Dibenzylbutane and aryltetralone lignans from seeds of Virola sebifera

Phytochemistry

Volumn 61, Issue 4, 2002, Pages 427-432

  Rezende, Kênnia R ^a   Kato, Massuo J ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Aryltetralone lignans; Atropisomerism; Benzylbutane; Lignans; Myristicaceae; Virola sebifera

Indexed keywords

2' HYDROXY 3,4:4',5' BIS(METHYLENEDIOXY) 7 OXO 2,7' CYCLOLIGNAN; 3,4:3',4' BIS(METHYLENEDIOXY) 7,7' DIOXOLIGNAN; LIGNAN DERIVATIVE; UNCLASSIFIED DRUG; 2' HYDROXY 3,4 4',5' BIS(METHYLENEDIOXY) 7 OXO 2,7' CYCLOLIGNAN; 2'-HYDROXY-3,4-4',5'-BIS(METHYLENEDIOXY)-7-OXO-2,7'-CYCLOLIGNAN; 3,4 3',4' BIS(METHYLENEDIOXY) 7,7' DIOXOLIGNAN; 3,4-3',4'-BIS(METHYLENEDIOXY)-7,7'-DIOXOLIGNAN; LIGNAN;

ACETYLATION; ARTICLE; DRUG ISOLATION; ISOMERISM; LOW TEMPERATURE; PLANT; PLANT SEED; PROTON NUCLEAR MAGNETIC RESONANCE; VIROLA SEBIFERA; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; MYRISTICACEAE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

MYRISTICACEAE; VIROLA; VIROLA SEBIFERA;

LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYRISTICACEAE; SEEDS;

EID: 0036774738     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00242-X     Document Type: Article

References (22)

1. Ahn, B.-T., Lee, S., Lee, S.-B., Lee, E.-S., Kim, J.-G., Bok, S.-H., Jeong, T.-S., 2001. Low-density lipoprotein-antioxidant constituents of Saururus chinensis. Journal of Natural Products 64, 1562-1565.
2. Biftu, T., Hazra, B.G., Stevenson, R., Williams, J.R., 1978. Syntheses of lignans from 2,3-diaroylbutanes. Journal of Chemical Society Perkin Transaction 1, 1147-1150.
3. Charlton, J.L., OLeschuk, C.J., Chee, G.-L., 1996. Hindered rotation of aryltetralene lignans. Journal of Organic Chemistry 62, 3452-3457.
4. Corothie, E., Nakano, T., 1969. Constituents of the bark of Virola sebifera. Planta Medica 17, 184-188.
5. Culp, T.W., Harlow, R.D., Lichfield, C., Reiser, R., 1965. Analysis of triglycerides by consecutive chromatographic techniques. II. Ucuuba kernel fat. Journal of American Oil Chemists Society 42, 974-978.
6. Danelutte, A.P., Cavalheiro, A.J., Kato, M.J., 2000. Lignoids in seedlings of Virola sebifera. Phytochemical Analysis 11, 383-386.
7. Fernandes, A.M.A.P., Barata, L.E.S., Ferri, P.H., 1993. Lignans and a neolignan from Virola oleifera leaves. Phytochemistry 32, 1567-1572.
8. Fraga, R. L., 1987. Master thesis dissertation. Universidade Federal de São Carlos, São Carlos, Brazil.
9. Fukuda, Y., Nagata, M., Osawa, T., Namiki, M., 1986. Contribution of lignan analogues to antioxidant activity of refined unroasted sesame seed oil. Journal of American Oil Chemists Society 63, 1027-1031.
10. Joshi, B.S., Viswanathan, N., Balakrishnan, V., Gawad, D.H., Ravindranath, K.R., 1979. Attenuol: Structure, stereochemistry and synthesis. Tetrahedron 35, 1665-1671.
11. Kato, M.J., Lopes, L.M.X., Paulino F°, H.F., Yoshida, M., Gottlieb, O.R., 1985. Acylresorcinols from Virola sebifera and Virola elongata. Phytochemistry 24, 533-536.
12. Kato, M.J., Yoshida, M., Gottlieb, O.R., 1990. Neolignans from fruits of Virola elongata. Phytochemistry 26, 1799-1810.
13. Kuo, Y.H., Kao, S.T., Lin, Y.T., 1976. Extractive Component from the Nutmeg of Myristica Simarum A. DC.: The structure of lignan ketone: Otobanone. Experientia 32, 828-829.
14. Lopes, L.M.X., Yoshida, M., Gottlieb, O.R., 1982. Lignoids and arylalkanones from fruits of Virola elongata. Phytochemistry 21, 751-755.
15. Lopes, L.M.X., Yoshida, M., Gottlieb, O.R., 1983. Dibenzylbutyrolactone lignans from Virola sebifera. Phytochemistry 22, 1516-1518.
16. Lopes, L.M.X., Yoshida, M., Gottlieb, O.R., 1984. Aryltetralone and arylindanone neolignans from Virola sebifera. Phytochemistry 23, 2021-2024.
17. Lopes, L.M.X., Yoshida, M., Gottlieb, O.R., 1984. Further lignoids from Virola sebifera. Phytochemistry 23, 2647-2652.
18. Martinez, V.J.C., Aldana, J.M.I., Cuca, S.L.E., 1999. Dibenzylbutane lignans from Virola sebifera. Phytochemistry 50, 883-886.
19. Silva, D.H.S., Lopes, N.P., Kato, M.J., Yoshida, M., 1997. Fatty acids from Myristicaceous seeds of myristic acid-rich species. Anais da Associação Brasileira de Quimica 46, 232-235.
20. Rodrigues, W.A., 1980. Revisão taxonômica das espécies de Virola Aublet (Myristicaceae) do Brasil. Acta Amazônica 10, 1-123.
21. Urzúa, A., Shamma, M., 1988. The 4-aryltetralones of Aristolochia chilensis. Journal of Natural Products 51, 117-121.
22. Wolf, C., Pirkle, W.H., Welch, C.J., Hochmulth, D.H., Konig, W.A., Chee, G., Charlton, J.L., 1997. Determination of enantiomerization barrier of arylnaphtalene lignans by cryogenic subcritical fluid chromatography and computer simulation. Journal of Organic Chemistry 62, 5208-5210.