Resin diterpenes from austrocedrus chilensis

Molecules

Volumn 16, Issue 12, 2011, Pages 10653-10667

  Olate, Verónica Rachel ^a   Usandizaga, Olatz Goikoetxeaundia ^b   Schmeda Hirschmann, Guillermo ^a  

^a UNIVERSIDAD DE TALCA   (Chile)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Abietanes; Andean gymnosperms; Austrocedrus chilensis; Diterpenes; Labdanes

Indexed keywords

DITERPENE; PLANT RESIN;

ARTICLE; CHEMISTRY; CUPRESSACEAE; GAS CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CHROMATOGRAPHY, GAS; CUPRESSACEAE; DITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; RESINS, PLANT;

EID: 84555189763     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules161210653     Document Type: Article

References (46)

1. Muñoz, M.; Barrera, E.; Meza, I. El Uso Medicinal Y Alimenticio De Plantas Nativas Y Naturalizadas en Chile; Museo Nacional de Historia Natural: Santiago, Chile, 1981; Publicacion Ocasional 33, pp. 3-89.
2. Hegnauer, R. Chemotaxonomie Der Pflanzen; Birkhäuser Verlag: Basel, Switzerland, 1962; Band 1.
3. Castro, M.A.; Gordaliza, M.; Miguel Del Corral, J.M.; San Feliciano, A. The distribution of lignanoids in the order coniferae. Phytochemistry 1996, 41, 995-1011.
4. Cairnes, D.A.; Eagan, R.L.; Ekundayo, O.; Kingston. D.G.I. Plant anticancer agents. XIII. Constituents of Austrocedrus chilensis. J. Nat. Prod. 1983, 46, 135-139. (Pubitemid 13115596)
5. Taylor and Francis Group. Dictionary of Natural Products on CDROM; CRC Press: Boca Raton, FL, USA, 2011; Version 20:1.
6. Gadek, P.A.; Quinn, C.J. Biflavones of the subfamily Callitroideae, Cupressaceae. Phytochemistry 1983, 33, 969-972.
7. Flores, C.; Alarcón, J.; Becerra, J.; Bittner, M.; Hoeneisen, M.; Silva, M. Extractable compounds of native trees. Chemical and biological study I: Bark of Prumnopytis andina (Podocarpaceae) and Austrocedrus chilensis (Cupressaceae). Bol. Soc. Chil. Quím. 2001, 46, 61-64. (Pubitemid 33265643)
8. Cox, R.E.; Yamamoto, S.; Otto, A.; Simoneit, B.R.T. Oxygenated di- and tricyclic diterpenoids of shouthern hemisphere conifers. Biochem. Syst. Ecol. 2007, 35, 342-362. (Pubitemid 46509822)
9. San Feliciano, A.; Miguel del Corral, J.M.; Lopez, J.L.; de Pascual-Teresa, B. Labdane acids from polar extracts of Juniperus thurifera. Phytochemistry 1992, 31, 1719-1722.
10. San Feliciano, A.; Miguel del Corral, J.M.; Lopez, J.L.; de Pascual-Teresa, B. Further diterpene acids from Juniperus thurifera. Phytochemistry 1993, 33, 1165-1167.
11. Piovetti, L.; Gonzalez, E.; Diara, A. Diterpene composition of Cupressus dupreziana and Cupressus sempervirens. Phytochemistry 1980, 19, 2772-2773.
12. Otto, A.; Walther, H.; Püttmann, W. Sesqui- and diterpenoid biomarkers preserved in Taxodiumrich Oligocene oxbow lake clays, Weisselster basin, Germany. Org. Geochem. 1997, 26, 105-115.
13. Otto, A.; Simoneit, B.R.T. Chemosystematics and diagenesis of terpenoids in fossil conifer species and sediment from the Eocene Zeitz formation, Saxony, Germany. Geochim. Cosmochim. Acta 2001, 65, 3505-3527. (Pubitemid 33122325)
14. Otto, A.; Simoneit, B.R.T.; Rember, W.C. Resin compounds from the seed cones of three fossil conifer species from the Miocene Clarkia flora, Emerald Creek, Idaho, USA, and from related extant species. Rev. Palaeobot. Palynol. 2003, 126, 225-241. (Pubitemid 37274209)
15. Mathe, C.; Culioli, G.; Archier, P.; Vieillescazes, C. Characterization of archaeological frankincense by gas chromatography-mass spectrometry. J. Chromatogr. A 2004, 1023, 277-285. (Pubitemid 37494801)
16. Lambert, J.B.; Kozminski, M.A.; Santiago-Blay, J.A. Distinctions among conifer exudates by proton magnetic resonance spectroscopy. J. Nat. Prod. 2007, 70, 1283-1294. (Pubitemid 47401568)
17. Su, W.-C.; Fang, J.-M.; Cheng, Y.-S. Labdanes from Cryptomeria japonica. Phytochemistry 1994, 37, 1109-1114.
18. Su, W.-C.; Fang, J.-M.; Cheng, Y.-S. Diterpenoids from leaves of Cryptomeria japonica. Phytochemistry 1996, 41, 255-261. (Pubitemid 126685893)
19. Yoshida, T.; Toyota, M.; Asakawa, Y. Scapaundulins A and B, two novel dimeric labdane diterpenoids and related compounds from the Japanese liverwort Scapania undulata (L.) Dum. Tetrahedron Lett. 1997, 38, 1975-1978. (Pubitemid 27117870)
20. Li, C.-J.; Zhang, D.-M.; Luo, Y.-M.; Yu, S.-S.; Li, Y.; Lu, Y. Bis-sesquiterpenes and diterpenes from Chloranthus henryi. Phytochemistry 2008, 69, 2867-2874.
21. Wang, Y.-Z.; Tang, C.-P.; Ke, C.-Q.; Weiss, H.-C.; Gesing, E.-R.; Ye, Y. Diterpenoids from the pericarp of Platycladus orientalis. Phytochemistry 2008, 69, 518-526.
22. Hall, S.F.; Oehlschlager, A.C. Cationic rearrangements and cyclizations of diterpenoid olefins. Tetrahedron 1972, 28, 3155-3173.
23. Oikawa, H.; Toshima, H.; Ohashi, S.; König, W.A.; Kenmoku, H.; Sassa, T. Diversity of diterpene hydrocarbons in fungus Phoma betae. Tetrahedron Lett. 2001, 42, 2329-2332. (Pubitemid 32200437)
24. Chamy, M.C.; Piovano, M.; Garbarino, J.A.; Gambaro, V. Diterpenes from Calceolaria polifolia. Phytochemistry 1991, 30, 3365-3368.
25. Garbarino, J.A.; Molinari, A. Diterpenes from Calceolaria latifolia. Phytochemistry 1990, 29, 3037-3039.
26. Yang, S.-J.; Fang, J.-M.; Cheng, Y.-S. Diterpenes from Taxus mairei. Phytochemistry 1998, 49, 2037-2043. (Pubitemid 28563817)
27. Fang, J.-M.; Sou, Y.-C.; Chiu, Y.-H.; Cheng, Y.-S. Diterpenes from the bark of Juniperus chinensis. Phytochemistry 1993, 34, 1581-1584.
28. Cambie, R.C.; Cox, R.E.; Sidwell, D. Phenolic diterpenoids of Podocarpus ferrugineus and other Podocarps. Phytochemistry 1984, 23, 333-336.
29. Inoue, M.; Hasegawa, S.; Hirose, Y. Terpenoids from the seed of Platycladus orientalis. Phytochemistry 1985, 24, 1602-1604.
30. Seca, A.M.L.; Silva, A.M.S.; Bazzocchi, I.L.; Jimenez, I.A. Diterpene constituents of leaves from Juniperus brevifolia. Phytochemistry 2008, 69, 498-505.
31. Barrero, A.F.; Quílez del Moral, J.F.; Herrador, M.M.; Akssira, M.; Bennamara, A.; Akkad, S.; Aitigri, N. Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry 2004, 65, 2507-2515. (Pubitemid 39286006)
32. Liu, Y.; Nair, M.G. Labdane diterpenes in Curcuma mangga rhizomes inhibit lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation. Food Chem. 2011, 124, 527-532.
33. Gordien, A.Y.; Gray, A.I.; Franzblau, S.G.; Seidel, V. Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae). J. Ethnopharmacol. 2009, 126, 500-505.
34. Areche, C.; Rodríguez, J.A.; Razmilic, I.; Yánez, T.; Theoduloz, C.; Schmeda-Hirschmann, G. Gastroprotective and cytotoxic effect of semisynthetic ferruginol derivatives. J. Pharm. Pharmacol. 2007, 59, 289-300. (Pubitemid 46203067)
35. Iwamoto, M.; Minami, T.; Tokuda, H.; Ohtsu, H.; Tanaka, R. Potencial antitumor promoting diterpenoids from the stem bark of Thuja standishii. Planta Med. 2003, 69, 69-72. (Pubitemid 36228462)
36. Bispo de Jesus, M.; Zambuzzi, W.F.; Ruela de Sousa, R.R.; Areche, C.; Santos de Souza, A.C.; Aoyama, H.; Schmeda-Hirschmann, G.; Rodríguez, J.A.; de Souza Brito, A.R.M.; Peppelenbosch, M.P.; den Hertog, J.; de Paula, E.; Ferreira, C.V. Ferruginol suppresses survival signaling pathways in androgen-independent human prostate cancer cells. Biochimie 2008, 90, 843-854.
37. Smith, E.C.J.; Williamson, E.M.; Wareham, N.; Kaatz, G.W.; Gibbons, S. Antibacterials and modulators of bacterial resistance from the immature cones of Chamaecyparis lawsoniana. Phytochemistry 2007, 68, 210-217. (Pubitemid 46043330)
38. Clarkson, C.; Musonda, C.; Chibale, K.; Campbell, W.E.; Smith, P. Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity. Bioorg. Med. Chem. 2003, 11, 4417-4422. (Pubitemid 37103112)
39. Shyur, L.-F.; Huang, C.-C.; Lo, C.-P.; Chiu, C.-Y.; Chen, Y.-P.; Wang, S.-Y.; Chang, S.-T. Hepatoprotective phytocompounds from Cryptomeria japonica are potent modulators of inflammatory mediators. Phytochemistry 2008, 69, 1348-1358.
40. Sepúlveda, B.; Astudillo, L.; Rodríguez, J.; Yáñez, T.; Theoduloz, C.; Schmeda-Hirschmann, G. Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives. Pharmacol. Res. 2005, 52, 429-437. (Pubitemid 41531163)
41. Son, K.-H.; Oh, H.-M.; Choi, S.-K.; Han, D.C.; Kwon, D.-M. Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens. Bioorg. Med. Chem. Lett. 2005, 15, 2019-2021. (Pubitemid 40445461)
42. Iwamoto, M.; Ohtsu, H.; Tokuda, H.; Nishino, H.; Matsunaga, S.; Tanaka, R. Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae). Bioorg. Med. Chem. 2001, 9, 1911-1921. (Pubitemid 32651927)
43. Pautasso, M.; Dehnen-Schmutz, K.; Holdenrieder, O.; Pietravalle, S.; Salama, N.; Jeger, M.J.; Lange, E.; Hehl-Lange, S. Plant health and global change-Some implications for landscape management. Biol. Rev. 2010, 85, 729-755.
44. Greslebin, A.G.; Hansen, E.M. Pathogenicity of Phytophthora austrocedrae on Austrocedrus chilensis and its relation with mal del ciprés in Patagonia. Plant Pathol. 2010, 59, 604-612.
45. Greslebin, A.G.; Hansen, E.M.; Sutton, W. Phytophthora austrocedrae sp. nov., a new species associated with Austrocedrus chilensis mortality in Patagonia (Argentina). Mycol. Res. 2007, 111, 308-316. (Pubitemid 46507748)
46. Amoroso, M.M.; Larson, B.C. Stand development patterns as a consequence of the mortality in Austrocedrus chilensis forests. For. Ecol. Manage. 2010, 259, 1981-1992.