Monolaterol, the first configurationally assigned phenylphenalenone derivative with a stereogenic center at C-9, from Monochoria elata

Journal of Natural Products

Volumn 69, Issue 11, 2006, Pages 1614-1617

  Hölscher, Dirk ^a   Reichert, Matthias ^b   Görls, Hilmar ^c   Ohlenschläger, Oliver ^d   Bringmann, Gerhard ^b   Schneider, Bernd ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^d FRITZ LIPMANN INSTITUTE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 8 (4 HYDROXYPHENYL) 1H PHENALEN 1 ONE; 2 HYDROXY 9 PHENYL 1H PHENALEN 1 ONE; 2,4 DIHYDROXY 9 PHENYL 1H PHENALEN 1 ONE; 2,6 DIHYDROXY 9 PHENYL 1H PHENALEN 1 ONE; CARBON; NATURAL PRODUCT; PHENYL GROUP; PHENYLPHENALENONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; GERMANY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENALENES; PLANT ROOTS; PONTEDERIACEAE;

MONOCHORIA;

EID: 33845961543     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np060192x     Document Type: Article

References (36)

1. Chen, P. H.; Kuo, W. H. J. Weed Res. 1999, 39, 107-115.
2. Wang, G.; Lin, Y.; Li, W.; Ito, M.; Itoh, K. Pestic. Biochem. Physiol. 2004, 80, 43-46.
3. Row, L.; Chen, C.; Ho, J. J. Chin. Chem. Soc. 2004, 51, 225-228.
4. Della Greca, M.; Lanzetta, R.; Molinaro, A.; Monaco, P.; Previtera, L. Bioorg. Med. Chem. Lett. 1992, 2, 311-314.
5. Hölscher, D.; Schneider, B. Phytochemistry 2005, 66, 59-64.
6. Luis, J.; Echeverri, F.; Quiñones, W.; Brito, I.; Lopez, M.; Torres, F.; Cardona, G.; Aguiar, Z.; Pelaez, C.; Rojas, M. J. Org. Chem. 1993, 58, 4306-4308.
7. Binks, R.; Greenham, J.; Luis, J.; Gowen, S. Phytochemistry 1997, 45, 47-49.
8. Kamo, T.; Hirai, N.; Tsuda, M.; Fujioka, M; Ohigashi, H. Biosci. Biotechnol. Biochem. 2000, 64, 2089-2098.
9. Edwards, J. M.; Weiss, U. Phytochemistry 1970, 9, 1653-1657.
10. Edwards, J. M. Phytochemistry 1974, 13, 290-291.
11. Otálvaro, F.; Quiñones, W.; Echeverri, F.; Schneider, B. J. Labelled Compd. Radiopharm. 2004, 47, 147-159.
12. Cooke, R. G.; Thomas, R. L. Austr. J. Chem. 1975, 28, 1053-1057.
13. Hölscher, D.; Schneider, B. Phytochemistry 1999, 50, 155-161.
14. Bringmann, G.; Mühlbacher, J.; Reichert, M.; Dreyer, M.; Kolz, J.; Speicher, A. J. Am. Chem. Soc. 2004, 126, 9283-9290.
15. Bracher, F.; Eisenreich, W. J.; Mühlbacher, J.; Dreyer, M.; Bringmann, G. J. Org. Chem. 2004, 69, 8602-8608.
16. Müller, M.; Lamottke, K.; Steglich, W.; Busemann, S.; Reichert, M.; Bringmann, G.; Spiteller, P. Eur. J. Org. Chem. 2004, 4580-4855.
17. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-264.
18. The CD spectra of those structures that lie energetically higher than 3 kcal/mol above the global minimum do not contribute to the overall CD curve obtained by superposition of the Boltzmann-weighted single spectra.
19. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
21. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
22. Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807-1813.
23. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
24. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
25. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835.
26. Bringmann, G.; Busemann, S. In Natural Product Analysis; Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden, 1998; pp 195-212.
27. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
28. Luis, J. G.; Fletcher, W. Q.; Echeverri, F.; Grillo, T. A. Tetrahedron 1994, 50, 10963-10970.
29. Frisch, M. J.; Trecks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gil, P. M. W.; Johnson, B.; Chen, M.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. SYBYL; Tripos, Inc.: St. Louis, MO, 2004.
31. Downing, J. W. Program Package BDZDO/MCDSPD; Department of Chemistry and Biochemistry, University of Colorado: Boulder, CO; modified by Fleischhauer, J.; Schleker, W.; Kramer, B.; ported to Linux by Gulden, K.-P.
32. Ahlrichs, R.; Bär, M.; Baron, H.-P.; Bauerschmitt, R.; Böcker, S.; Deglmann, P.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Haase, F.; Häser, M.; Horn, H.; Hättig, C.; Huber, C.; Huniar, U.; Kattannek, M.; Köhn, A.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Patzelt, H.; Rubner, O.; Schäfer, A.; Schneider, U.; Sierka, M.; Treutler, O.; Unterreiner, B.; Arnim, M. V.; Weigend, F.; Weis, P.; Weiss, H. TURBOMOLE, Version 5.6; Universität Karlsruhe: Karlsruhe, Germany, 2002.
33. Otinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
34. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, 46, 467-473.
35. Sheldrick, G. M. SHELXL-97 (Release 97-2); University of Göttingen: Göttingen, Germany, 1997.
36. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC 289522). 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).