Antitumour activity of 3-chlorodeoxylapachol, a naphthoquinone from Avicennia germinans collected from an experimental plot in southern Florida

Journal of Pharmacy and Pharmacology

Volumn 57, Issue 9, 2005, Pages 1101-1108

  Jones, William P ^a,b   Lobo Echeverri, Tatiana ^a,c   Mi, Qiuwen ^a   Chai, Heebyung ^a   Lee, Dongho ^a,d   Soejarto, Djaja D ^a   Cordell, Geoffrey A ^a   Pezzuto, John M ^a,e   Swanson, Steven M ^a   Kinghorn, A Douglas ^a,b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSIDAD DE ANTIOQUIA   (Colombia)

^d Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^e PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORODEOXYLAPACHOL; AVICENNIA GERMINANS EXTRACT; NAPHTHOQUINONE; PETROLEUM ETHER; PLANT EXTRACT; SOLVENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; AVICENNIA GERMINANS; CARCASS; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FRACTIONATION; HOLLOW FIBER; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LUNG CANCER; MANGROVE; MASS SPECTROMETRY; MEDICINAL PLANT; MOUSE; NONHUMAN; PLANT LEAF; PROSTATE CANCER; SQUAMOUS CELL CARCINOMA; UNITED STATES;

ANTINEOPLASTIC AGENTS; AVICENNIA; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEUTERIUM; DRUG SCREENING ASSAYS, ANTITUMOR; FLORIDA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GEOGRAPHY; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PLANT EXTRACTS; PLANT LEAVES; PLANT STEMS;

EID: 25844526511     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.57.9.0005     Document Type: Article

References (31)

1. Araki, S., Katsumura, N., Butsugan, Y. (1991) Allylation of quinones by allylic indium reagents. J. Organomet. Chem. 415: 7-24
2. Boyd, M. R., Paull, K. D (1995) Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev. Res. 34: 91-109
3. Calderon, A. I., Angerhofer, C. K., Pezzuto, J. M., Farnsworth, N. R., Foster, R., Condit, R., Gupta, M. P., Soejarto, D. D. (2000) Forest plot as a tool to demonstrate the pharmaceutical potential of plants in a tropical forest of Panama. Econ. Bot. 54: 278-294
4. Casciari, J. J., Hollingshead, M. G., Alley, M. C., Mayo, J. G., Malspeis, L., Miyauchi, S., Grever, M. R., Weinstein, J. N. (1994) Growth and chemotherapeutic response of cells in a hollow-fiber in vitro solid tumor model. J. Natl Cancer. Inst. 86: 1846-1852
5. 13C NMR of lapachol and some related naphthoquinones. Magn. Resort. Chem. 27: 1176-1177
6. Driscoll, J. S., Hazard, G. F., Jr, Wood, H. B., Jr, Goldin, A. (1974) Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother. Rep. (Part 2) 4: 1-27
7. Fauvel, M. T., Taoubi, K., Gleye, J., Fourasté, I. (1993) Phenylpropanoid glycosides from Avicennia marina. Planta Med. 59: 387
8. Gribble, G. W. (2003) The diversity of naturally produced organohalogens. Chemosphere 52: 289-297
9. Gu, J. -Q., Graf, T. N., Lee, D., Chai, H. -B., Mi, Q., Kardono, L. B. S., Setyowati, F. M., Ismail, R., Riswan, S., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Swanson, S. M., Kroll, D. J., Falkinham, J. O., III, Wall, M. E., Wani, M. C., Kinghorn, A. D., Oberlies, N. H. (2004) Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. J. Nat. Prod. 67: 1156-1161
10. Ham, S. W., Park, J., Lee, S. -J., Kim, W., Kang, K., Choi, K. H. (1998) Naphthoquinone analogs as inactivators of cdc25 phosphatase. Bioorg. Med. Chem. Lett. 8: 2507-2510
11. Hollingshead, M. G., Alley, M. C., Camalier, R. F., Abbott, B. J., Mayo, J. G., Malspeis, L., Grever, M. R. (1995) In vivo cultivation of tumor cells in hollow fibers. Life Sci. 57: 131-141
12. Itoigawa, M., Ito, C., Tan, H. T. -W., Okuda, M., Tokuda, H., Nishino, H., Furukawa, H. (2001) Cancer chemopreventive activity of naphthoquinones and their analogs from Avicennia plants. Cancer Lett. 174: 135-139
13. Kapoor, N. K., Gupta, R. B., Khanna, R. N. (1982) Synthesis of naturally occurring naphthoquinones: deoxylapachol, 2,3-di-(3-methyl-but-2-enyl)-1,4- naphthoquinone, 2-methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone and lapachol. Indian J. Chem. (Section B) 21: 189-191
14. Kinghorn, A. D. (2001) Pharmacognosy in the 21st century. J. Pharm. Pharmacol. 53: 135-148
15. Kinghorn, A. D., Farnsworth, N. R., Soejarto, D. D., Cordell, G. A., Swanson, S. M., Pezzuto, J. M., Wani, M. C., Wall, M. E., Oberlies, N. H., Kroll, D. J., Kramer, R. A., Rose, W. C., Vite, G. D., Fairchild, C. R., Peterson, R. W., Wild, R. (2003) Novel strategies for the discovery of plant-derived anticancer agents. Pharm. Biol. 41S: 53-67
16. Kingston, D. G. I., Newman, D. J. (2002) Mother nature's combinatorial libraries; their influence on the synthesis of drugs. Curr. Opin. Drug Discov. Dev. 5: 304-316
17. König, G., Rimpler, H., Hunkler, D. (1987) Iridoid glucosides in Avicennia officinalis. Phytochemistry 26: 423-427
18. Mabberly, D. J. (1997) The plant book: a portable dictionary of vascular plants, 2nd edn. Cambridge University Press, Cambridge, UK
19. Mi, Q., Lantvit, D., Reyes-Lim, E., Chai, H., Zhao, W., Lee, I. -S., Peraza-Sánchez, S., Ngassapa, O., Kardono, L. B. S., Riswan, S., Hollingshead, M. G., Mayo, J. G., Farnsworth, N. R., Cordell, G. A., Kinghorn, A. D., Pezzuto, J. M. (2002) Evaluation of the potential cancer chemotherapeutic efficacy of natural product isolates employing in vivo hollow fiber tests. J. Nat. Prod. 65: 842-850
20. Monde, K., Satoh, H., Nakamura, M., Tamura, M., Takasugi, M. (1998) Organochlorine compounds from a terrestrial higher plant: structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii. J. Nat. Prod. 61: 913-921
21. Newman, D. J., Cragg, G. M., Snader, K. M. (2003) Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66: 1022-1037
22. Perry, N. B., Blunt, J. W., Munro, M. H. G. (1991) A cytotoxic and antifungal 1,4-naphthoquinone and related compounds from a New Zealand brown alga, Landsburgia quercifolia. J. Nat. Prod. 54: 978-985
23. Scholander, P. F., Hammel, H. T., Hemmingsen, E., Garey, W. (1962) Salt balance in mangroves. Plant Physiol. 37: 722-729
24. Seo, E.-K., Kim, N.-C., Mi, Q., Chai, H., Wall, M. E., Wani, M. C., Navarro, H. A., Burgess, J. P., Graham, J. G., Cabieses, F., Tan, G. T., Farnsworth, N. R., Pezzuto, J. M., Kinghorn, A. D. (2001) Macharistol, a new cytotoxic cinnamylphenol from the stems of Machaerium aristulatum. J. Nat. Prod. 64: 1483-1485
25. Sharaf, M., El-Ansari, M. A., Saleh, N. A. M. (2000) New flavonoids from Avicennia marina. Fitoterapia 71: 274-277
26. Sharp, H., Thomas, D. Currie, F, Bright, C., Latif, Z., Sarker, S. D., Nash, R. J. (2001) Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae). Biochem. Syst. Ecol. 29: 325-327
27. Siuda, J. F., DeBernardis, J. F. (1973) Naturally occurring halogenated organic compounds. Lloydia 36: 107-143
28. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., Boyd, M. R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl Cancer. Inst. 82: 1106-1112
29. Sobrado, M. A., Greaves, E. D. (2000) Leaf secretion composition of the mangrove species Avicennia germinans (L.) in relation to salinity: a case study by using total-reflection X-ray fluorescence analysis. Plant Sci. 159: 1-5
30. Subramanian, S. S., Vedantham, T. N. C. (1974) Chemical components of Avicennia officinalis. Indian J. Pharm. 36: 105-106
31. Wall, M. E., Wani, M. C., Brown, D. M., Fullas, F., Oswald, J. B., Josephson, F. F., Thornton, N. M., Pezzuto, J. M., Beecher, C. W. W., Farnsworth, N. R., Cordell, G. A., Kinghorn, A. D. (1996) Effect of tannins on screening of plant extracts for enzyme inhibitory activity and techniques for their removal. Phytomedicine 3: 281-285