Sterols In Marine Invertebrates Research Articles

Sterols in marine invertebrates

: The sterol composition of marine invertebrates, crustaceans, molluscs, echinoderms, coelenterates, and sponges has been re-examined by using improved analytical techniques. As a result, the sterol composition of marine invertebrates has been shown to be more complex mixtures including many new types of sterols with unusual steroid nuclei or with non-conventional side chains. Some crustaceans and molluscs are of importance as seafood and aquaculture species. Crustaceans and some molluscs require dietary sources of sterol for growth and survival because of the absence of de novo sterol-synthesizing ability. The present paper gives a review of the requirement and nutritive value of sterols, biosynthesis and metabolism of sterols, and composition and structure of sterols in marine invertebrates.

Minor and trace sterols in marine invertebrates 65. 23-Epidihydrocalysterol: a new cyclopropane-containing sponge sterol

A new cyclopropane-containing sterol was isolated from the marine sponge Cribrochalina vasculum. The new sterol was characterized by nuclear magnetic resonance and mass spectrometry and the structure was shown to be (23R,24S,28R)-dihydrocalysterol. Implications concerning the biosynthesis of cyclopropane and cyclopropene sterols in sponges are discussed. ( Steroids 57:258–261, 1992)

Sterols of marine invertebrates. 63. Isolation and structure elucidation of sutinasterol, the major sterol of the marine sponge Xestospongia sp

Sterols of marine invertebrates. 63. Isolation and structure elucidation of sutinasterol, the major sterol of the marine sponge Xestospongia sp

Minor and trace sterols in marine invertebrates. 62. novel coprostanols with unusual side chains from the marine sponge Calyx nicaeensis

Seventeen stanols with a variety of unusual side chains and possessing the rare 5β-dihydro nucleus have been isolated from the sponge Calyx nicaeensis. These stanols probably result from bacterial metabolism of the endogenous sponge sterols.

Minor and trace sterols in marine invertebrates. 61. Isolation and structure elucidation of new A-nor sterols from the marine sponge Phakellia aruensis

An examination of the Australian sponge Phakellia aruensis led to the isolation and identification of sterols with six different nuclei. Eight new sterols were isolated which included three Δ 15-A-nor sterols, three Δ 7 -A-nor sterols, and two saturated A-nor sterols. Their structures were established through mass spectrometry and 1H-NMR spectral studies.

Sterols in marine invertebrates. 60. Isolation and structure elucidation of four new steroidal cyclopropenes from the sponge Calyx podatypa

Sterols in marine invertebrates. 60. Isolation and structure elucidation of four new steroidal cyclopropenes from the sponge Calyx podatypa

Sterols in marine invertebrates. Part 57. Stereostructure, synthesis, and acid-catalysed isomerization of hebesterol—a biosynthetically significant cyclopropyl-containing marine sterol

Three new cyclopropane-containing sterols hebesterol (11), petrostanol (8), and 23,24-dihydro-5α-calystanol (10) have been isolated from the sponge, Petrosia hebes, together with the principal sterol, petrosterol (7), and 21 known sterols. The structure elucidation of the new trace sterols was accomplished by spectroscopic methods and partial synthesis. Hebesterol (11) and its trans-diastereoisomers (31)–(33) have been synthesized and their acid-catalysed cyclopropane ring-opening studied. Each hebesterol isomer (11), (31)–(33) was correlated with the recently synthesized ficisterol isomers (5), (53), (56), and (58) of known absolute stereochemistry, thus leading to an unambiguous assignment of the absolute stereochemistry of hebesterol. The other products from the acid-catalysed isomerizations were characterized by spectroscopic methods, synthesis, and mechanistic considerations. Two of these products, (23R)-23-ethyldesmosterol (51) and (23S)-23-ethyldesmosterol (59), provided a relay to the absolute stereochemistry of the 23-ethylcholestanols, which had previously been synthesized without assignment of absolute stereochemistry. Hebesterol (11) is the key ‘missing link’ with the predicted stereochemistry in a proposed biosynthetic sequence encompassing the unusual marine sterols dihydrocalysterol (9), petrosterol (7), and ficisterol (5).

Minor and trace sterols in marine invertebrates 52 : Tam Ha, T.B. and Carl Djerassi, 1985. Isolation, structure elucidation and partial synthesis of 24-propyl-24, 28-methylenecholest-5-EN-3β-OL. Tetrahedron Letts, 26(34):4031–4034. Dept. of Chem., Stanford Univ., Stanford, CA 94305, USA

Minor and trace sterols in marine invertebrates 52 : Tam Ha, T.B. and Carl Djerassi, 1985. Isolation, structure elucidation and partial synthesis of 24-propyl-24, 28-methylenecholest-5-EN-3β-OL. Tetrahedron Letts, 26(34):4031–4034. Dept. of Chem., Stanford Univ., Stanford, CA 94305, USA

ChemInform Abstract: STEROLS IN MARINE INVERTEBRATES. 51. ISOLATION AND STRUCTURE ELUCIDATION OF C‐18 FUNCTIONALIZED STEROLS FROM THE SOFT CORAL SINULARIA DISSECTA

Chemischer InformationsdienstVolume 16, Issue 52 Natural Products ChemInform Abstract: STEROLS IN MARINE INVERTEBRATES. 51. ISOLATION AND STRUCTURE ELUCIDATION OF C-18 FUNCTIONALIZED STEROLS FROM THE SOFT CORAL SINULARIA DISSECTA B. M. JAGODZINSKA, B. M. JAGODZINSKASearch for more papers by this authorJ. S. TRIMMER, J. S. TRIMMERSearch for more papers by this authorW. FENICAL, W. FENICALSearch for more papers by this authorC. DJERASSI, C. DJERASSISearch for more papers by this author B. M. JAGODZINSKA, B. M. JAGODZINSKASearch for more papers by this authorJ. S. TRIMMER, J. S. TRIMMERSearch for more papers by this authorW. FENICAL, W. FENICALSearch for more papers by this authorC. DJERASSI, C. DJERASSISearch for more papers by this author First published: December 31, 1985 https://doi.org/10.1002/chin.198552289AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume16, Issue52December 31, 1985 RelatedInformation

ChemInform Abstract: STEROLS IN MARINE INVERTEBRATES. 49. ISOLATION AND STRUCTURE ELUCIDATION OF EIGHT NEW POLYHYDROXYLATED STEROLS FROM THE SOFT CORAL SINULARIA DISSECTA

Chemischer InformationsdienstVolume 16, Issue 39 Natural Products ChemInform Abstract: STEROLS IN MARINE INVERTEBRATES. 49. ISOLATION AND STRUCTURE ELUCIDATION OF EIGHT NEW POLYHYDROXYLATED STEROLS FROM THE SOFT CORAL SINULARIA DISSECTA B. M. JAGODZINSKA, B. M. JAGODZINSKASearch for more papers by this authorJ. S. TRIMMER, J. S. TRIMMERSearch for more papers by this authorW. FENICAL, W. FENICALSearch for more papers by this authorC. DJERASSI, C. DJERASSISearch for more papers by this author B. M. JAGODZINSKA, B. M. JAGODZINSKASearch for more papers by this authorJ. S. TRIMMER, J. S. TRIMMERSearch for more papers by this authorW. FENICAL, W. FENICALSearch for more papers by this authorC. DJERASSI, C. DJERASSISearch for more papers by this author First published: October 1, 1985 https://doi.org/10.1002/chin.198539330AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume16, Issue39October 1, 1985 RelatedInformation

Sterols in marine invertebrates. 51. Isolation and structure elucidation of C-18 functionalized sterols from the soft coral Sinularia dissecta

Sterols in marine invertebrates. 51. Isolation and structure elucidation of C-18 functionalized sterols from the soft coral Sinularia dissecta

Minor and trace sterols in marine invertebrates 55. The isolation, structure elucidation and synthesis of ergosta-5, 24(28), 25-trien-3 beta-ol.

The isolation, structure determination and synthesis of ergosta-5, 24(28), 25-trien-3 beta-ol, as well as the synthesis of its 28-14C analog--a possible biosynthetic precursor of several marine sterols--is described.

Sterols in marine invertebrates. 49. Isolation and structure elucidation of eight new polyhydroxylated sterols from the soft coral Sinularia dissecta

1316 cm-'; MS, mle (relative intensity) 217 (M', 4), 175 (13), 174 (loo), 162 (16), 159 (28), 56 (15), 43 (36). Anal. Calcd for Cl3HI5NO2: C, 71.86; H, 6.86; N, 6.45. Found: C, 72.10; H, 6.98; N, 6.49. The ketone 32 was reduced in a similar way as that of 7a to give 33 (85%). 6,7-Dihydro-5hydroxy1,6,6-trimethyl-3,4-benzazepin-2(5H)-one (33): mp 188-189 C (from ethanol); 'H NMR (CDC13) b 1.14 (s,3 H, MeCMe), 2.10 (s,3 H, MeCMe), 2.62 and 2.90 (ABq, J = 14 Hz, 2 H,NCH,),3.08 (9, 3 H,NMe),3.57 (8, 1 H,HCOH), 4.20 (s, 1 H, OH), 7.2-7.8 (m, 4 H, Ar H); IR (KBr) 3305 (OH), 1625 (amide), 1595, 1428, 1256, 1058 cm-l; MS, mle relative intensity) 219 (M', 100), 190 (61), 161 (56), 44 (100). Anal. Calcd for C13H1,N02: C, 71.20; H, 7.82; N, 6.39. Found C, 71.20; H,

Minor and trace sterols in marine invertebrates 53: Further novel marine sterols resulting from triple and quadruple biomethylation of the cholesterol side-chain

The isolation and structure elucidation of nine new trace sterols with highly branched side chains from a Pseudaxinyssa species from the Australian Great Barrier Reef are described.

Minor and trace sterols in marine invertebrates 52. isolation, structure elucidation and partial synthesis of 24-propyl-24,28-methylenecholest-5-en-3β-ol

The isolation and structure elucidation of the first cyclopropyl-containing sterol (1) resulting from quadruple bioalkylation of the sterol side chain is reported.

ChemInform Abstract: Sterols in Marine Invertebrates. Part 42. Isolation, Partial Synthesis and Structure Determination of Sterols with the Four Possible 23,24‐Dimethy1‐Substituted Side Chains.

AbstractVier isomere methylierte Cholestan‐Derivate werden isoliert und identifiziert.

Minor and trace sterols in marine invertebrates 48. The isolation, structure elucidation and synthesis of 23(R),24(R)-methylenecholesterol.

The isolation, structure determination and synthesis of 23(R),24(R)-methylene-cholesterol—a possible biosynthetic precursor of brassicasterol—is described.

Sterols of marine invertebrates. 44. Isolation, structure elucidation, partial synthesis, and determination of absolute configuration of pulchrasterol. The first example of double bioalkylation of the sterol side chain at position 26

Sterols of marine invertebrates. 44. Isolation, structure elucidation, partial synthesis, and determination of absolute configuration of pulchrasterol. The first example of double bioalkylation of the sterol side chain at position 26

Sterols in marine invertebrates. Part 42. Isolation, partial synthesis and structure determination of sterols with the four possible 23,24-dimethyl-substituted side chains

Sterols in marine invertebrates. Part 42. Isolation, partial synthesis and structure determination of sterols with the four possible 23,24-dimethyl-substituted side chains

Minor and trace sterols in marine invertebrates 47. A re-investigation of the 19-nor stanols isolated from the sponge [formula omitted

The aim of this research was to establish the true composition of the 19-nor stanols isolated from the sponge Axinella polypoides and to determine accurate stereochemistry for each 19-nor stanol isolated. The following new 19-nor stanols were collected from this sponge: (i) (22E,24 S )-24-methyl-19,27-bisnor-5α-cholest-22-en-3β-ol, (ii) (22 R , 23 R )-22,23-methylene-19-nor-5α-cholestan-3β-ol, (iii) (24ξ)-24-propyl-19-nor-5α-cholestan-3β-ol and (iv) (23 R ,24 R )-23,24-dimethyl-19-nor-5α-cholestan-3β-ol. The general structure and stereochemistry of all fifteen 19-nor stanols were established by analysis of the MS and H-NMR (300 MHz, CDCl 3) data measured for each compound. The relative percentage of 19-nor stanols having Δ 22 double bonds should be sufficient to suggest that this sponge could be a potential source of starting material for the partial synthesis of certain oral contraceptives, which also have a 19-nor steroid nucleus.