Daphnane- and tigliane-type diterpenoid esters and orthoesters from Pimelea elongata

Journal of Natural Products

Volumn 73, Issue 11, 2010, Pages 1907-1913

  Hayes, Patricia Y ^a   Chow, Sharon ^b   Somerville, Michael J ^b   Fletcher, Mary T ^b   De Voss, James J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b DEPARTMENT OF AGRICULTURE AND FISHERIES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDRO 5 HYDROXY 9' METHYL 6ALPHA,7ALPHA EPOXY 12BETA ACETOXY 9,13,14 ORTHO 1ALPHA DECENOATE RESINIFERONOL 10' OIC ACID; 12 BETA ACETOXYHURATOXIN; 12 O CTANOYLPHORBOL 13 ACETATE; 12 O DECA 4 ENOYLPHORBOL 13 ACETATE; 12 O DECA 4,7 DIENOYLPHORBOL 13 ACETATE; 6ALPHA,7ALPHA EPOXY 4BETA,5BETA,9ALPHA,20 TETRAHYDROXY 13ALPHA (2E,4E) TETRADECA 2,4 DIENOYL 1 TIGLIEN 3 ONE; 6ALPHA,7ALPHA EPOXY 5BETAHYDROXY 12 DEOXYPHORBOL 13 DECANOATE; CYTOTOXIC AGENT; DITERPENOID; ESTER DERIVATIVE; GNIDIGLAUCIN; HURATOXIN; KIRKININE D; PHORBOL 13 ACETATE 12 DECANOATE; PIMELOTIDE A; PIMELOTIDE B; PIMELOTIDE C; PIMELOTIDE D; PLANT EXTRACT; SIMPLEXIN; TIGLIANE DERIVATIVE; UNCLASSIFIED DRUG; WIKSTROELIDE E;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; NONHUMAN; PIMELEA ELONGATA; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; THYMELAEACEAE;

DITERPENES; ESTERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; THYMELAEACEAE;

PIMELEA;

EID: 78650210589     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np1005746     Document Type: Article

References (39)

1. Everist, S. L. Poisonous Plants of Australia; Angus & Robertson: Sydney, 1981.
2. Wilson, S. J., Taylor, J. D., and McKenzie, R. A. Aust. Vet. J. 2007, 85, 201
3. Dadwell, L. P. In Plant-associated Toxins; Agricultural, Phytochemical and Ecological Aspects; Colegate, S. M. and Dorling, P. R., Eds.; CAB International: Wallingford, UK, 1994.
4. Rye, B. L. and Heads, M. J. Flora Aust. 1990, 18, 122-215
5. Freeman, P. W., Ritchie, E., and Taylor, W. C. Aust. J. Chem. 1979, 32, 2495-2506
6. Liao, S.-G., Chen, H.-D., and Yue, J.-M. Chem. Rev. 2009, 109, 1092-1140
7. Stanoeva, E., He, W., and De Kimpe, N. Bioorg. Med. Chem. 2004, 13, 17-28
8. He, W., Cik, M., Appendino, G., Van Puyvelde, L., Leysen, J. E., and De Kimpe, N. Mini Rev. Med. Chem. 2002, 2, 185-200
9. Schmidt, R. J. Naturally Occurring Phorbol Esters; Evans, F. J., Ed.; CRC Press: Boca Raton, FL, 1986; pp 217 - 243.
10. Chow, S., Fletcher, M. T., and McKenzie, R. A. J. Agric. Food Chem. 2010, 58, 7482-7487
11. Hayes, P. Y., Chow, S., Somerville, M. J., De Voss, J. J., and Fletcher, M. T. J. Nat. Prod. 2009, 72, 2081-2083
12. Erdelmeier, C. A. J., Van Leeuwen, P. A. S., and Kinghorn, A. D. Planta Med. 1988, 54, 71-75
13. Kupchan, S. M., Shizuri, Y., Sumner, W. C., Jr., Haynes, H. R., Leighton, A. P., and Sickles, B. R. J. Org. Chem. 1976, 41, 3850-3853
14. Zayed, S., Adolf, W., Hafez, A., and Hecker, E. Tetrahedron Lett. 1977, 39, 3481-3482
15. Abe, F., Iwase, Y., Yamauchi, T., Kinjo, K., and Yaga, S. Phytochemistry 1997, 44, 643-647
16. Roberts, H. B., McClure, T. J., Ritchie, E., Taylor, W. C., and Freeman, P. W. Aust. Vet. J. 1975, 51, 325-326
17. Powell, R. G., Weisleder, D., and Smith, C. R., Jr. J. Nat. Prod. 1985, 48, 102-107
18. Jolad, S. D., Hoffmann, J. J., Timmermann, B. N., Schram, K. H., Cole, J. R., Bates, R. B., Klenck, R. E., and Tempesta, M. S. J. Nat. Prod. 1983, 46, 675-680
19. Adolf, W. and Hecker, E. Planta Med. 1982, 45, 177-182
20. Zayed, S., Hafez, A., Adolf, W., and Hecker, E. Experientia 1977, 33, 1554-1555
21. Sakata, K., Kawazu, K., Mitsui, T., and Masaki, N. Tetrahedron Lett. 1971, 16, 1141-1144
22. Yaga, S., Kinjo, K., Hayashi, H., Matsuo, N., Abe, F., and Yamauchi, T. Phytochemistry 1993, 32, 141-143
23. Adolf, W., Dossaji, S. F., Seip, E. H., and Hecker, E. Phytochemistry 1985, 24, 2047-2049
24. Adolf, W., Seip, E. H., and Hecker, E. J. Nat. Prod. 1988, 51, 662-674
25. Zhang, S., Li, X., Zhang, F., Yang, P., Gao, X., and Song, Q. Bioorg. Med. Chem. 2006, 14, 3888-3895
26. Niwa, M., Takamizawa, H., Tatematsu, H., and Hirata, Y. Chem. Pharm. Bull. 1982, 30, 4518-4520
27. Naef, R., Velluz, A., and Jaquier, A. Eur. Food Res. Technol. 2006, 222, 554-558
28. Levin, D. and Warren, S. J. Chem. Soc., Perkin Trans. 1 1988, 7, 1799-1807
29. Bresch, H., Kreibich, G., Kubinyi, H., Schairer, H. U., Thielmann, H. W., and Hecker, E. Z. Naturforsch., B: Chem. Sci. 1968, 23, 539-547
30. Kirira, P. G., Rukunga, G. M., Wanyonyi, A. W., Muthaura, C. N., Mungai, G. M., Machocho, A. K., and Ndiege, I. O. J. Nat. Prod. 2007, 70, 842-845
31. Garigipati, R. S., Freyer, A. J., Whittle, R. R., and Weinreb, S. M. J. Am. Chem. Soc. 1984, 106, 7861-7867
32. Cow, C., Valentini, D., and Harrison, P. Can. J. Chem. 1997, 75, 884-889
33. Tyler, M. I. and Howden, M. E. H. J. Nat. Prod. 1985, 48, 440-445
34. The proposed assignment is based on the fact that all naturally occurring daphnane esters isolated to date are R -configured at C-4 and since all the 1α-alkyldaphnane orthoesters reported so far possess an S -configured methyl group (C-19) at C-2. (4)
35. Kupchan, S. M., Shizuri, Y., Murae, T., Sweeny, J. G., Haynes, H. R., Shen, M.-S., Barrick, J. C., Bryan, R. F., Van der Helm, D., and Wu, K. K. J. Am. Chem. Soc. 1976, 98, 5719-5720
36. Hafez, A., Adolf, W., and Hecker, E. Planta Med. 1983, 49, 3-8
37. Trudgill, P. W. Biodegradation 1990, 1, 93-105
38. Nomura, T., Kushiro, T., Yokota, T., Kamiya, Y., Bishop, G. J., and Yamaguchi, S. J. Biol. Chem. 2005, 18, 17873-17879
39. Kim, T.-W., Hwang, J.-Y., Kim, Y.-S., Joo, S.-H., Chang, S. C., Lee, J. S., Takatsuto, S., and Kim, S.-K. Plant Cell 2005, 17, 2397-2412