New terpenoid constituents from Eunicea pinta

Journal of Natural Products

Volumn 65, Issue 9, 2002, Pages 1232-1241

  Shi, Yan Ping ^a   Rodríguez, Abimael D ^a   Barnes, Charles L ^a   Sánchez, Juan A ^a   Raptis, Raphael G ^a   Baran, Peter ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

12 EPIUPALMERONE; 3BETA PREGNA 5,20 DIENE BETA DEXTRO XYLOPYRANOSIDE; CEMBRANOLIDE DERIVATIVE; EUNIOLIDE; SAPONIN; SUCCINOLIDE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; UPROLIDE H; UPROLIDE I; UPROLIDE J; UPROLIDE K; UPROLIDE K ACETATE; UPROLIDE L; UPROLIDE M;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CORAL; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; EUNICEA PINTA; SPECTROSCOPY; STEREOCHEMISTRY; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, NON-SMALL-CELL LUNG; CNIDARIA; COLOMBIA; CRYSTALLOGRAPHY, X-RAY; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; KIDNEY NEOPLASMS; LUNG NEOPLASMS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SAPONINS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; T-LYMPHOCYTES; TUMOR CELLS, CULTURED;

ANTHOZOA; EUNICEA; EUNICEA PINTA; GORGONIA;

EID: 0036742078     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0200820     Document Type: Article

References (33)

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14. 3-20], C-13 [H-11αβ, H-12, H-14, H3-20], C-14 [H-2β], C-15 [H-2αβ, H-17α], C-16 [H-14, H-17αβ], C-19 [H-7], C-20 [H-12].
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27. C-7 85-9) and uprolide C acetate (δC-7 89.8) (i.e., members of the "uprolide-C series") there should appear a hydroperoxide at C-7 and not a hydroxyl group (see Table 3). Reinterpretation of the spectral data (in particular the mass spectra) for the above-mentioned compounds supported these revisions. The structural revision of some of these analogues also includes an inversion of configuration at the C-8 position.
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29. These trends seem to hold whether there is a hydroxyl, a hydroperoxyl, or an acetyl group attached to C-8. Seemingly, uprolide L (9) and uprolide M (10), each having the C-8(S*) configuration, represent exceptions to this empirical rule.
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31. The poor quality of the crystals of 3 have only allowed a preliminary structural study. However, the stereochemistry and the atom coordinates of 3, as depicted in Figure 1, are established with certainty.
32. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: 44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
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