Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 58, Issue 7-8, 2003, Pages 521-526

  Chang, Yuh Chwen ^a,b   Chang, Fang Rong ^a   Khalil, Ashraf T ^a   Hsieh, Pei Wen ^a   Wu, Yang Chang ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b KAO YUAN INSTITUTE OF TECHNOLOGY   (Taiwan)

Author keywords

Argemone mexicana; Cytotoxicity; N Demethyloxysanguinarine

Indexed keywords

ARGEMONE; ARGEMONE MEXICANA;

EID: 0042657819     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2003-7-813     Document Type: Article

References (25)

1. Bjornland T., Lianen-Jensen S., and Throndsen J. (1989), Carotenoids of the marine chrysophyte Pelagococcus subviridis. Phytochemistry 28, 3347-3353.
2. Capasso A., Piacente S., Pizza C., Tommasi N. D., Jativa C., and Sorrentino L. (1997), Isoquinoline alkaloids from Argemone mexicana reduce morphine withdrawal in guinea pig isolated ileum. Planta Med. 63, 326-28.
3. Castro O. C., Lopez J. V., and Vergara A. G. (1985), Aporphine alkaloids from Phoebe pittieri. Phytochemistry 24, 203-204.
4. Chang Y.C, Hsieh P. W., Chang F. R., Wu R. R., Liaw, C. C., Lee K. H., and Wu Y. C. (2003), New protopine and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana. Planta Med. 69, 148-152.
5. Chen C. Y., Chang F. R., and Wu Y. C. (1997), The constituents from the stems of Annona cherimola. J. Chin. Chem. Soc. 44, 313-319.
6. Chen I. S., Chen J. J., Duh C. Y., Tsai I. L., and Chang C. T. (1997), New aporphine alkaloids and cytotoxic constituents of Hernandia nymphaeifolia. Planta Med. 63, 154-157.
7. Dinda B., and Bandyopadhyay M. J. (1986), Free amino acids of Argemone mexicana. J. Indian. Chem. Soc. 63, 934-36.
8. Gunstone F. D., Holliday J. A., and Scrimgeour C. M. (1977), Fatty acids, Part 51. The long-chain oxoacids (argemonic acids) in Argemone mexicana seed oil. Chem. Phys. Lipids 20, 331-335.
9. Hanaoka M., Nagami K., Inoue M., and Yasuda S. (1983), Chemical transformation of Protoberberines. IV. A novel, simple synthesis of (±)-canadaline and a retroprotoberberine from tetrahydroberberine. Chem. Pharm. Bull. 31, 2685-90.
10. Harborne J. B. and Mabry T. J. (1982), The Flavonoids: Aadvances in Research. Chapman and Hall, London.
11. Harborne J. B. and Williams C. A. (1983), Flavonoids in the seeds of Argemone mexicana: a reappraisal. Phytochemistry 22, 1520-1521.
12. Hussain S. F., Nakkady S., Khan L., and Shamma M. (1983), oxyhydrastinine, an isoquinoline alkaloid from the Papaveraceae. Phytochemistry 22, 319-320.
13. Itokawa H., Akasu M., and Fujita M. (1973), Several oxidized sterols isolated from callus tissue of Stephania cepharantha. Chem. Pharm. Bull. 21, 1386-1387.
14. Kawahara N., Sekita S., Satake M., and Udagawa S. I. (1992), A nucleoside derivative from Emericellia nidulans. Phytochemistry 31, 1409-1410.
15. Kim S. R., Hwang S. Y., Jang Y. P., Park M. J., Markelonis G..J., Oh T. H., and Kim Y. C. (1999), Protopine from Corydalis ternate has anticholinesterase and antiamnesic activities. Planta Med. 65, 218-21.
16. Krane B. D., Fagbule M. O., Shamma M., and Gozler B. (1984), The benzophenanthridine alkaloids. J. Nat. Prod. 47, 1-43.
17. Malich G., Markovic B., and Winder C. (1997), The sensitivity and specificity of the MTS tetrazolium assay for detecting the in vitro cytotoxicity of 20 chemicals using human cell lines. Toxicology 124, 179-192.
18. Mozawa M., Takahashi K., Kato K., and Akita H. (2000), Enantioselective synthesis of (2R,4′R,8′R)-α-tocopherol (vitamin E) based on enzymatic function. Chem. Pharm. Bull. 48, 272-277.
19. Nakkady S. and Shamma, M. (1988), Studies on the chemical constituents of Argemone mexicana. Egypt. J. Pharm. Sci. 29, 53-61.
20. Pandey V. B., Ray A. B., and Dasgupta B. (1979), Minor alkaloids of Fumaria indica seeds. Phytochemistry 18, 695-696.
21. Shamma M., Minard R. D., Freyer A. J., and Guinaudeau H. (1983), Novel biogenetic pathways from (+)-reticuline. Three dimeric alkaloids: (+)-vanuatine, (+)-vateamine, and (+)-Malekulatine. J. Org. Chem. 48, 3957-3960.
22. Shin J. S., Yun-Choi H. S., Kim E. I., and Lee M. K. (1999), Inhibitory effects of higenamine on dopamine content in PC12 cells. Planta Med. 65, 452-455.
23. Tanaka S., Sakata Y., Morimoto K., Tambe Y., Watanabe Y., Honda G., Tabata M., Oshima T., Masuda T., Umezawa T., Shimada M., Nagakura N., Kamisako W., Kashiwada Y., and Ikeshiro T. (2001), Influence of natural and synthetic compounds on cell surface expression of cell adhesion molecules, ICAM-1 and VCAM-1. Planta Med. 67, 108-113.
24. Williams R. D. and Ellis B. E. (1993), Alkaloids from Agrobacterium rhizogenes- transformed Papaver somniferum cultures. Phytochemistry 32, 719-723.
25. Xu Q. and Lin M. (1999), Benzylisoquinoline alkaloids from Gnetum parvifolium. J. Nat. Prod. 62, 1025-1027.