Letters 389
Alkaloids from Dehaasia
The third and more polar component had
incrassata
UV (MeOH) maxima at 223 and 283 nm and a mass of 608 which fits the molecular formula C37H40N206. The 1H-NMR spectrum shows the presence of 3 methoxyl groups and two
IlcramM. Said1'4, A. Latiff2, Sarah J. Partridge3, and J. David Phillipson3
N-methyl groups. The MS fragmentation pattern with major peaks at in/z = 608, 607, 397, 396, 395, 382, 381, 199, 198, 175, 174, 146, and 145 suggests a bisben-
1
Department of Chemistry, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Malaysia 2 Department of Botany, Universiti Kebangsaan Malaysia, 43600 UKM Bangi. Malaysia
'
Department of Pharmacognasy, The School of Pharmacy, University of London, 29—39 Brunswick Square, London WC1N lAX, U. K. Address for correspondence
zylisoquinoline alkaloid with the three OMe groups all in the
upper portion of the molecule and one OH group in the lower portion (4). The NMR pattern (5) suggests a 1R,1'S configuration with the ether linkages between 7—8' and
11—12' carbons. The above data show the bisbenzylisoquinoline alkaloid to be oxyacanthine which was further confirmed by comparison with the NMR and mass
Received: April 3, 1990
spectra of an authentic sample of oxyacanthine hy-
Dehaasia incrassata (Lauraceae) is a medium-sized tree that can grow up to 25 m high and is found in the jungles throughout the Malaysian Peninsula, The leaves are large and oblong (Ca. 25 x 10cm) while the fruits (ca. 5 x 2 cm) are shiny black on bright red stout stalks (3 cm). The tree has no known medicinal use but the wood
is said to be useful as timber for house building and the fruits are said to be very poisonous (1). There have been very few detailed studies on the alkaloids of Dehaasia except for D. triandra (2) which was shown to contain apor-
Acknowledgements The research was partly funded by IFS F/1082 — 4-07-03-005, and the British Council under its CICHE programme and their support is greatly appreciated. 1, IRPA
References 1
phines and bisbenzylisoquinoline alkaloids.
Extraction of the fresh leaves (500 g) and
2
the bark (350g) was carried out at room temperature (30 °C) for two weeks using ethanol. On evaporation of the solvent, the residue from the extract was taken into dilute hydrochloric acid, filtered and basified with 10% Na2CO3 solution which was then extracted with dichloromethane. It was found that the leaves contained more alkaloids (1.6%) when compared to the bark (0.6%) and showed a slightly different TLC profile. The alkaloids from the bark did not show any antimicrobial activity whereas the alkaloid mix-
ture from the leaves was active against Streptococcus
pneumoniae, Proteus inirabilis, and Pseudornonas pseudoinallei. Further fractionation of the crude alkaloid mixture from the leaves by column chromatography (silica gel, Merck, 70—230mesh) using CHC13-MeOH mixtures (9 : 1 to 6: 4) as eluent gave three major components. The first component was obtained from the 9: 1 mixture, the second from the 7: 3 mixture, while the third was from the 6 : 4 mixture.
The first two components had UV (MeOH) absorption maxima at 210, 267, and 302 nm, indicatingthe
presence of an aporphine ring system. The 1H-NMR (300 MHz) spectra looked similar for both compounds except one did not have a singlet at b = 2.54 ppm due to anN-
methyl group. This was further reflected in the mass spectra when one component had fragments of m/z = 341
(M), 340,327,326,324, 3l0whiletheotherhadm/z= 327 (M), 326, 312, 310,297,296. Comparison ofotherphysical data (m.p. and optical rotation) with the literature (3) indi-
cated the two aporphines to be isocorydine and norisocorydine.
6
Burkill, I. H. (1935) A Dictionary of Economic Products of the Malay Peninsula, 2 Vols., Crown agents for the colonies, London, (Reprint 1966, Ministry of Agriculture and Cooperatives, Kuala Lumpur), p.
788.
Lu, S. T., Tsai, I. L., Leou, S. P. (1989) Phytochemistry 28,615—620. Guinaudeau, FL, I,eboeuf, M., Cave, A. (1975) Lloydia 38, 275—338. Baldas, J., Bick, I. R. C., Ibuka, T., Kapil, R. S., Porter, Q. N. (1972) J.
Chem. Soc., Perkin Trans. 1,592—596. Guinaudeau, H., Freyer, A. J., Shamma, M. (1986) Nat. Prod. Report 477—488. O'Neill, M. J., Bray, D. H., Boardman, P., Chan, K. L., Phillipson, J. D. (1987)J. Nat. Prod. 50, 41—48.
Downloaded by: University of Arizona Library. Copyrighted material.
drochloride. Oxyacanthine was also screened for antimalarial activity against Plasmodium falciparum KI strain (6) and found to be active with an IC50 value of 0.31 jg/ml.
Alkaloids from Dehaasia
The third and more polar component had
incrassata
UV (MeOH) maxima at 223 and 283 nm and a mass of 608 which fits the molecular formula C37H40N206. The 1H-NMR spectrum shows the presence of 3 methoxyl groups and two
IlcramM. Said1'4, A. Latiff2, Sarah J. Partridge3, and J. David Phillipson3
N-methyl groups. The MS fragmentation pattern with major peaks at in/z = 608, 607, 397, 396, 395, 382, 381, 199, 198, 175, 174, 146, and 145 suggests a bisben-
1
Department of Chemistry, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Malaysia 2 Department of Botany, Universiti Kebangsaan Malaysia, 43600 UKM Bangi. Malaysia
'
Department of Pharmacognasy, The School of Pharmacy, University of London, 29—39 Brunswick Square, London WC1N lAX, U. K. Address for correspondence
zylisoquinoline alkaloid with the three OMe groups all in the
upper portion of the molecule and one OH group in the lower portion (4). The NMR pattern (5) suggests a 1R,1'S configuration with the ether linkages between 7—8' and
11—12' carbons. The above data show the bisbenzylisoquinoline alkaloid to be oxyacanthine which was further confirmed by comparison with the NMR and mass
Received: April 3, 1990
spectra of an authentic sample of oxyacanthine hy-
Dehaasia incrassata (Lauraceae) is a medium-sized tree that can grow up to 25 m high and is found in the jungles throughout the Malaysian Peninsula, The leaves are large and oblong (Ca. 25 x 10cm) while the fruits (ca. 5 x 2 cm) are shiny black on bright red stout stalks (3 cm). The tree has no known medicinal use but the wood
is said to be useful as timber for house building and the fruits are said to be very poisonous (1). There have been very few detailed studies on the alkaloids of Dehaasia except for D. triandra (2) which was shown to contain apor-
Acknowledgements The research was partly funded by IFS F/1082 — 4-07-03-005, and the British Council under its CICHE programme and their support is greatly appreciated. 1, IRPA
References 1
phines and bisbenzylisoquinoline alkaloids.
Extraction of the fresh leaves (500 g) and
2
the bark (350g) was carried out at room temperature (30 °C) for two weeks using ethanol. On evaporation of the solvent, the residue from the extract was taken into dilute hydrochloric acid, filtered and basified with 10% Na2CO3 solution which was then extracted with dichloromethane. It was found that the leaves contained more alkaloids (1.6%) when compared to the bark (0.6%) and showed a slightly different TLC profile. The alkaloids from the bark did not show any antimicrobial activity whereas the alkaloid mix-
ture from the leaves was active against Streptococcus
pneumoniae, Proteus inirabilis, and Pseudornonas pseudoinallei. Further fractionation of the crude alkaloid mixture from the leaves by column chromatography (silica gel, Merck, 70—230mesh) using CHC13-MeOH mixtures (9 : 1 to 6: 4) as eluent gave three major components. The first component was obtained from the 9: 1 mixture, the second from the 7: 3 mixture, while the third was from the 6 : 4 mixture.
The first two components had UV (MeOH) absorption maxima at 210, 267, and 302 nm, indicatingthe
presence of an aporphine ring system. The 1H-NMR (300 MHz) spectra looked similar for both compounds except one did not have a singlet at b = 2.54 ppm due to anN-
methyl group. This was further reflected in the mass spectra when one component had fragments of m/z = 341
(M), 340,327,326,324, 3l0whiletheotherhadm/z= 327 (M), 326, 312, 310,297,296. Comparison ofotherphysical data (m.p. and optical rotation) with the literature (3) indi-
cated the two aporphines to be isocorydine and norisocorydine.
6
Burkill, I. H. (1935) A Dictionary of Economic Products of the Malay Peninsula, 2 Vols., Crown agents for the colonies, London, (Reprint 1966, Ministry of Agriculture and Cooperatives, Kuala Lumpur), p.
788.
Lu, S. T., Tsai, I. L., Leou, S. P. (1989) Phytochemistry 28,615—620. Guinaudeau, FL, I,eboeuf, M., Cave, A. (1975) Lloydia 38, 275—338. Baldas, J., Bick, I. R. C., Ibuka, T., Kapil, R. S., Porter, Q. N. (1972) J.
Chem. Soc., Perkin Trans. 1,592—596. Guinaudeau, H., Freyer, A. J., Shamma, M. (1986) Nat. Prod. Report 477—488. O'Neill, M. J., Bray, D. H., Boardman, P., Chan, K. L., Phillipson, J. D. (1987)J. Nat. Prod. 50, 41—48.
Downloaded by: University of Arizona Library. Copyrighted material.
drochloride. Oxyacanthine was also screened for antimalarial activity against Plasmodium falciparum KI strain (6) and found to be active with an IC50 value of 0.31 jg/ml.
