Gloriosaols A and B, two novel phenolics from Yucca gloriosa: structural characterization and configurational assignment by a combined NMR-quantum mechanical strategy

Tetrahedron

Volumn 63, Issue 1, 2007, Pages 148-154

  Bassarello, Carla ^a   Bifulco, Giuseppe ^a   Montoro, Paola ^a   Skhirtladze, Alexandre ^b   Kemertelidze, Ether ^b   Pizza, Cosimo ^a   Piacente, Sonia ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b Institute of Pharmacochemistry   (Georgia)

Author keywords

DFT calculations; GIAO NMR; Gloriosaols A and B; Resveratrol; Yucca gloriosa

Indexed keywords

GLORIOSAOL A; GLORIOSAOL B; PHENOL DERIVATIVE; PLANT EXTRACT; YUCCA GLORIOSA EXTRACT;

ARTICLE; CALCULATION; CONTROLLED STUDY; DIASTEREOISOMER; DRUG ISOLATION; DRUG STRUCTURE; ISOMER; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT; PRIORITY JOURNAL; QUANTUM MECHANICS; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY; YUCCA GLORIOSA;

YUCCA GLORIOSA;

EID: 34548502717     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.034     Document Type: Article

References (34)

1. Kemertelidze E.P., and Pkheidze T.A. Khim.-Farm. Zh. 6 (1972) 44-47
2. Nakano K., Yamasaki T., Imamura Y., Murakami K., Takaishi Y., and Tomimatsu T. Phytochemistry 28 (1989) 1215-1217
3. Nakano K., Hara Y., Yamasaki T., Murakami K., Takaishi Y., and Tomimatsu T. Phytochemistry 30 (1991) 1993-1995
4. Kemertelidze E., and Benidze M. Bull. Georgian Acad. Sci. 164 (2001) 91-93
5. Oleszek W., Sitek M., Stochmal A., Piacente S., Pizza C., and Cheeke P. J. Agric. Food Chem. 49 (2001) 747-752
6. Piacente S., Bifulco G., Pizza C., Stochmal A., and Oleszek W. Tetrahedron Lett. 43 (2002) 9133-9136
7. Piacente S., Montoro P., Oleszek W., and Pizza C. J. Nat. Prod. 67 (2004) 882-885
8. Piacente S., Pizza C., and Oleszek W. Phytochem. Rev. 4 (2005) 177-190
9. Calderon A.A., Zapata J.M., Munoz R., Pedreno M.A., and Ros Barcelo A. New Phytol. 124 (1993) 455-463
10. Jeandet P.R., Bessis M., Sbaghi M., and Meunier P. J. Phytopathol. 143 (1995) 135-139
11. Langcake P., and Price R.J. Physiol. Plant Pathol. 9 (1976) 77-86
12. Kimura Y., Okuda H., and Kubo M. J. Ethnopharmacol. 45 (1995) 131-139
13. Orsini F., Pellizzoni F., Verotta L., Aburjai T., and Rogers C.B. J. Nat. Prod. 60 (1997) 1082-1087
14. Orallo F. Curr. Med. Chem. 13 (2006) 87-98
15. Tsai S.H., Lin Shiau S.H., and Lin J.K. Br. J. Pharmacol. 126 (1999) 673-680
16. Bhat K.P., and Pezzuto J.M. Ann. N.Y. Acad. Sci. 957 (2002) 210-229
17. Pellecchia M., and Reed J.C. Curr. Pharm. Des. 10 (2004) 1387-1398
18. Ragione F.D., Cucciola V., Borriello A., Pietra V.D., Racioppi L., Soldati G., Manna C., Galletti P., and Zappia V. Biochem. Biophys. Res. Commun. 1250 (1998) 53-58
19. Olas B., Wachowicz B., Stochmal A., and Oleszek W. Platelets 13 (2002) 167-173
20. Olas B., Wachowicz B., Stochmal A., and Oleszek W. Nutrition 19 (2003) 633-640
21. Marzocco S., Piacente S., Pizza C., Oleszek W., Stochmal A., Pinto A., Sorrentino R., and Autore G. Life Sci. 75 (2004) 1491-1501
22. Balestrieri C., Felice F., Piacente S., Pizza C., Montoro P., Oleszek W., Visciano V., and Balestrieri M.L. Biochem. Pharmacol. 71 (2006) 1479-1487
23. Barone G., Duca D., Silvestri A., Gomez-Paloma L., Riccio R., and Bifulco G. Chem.-Eur. J. 8 (2002) 3240-3245
24. Bifulco G., Bassarello C., Riccio R., and Gomez-Paloma L. Org. Lett. 6 (2004) 1025-1028
25. Plaza A., Piacente S., Perrone A., Hamed A., Pizza C., and Bifulco G. Tetrahedron 60 (2004) 12201-12209
26. Bassarello C., Zampella A., Monti M.C., Gomez-Paloma L., D'Auria M.V., Riccio R., and Bifulco G. Eur. J. Org. Chem. 3 (2006) 604-609
27. Adamo C., and Barone V. J. Chem. Phys. 108 (1998) 664-675
28. Ditchfield R. J. Chem. Phys. 56 (1972) 5688-5691
29. Wolinski K., Hinton J.F., and Pulay P. J. Am. Chem. Soc. 112 (1990) 8251-8260
30. Cimino P., Duca D., Gomez-Paloma L., Riccio R., and Bifulco G. Magn. Reson. Chem. 42 (2004) S26-S33
31. Norwood T.J., Boyd J., Heritage J.E., Soffe N., and Campbell I.D. J. Magn. Reson. 87 (1990) 488-501
32. Bax A., and Summers M.F. J. Am. Chem. Soc. 108 (1986) 2093-2094
33. Bax A., and Davis D.G. J. Magn. Reson. 63 (1985) 207-213
34. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03W, revision 6.0 (2003), Gaussian, Pittsburgh, PA