Two new Δ5,7-sterols from two spongiidae sponges

doi:10.1016/0305-0491(84)90128-7

Comparative Biochemistry and Physiology Part B: Comparative Biochemistry

Volume 78, Issue 3, 1984, Pages 741-744

https://doi.org/10.1016/0305-0491(84)90128-7 Get rights and content

Abstract

1.
1. The sterol composition of Ircinia foetida and Ircinia variabilis (phylum Porifera, order Dictyoceratida, family Spongiidae) was investigated by silver nitrate-silica gel column chromatography and by spectroscopy methods.
2.
2. Sponges contain mainly Δ^5,7-sterols accompanied by Δ⁷-sterols; a small quantity of cholesterol is also present. The sterols from I. foetida and I. variabilis are qualitatively similar, while the quantitative content of some components is different.
3.
3. In addition to known sterols the sponges contain two new sterols which were identified as (24E)-24-ethylcholesta-5,7,24(28)-trien-3β-ol and 24-propylcholesta-5,7,24(28)-trien-3β-ol, respectively.

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5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: Isolation and evaluation of their antiproliferative activity
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Three new (1, 4, 9) and nine previously reported (2, 3, 5–8, 10–12) 5α,8α-epidioxysterols were isolated from the organic extracts of the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum. The structures and relative configurations of 1–12 were established on the basis of detailed NMR spectroscopic analyses and comparison with the literature. The growth inhibitory effects of 1–12 were evaluated against MCF-7 human breast cancer cells. Compound 1, bearing a cyclopropyl moiety in the side chain, exhibited the highest antiproliferative activity.
Δ<sup>5,7</sup>Sterols from the sponges Ircinia pipetta and Dysidea avara identification of cholesta-5,7,24-trien-3B-OL
1987, Comparative Biochemistry and Physiology -- Part B: Biochemistry and
- 1.
  1. Δ^5,7-sterols have been isolated as pure compounds from the marine sponges Ircinia pipetta (Dictyoceratida:Thorectidae) and Dysidea avara (Dictyoceratida:Dysideidae) by reverse phase HPLC and analyzed by GLC, u.v., mass spectrometry and ¹H-NMR.
- 2.
  2. Ircinia pipetta and D. avara have rather similar sterol compositions and contain predominantly Δ^5,7-sterols, accompaned by Δ⁵-sterols. Ergosterol, cholesta-5,7-dien-3β-ol and 24-ethylcholesta-5,7-dien-3β-ol are the major sterols in I. pipetta, while D. avara contains in addition to these three sterols, (24Z)-24-ethylcholesta-5,7,24(28)-trien-3β-ol as the fourth major sterol.
- 3.
  3. Cholesta-5,7,24-trien-3β-ol which previously was not isolated from a marine organism is also present.
A new C<inf>30</inf> sterol, (24Z)-24-propylcholesta-5,7,24(28)-trien-3β-ol, and other Δ<sup>5,7</sup> sterols from the sponge Spongionella gracilis
1985, Comparative Biochemistry and Physiology -- Part B: Biochemistry and
- 1.
  1. The sterol mixture of the marine sponge Spongionella gracilis (Dictyoceratida: Dysideidae) was fractionated by reverse-phase HPLC and argentic TLC and analyzed by spectroscopic methods.
- 2.
  2. Sponge contains mainly Δ^5,7-sterols (92%) accompanied by Δ⁵-sterols. The Δ^5,7-sterols were isolated and characterized by u.v., ¹H-NMR and mass spectra. Ergosterol and 24-ethylcholesta-5,7-dien-3β-ol were the major components of the sterol mixture.
- 3.
  3. A new C₃₀ sterol was detected as a minor component and characterized as (24Z)-24-propylcholesta-5,7,24(28)-trien-3β-ol. A rare marine sterol, identified as 24-methylcholesta-5,7,24(28)-trien-3β-ol, is also present.
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2023, Marine Drugs
Organic Synthesis of New Secosteroids from Fucosterol, Its Intestinal Absorption by Caco-2 Cells, and Simulation of the Biological Activities of Vitamin D
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Sulfur-Containing Aristoloxazines and Other Constituents of the Roots of Aristolochia orbicularis
2017, Journal of Natural Products

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Comparative Biochemistry and Physiology Part B: Comparative Biochemistry

Abstract

References (20)

Metabolism in Porifera—II. Distribution of sterols

Comp. Biochem. Physiol.

Sterols from the sponge Agelas oroides

Comp. Biochem. Physiol.

Stereochemistry of 7,24(28)-stigmastadien-3β-ol and the fucosterols

Tetrahedron Lett.

Mass spectrometric investigations of some unsaturated sterols biosynthetically related to cholesterol

Steroids

The sterols of marine invertebrates: composition, biosynthesis and metabolites

Conformational analysis of the enzyme-substrate complex in the dehydrogenation of sterols by Tetrahymena pyriformis

J. biol. Chem.

The 220 MHz spectra of phytosterols

Phytochemistry

Ergosta-5,7,9(11), 22-tetraen-3β-ol and its 24 ξ-ethyl homolog, two new marine sterols from the Red Sea sponge Biemna fortis

Helv. chim. Acta

5α-24-Norcholestan-3β-ol and (24Z)-stigmasta-5,7,24(28)-trien-3β-ol, two new marine sterols from Pacific sponges Terpios zeteki and Dysidea herbacea

Helv. chim. Acta

Cited by (8)

5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: Isolation and evaluation of their antiproliferative activity

Δ<sup>5,7</sup>Sterols from the sponges Ircinia pipetta and Dysidea avara identification of cholesta-5,7,24-trien-3B-OL

A new C<inf>30</inf> sterol, (24Z)-24-propylcholesta-5,7,24(28)-trien-3β-ol, and other Δ<sup>5,7</sup> sterols from the sponge Spongionella gracilis

Comparative Chemical Profiling and Antimicrobial/Anticancer Evaluation of Extracts from Farmed versus Wild Agelas oroides and Sarcotragus foetidus Sponges

Organic Synthesis of New Secosteroids from Fucosterol, Its Intestinal Absorption by Caco-2 Cells, and Simulation of the Biological Activities of Vitamin D

Sulfur-Containing Aristoloxazines and Other Constituents of the Roots of Aristolochia orbicularis

General paperTwo new Δ5,7-sterols from two spongiidae sponges

Abstract

Comp. Biochem. Physiol.

Comp. Biochem. Physiol.

Tetrahedron Lett.

Steroids

J. biol. Chem.

Phytochemistry

Ergosta-5,7,9(11), 22-tetraen-3β-ol and its 24 ξ-ethyl homolog, two new marine sterols from the Red Sea sponge Biemna fortis

Helv. chim. Acta

5α-24-Norcholestan-3β-ol and (24Z)-stigmasta-5,7,24(28)-trien-3β-ol, two new marine sterols from Pacific sponges Terpios zeteki and Dysidea herbacea

Helv. chim. Acta

General paper
Two new Δ^5,7-sterols from two spongiidae sponges