ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia

Phytochemistry

Volumn 68, Issue 4, 2007, Pages 546-553

  Grace, Mary H ^a   Faraldos, Juan A ^a   Lila, Mary Ann ^a   Coates, Robert M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Cytotoxicity; Diosphenols; Diterpenoids; ent Beyeranes; Euphorbiaceae; Excoecaria parvifolia; Heartwood; L1210

Indexed keywords

DITERPENE; VEGETABLE OIL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; EUPHORBIA; ISOLATION AND PURIFICATION; WOOD;

DITERPENES; EUPHORBIACEAE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT OILS; WOOD;

EUPHORBIA; EUPHORBIACEAE; EXCOECARIA PARVIFOLIA;

EID: 33846563961     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.11.010     Document Type: Article

References (39)

1. Anjaneyulu A.S.R., Anjaneyulu V., and Rao V.L. New beyerane and isopimarane diterpenoids from Rhizophora mucronata. J. Asian Nat. Prod. Res. 4 (2002) 53-61
2. Anjaneyulu A.S.R., and Rao V.L. Five diterpenoids (agallochins A-E) from the mangrove plant Excoecaria agallocha Linn. Phytochemistry 55 (2000) 891-901
3. Baarschers W.H., Horn D.H.S., and Johnson L.F. The structure of some diterpenes from tambooti wood Spirostachys africana. J. Chem. Soc. (1962) 4046-4055
4. Bakker H.J., Ghisalberti E.L., and Jefferries P.R. Biosynthesis of diterpenes in Beyeria leschenaultia. Phytochemistry 11 (1972) 2221-2231
5. Buckingham J. (Exec. Ed.). Dictionary of Natural Products (1994), Chapman & Hall, London
6. 13C NMR spectra and investigation of hindered side-chain rotation in lupeol derivatives. Magn. Reson. Chem 38 (2000) 488-493
7. Chalmers A.A., Gorst-Allman C.P., and Piacenza L.P.L. Carbon-13 NMR spectra of stachenol and related derivatives. Tetrahedron Lett. 18 (1977) 1665-1668
8. Coates R.M., Conradi R.A., Ley D.A., Akeson A., Harada J., Lee S.C., and West C.A. Enzymatic cyclization of (R,S)-14,15-oxidogeranylgeranyl pyrophosphate to 3α- and 3β-hydroxykaurene. J. Am. Chem. Soc. 98 (1976) 4659-4661
9. Connolly J.D., and Hill R.A. Dictionary of Terpenoids Di- and Higher Terpenoids vol. 2 (1991), Chapman & Hall, London
10. Croteau R. Biosynthesis and catabolism of monoterpenoids. Chem. Rev. 87 (1987) 929-954
11. Davis E.M., and Croteau R. Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes. Top. Curr. Chem. 209 (2000) 53-95
12. Dürr C., Schnell H.-J., Luzhetskyy A., Murillo R., Weber M., Welzel K., Vente A., and Bechthold A. Biosynthesis of the terpene phenalinolactone in Streptomyces sp. Tü6071: analysis of the gene cluster and generation of derivatives. Chem. Biol. 13 (2006) 365-377
13. Erickson K.L., Beutler J.A., Cardellina II J.H., McMahon J.B., Newman D.J., and Boyd M.R. A novel phorbol ester from Excoecaria agallocha. J. Nat. Prod. 58 (1995) 769-772
14. Grace M.H., Jin Y., Wilson G.R., and Coates R.M. Structures, biogenetic relationships, and cytotoxicity of pimarane-derived diterpenes from Petalostigma pubescens. Phytochemistry 67 (2006) 1708-1715
15. Grant P.K., and Carman R.M. Colensenone. J. Chem. Soc. (1962) 3740-3746
16. Grant P.K., Huntrakul C., and Robertson J.M. The diterpenes of Dacrydium colensoi. VIII. Sandaracopimaradien-19-ol and 2α-carboxycolensen-2β-ol. Aust. J. Chem. 22 (1969) 1265-1270
17. Hanson J.R. Chemistry of the tetracyclic diterpenoids. X. Beyerene 2 and 3-alcohols. Tetrahedron 26 (1970) 2711-2715
18. Hedden P., Phillips A.L., Rojas M.C., Carrera E., and Tudzynski B. Gibberellin biosynthesis in plants and fungi: a case of convergent evolution?. J. Plant Growth Regul. 20 (2002) 319-331
19. Jayaweera D.M.A. Medicinal plants used in Ceylon. Natl. Sci. Council Sri Lanka 2 (1980) 214-215
20. Jefferies P.R., Rosich R.S., and White D.E. Absolute configuration of beyerol. Tetrahedron Lett. 14 (1973) 1793-1799
21. Jones P.R. Ring-chain tautomerism. Chem. Rev. 63 (1963) 461-487
22. Kametani T., Toya T., Ueda K., Tsubuki M., and Honda T. A novel synthesis of cyclobutane monoterpenes, (±)-grandisol and (±)-lineatin. J. Chem. Soc. Perkin Trans. I (1988) 2433-2438
23. Karalai C., Wiriyachitra P., Opferkuch H.J., and Hecker E. Medicinal plants of Euphoribiaceae occurring and utilized in Thailand. II. Cryptic and free skin irritants of the daphnane and tigliane types in latex of Excoecaria agallocha. Planta Med. 60 (1994) 351-355
24. Konishi T., Konoshima T., Fujiwara Y., and Kiyosawa S. Excoecarins D, E and K from Excoecaria agallocha. J. Nat. Prod. 63 (2000) 344-346
25. Konishi T., Yamazoe K., Konoshima T., and Fujiwara Y. Seco-labdane type diterpenoids from Excoecaria agallocha. Phytochemistry 64 (2003) 835-840
26. Kono K., Kojima A., Nagai R., Watanabe M., Kawashima T., Onizawa T., Teraoka T., Watanab M., Koshino H., Uzawa J., Suzuki Y., and Sakurai A. Antibacterial diterpenoids and their fatty acid conjugates from rice leaves. Phytochemistry 65 (2004) 1291-1298
27. Maguire T.L., and Saenger P. The taxonomic relationships within the genus Excoecaria L. (Euphorbiaceae) based on leaf morphology and rDNA sequence data. Wetlands Ecol. Manage. 8 (2000) 19-28
28. MacMillan J. The biosynthesis of gibberellin plant hormones. Nat. Prod. Rep. 14 (1997) 221-243
29. MacMillan J., and Beale M.H. In: Cane D.E. (Ed). Isoprenoids Including Carotenoids and Steroids. In: Barton D., Nakanishi K., and Meth-Cohn O. (Eds). Comprehensive Natural Products Chemistry vol. 2 (1999), Elsevier, Amsterdam 217-243
30. Munkombwe N.M., Maswabi T., and Hughes N.A. Diosphenols from Spirostachys africana. Phytochemistry 45 (1997) 1217-1220
31. Munkombwe N.M., Hughes N.A., and Duri Z.J. Acid metabolites from Spirostachys africana. Phytochemistry 47 (1998) 1653-1655
32. Ohigashi H., Katsumata H., Kawazu K., Koshimizu K., and Mitsui T. Piscicidal constituent of Excoecaria agallocha. Agric. Biol. Chem. 38 (1974) 1093-1095
33. Petrini M., Ballini R., and Marcantoni E. Amberlyst 15: a practical, mild and selective catalyst for methyl esterification of carboxylic acids. Synth. Commun. 18 (1988) 847-853
34. Pretsch E., Clerc T., Seibl J., and Simon W. Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Methoden (1976), Springer-Verlag, Berlin pp. C175
35. Sakai T., and Nakagawa Y. Diterpenic stress metabolites from cassava roots. Phytochemistry 27 (1988) 3769-3779
36. Stahl E. Thin Layer Chromatography. 2nd ed. (1969), Springer-Verlag, Berlin pp. 857
37. West C.A. In: Porter J.W., and Spurgeon S.L. (Eds). Biosynthesis of Isoprenoid Compounds vol. 1 (1983), Wiley, New York (Chapter 7)
38. Wills J.C. A Dictionary of the Flowering Plants and Ferns. eighth ed. (1973), Cambridge University Press, Cambridge pp. 450
39. Wiriyachitra P., Hajiwangoh H., Boonton P., Adolf W., Opferkuch H.J., and Hecker E. Investigations of medicinal plants of Euphorbiaceae and Thymelaeaceae occurring and used in Thailand; II. Cryptic irritants of the diterpene ester type from three Excoecaria species. Planta Med. 5 (1985) 368-371