(+)-Germacrene A biosynthesis - The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory

Plant Physiology

Volumn 117, Issue 4, 1998, Pages 1381-1392

  De Kraker, Jan Willem ^a   Franssen, Maurice C R ^a   De Groot, Aede ^a   König, Wilfried A ^b   Bouwmeester, Harro J ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000839814     PISSN: 00320889     EISSN: None     Source Type: Journal    
DOI: 10.1104/pp.117.4.1381     Document Type: Article

References (15)

1. Bachelor FW, Ito S (1973) A revision of the stereochemistry of lactucin. Can J Chem 51: 3626-3630
2. Back K, Chappell J (1995) Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamos muticus and its molecular comparison to related terpene cyclases. J Biol Chem 270: 7375-7381
3. Back K, Chappell J (1996) Identifying functional domains within terpene cyclases using a domain swapping strategy. Proc Natl Acad Sci USA 93: 6841-6845
4. 20 terpenoid compounds. Nat Prod Rep 7: 387-407
5. Belingheri L, Cartayrade A, Pauly G, Gleizes M (1992) Partial purification and properties of the sesquiterpene β-selinene cyclase from Citronella mitis fruits. Plant Sci 84: 129-136
6. Bohlman F, Zdero C (1978) New sesquiterpenes and acetylenes from Athanasia and Pentzia species. Phytochemistry 17: 1595-1599
7. Bowers WS, Nishino C, Montgomery ME, Nault LR, Nielson MW (1977) Sesquiterpene progenitor, germacrene A: an alarm pheromone in aphids. Science 196: 680-681
8. Brown ED, Sutherland JK, Sam TW (1975) Medium-ring 1:5-dienes. Part III. Cyclization of germacra-1(10),4,7-(11)-triene oxides. J Chem Soc Perkin Trans I 2332-2336
9. Cane DE (1990) Enzymatic formation of sesquiterpenes. Chem Rev 90: 1089-1103
10. Cane DE, Tsantrizos YS (1996) Aristolochene synthase: elucidation of the cryptic germacrene A synthase activity using the anomalous substrate dihydrofarnesyl diphosphate. J Am Chem Soc 118: 10037-10040
11. Cane DE, Wu Z, Proctor RH, Hohn TM (1993) Overexpression in Escherichia coli of soluble aristolochene synthase from Penicillium roqueforti. Arch Biochem Biophys 30: 415-419
12. Threlfall DR, Whitehead IM (1988) Co-ordinated inhibition of squalene synthetase and induction of enzymes of sesquiterpe-noid phytoalexin biosynthesis in cultures of Nicotiana tabacum. Phytochemistry 27: 2567-2580
13. van Beek TA, Maas P, King BM, Leclercq E, Voragen AGJ, de Groot Ae (1990) Bitter sesquiterpene lactones from chicory roots. J Agric Food Chem 38: 1035-1038
14. Weinheimer AJ, Youngblood WW, Washecheck PH, Karns TKB, Ciereszko LS (1970) Isolation of the elusive (-)-germacrene-A from the gorgonian, Eunicea mammosa: chemistry of coelenterates XVIII. Tetrahedron Lett 7: 497-500
15. Whitehead IM, Threlfall DR, Ewing DE (1989) 5-Epi-aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 28: 775-779