Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp.

Steroids

Volumn 70, Issue 13, 2005, Pages 873-878

  Mandeau, Anne ^a   Debitus, Cecile ^a   Ariès, Marie Françoise ^a   David, Bruno ^a  

^a INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

3 Hydroxy 26 norcampest 5 en 25 oic acid; Absolute configuration; Euryspongia n. sp.; Phenylglycine methyl ester

Indexed keywords

3BETA HYDROXY 24 NORCHOL 5 EN 23 OIC ACID; 3BETA HYDROXY 26 NORCAMPEST 5 EN 25 OIC ACID; 6 OXOPROSTAGLANDIN F1 ALPHA; ESTER DERIVATIVE; PETROSTEROL; STEROID; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; BIOASSAY; CELL LINE; CHROMATOGRAPHY; CONTROLLED STUDY; DATA ANALYSIS; DRUG ISOLATION; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; KERATINOCYTE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA);

6-KETOPROSTAGLANDIN F1 ALPHA; ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; HUMANS; KERATINOCYTES; MAGNETIC RESONANCE SPECTROSCOPY; PORIFERA; STEREOISOMERISM; STEROIDS; STEROLS;

EURYSPONGIA; PORIFERA;

EID: 27644525200     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.05.006     Document Type: Article

References (18)

1. J. Cho, and C.J. Djerassi Sterols in marine invertebrates. Part 57. Stereostructure, synthesis, and acid-catalysed isomerization of hebesterol - a biosynthetically significant cyclopropyl-containing marine sterol Chem Soc Perkin Trans 1 1987 1307 1318
2. R.G. Kerr, and B.J. Baker Marine sterols Nat Prod Rep 8 1991 465 497
3. E.A. Santalova, T.N. Makarieva, I.A. Gorshkova, A.S. Dmitrenok, V.B. Krasokhin, and V.A. Stonik Sterols from six marine sponges Biochem Syst Ecol 32 2004 153 167
4. E. Finamore, L. Minale, R. Riccio, G. Rinaldo, and F. Zollo Novel marine polyhydroxylated steroids from the starfish Myxoderma platy acanthum J Org Chem 56 1991 1146 1153
5. S.W. Ayer, and R.J. Andersen Steroidal antifeedants from the dorid nudibranch Aldisa sanguinea cooperi Tetrahedron Lett 23 1982 1039 1042
6. M. Kobayashi, B. Haribabu, and V. Anjaneyulu Marine sterols. XXI. Isolation of (24S)-3β-hydroxyergost-5-en-21-oic acid from a Sclerophytum sp. of soft coral Chem Pharm Bull 40 1992 233 234
7. F. Kong, and R.J. Andersen Polymastiamides B-F, novel steroid/amino acid conjuguates isolated from the Norwegian marine sponge Polymastia boletiformis J Nat Prod 59 1996 379 385
8. C.A. Mattia, L. Mazzarella, R. Puliti, D. Sica, and F. Zollo X-ray crystal structure determination of petrosterol p-bromobenzoate. A revision Tetrahedron Lett 19 1978 3953 3954
9. 24-sterol reductase enzyme system(s) in the tobacco hornworm, Manduca sexta (Johannson) Steroids 12 1968 559 570
10. J.E. Van Lier, and L.L. Smith Sterol metabolism X: epimeric 23-hydroxycholesterols J Pharm Sci 59 1970 719 721
11. D. Sica, and F. Zollo Petrosterol, the major sterol with a cyclopropane side chain in the sponge Petrosia ficiformis Tetrahedron Lett 19 1978 837 838
12. J.L. Giner, S.P. Gunasekera, and S.A. Pomponi Sterols of the marine sponge Petrosia weinbergi: implications for the absolute configurations of the antiviral orthosterols and weinbersterols Steroids 64 1999 820 824
13. J.A. Dale, and H.S. Mosher Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate. O-methylmandelate, and α-methoxy- α-trifluoromethylphenylacetate (MTPA) esters J Am Chem Soc 95 1973 512 519
14. T. Yabuuchi, and K. Takenori Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids J Org Chem 65 2000 397 404
15. P. Boukamp, R.T. Petrussevska, D. Breitkreutz, J. Hornung, A. Markham, and N.E. Fusenig Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line J Cell Biol 106 1988 761 771
16. I. Rubinstein, L.J. Goad, Clague ADH, and L.J. Mulheirn The 220 MHz NMR spectra of phytosterols Phytochemistry 15 1976 195 200
17. Y. Nagai, and T. Kusumi New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids Tetrahedron Lett 36 1995 1853 1856
18. Q. Zhao, S.Y. Lee, J. Hong, C.O. Lee, K.S. Im, C.J. Sim, D.S. Lee, and J.H. Jung New acetylenic acids from the marine sponge Stelletta species J Nat Prod 66 2003 408 411