Germacrene D, A common sesquiterpene in the genus Bursera (Burseraceae)

Molecules

Volumn 14, Issue 12, 2009, Pages 5289-5297

  Noge, Koji ^a,b   Becerra, Judith X ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b AKITA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Bursera; Burseraceae; Germacrene D; Monoterpenes; Sesquiterpenes

Indexed keywords

GERMACRENE D; SESQUITERPENE;

ARTICLE; BURSERACEAE; CHEMISTRY; MASS FRAGMENTOGRAPHY; SPECIES DIFFERENCE;

BURSERA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; SESQUITERPENES, GERMACRANE; SPECIES SPECIFICITY;

EID: 73849092890     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14125289     Document Type: Article

References (43)

1. Rzedowski, J.; Kruse, H. Algunas tendencias evolutiv as en Bursera (Burseraceae). Taxon 1979, 28, 103-116.
2. Becerra, J.X.; Venable, D.L. Nuclear ribosomal DNA phylogeny and ITS implication for evolutionary trends in Mexican Bursera (Burseraceae). Am. J. Bot. 1999, 86, 1047-1057.
3. Becerra, J.X. Evolution of Mexican Bursera (Burseraceae) inferred from ITS, ETS, and 5S nuclear ribosomal DNA sequences. Mol. Phyl. Evol. 2003, 26, 300-309.
4. Becerra, J.X.; Venable, D.L. Rapid-terpene-bath and "squirt- gun" defense in Bursera schlechtendalii and the counterploy of chrysomelid beetles. Biotropica 1990, 22, 320-323.
5. Becerra, J.X. Squirt-gun defense in Bursera and the Chrysomelid counterploy. Ecology 1994, 75, 1991-1996.
6. Becerra, J.X.; Venable, D.L.; Evans, P.H.; Bowers, W.S. Interactions between chemical and mechanical defenses in the plant genus Bursera and their implications for herbivores. Amer. Zool. 2001, 41, 865-876.
7. Evans, P.H.; Becerra, J.X.; Venable, D.L.; Bowers, W.S. Chemical analysis of squirt-gun defense in Bursera and counterdefense by chrysomelid beetles. J. Chem. Ecol. 2000, 26, 745-754.
8. Evans, P.H.; Becerra, J.X. Non-terpenoid essential oils from Bursera chemapodicta. Flavour Fragr. J. 2006, 21, 616-618.
9. Sylvestre, M.; Longtin, A.P.A.; Legault, J. Volatile leaf constituents and anticancer activity of Bursera simaruba (L.) Sarg. essential oil. Nat. Prod. Commun. 2007, 2, 1273-1276.
10. Young, D.G.; Chao, S.; Casabiana, H.; Bertrand, M.C.; Minga, D. Essential oil of Bursera graveolens (Kunth) Triana et Planch from Ecuador. J. Essent. Oil Res. 2007, 19, 525-526.
11. Birkett, M.A.; Al Abassi, S.; Krober, T.; Chamberlain, K.; Hooper, A.M.; Guerin, P.M.; Pettersson, J.; Pickett, J.A.; Slade, R.; Wadhams, L.J. Antiectoparasitic activity of the gum resin, gum haggar, from the East Africa plant, Commiphora holtziana. Phytochemistry 2008, 69, 1710-1715.
12. 2 extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L. J. Agric. Food Chem. 2005, 53, 7939-7943.
13. Bülow, N.; König, W.A. The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigation of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemistry 2000, 55, 141-168.
14. Telascrea, M.; de Araújo, C.C.; Marques, M.O.M.; Facanali, R.; de Moraes, P.L.R.; Cavalheiro, A.J. Essential oil leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability. Biochem. Syst. Ecol. 2007, 35, 222-232.
15. Langenheim, J.H. Higher plant terpenoids: A phytocentric overview of their ecological roles. J. Chem. Ecol. 1994, 20, 1223-1280.
16. Kiran, S.R.; Devi, P.S. Evaluation of mosquitocidal activity of essential oil and sesquiterpenes from leaves of Chloroxylon swietenia DC. Parasitol. Res. 2007, 101, 413-418.
17. Bruce, T.J.A.; Birkett, M.A.; Blande, J.; Hooper, A.M.; Martin, J.L.; Khambay, B.; Prosser, I.; Smart, L.E.; Wadhams, L.J. Response of economically important aphids to components of Hemizygia petiolata essential oil. Pest Manag. Sci. 2005, 61, 1115-1121.
18. Becerra, J.X. Insects on plants: Macroevolutionary chemical trends in host use. Science 1997, 276, 253-256.
19. Al-Harrasi, A.; Al-Saidi, S. Phytochemical analysis of the essential oil from botanically certified oleogum resin of Boswellia sacra (Omani Luban). Molecules 2008, 13, 2181-2189.
20. Siani, A.C.; Garrido, I.S.; Monteiro, S.S.; Carvalho, E.S.; Ramos, M.F.S. Protium icicariba as a source of volatile essences. Biochem. Syst. Ecol. 2004, 32, 477-489.
21. Zini, C.A.; Zanin, K.D.; Christensen, E.; Caramão, E.B.; Pawliszyn, J. Solid-phase microextraction of volatile compounds from the chopped leaves of three species of Eucalyptus. J. Agric. Food Chem. 2003, 51, 2679-2686.
22. Melo, R.M.; Corrêa, V.F.S.; Amorim, A.C.L.; Miranda, A.L.P.; Rezende, C.M. Identification of impact aroma compounds in Eugenia uniflora L. (Brazilian pitanga) leaf essential oil. J. Braz. Chem. Soc. 2007, 18, 179-183.
23. Phi, N.T.L.; Nishiyama, C.; Choi, H.-S.; Sawamura, M. Evaluation of characteristic aroma compounds of Citrus matsudaidai Hayata (Natsudaidai) cold-pressed peel oil. Biosci. Biotechnol. Biochem. 2006, 70, 1832-1838.
24. Boehme, A.K.; Noletto, J.A.; Haber, W.A.; Setzer, W.N. Bioactivity and chemical composition of the leaf essential oils of Zanthoxylum rhoifolium and Zanthoxylum setulosum from Monteverde, Costa Rica. Nat. Prod. Res. 2008, 22, 31-36.
25. Agnihotri, V.K.; Thappa, R.K.; Meena, B.; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N.; Agarwal, S.G. Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India). Phytochemistry 2004, 65, 2411-2413.
26. Itokawa, H.; Matsumoto, H.; Mihashi, S. Isolation of oppositane- and cycloeudesmane-type sesquiterpenoids from Torilis japonica D.C. Chem. Lett. 1983, 1253-1256.
27. Tellez, M.R.; Canel, C.; Rimando, A.M.; Duke, S. O. Differential accumulation of isoprenoids in glanded and glandless Artemisia annua L. Phytochemistry 1999, 52, 1035-1040.
28. Rivero-Cruz, B.; Rivero-Cruz, I.; Rodríguez, J.M.; Cerda-García-Rojas, C.M.; Mata, R. Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. J. Nat. Prod. 2006, 69, 1172-1176.
29. Niwa, M.; Iguchi, M.; Yamamura, S. Co-occurence of (-) and (+)-germacrene-D in Solidago altissima L.: Determination of the optical rotation of optically pure germacrene-D. Chem. Pharm. Bull. 1980, 28, 997-999.
30. König, W.A.; Bülow, N.; Saritas, Y. Identification of sesquiterpene hydrocarbons by gas phase analytical methods. Flavour Fragr. J. 1999, 14, 367-378.
31. Celik, S.; Gokturk, R.S.; Flamini, G.; Cioni, P.L.; Morelli, I. Essential oils of Phlomis leucophracta, Phlomis chimerae and Phlomis grandiflora from Turkey. Biochem. Syst. Ecol. 2005, 33, 617-623.
32. Radulović, N.; Lazarević, J.; Ristić, N.; Palić, R. Chemotaxonomic significance of the volatiles in the genus Stachys (Lamiaceae): Essential oil composition of four Balkan Stachys species. Biochem. Syst. Ecol. 2007, 35, 196-208.
33. van der Hoeven, R.S.; Monforte, A.J.; Breeden, D.; Tanksley, S.D.; Steffens, J.C. Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum. Plant Cell 2000, 12, 2283-2294.
34. Naik, J.P.; Rao, L.J.M.; Kumar, T.M.M.; Sampathu, S.R. Chemical composition of the volatile oil from the pericarp (husk) of large cardamon (Amomum subulatum Roxb.). Flavour Fragr. J. 2004, 19, 441-444.
35. Yang, F.Q.; Li, S.P.; Chen, Y.; Lao, S.C.; Wang, Y.T.; Dong, T.T.X.; Tsim, K.W.K. Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J. Pharm. Biomed. Anal. 2005, 39, 552-558.
36. Stashenko, E.E.; Prada, N.Q.; Martínez, J.R. HRGC/FID/NPD and HRGC/MSD study of Colombian ylang-ylang (Cananga odorata) oils obtained by different extraction techniques. J. High Resol. Chromatogr. 1996, 19, 353-358.
37. Stefanello, M.E.A.; Salvador, M.J.; Ito, I.Y.; Wisniewski, A.; Simionatto, E.L.; de Mello-Silva, R. Chemical composition, seasonal variation and evaluation of antimicrobial activity of essential oils of Talauma ovata A. St. Hil. (Magnoliaceae). J. Essent. Oil Res. 2008, 20, 565-569.
38. Mundina, M.; Vila, R.; Tomi, F.; Tomàs, X.; Cicció, J.F.; Adzet, T.; Casanova, J.; Cañigueral, S. Composition and chemical polymorphism of the essential oils from Piper lanceaefolium. Biochem. Syst. Ecol. 2001, 29, 739-748.
39. Pietsch, M.; König, W.A. Enantiomers of sesquiterpene and diterpene hydrocarbons in Araucaria species. Phytochem. Anal. 2000, 11, 99-105.
40. Cool, L.; Zavarin, E. Terpene variability of mainland Pinus radiata. Biochem. Syst. Ecol. 1992, 20, 133-144.
41. Hayman, A.R.; Weavers, R.T. Terpenes of foliage oils from Halocarpus bidwillii. Phytochemistry 1990, 29, 3157-3162.
42. Lorimer, S.D.; Weavers, R.T. Foliage sesquiterpenes and diterpenes of Podocarpus spicatus. Phytochemistry 1987, 26, 3207-3215.
43. König, W.A.; Bülow, N.; Fricke, C.; Melching, S.; Rieck, A.; Muhle, H. The sesquiterpene constituents of the liverwort Preissia quadrata. Phytochemistry 1996, 43, 629-633.