(6,7-Dimethoxy-4-methylisoquinolinyl)-(4’-methoxyphenyl)-methanone, a New Benzylisoquinoline Alkaloid from Beilschmiedia brevipes
Abstract
:1. Introduction
2. Results and Discussion
Alkaloid | ||||||
---|---|---|---|---|---|---|
Positions | (1) | (2) | (3) | (1) | (2) | (3)* |
1 | 152.7 | 156.6 | 153.5 | |||
α | 6.23 s | 194.0 | 72.1 | 187.0 | ||
3 | 8.24 s | 8.40 d (6.0) | 8.42 d (5.6) | 140.0 | 137.5 | 139.9 |
4 | 7.52 d (6.0) | 7.53 d (5.6) | 128.2 | 120.0 | 121.1 | |
4a | 132.9 | 133.9 | 133.8 | |||
5 | 7.24 s | 7.06 s | 6.61 s | 101.4 | 105.3 | 104.7 |
6 | 152.1 | 153.1 | 153.0 | |||
7 | 150.4 | 150.1 | 150.9 | |||
8 | 7.58 s | 7.11 s | 7.20 s | 104.7 | 103.5 | 104.0 |
8a | 122.7 | 120.8 | 122.6 | |||
1′ | 129.9 | 135.2 | 129.7 | |||
2′ | 7.90 d (10.9) | 7.24 d (8.4) | 7.92 d (8.0) | 133.1 | 128.9 | 133.1 |
3′ | 6.90 d (10.9) | 6.78 d (8.4) | 6.93 d (8.0) | 113.5 | 114.1 | 113.6 |
4′ | 163.8 | 159.2 | 163.0 | |||
5′ | 6.90 d (10.9) | 6.78 d (8.4) | 6.93 d (8.0) | 113.5 | 114.1 | 113.6 |
6′ | 7.90 d (10.9) | 7.24 d (8.4) | 7.92 d (8.0) | 133.1 | 128.9 | 133.1 |
CH3-4 | 2.71 s | 16.4 | ||||
OMe-6 | 4.12 s | 3.97 s | 4.03 s | 55.9 | 56.1 | 56.0 |
OMe-7 | 3.99 s | 3.78 s | 3.93 s | 55.4 | 55.9 | 56.0 |
OMe-4′ | 3.93 s | 3.72 s | 3.85 s | 55.3 | 55.2 | 55.6 |
Biological Activity
Compounds | IC50 (μg/mL) |
---|---|
(6,7-Dimethoxy-4-methylisoquinolinyl)-(4’-methoxyphenyl)-methanone (1) | >100 |
(6,7-Dimethoxyisoquinolinyl)-(4’-methoxyphenyl)-methanone (3) [13] | 18.7 |
O,O-Dimethylcoclaurine [12] | 6.5 |
O-Methylvelucryptine [14] | 17.3 |
Armepavine [15] | 42.2 |
Norarmepavine [16]. | 44.5 |
3. Experimental
3.1. General
3.2. Plant Materials
3.3. Extraction and Isolation of the Alkaloids
3.3. Cytotoxic Assays
4. Conclusions
Acknowledgements
References
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Pudjiastuti, P.; Mukhtar, M.R.; Hadi, A.H.A.; Saidi, N.; Morita, H.; Litaudon, M.; Awang, K. (6,7-Dimethoxy-4-methylisoquinolinyl)-(4’-methoxyphenyl)-methanone, a New Benzylisoquinoline Alkaloid from Beilschmiedia brevipes. Molecules 2010, 15, 2339-2346. https://doi.org/10.3390/molecules15042339
Pudjiastuti P, Mukhtar MR, Hadi AHA, Saidi N, Morita H, Litaudon M, Awang K. (6,7-Dimethoxy-4-methylisoquinolinyl)-(4’-methoxyphenyl)-methanone, a New Benzylisoquinoline Alkaloid from Beilschmiedia brevipes. Molecules. 2010; 15(4):2339-2346. https://doi.org/10.3390/molecules15042339
Chicago/Turabian StylePudjiastuti, Pratiwi, Mat Ropi Mukhtar, A. Hamid A. Hadi, Nurdin Saidi, Hiroshi Morita, Marc Litaudon, and Khalijah Awang. 2010. "(6,7-Dimethoxy-4-methylisoquinolinyl)-(4’-methoxyphenyl)-methanone, a New Benzylisoquinoline Alkaloid from Beilschmiedia brevipes" Molecules 15, no. 4: 2339-2346. https://doi.org/10.3390/molecules15042339