coworkers in 1949. Obtained from Hawaii, the acetone extract yielded cholestanol and neospongosterol [27]. Further research work executed on the Hawaiiansourced organism in 1979 led to the isolation of the steroids including 5α-stanols and traces of 5α-24-norcholestan-3β-ol.…”

Section: Species:t Zetekimentioning

confidence: 99%

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

Gallimore

2018

JAC

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Research efforts to examine the chemistry of marine organisms collected from the Ramsar site of Port Royal, Jamaica, has led to the isolation of a range of compounds as diverse as the species from which they were derived. Six sponges, two algal species, one ascidian and one soft coral collected from the mangrove area and the shallow coastal reefs were studied to yield compounds including steroids, aromatic compounds and terpenoids.

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CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. XXVI.¹ STEROLS FROM SPONGES OF THE FAMILY SUBERITIDAE²

Cited by 13 publications

References 6 publications

5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

In vitro anti-proliferative activities of the sterols and fatty acids isolated from the Persian Gulf sponge; Axinella sinoxea

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

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CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. XXVI.1 STEROLS FROM SPONGES OF THE FAMILY SUBERITIDAE2

Cited by 13 publications

References 6 publications

5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

5α‐24‐Norcholestan‐3β‐ol and (24Z)‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

In vitro anti-proliferative activities of the sterols and fatty acids isolated from the Persian Gulf sponge; Axinella sinoxea

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

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CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. XXVI.¹ STEROLS FROM SPONGES OF THE FAMILY SUBERITIDAE²