BENZYLISOQUINOLINE ALKALOIDS FROM BARK OF Cryptocarya rugulosa

https://doi.org/10.22146/ijc.21421

Nurdin Saidi(1*), Hiroshi Morita(2), Marc Litaudon(3), Mat Ropi Mukhtar(4), Khalijah Awang(5), A. Hamid A. Hadi(6)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Syiah Kuala University, Banda Aceh, 23111
(2) Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa, Tokyo 142-8501
(3) Institut de Chimie des Substances Naturelles, Centre Nationale des Recherches Scientifique, 91198, Gif-sur Yvette, Cedex
(4) Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur
(5) Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur
(6) Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur
(*) Corresponding Author

Abstract


Seven known Benzylisoquinoline alkaloids, Papraline 1, (+)-norcinnamolaurine 2, (+)-codamine 3, (+)-6-methoxy-1-(3'-methoxybenzyl)-N-methyl-7-isoquinolinol 4, (+)-reticuline N-oxide 5, (+)-reticuline 6 and (-)-N-methylisococlaurine 7 were isolated from bark of Cryptocarya rugulosa. A combination of 1D-NMR (1H, 13C, DEPT, NOE), 2D-NMR (COSY, NOESY, HMQC, HMBC), MS (HRESI+, FAB+ and EI) spectroscopy used to elucidate the structure.

Keywords


Cryptocarya rugulosa; lauraceae; benzylisoquinoline alkaloid

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References

[1] Ng, F.S.P., 1989, Tree Flora of Malaya; A Manual for Forester, Longman Malaysia, Kuala Lumpur, 132–138.

[2] Khalijah, A., Hadi, A.H.A., Saidi, N., Mukhtar, M.R., Morita, H., and Litaudon, M., 2008, Fitoterapia, 79, 308–310.

[3] Borthakur, N., Mahanta, P.K., and Rastogi, R.C., 1981, Phytochem., 20, 501–504.

[4] Saidi, N., Hadi, A.H.A., Khalijah, A., and Mukhtar, M.R., 2009, Indo. J. Chem., 9, 3, 461–465.

[5] Lee, S.S., Chen, C.H., and Liu, Y.C., 1993, J. Nat. Prod., 56, 2, 227–232.

[6] Chang, W.T., Lee, S.S., Chueh, F.S., and Liu, K.C.S., 1998, Phytochem., 48, 1, 119–124.

[7] Lin, F.W., Wu, P.L., and Wu, T.S., 2001, Chem, Pharm. Bull., 49, 10, 1292–1294.

[8] Lee, S.S., Liu, Y.C., and Chen, C.H., 1990, J. Nat. Prod., 53, 5, 1267–1271.

[9] Lee, S.S., Lin, Y.J., Chen, C.K., Liu, K.S., and Chen, C.H., 1993, J. Nat. Prod., 56, 11, 1971–1976.

[10] Bick, I.R.C., Sevenet, T., Sinchai, W., Skelton, B.W., and White, A.H., 1981, Aust. J. Chem., 34, 195–200.

[11] Lamberton, J.A., and Vashist, V.N., 1972, Aust. J. Chem., 25, 2737–2738.

[12] Atta-Ur-Rahman, Ahmad, S., Bhatti M.K., and Choudhary, M.I., 1995, Phytochem., 40, 2, 593–596.

[13] Richard, A.M., Janssen, M., Robert, J., Lousberg, J.Ch., Wijkens, P., Kruk, C., and Theuns, H.G., 1989, Phytochem., 28, 10, 2833–2839.

[14] Debourges, D., Roblot, F., Hocquemiller, R., and Cave, A., 1987, J. Nat. Prod., 50, 5, 852–859.

[15] Kashiwada, Y., Aoshima, A., Ikeshiro, Y., Chen, Y.P., Furukawa, H., Itoigawa, M., Fujioka, T., Mihashi, K., Cosentino, L.M., Morris-Natschke S.L., and Lee, K.H., 2005, Bioinorg. Med. Chem., 13, 443–448.

[16] Gellert, E., and Summons, R.E., 1970, Aust. J. Chem., 23, 2095–2099.

[17] Chowdhury, B.K., Sethi M.L., and Lloyd, H.A., 1976, Phytochem., 15, 1803–1804.

[18] Gellert, E., and Summons, R.E., 1969, Tetrahedron Lett., 58, 5055–5058.

[19] Richard, A.M., Janssen, M., Wijkens, P., Kruk, C., Biessels, H.W.A., Menichini F., and Theuns, H.G., 1990, Phytochem., 29, 10, 3331–3339.

[20] Marsaioli, A.J., Ruveda, E.A., and Reis, F. de A.M., 1978, Phytochem., 17, 1655–1658.

[21] Atta-Ur-Rahman, Wahab, A.T., Ahmad, S., Nawaz, S.A., and Choudhary, M.I., 2004, Chem. Pharm. Bull. 52, 7, 802–806.

[22] Dasgupta, S., and Ray, A.B., 1979, J. Nat. Prod., 42, 4, 399–406.

[23] Israilov, I.A., Irgashev, T., and Yunusov, M.S., 1985, Chem. Nat. Comp., 69, 842–843.

[24] Kametami, T., and Ihara, M., 1980, J. Chem. Soc., Perkin Trans. 1, 629–631.

[25] Ohiri, F.C., Verpoorte, R., and Svendsen, A.B., 1983, Planta Med., 47, 87.

[26] El-Shabrawiy, A.O., Schiff, Jr, P.L., Slatkin, D.J., Dasgupta, S., Ray, A.B., and Tripathi, V.J., 1984, Heterocycles, 22, 993.

[27] Leet, J.E., Freyer, A.J., Minard, R.D., and Shamma, M., 1985, J. Chem. Soc., Perkin Trans. 1, 1565.

[28] Al-Amri, A.M., Smith, R.M., EL-Haj, B.M., and Juma’a, M.H., 2004, Forensic Sci. Int., 140, 175–183.

[29] Castro, O.C., Lopes, J.L. and Vergera, A.G. 1985, Phytochem., 24, 1, 203–204.

[30] Jendrzejewski, S., 1990, Phytochem., 29, 1, 135–139.

[31] Brochmann-Hanssen, E., and Nielsen, B., 1965, Tetrahedron Lett., 18, 1271–1274.

[32] Bhakuni, D.S., Satish, S., and Dhar, M.M., 1972, Tetrahedron, 28, 4579–4582.

[33] Kunitomo, J., Yoshikawa, Y., Tanaka, S., Imori, Y., and Isoi, K., 1973, Phytochem., 12, 699–701.



DOI: https://doi.org/10.22146/ijc.21421

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