Mechanisms of the biosynthesis of sesquiterpene enantiomers (+)- and (- )-germacrene D in solidago canadensis

Chirality

Volumn 11, Issue 5-6, 1999, Pages 353-362

  Schmidt, Claus O ^a   Bouwmeester, Harro J ^b   Franke, Stephan ^a   König, Wilfried A ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Biosynthesis of enantiomers; Deuterated farnesyl diphosphate; Enzymatic mechanism; Germacrene D; Labeled precursors; Mass spectrometry; Sesquiterpene synthases; Sesquiterpenes

Indexed keywords

GERANYLTRANSFERASE; GERMACRENE D; SESQUITERPENE DERIVATIVE; SOLIDAGO CANADENSIS EXTRACT;

CHIRALITY; CONFERENCE PAPER; DRUG ISOLATION; ENANTIOMER; ENZYME ANALYSIS; ENZYME MECHANISM; MASS SPECTROMETRY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032997636     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:5/6<353::AID-CHIR2>3.0.CO;2-L     Document Type: Conference Paper

References (36)

1. Rücker G. Sesquiterpene. Angew Chem 1973;85:895-907.
2. Ohloff G. Scent and fragrances. Berlin: Springer; 1994.
3. Persoons CJ, Verwiel PEJ, Ritter FJ, Talman E, Nooijen PJF, Nooijen WJ. Sex pheromones of the american cockroach, Periplanata americana: A tentative structure of periplanone-B. Tetrahedron Lett 1976;2055-2058.
4. Jain SC, Nowicki S, Eisner T, Meinwald J. Insect repellents from vetiver oil: I. Zizanal and epizizanal. Tetrahedron Lett 1982;4639-4642.
5. Cane DE, Oliver JS, Harrison PHM, Abell C, Hubbard BR, Kane CT, Lattman R. Biosynthesis of pentalenene and pentalenolactone. J Am Chem Soc 1990;112:4513-4524.
6. (a) Ayer WA, Browne LM. terpenoid metabolites of mushrooms and related basidiomycetes. Tetrahedron 1981;37:2199-2248.
7. (b) Izac RR, Schneider P, Swain M, Fenical W. New nor-sesquiterpenoids of apparent nardosinane origin from the pacific soft-coral Paralemnalia thyrsoides. Tetrahedron Lett 1982;23:817-820.
8. Rodriguez AD. The natural product chemistry of West Indian gorgonian octocorals. Tetrahedron 1995;51:4571-4618.
9. König GM, Wright AD. New and unusual sesquiterpenes: Kelsoene, prespatane, epi-γ-gurjunene, and T-cadinthiol, from the tropical marine sponge Cymbastela hooperi. J Org Chem 1997; 62:3837-3840.
10. König WA, Rieck A, Hardt I, Gehrcke B, Kubeczka K-H, Muhle H. Enantiomeric composition of the chiral constituents of essential oils. Part 2. Sesquiterpenes. J High Res Chromatogr 1994;17:315-320.
11. König WA, Rieck A, Saritas Y, Hardt IH, Kubeczka K-H. Sesquiterpene hydrocarbons in the essential oil of Meum athamanticum. Phytochemistry 1996;42:461-464.
12. Cane DE. Enzymatic formation of sesquiterpenes. Chem Rev 1990;90: 1089-1103.
13. Croteau R, Cane DE. Methods Enzymol 1985;110:383-405.
14. (a) Salin F, Pauly G, Charon J, Gleizes M. Purification and characterization of trans-β-farnesene synthase from maritime pine (Pinus pinaster Ait.) needles. J Plant Physiol 1995;146:203-209.
15. (b) Banthorpe DV, Brown JT, Morris GS. Partial purification of farnesyl pyrophosphate: Drimenol cyclase and geranylgeranyl pyrophosphate, sclareol cyclase, using cell culture as a source of material. Phytochemistry 1992;31: 3391-3395.
16. Cano-Camacho H, López-Romero E, Lozoya-Gloria E. Partial purification and characterization of an elicitor stimulated sesquiterpene cyclase from chili pepper (Capsicum annuum L.) fruits. Plant Sci 1997;124:23-31.
17. Starks CM, Back K, Chappell J, Noel JP. Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science 1997;277:1815-1820.
18. Cane DE, Tandon M, Prabhakaran PC. Epicubenol synthase and the enzymatic cyclization of farnesyl diphosphate. J Am Chem Soc 1993; 115:8103-8106.
19. Colby SM, Crock J, Dowdle-Rizzo B, Lemaux PG, Croteau R. Germacrene C synthase from Lycopersicon esculentum cv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Biochemistry 1998;95:2216-2221.
20. Steele CL, Crock J, Bohlmann J, Croteau R. Sesquiterpene synthases from grand fir (Abies grandis). J Biol Chem 1998;273:2078-2089.
21. Kitamura C, Takahashi S, Tahara S, Mizutani J. A sex stimulant to the male american cockroach in plants. Agric Biol Chem 1976;40:1965-1969.
22. Peterson JK, Horvat RJ, Elsey KD. Squash leaf glandular trichome volatiles: identification and influence on behavior of female pickleworm moth. J Chem Ecol 1994;20:2099-2109.
23. Weissbecker B, Schütz S, Klein A, Hummel HE. Analysis of volatiles emitted by potato plants by means of a Colorado beetle electroantennographic detector. Talanta 1997;44:2217-2224.
24. Yoshihara K, Ohta Y, Sakai T, Hirose Y, Germacrene D, a key intermediate of cadinene group compounds and bourbonenes. Tetrahedron Lett 1969;2263-2264.
25. König WA, Bülow N, Fricke C, Melching S, Rieck A, Muhle H. The sesquiterpenes of the liverwort Preissia quadrata. Phytochemistry 1996;43:629-633.
26. Lorimer SD, Weavers RT. Foliage sesquiterpenes and diterpenes of Podocarpus spicatus. Phytochemistry 1987;26:3207-3215.
27. 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(3): 997-999.
28. Bülow N, König WA. Essential oils: Basic and applied research. In: Franz Ch, Mathe A, Buchbauer G, editors. Proceedings of the 27th International Symposium on Essential Oils, Vienna, 1996. Carol Stream, IL: Allured Publ. Corp. p 209-213.
29. Schmidt CO, Bouwmeester HJ, De Kraker J-W, König WA. Biosynthesis of (+)-and (-)-germacrene D in Solidago canadensis: Isolation and characterization of two enantioselective germacrene D synthases. Angew Chem, Int Ed 1998;37:1400-1402.
30. Cane DE, Iyengar R, Shiao M-S. Cyclonerolidol biosyntheis and the enzymatic conversion of farnesyl to nerolidyl pyrophosphate. J Am Chem Soc 1981;103:914-931.
31. De Kraker J-W, Bouwmeester HJ, Franssen MCR, König WA, deGroot, A. (+)-Germacrene a biosynthesis: The first committed step in the biosynthesis of bitter sesquiterpene lactones in chicory (Cichorium intybus L.). Plant Physiol 1998;117:1381-1392.
32. Munck SL, Croteau R. purification and characterization of the sesquiterpene cyclase patchoulol synthase from Pogostemon cablin. Arch Biochem Biophys 1990;282:58-64.
33. Bouwmeester HJ, Gershenzon J, Konings MCJM, Croteau R. Biosynthesis of the monoterpenes limonene and carvone in the fruits of caraway (Carum carvi L.). Demonstration of enzyme activities and their changes with development. Plant Physiol 1998;117:901-912.
34. Dehal SS, Croteau R. Partial purification and characterization of two sesquiterpene cyclases from sage (Salvia officinalis) Which Catalyze the Respective Conversion of Farnesyl Pyrophosphate to Humulene and Caryophyllene. Arch Biochem Biophys 1988;261:346-356.
35. Boyd RK, Beynon JH. Scanning of sector mass spectrometers to observe the fragmentations of metastable ions. Org Mass Spectrom 1977; 12:163-165.
36. Haddon WF. The constant neutral linked magnetic field-electric sector scan. Org Mass Spectrom 1980;15:539-543.