Structural modifications of plumieride isolated from Plumeria bicolor and the effect of these modifications on in vitro anticancer activity

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6165-6172

  Dobhal, Mahabeer P ^a,b   Li, Guolin ^a   Gryshuk, Amy ^a   Graham, Andrew ^a   Bhatanager, Atul K ^b   Khaja, Sirajud D ^a   Joshi, Yogesh C ^b   Sharma, Mahesh C ^b   Oseroff, Allan ^a   Pandey, Ravindra K ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

^b UNIVERSITY OF RAJASTHAN   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CORRELATION METHODS; CYTOLOGY; DERIVATIVES; EXTRACTION; METHANOL; TOXICITY; TUMORS;

CYTOTOXIC ACTIVITY; LIPOPHILICITY; STRUCTURAL MODIFICATIONS;

BIOCHEMICAL ENGINEERING;

ANTINEOPLASTIC AGENT; PLUMERIA BICOLOR EXTRACT; PLUMIERIDE; PLUMIERIDE PENTAACETATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BARK; DRUG CYTOTOXICITY; DRUG ISOLATION; FIBROSARCOMA; HIGHER PLANT; HUMAN; HUMAN CELL; IC 50; PARTITION COEFFICIENT; PLUMERIA BICOLOR; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APOCYNACEAE; CARBOHYDRATE SEQUENCE; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPIRO COMPOUNDS;

EID: 4644280831     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0491408     Document Type: Article

References (34)

1. Dev, S. Curr. Sci. 1997, 73, 909.
2. Ho, C.-T., Li, J.-K., Zheng, Q. Y., Eds.; Oriental Foods and Herbs, Chemistry and Health Effects; ACS Symposium Series 859, American Chemical Society: Washington, DC, 2003.
3. Corey, E. J.; Chung, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989.
4. Pandey, R. K. Synthetic Strategies in Designing Porphyrin-Based Photosensitizers for Photodynamic Therapy, Organic Photochemistry and Photobiology; Hosspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, 2004.
5. Chen, Y.; Li, G.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105-1134.
6. (a) Pandey, R. K.; Sumlin, A. B.; Potter, W. R.; Bellnier, D. A.; Henderson, B. W.; Constantine, S.; Aoudia, A.; Rodgers, M. A. J.; Smith, K. M.; Dougherty, T. J. Photochem. Photobiol. 1996, 63, 194.
7. (b) Henderson, B. W.; Bellnier, D. A.; Graco, W. R.; Sharma, A.; Pandey, R. K.; Vaughan, L.; Weishaupt, K. R.; Dougherty, T. J. Cancer Res. 1997, 57, 4000.
8. (c) Zheng, G.; Potter, W. R.; Camacho, S.; Missert, J. R.; Wang, G.; Bellnier, D. A.; Henderson, B. W.; Rodgers, M. A. J.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2001, 44, 1540.
9. (d) Chen, Y.; Graham, A.; Potter, W.; Morgan, J.; Vaughan, L.; Bellnier, D. A.; Henderson, B. W.; Oseroff, A.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2002, 45, 255.
10. (e) Li, G.; Graham, A.; Chen, Y.; Dobhal, M. P.; Morgan, J.; Zheng, G.; Kozyrev, A.; Oseroff, A.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2003, 46, 5349.
11. Dougherty, T. J.; Levy, J. Photodynamic Therapy (PDT) and Clinical Applications, Biomedical Photonics Handbook; Vo-Dinh, T., Ed.; CRC Press: Boca Raton, 2002.
12. Rungta, A.; Zheng, G.; Missert, J. R.; Potter, W.; Dougherty, T. J.; Pandey, R. K. Bioorg. Med. Chem. Lett. 2000, 10, 1463.
13. Gryshuk, A.; Graham, A.; Pandey, S. K.; Potter, W. R.; Missert, J. R.; Oseroff, A.; Dougherty, T. J.; Pandey, R. K. Photochem. Photobiol. 2002, 76, 555.
14. Pandey, R. K. et al. Unpublished results.
15. (a) Unny, R.; Chauhan, A. K.; Joshi, Y. C.; Dobhal, M. P.; Gupta, R. S. Phytomedicine 2003, 10, 233.
16. (b) Gupta, R. S.; Bhatnager, A. K.; Joshi, Y. C.; Sharma, R.; Sharma, A. Phytomedicine 2004, 11, 169.
17. (c) Gupta, R. S.; Sharma, R.; Sharma, A.; Chaudhary, R.; Bhatnager, A. K.; Dobhal, M. P.; Joshi, Y. C.; Sharma, M. C. Pharm. Biol. 2002, 40, 411.
18. (d) Gupta, R. S.; Sharma, R.; Sharma, A.; Bhatnager, A. K.; Dobhal, M. P.; Joshi, Y. C.; Sharma, M. C. Asian J. Androl. 2002, 4, 175.
19. Perry, L. M.; Metzger, J. Med. Plants East South Asia 1980, 29.
20. (a) Kupchan, S. M.; Dessertine, A. I.; Blaylock, B. T.; Bryan, R. F. J. Org. Chem. 1974, 39, 2466.
21. (b) Kardono, L. B. S.; Tsauri, S.; Padmawinta, K.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 1990, 53, 1447.
22. (c) Coppen, J. J. W.; Cobb, A. L. Phytochemistry 1983, 22, 125.
23. (d) Kardono, L. B. S.; Tsauri, S.; Padmawinta, Kinghorn, A. D. Phytochemistry 1990, 29, 2995.
24. (a) Anderson, J. E.; Chang, C. J.; McLaughlin, J. L. J. Nat. Prod. 1988, 51, 307.
25. (b) Adam, G.; Khoi, N. H.; Bergner, C.; Lien, N. T. Phytochemistry 1979, 18, 1399.
26. (a) Misra, T. N.; Singh, R. S. Upadhyay, J. Phytochemistry 1983, 22, 603.
27. (b) Dobhal, M. P.; Hasan, A. M.; Sharma, M. C.; Joshi, Y. C. Phytochemistry 1999, 51, 319.
28. (c) Barreta, A. de sa; Carvalho, M. G. De; Nery, I De A.; Kaplan, M. A. C. J. Braz. Chem. Soc. 1998, 9, 430.
29. (d) Abe, F.; Mori, T.; Yamauchi, T. Chem. Pharm. Bull. 1984, 32, 2947.
30. Rini, J. M. Annu. Tev. Biophys. Biomol. Struct. 1995, 24, 551.
31. Brewer, C. F.; Miceli, M. C.; Baum, L. G. Curr. Opin. Struct. Biol. 2002, 12, 616.
32. Hirabayashi, J.; Hashidate, T.; Arata, Y.; Nishi, N.; Nakamura, Takanori; Hirashima, M.; Urashima, T.; Oka, Toshihiko; Futai, M.; Muller, W. F. G.; Yagi, F.; Kasai, K. Biochem. Biophys. Acta 2002, 1572, 232.
33. (a) Riss, D.; Jin, L.; Qian, X.; Nayliss, J.; Scheithauer, B. W.; Young, W. F.; Vidal, S.; Kovacs, K.; Raz, A. Lloyd, R. V. Cancer Res. 2003, 63, 2251.
34. (b) Zheng, G.; Graham, A.; Shibata, M.; Missert, J. R.; Oseroff, A.; Dougherty, T. J.; Pandey, R. K. J. Org. Chem. 2001, 66, 8709.