Diterpene constituents of leaves from Juniperus brevifolia

Phytochemistry

Volumn 69, Issue 2, 2008, Pages 498-505

  Seca, Ana M L ^a   Silva, Artur M S ^b   Bazzocchi, Isabel L ^c   Jimenez, Ignacio A ^c  

^a UNIVERSITY OF THE AZORES   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Abietanes; Cedro do mato; Cupressaceae; Fatty acid diterpenol ester; Juniperus brevifolia; Sadaracopimaranes

Indexed keywords

DITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; JUNIPERUS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF;

DITERPENES; JUNIPERUS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT LEAVES;

CUPRESSACEAE; JUNIPERUS; JUNIPERUS BREVIFOLIA;

EID: 37549010342     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.07.026     Document Type: Article

References (40)

1. Aboul-Ela M.A. New abietane diterpene quinone fatty acid esters from Salvia lanigera. Alex. J. Pharm. Sci. 20 (2006) 32-34
2. Adams R.P. Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting. Biochem. Sys. Ecol. 27 (1999) 709-725
3. Ara I., Siddiqui B.S., Faizi S., and Siddiqui S. Tricyclic diterpenoids from the stem bark of Azadirachta indica. J. Nat. Prod. 51 (1988) 1054-1061
4. Audier H.E., Bory S., Fétizon M., and Anh N.-T. Spectres de mass des terpènes. III - influence dês liaisons éthyléniques sur la fragmentation des diterpénes. Bull. Soc. Chim. Fr. (1966) 4002-4010
5. Bajda M., Boryczka S., Wietrzyk J., and Malawska B. Investigation of lipophilicity of anticancer-active thioquinoline derivatives. Biomed. Chromatogr. 21 (2007) 123-131
6. Barrero A.F., del Moral J.F.Q., Herrador M.M., Akssira M., Bennamara A., Akkad S., and Aitigri M. Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. Africana. Phytochemistry 65 (2004) 2507-2515
7. Burnell R.H., Côté C., and Théberge N. Approaches to the synthesis of aromatic diterpenes oxygenated in the A ring. Synthesis of margocin. J. Nat. Prod. 56 (1993) 1459-1467
8. Cambie R.C., Burfitt I.C., Goodwin T.E., and Wenkert E. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XXXVII. Structure of hallol. J. Org. Chem. 40 (1975) 3789-3791
9. Cerqueira F., Cordeiro-da-Silva A., Gaspar-Marques C., Simões F., Pinto M.M.M., and Nascimento M.S.J. Effect of abietane diterpenes from Plectranthus grandidentatus on T- and B-lymphocyte proliferation. Bioorg. Med. Chem. 12 (2004) 217-223
10. Chamy M.C., Piovano M., Gambaro V., Garbarino J.A., and Nicoletti M. Dehydroabietane diterpenoids from Calceolaria ascendis. Phytochemistry 26 (1987) 1763-1765
11. Chang L.C., Song L.L., Park E.J., Luyengi L., Lee K.J., Farnsworth N.R., Pezzuto J.M., and Kinghorn A.D. Bioactive constituents of Thuja occidentalis. J. Nat. Prod. 63 (2000) 1235-1238
12. Da Silva J.A., Pedro L.G., Santos P.A.G., Figueiredo A.C., Barroso J.G., Tenreiro R.P., Ribeiro C.A., Deans S.G., Looman A., and Scheffer J.J.C. Essential oils from seven populations of Juniperus brevifolia (Seub.) Antoine, an endemic species of the Azores. Flavour Fragr. J. 15 (2000) 31-39
13. Enzell C.R., and Ryhage R. Mass spectrometric studies of diterpenes. 5 Aromatic diterpenes. Arkiv Kemi 27 (1967) 213-229
14. Fang J.-M., Sou Y.-C., Chiu Y.-H., and Cheng Y.-S. Diterpenes from the bark of Juniperus chinensis. Phytochemistry 34 (1993) 1581-1584
15. Fang J.-M., Chen Y.-C., Wang B.-W., and Cheng Y.-S. Terpenes from heartwood of Juniperus chinensis. Phytochemistry 41 (1996) 1361-1365
16. Fraga B.M., Hernández M.G., Artega J.M., and Suárez S. The microbiological transformation of the diterpenes dehydroabietanol and teideadiol by Mucor plumbeus. Phytochemistry 63 (2003) 663-668
17. Inoue M., Hasegawa S., and Hirose Y. Terpenoids from the seed of Platyclaudus orientalis. Phytochemistry 24 (1985) 1602-1604
18. Kenmoku H., Tanaka M., Ogiyama K., Kato N., and Sassa T. Identification of (+)-phyllocladene, (-)-sandaracopimaradiene, and (+)-kaurene as new fungal metabolites from fusicoccin-producing Phomopsis amygdali F6. Biosci. Biotech. Biochem. 68 (2004) 1574-1577
19. Mahmood U., Kaul V.K., Acharya R., and Jirovetz L. p-Coumaric acid from Tanacetum longifolium. Phytochemistry 64 (2003) 851-853
20. Maliepaard M., De Mol N.J., Janssen L.H.M., Van der Neut W., Verboom W., and Reinhoudt D.N. Role of lipophilicity in the in vitro antitumor activity of a series of new mitosene compounds. Anticancer Drug Des. 7 (1992) 415-425
21. Marques C., Pedro M., Simões M., Nascimento M.S.J., Pinto M., and Rodríguez B. Effect of abietane diterpenes from Plectranthus grandidentatus on the growth of human cancer cell lines. Planta Med. 68 (2002) 839-840
22. Miyazawa M., Nakamura Y., and Ishikawa Y. Insecticidal sesquiterpene from Alpinia oxyphylla against Drosophila melanogaster. J. Agric. Food Chem. 48 (2000) 3639-3641
23. Muhammad I., Mossa J.S., Al-Yahya M.A., Ramadan A.F., and El-Feraly F.S. Futher antibacterial diterpenes from the bark and leaves of Juniperus procera Hochst. ex Endl. Phytother. Res. 9 (1995) 584-588
24. Muhammad I., Mossa J.S., and El-Feraly F.S. Additional antibacterial diterpenes from the bark of Juniperus procera. Phytother. Res. 10 (1996) 604-607
25. Otto A., and Wilde V. Sesqui-, di-, and triterpenoids as chemosystematic markers in extand conifers - a review. Bot. Rev. 67 (2001) 141-238
26. Richomme P., Godet M.-C., Foussard F., Toupet L., Sévenet T., and Bruneton J. A novel leishmanicidal labdane from Polyalthia macropoda. Planta Med. 57 (1991) 552-554
27. Sakar M.K., and San Feliciano A. Diterpenoids of Juniperus foetidissima unripe berries. Fitoterapia 65 (1994) 304-306
28. San Feliciano A., del Corral J.M.M., Gordaliza M., and Salinero M.A. Diterpenoides neutros y compuestos aromaticos de las hojas de Juniperus phoenicea subsp. turbinate. An. Quim. 88 (1992) 512-516
29. Schäfer H. Flora of the Azores: A Field Guide (2002), Margraf Verlag, Weikersheim
30. Schneider I., Gibbons S., and Bucar F. Inhibitory activity of Juniperus communis on 12(S)-HETE production in human platelets. Planta Med. 70 (2004) 471-474
31. Seca A.M.L., Silva A.M.S., Silvestre A.J.D., Cavaleiro J.A.S., Domingues F.M.J., and Neto C.P. Chemical composition of the light petroleum extract of Hibiscus cannabinus bark and core. Phytochem. Anal. 11 (2000) 345-350
32. Seca A.M.L., and Silva A.M.S. The chemical composition of Juniperus genus (1970-2004). In: Govil J.N., and Singh V.K. (Eds). Recent Progress in Medicinal Plants vol. 16 (2006), Studium Press LLC, Houston 401-522
33. Seca, A.M.L., Silva, A.M.S., in press. The chemical composition of hexane extract from bark of Juniperus brevifolia. Nat. Prod. Res.
34. Sepúlveda B., Astudillo L., Rodríguez J.A., Yáñez T., Theoduloz C., and Schmeda-Hirschmann G. Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives. Pharmacol. Res. 52 (2005) 429-437
35. Tanaka R., Ohtsu H., and Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi. Phytochemistry 46 (1997) 1051-1057
36. Teixeira A.P., Batista O., Simões F., Nascimento J., Duarte A., de la Torre M.C., and Rodríguez B. Abietane diterpenoids from Plectranthus grandidentatus. Phytochemistry 44 (1997) 325-327
37. Ulubelen A., and Topcu G. Abietane diterpenoids from Salvia pomifera. Phytochemistry 31 (1992) 3949-3951
38. Wang S.-Y., Wu J.-H., Shyur L.-F., Kuo Y.-H., and Chang S.-T. Antioxidant activity of abietane-type diterpenes from heartwood of Taiwania cryptomerioides Hayata. Holzforschung 56 (2002) 487-492
39. Wenkert E., and Buckwalter B.L. Cabon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes. J. Am. Chem. Soc. 94 (1972) 4367-4369
40. Yang S.-J., Fang J.-M., and Cheng Y.-S. Diterpenes from Taxus mairei. Phytochemistry 49 (1998) 2037-2043