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Secondary Plant Substances. Diterpenes

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Progress in Botany

Part of the book series: Progress in Botany/Fortschritte der Botanik ((BOTANY,volume 58))

Abstract

Diterpenes are 20-carbon compounds derived biogenetically from an acyclic precursor containing four isoprenoid units linked together in a regular (i.e., head-to-tail) manner. All-trans-geranylgeranyl pyrophosphate (GGPP; III) is considered to be the general acyclic precursor of this class of terpenes (Ruzicka 1953; West 1981). The structure of well over 1000 natural diterpenes and diterpenoid substances has been elucidated, and the pace at which new structures are being described is increasing (Connolly and Hill 1992; Hanson 1992, 1993, 1994, 1995; Buckingham 1994). Some acyclic diterpenes are known, but the vast majority are carbocyclic compounds containing from one to as many as five rings. Many different carbon skeletons are represented among these cyclic substances. Diterpenes at many different states of oxidation ranging from hydrocarbons to highly oxygenated are known. The clero-dane diterpenoids have attached attention because some of them possess antifeedant activity which appears to be specific to certain insects (Malekov et al. 1994; Rodriguez-Hahn et al. 1994). Also the biological and pharmacological effects of cembranoids (Weinheimer et al. 1979; Wahlberg and Enzell 1984; Wahlberg and Eklund 1992) and of forskolin (Bhat 1993) are important.

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References

  • Akatsuka T, Kodama O, Sekido H, Kono Y, Takeuchi S (1985) Agric Biol Chem 49: 1689–1694.

    CAS  Google Scholar 

  • Anderson JD, Moore TC (1967) Plant Physiol 42: 1527–1534.

    PubMed  CAS  Google Scholar 

  • Ashman PJ, Mackenzie A, Bramley PM (1990) Biochim Biophys Acta 1036: 151–157.

    PubMed  CAS  Google Scholar 

  • Barendse GWM, Dijkstra A, Moore TC (1983) J Plant Growth Regul 2: 165–175.

    CAS  Google Scholar 

  • Barendse GWM, Kepczynski CM, Karssen CM, Koornneef M (1986) Physiol Plant 67: 315–319.

    CAS  Google Scholar 

  • Begley MJ, Jackson CB, Pattenden G (1990) Tetrahedron 46: 4907–4924.

    CAS  Google Scholar 

  • Benson RJ, Zeevaart JAD (1990) J Plant Growth Regul 9: 237–242.

    Google Scholar 

  • Bhat SV (1993) Prog Chem Org Nat Prod 62: 1–74.

    CAS  Google Scholar 

  • Birch AJ, Brown WV, Corrie JET, Moore BP (1972) J Chem Soc Perkin Trans I 2653–2658.

    Google Scholar 

  • Blechert S, Guenard D (1990) In: Brossi A (ed) The alkaloids, vol 39. Academic Press, New York, pp 195–238.

    Google Scholar 

  • Bolwell GP, Bozak K, Zimmerlin A (1994) Phytochemistry 37:1491–1506.Borman S (1994) Chem Eng News 72 (8): 32–34.

    PubMed  CAS  Google Scholar 

  • Briggs LH, Cain BF, Cambie RC, Davis BR, Rutledge PS, Wilmshurst JK (1963) J Chem Soc 1345–1355.

    Google Scholar 

  • Bruce RJ, West CA (1982) Plant Physiol 69: 1181–1188.

    PubMed  CAS  Google Scholar 

  • Buckingham J (ed) (1994) Dictionary of natural products, vols 1–8.

    Google Scholar 

  • Chapman and Hall, London.

    Google Scholar 

  • Carman RM, Duffield AR (1993) Aust J Chem 46: 1105–1114.

    CAS  Google Scholar 

  • Cartwright DW, Langcake PW, Pryce RJ, Leworthy DW, Ride JP (1981) Phytochemistry 20: 535–537.

    CAS  Google Scholar 

  • Ceccarelli N, Lorenzi R (1983) Phytochemistry 22: 2203–2205.

    CAS  Google Scholar 

  • Ceccarelli N, Lorenzi R, Alpi A (1979) Phytochemistry 18: 1657–1658.

    CAS  Google Scholar 

  • Ceccarelli N, Lorenzi R, Alpi A (1981) Experientia 37: 478.

    CAS  Google Scholar 

  • Cheniclet C (1987) J Exp Bot 38: 1557–1572.

    CAS  Google Scholar 

  • Choinski JS, Moore TC (1980) Plant Physiol 65: 1031–1035.

    PubMed  CAS  Google Scholar 

  • Chung HC, Coolbaugh RC (1986) Plant Physiol 80: 544–548.

    PubMed  CAS  Google Scholar 

  • Coates RM, Cavender PL (1980) J Am Chem Soc 102: 6358–6359.

    CAS  Google Scholar 

  • Colby SM, Alonso WR, Katahira EJ, McGarvey DJ, Croteau R (1993) J Biol Chem 268: 23016–23024.

    PubMed  CAS  Google Scholar 

  • Connolly JD, Hill RA (1992) Dictionary of terpenoids, vols 1–3.

    Google Scholar 

  • Chapman and Hall, London.

    Google Scholar 

  • Coolbaugh RC (1983) In: Crozier A (ed) The biochemistry and physiology of gibberellins, vol 1. Praeger, New York, pp 53–89.

    Google Scholar 

  • Coolbaugh RC, Hamilton R (1976) Plant Physiol 57: 245–248.

    PubMed  CAS  Google Scholar 

  • Coolbaugh RC, Hirano SS, West CA (1978) Plant Physiol 62: 571–576.

    PubMed  CAS  Google Scholar 

  • Cragg GM, Schepartz SA, Suffness M, Grever MR (1993) J Nat Prod 56: 1657–1668.

    PubMed  CAS  Google Scholar 

  • Cross BE, Gait RHB, Hanson JR, Curtis PJ, Grove JF, Morrison A (1963) J Chem Soc 2937–2943.

    Google Scholar 

  • Croteau R (1987) Chem Rev 87: 929–954.

    CAS  Google Scholar 

  • Croteau R, Johnson MA (1985) In: Higuchi T (ed) Biosynthesis and biodegradation of wood components. Academic Press, New York, pp 379–439.

    Google Scholar 

  • Croteau R, Gurkewitz S, Johnson MA, Fisk HJ (1987a) Plant Physiol 85: 1123–1128.

    CAS  Google Scholar 

  • Croteau R, Wheeler CJ, Cane DE, Ebert R, Ha HJ (1987b) Biochemistry 26: 5383–5389.

    CAS  Google Scholar 

  • Dell B, McComb AJ (1978a) Adv Bot Res 6: 276–316.

    Google Scholar 

  • Dell B, McComb AJ (1978b) J Exp Bot 29: 89–95.

    CAS  Google Scholar 

  • Denis JN, Greene AE, Guenard D, Gueritte-Voegelein F, Mangatal L, Potier P (1988) J Am Chem Soc 110: 5917–5919.

    CAS  Google Scholar 

  • Dennis DT, West CA (1967) J Biol Chem 242: 3293–3300.

    PubMed  CAS  Google Scholar 

  • Dickson RE, Isebrands JG (1991) In: Mooney HA, Winner WE, Pell EJ, Chu E (eds) Response of plants to multiple stresses. Academic Press, San Diego, pp 4–29.

    Google Scholar 

  • Donaldson RP, Luster DG (1991) Plant Physiol 96: 669–674.

    PubMed  CAS  Google Scholar 

  • Drengler KA, Coates RM (1980) Chem Commun 856–857.

    Google Scholar 

  • Dudley MW, Dueber MT, West CA (1986a) Plant Physiol 81: 335–342.

    CAS  Google Scholar 

  • Dudley MW, Green TR, West CA (1986b) Plant Physiol 81: 343–348.

    CAS  Google Scholar 

  • Dueber MT, Adolf W, West CA (1978) Plant Physiol 62: 598–603.

    PubMed  CAS  Google Scholar 

  • Duncan JD, West CA (1981) Plant Physiol 68: 1128–1134.

    PubMed  CAS  Google Scholar 

  • Elliger CA, Zinkel DF, Chan BG, Waiss AC (1976) Experientia 32: 1364–1366.

    PubMed  CAS  Google Scholar 

  • Facchini PJ, Chappell J (1992) Proc Natl Acad Sci USA 89: 11088–11092.

    PubMed  CAS  Google Scholar 

  • Fahn A (1988) New Phytol 108: 229–257.

    Google Scholar 

  • Fall RR, West CA (1971) J Biol Chem 246: 6913–6928.

    PubMed  CAS  Google Scholar 

  • Fenical W (1978) In: Scheuer PJ (ed) Marine natural products: chemical and biological perspectives, vol 2. Academic Press, New York, pp 173–245.

    Google Scholar 

  • Fett-Neto AG, DiCosmo F (1992) Planta Med 58: 464–466.

    PubMed  CAS  Google Scholar 

  • Fett-Neto AG, DiCosmo F, Reynolds WF, Sakata K (1992) Bio/Technology 10: 1572–1575.

    PubMed  CAS  Google Scholar 

  • Fleming PE, Mocek U, Floss HG (1993) J Am Chem Soc 115: 805–807.

    CAS  Google Scholar 

  • Fleming PE, Knaggs AR, He XG, Mocek U, Floss HG (1994) J Am Chem Soc 116: 4137–4138.

    CAS  Google Scholar 

  • Frost RG, West CA (1977) Plant Physiol 59: 22–29.

    PubMed  CAS  Google Scholar 

  • Funk C, Croteau R (1994) Arch Biochem Biophys 308: 258–266.

    PubMed  CAS  Google Scholar 

  • Funk C, Lewinsohn E, Stofer-Vogel B, Steele CL, Croteau R (1994) Plant Physiol 106: 999–1005.

    PubMed  CAS  Google Scholar 

  • Geiger DR, Servaites JC (1991) In: Mooney HA, Winner WE, Pell EJ, Chu E (eds) Response of plants to multiple stresses. Academic Press, San Diego, pp 104–124.

    Google Scholar 

  • Georg GI, Cheruvallath ZS (1994) J Org Chem 59: 4015–4018.

    CAS  Google Scholar 

  • Georg GI, Gollapudi SR, Grunewald GL, Gunn CW, Himes RH, Rao BK, Liang XZ, Mirhom YW, Mitcher LA (1993a) Bioorg Med Chem Lett 3: 1345–1348.

    CAS  Google Scholar 

  • Georg GI, Cheruvallath ZS, Vander Velde D, Ye QM, Mitcher LA, Himes RH (1993b) Bioorg Med Chem Lett 3: 1349–1350.

    CAS  Google Scholar 

  • Georg GI, Cheruval¬lath ZS, Harriman GCB, Hepperle M, Park H (1993c) Bioorg Med Chem Lett 3: 2467–2470.

    CAS  Google Scholar 

  • Georg GI, Ali SM, Zygmut J, Jayasinghe LR (1994) Exp Opin Ther Patents 4: 109–120.

    CAS  Google Scholar 

  • Georg GI, Harriman GCB, Vander Velde D, Boge TC, Cheruvallath ZS, Datta A, Hepperle M, Park H, Himes RH, Jayasinghe LR (1995) In: Georg GI, Chem TT, Ojima I, Vyas DM (eds) Taxane anticancer agents: basic science and current status. American Chemical Society Symp 583. American Chemical Societey, Washington, DC, pp 217–232.

    Google Scholar 

  • Gibson DM, Ketchum REB, Vance NV, Christen AA (1993) Plant Cell Rep 12: 479–482.

    CAS  Google Scholar 

  • Gijzen M, Lewinsohn E, Croteau R (1991) Arch Biochem Biophys 289: 267–273.

    PubMed  CAS  Google Scholar 

  • Gijzen M, Lewinsohn E, Croteau R (1992) Arch Biochem Biophys 294: 670–674.

    PubMed  CAS  Google Scholar 

  • Gijzen M, Lewinsohn E, Savage TJ, Croteau R (1993) In: Teranishi R, Butterry RG, Sugisawa H (eds) Bioactive volatile compounds from plants. American Chemical Society Symp Ser 525. American Chemical Society, Washington, DC, pp 8–22.

    Google Scholar 

  • Gilmour SJ, Zeevaart JAD, Schwenen L, Graebe JE (1986) Plant Physiol 82: 190–195.

    PubMed  CAS  Google Scholar 

  • Gleizes M, Pauly G, Bernard-Dagan C, Jacques R (1980) Physiol Plant 50: 16–20.

    CAS  Google Scholar 

  • Graebe JE (1968) Phytochemistry 7: 2003–2020.

    CAS  Google Scholar 

  • Graebe JE (1969) Planta 85: 171–174.

    Google Scholar 

  • Graebe JE (1982) In: Wareing PF (ed) Plant growth substances. Academic Press, London, pp 71–80.

    Google Scholar 

  • Graebe JE (1987) Annu Rev Plant Physiol 38: 419–465.

    CAS  Google Scholar 

  • Graebe JE, Dennis DT, Upper CD, West CA (1965) J Biol Chem 240: 1847–1854.

    PubMed  CAS  Google Scholar 

  • Graebe JE, Bowen DH, MacMillan J (1972) Planta 102: 261–271.

    CAS  Google Scholar 

  • Gref R, Ericsson A (1985) Can J For Res 15: 92–96.

    CAS  Google Scholar 

  • Gref R, Tenow O (1987) Can J For Res 17: 346–349.

    CAS  Google Scholar 

  • Großelindemann E, Graebe JE, Stoeckl D, Hedden P (1991) Plant Physiol 96: 1099–1104.

    PubMed  Google Scholar 

  • Guenard D, Gueritte-Voegelein F, Potier P (1993) Acc Chem Res 26: 160–167.

    CAS  Google Scholar 

  • Gueritte-Voegelein F, Senilh V, David B, Guenard D, Potier P (1986) Tetrahedron 42: 4451–4460.

    CAS  Google Scholar 

  • Gueritte-Voegelein F, Guenard D, Potier P (1987) J Nat Prod 50: 9–18.

    PubMed  CAS  Google Scholar 

  • Guo Z, Severson RF, Wagner GJ (1994) Arch Biochem Biophys 308: 103–108.

    PubMed  CAS  Google Scholar 

  • Hanson JR (1992) Nat Prod Rep 9: 1–16.

    PubMed  CAS  Google Scholar 

  • Hanson JR (1993) Nat Prod Rep 10: 159–174.

    CAS  Google Scholar 

  • Hanson JR (1994) Nat Prod Rep 11: 265–277.

    PubMed  CAS  Google Scholar 

  • Hanson JR (1995) Nat Prod Rep 12: 207–218.

    CAS  Google Scholar 

  • Harrison JW, Scrowston RM, Lythgoe B (1966) J Chem Soc C 1933–1945.

    Google Scholar 

  • Hedden P, Phinney BO (1979) Phytochemistry 18: 1475–1479.

    CAS  Google Scholar 

  • Hedden P, MacMillan J, Phinney BO (1978) Annu Rev Plant Physiol 29: 149–192.

    CAS  Google Scholar 

  • Hendry G (1986) New Phytol 102: 239–247.

    CAS  Google Scholar 

  • Hezari M, Lewis NG, Croteau R (1995) Arch Biochem Biophys 322: 437–444.

    PubMed  CAS  Google Scholar 

  • Hodges JD, Elam WW, Watson WF, Nebeker TE (1979) Can Entomol 111: 889–896.

    CAS  Google Scholar 

  • Holmes FA, Kudelka AP, Kavanagh JJ, Huber MH, Ajani JA, Valero V (1995) In: Georg GI, Chen TT, Ojima I, Vyas DM (eds) Taxane anticancer agents: basic science and current status. American Chemical Society, Washington, DC, pp 31–57.

    Google Scholar 

  • Honda K, Shishibori T, Suga T (1980) J Chem Res (Synop) 218–219.

    Google Scholar 

  • Jin DF, West CA (1984) Plant Physiol 74: 989–992.

    Google Scholar 

  • Johnson M, Croteau R (1987) In: Fuller G, Nes WD (eds) Ecology and metabolism of plant lipids. American Chemical Society Symposium Series 325, American Chemical Society, Washington, DC, pp 76–92.

    Google Scholar 

  • Jones MG, Zeevaart JAD (1980) Planta 149: 269–273.

    CAS  Google Scholar 

  • Kandra L, Wagner GJ (1988) Arch Biochem Biophys 265: 425–432.

    PubMed  CAS  Google Scholar 

  • Kato T, Aizawa H, Tsunakawa M, Sasaki N, Kitahara Y, Takahashi N (1977) J Chem Soc Perkin Trans I 250–254.

    Google Scholar 

  • Keene CK, Wagner GJ (1985) Plant Physiol 79: 1026–1032.

    PubMed  CAS  Google Scholar 

  • Kelsey RG, Vance NC (1992) J Nat Prod 55: 912–917.

    CAS  Google Scholar 

  • Kingston DGI (1995) In: Georg GI, Chen TT, Ojima I, Vyas DM (eds) Taxane anticancer agents: basic science and current status. American Chemical Society Symp Ser 583. American Chemical Society, Washington, DC, pp 203–216.

    Google Scholar 

  • Kingston DGI, Molinero AA, Rimoldi JM (1993) Prog Chem Org Nat Prod 61: 1–192.

    CAS  Google Scholar 

  • Knotz J, Coolbaugh RC, West CA (1977) Plant Physiol 60: 81–85.

    PubMed  CAS  Google Scholar 

  • Koepp AE, Hezari M, Zajicek J, Stofer-Vogel B, LaFever RE, Lewis NG, Croteau R (1995) J Biol Chem 270: 8686–8690.

    PubMed  CAS  Google Scholar 

  • Kono Y, Takeuchi S, Kodama O, Sekido H, Akatsuka T (1985) Agric Biol Chem 49: 1695–1701.

    CAS  Google Scholar 

  • Kwak SS, Choi MS, Park YG, Yoo JS, Lin JR (1995) Phytochemistry 40: 29–32.

    CAS  Google Scholar 

  • LaFever RE, Stofer-Vogel B, Croteau R (1994) Arch Biochem Biophys 313: 139–149.

    PubMed  CAS  Google Scholar 

  • Lee SC, West CA (1981a) Plant Physiol 67: 633–639.

    Google Scholar 

  • Lee SC, West CA (1981b) Plant Physiol 67: 640–645.

    Google Scholar 

  • Leete E, Bodem GB (1966)Tetrahedron Lett 33:3925–3927.

    Google Scholar 

  • Lewinsohn E, Gijzen M, Savage TJ, Croteau R (1991a) Plant Physiol 96: 38–43.

    Google Scholar 

  • Lewinsohn E, Gijzen M, Croteau R (1991b) Plant Physiol 96: 44–49.

    Google Scholar 

  • Lewinsohn E, Gijzen M, Croteau R (1992a) Arch Biochem Biophys 293: 167–173.

    Google Scholar 

  • Lewinsohn E, Gijzen M, Croteau R (1992b) In: Nes WD, Parish EJ, Trzaskos JM (eds) Regulation of isopentenoid metabolism. ACS Symp Ser 497. American Chemical Society, Washington, DC, pp 8–17.

    Google Scholar 

  • Lewinsohn E, Savage TJ, Gijzen M, Croteau R (1993a) Phytochem Anal 4: 220–225.

    CAS  Google Scholar 

  • Lewinsohn E, Gijzen M, Muzika RM, Barton K, Croteau R (1993b) Plant Physiol 101: 1021–1028.

    CAS  Google Scholar 

  • Lewinsohn E, Steele CL, Croteau R (1994a) Plant Mol Biol Rep 12: 20–25.

    Google Scholar 

  • Lewinsohn E, Worden E, Croteau R (1994b) Phytochemistry 36: 651–656.

    Google Scholar 

  • Lois AF, West CA (1990) Arch Biochem Biophys 276: 270–277.

    PubMed  CAS  Google Scholar 

  • Lorio PL Jr (1988) In: Mattson WJ, Levieux J, Bernard-Dagan C (eds) Mechanisms of woody plant defense against insect: search for pattern. Springer, Berlin Heidelberg New York, pp 73–92.

    Google Scholar 

  • Lythgoe B (1968) In: Manske RHF (ed) The Alkaloids, vol 10, Chemistry and physiology. Academic Press, New York, pp 597–626.

    Google Scholar 

  • Magri NF, Kingston DGI, Jitrangsri C, Piccariello T (1986) J Org Chem 51: 3239–3242.

    CAS  Google Scholar 

  • Malekov PY, Papanov GY, Rodriguez B, De La Torre MC, Simmonds MSJ, Blaney WM, Boneva IM (1994) Phytochemistry 37: 147–157.

    Google Scholar 

  • Mau CJD, West CA (1994) Proc Natl Acad Sci USA 91: 8497–8501.

    PubMed  CAS  Google Scholar 

  • McGimpsey JR, Murray J (1960) J Appl Chem 10: 340–364.

    Google Scholar 

  • Meinwald J, Prestwich GD, Nakanishi K, Kubo I (1978) Science 199: 1167–1173.

    PubMed  CAS  Google Scholar 

  • Mellon JE, West CA (1979) Plant Physiol 64: 406–410.

    PubMed  CAS  Google Scholar 

  • Metzger JD, Zeevaart JAD (1982) Plant Physiol 69: 287–291.

    PubMed  CAS  Google Scholar 

  • Mihaliak CA, Karp F, Croteau R (1993) In: Lea PJ (ed) Methods in plant biochemistry, enzymes of secondary metabolism, vol 9. Academic Press, London, pp 261–279.

    Google Scholar 

  • Miller RH, Berryman AA, Ryan CA (1986) Phytochemistry 25: 611–612.

    CAS  Google Scholar 

  • Moesta P, West CA (1985) Arch Biochem Biophys 238: 325–333.

    PubMed  CAS  Google Scholar 

  • Moore TC, Moore JA (1991) J Plant Growth Regul 10: 91–95.

    CAS  Google Scholar 

  • Moss ML, Frey PA (1990) J Biol Chem 265: 18112–18115.

    PubMed  CAS  Google Scholar 

  • Murphy PJ, West CA (1969) Arch Biochem Biophys 133: 395–407.

    Google Scholar 

  • Nicolaou KC, Dai WM, Guy RK (1994) Angew Chem Int Ed Engl 33:15–44

    Google Scholar 

  • Angew Chem 106:38–69.

    Google Scholar 

  • Noma M, Suzuki F, Gamou K, Kawashima N (1983) Phytochemistry 22: 133–135.

    Google Scholar 

  • Norin T (1972) Phytochemistry 11: 1231–1242.

    CAS  Google Scholar 

  • Paine TD, Blanche CA, Nebeker TE, Stephen FM (1987) Can J For Res 17: 1202–1206.

    CAS  Google Scholar 

  • Phinney BO, Spray CR (1990) In: Towers GHN, Stafford HA Biochemistry of the mevalonic acid pathway to terpenoids. Plenum Press, New York, pp 203–218.

    Google Scholar 

  • Piatt RV, Opie CT, Haslam E (1984) Phytochemistry 23: 2211–2217.

    Google Scholar 

  • Proctor RH, Hohn TM (1993) J Biol Chem 268: 4543–4548.

    PubMed  CAS  Google Scholar 

  • Puritch GS (1973) Can J For Res 3: 293–298.

    Google Scholar 

  • Puritch GS, Mullick DB (1975) J Exp Bot 26: 903–910

    Google Scholar 

  • Raffa KF (1991) In: Tallamy DW, Raupp MJ (eds) Phytochemical induction by herbivores. Academic Press, New York, pp 245–276.

    Google Scholar 

  • Raffa KF, Berryman AA (1982a) Can Entomol 114: 797–810.

    Google Scholar 

  • Raffa KF, Berryman AA (1982b) Environ Entomol 11: 486–492.

    Google Scholar 

  • Raffa KF, Berryman AA, Simasko J, Teal W, Wong BL (1985) Environ Entomol 14: 552–556.

    CAS  Google Scholar 

  • Railton ID, Fellows B, West CA (1984) Phytochemistry 23: 1261–1267.

    Google Scholar 

  • Reid RW, Whitney HS, Watson JA (1967) Can J Bot 45: 1115–1128.

    Google Scholar 

  • Robinson DL, West CA (1970a) Biochemistry 9: 70–79.

    Google Scholar 

  • Robinson DR, West CA (1970b) Biochemistry 9: 80–89.

    Google Scholar 

  • Rodriguez-Hahn L, Esquivel B, Cardenas J (1994) Prog Chem Org Nat Prod 63: 107–196.

    Google Scholar 

  • Ruzicka L (1953) Experientia 9: 357–367.

    Google Scholar 

  • Saito T, Kamiya Y, Yamane H, Murofushi N, Sakurai A, Takahashi N (1993) Plant Physiol 102:349 (Suppl).

    Google Scholar 

  • Savage TJ, Hatch MW, Croteau R (1994) J Biol Chem 269: 4012–4020.

    PubMed  CAS  Google Scholar 

  • Schneider B (1994) Dtsch Apoth Ztg 134: 3389–3400.

    Google Scholar 

  • Schuck HJ (1982a) In: Heybroek HM, Stephan BR, von Weissenberg K (eds) Resistance to disease and pests in forest trees. PUDOG, Wageningen, pp 169–175.

    Google Scholar 

  • Schuck HJ (1982b) Eur J For Pathol 12: 175–181.

    Google Scholar 

  • Schütte W, Reppe I, Schüdlich S, Füchsel G (1995) Ärzteblatt Sachsen-Anhalt 6:46–48.

    Google Scholar 

  • Sekido H, Endo T, Suga R, Kodama O, Akatsuka T, Kono Y, Takeuchi S (1986) J Pestic Sci 11: 369–372.

    CAS  Google Scholar 

  • Shechter I, West CA (1969) J Biol Chem 244: 3200–3209.

    Google Scholar 

  • Shen-Miller J, West CA (1982) Plant Physiol 69: 637–641.

    PubMed  CAS  Google Scholar 

  • Shen-Miller J, West CA (1984) Plant Physiol 74:439– 441.

    Google Scholar 

  • Shen-Miller J,West CA (1985) Phytochemistry 24: 461–464.

    Google Scholar 

  • Shrimpton DM (1972) Can J Bot 51: 527–534.

    Google Scholar 

  • Sitton D, West CA (1975) Phytochemistry 14: 1921–1925.

    Google Scholar 

  • Spickett CM, Ponnamperuma K, Abell C (1994) Phytochemistry 37: 971–973.

    CAS  Google Scholar 

  • Steele CL, Lewinsohn E, Croteau R (1995) Proc Natl Acad Sci 92: 4164–4168.

    PubMed  CAS  Google Scholar 

  • Stekoll M, West CA (1978) Plant Physiol 61: 38–45.

    PubMed  CAS  Google Scholar 

  • Stierle A, Strobel G, Stierle D (1993) Science 260: 214–216.

    PubMed  CAS  Google Scholar 

  • Strobel GA, Stierle A, van Kuijk FJGM (1992) Plant Sci 84: 65–74.

    CAS  Google Scholar 

  • Strobel GA, Stierle A, Hess WM (1993) Plant Sci 92: 1–12.

    CAS  Google Scholar 

  • Suffness M, Cordell GA (1985) In: Brossi A (ed) The Alkaloids, chemistry and pharmacology, vol 25. Academic Press, New York, pp 6–18.

    Google Scholar 

  • Sun T-p, Ka¬miya Y (1994) Plant Cell 6: 1509–1518.

    PubMed  CAS  Google Scholar 

  • Sun T-p, Goodman HM, Ausubel FM (1992) Plant Cell 4: 119–128.

    PubMed  CAS  Google Scholar 

  • Talon M, Zeevaart JAD (1990) Plant Physiol 92: 1094–1100.

    PubMed  CAS  Google Scholar 

  • Talon M, Tadeo FR, Zeevaart JAD (1991a) Planta 185: 487–493.

    Google Scholar 

  • Talon M, Zeevaart JAD, Gage DA (1991b) Plant Physiol 97: 1521–1526.

    Google Scholar 

  • Turnbull CGN, Crozier A, Schwenen L, Graebe JE (1986) Phytochemistry 25: 97–101.

    CAS  Google Scholar 

  • Tursch B, Braekman JC, Daloze D, Kaisin M (1978) In: Scheuer PJ (ed) Marine natural products: chemical and biological perspectives, vol 2. Academic Press, New York, pp 247–296.

    Google Scholar 

  • Upper CD, West CA (1967) J Biol Chem 242: 3285–3292.

    PubMed  CAS  Google Scholar 

  • Vance NC, Kelsey RG, Sabin TE (1994) Phytochemistry 36: 1241–1244.

    PubMed  CAS  Google Scholar 

  • Vidensek N, Lim P, Campbell A, Carlson C (1990) J Nat Prod 53: 1609–1610.

    PubMed  CAS  Google Scholar 

  • Wagner GJ (1991) Plant Physiol 96: 675–679.

    PubMed  CAS  Google Scholar 

  • Wagschal K, Savage TJ, Croteau R (1991) Tetrahedron 47: 5933–5944.

    CAS  Google Scholar 

  • Wagschal K, Pyun HJ, Coates RM, Croteau R (1994) Arch Biochem Biophys 308: 477–487.

    PubMed  Google Scholar 

  • Wahlberg I, Enzell CR (1984) Beitr Tabakforsch Int 12: 93–104.

    Google Scholar 

  • Wahlberg I, Eklung AM (1992) Prog Chem Org Nat Prod 60: 1–141.

    CAS  Google Scholar 

  • Walker-Simmons M, Jin D, West CA, Hadwiger L, Ryan CA (1984) Plant Physiol 76: 833–836.

    Google Scholar 

  • Wall ME, Wani MC (1995) In: Georg GI, Chen TT, Ojima I, Vyas DM (eds) Taxane anticancer agents: basic science and current status. American Chemical Society Symp Ser 583. American Chemical Society, Washington, DC, pp 18–30.

    Google Scholar 

  • Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT (1971) J Am Chem Soc 93: 2325–2327.

    PubMed  CAS  Google Scholar 

  • Weinheimer AJ, Chang CWJ, Matson JA (1979) Prog Chem Org Nat Prod 36: 286–387.

    Google Scholar 

  • West CA (1981) In: Porter JW, Spurgeon SL (eds) Biosynthesis of isoprenoid compounds, vol 1. Wiley, New York, pp 375–411.

    Google Scholar 

  • West CA, Dudley MW, Dueber MT (1979) In: Swain T, Waller GR (eds) Recent advances in phytochemistry. Topics in the biochemistry of natural products, vol 13. Plenum Press, New York, pp 163–198.

    Google Scholar 

  • West CA, Shen-Miller J, Railton ID (1982) In: Wareing PF (ed) Plant growth substances. Academic Press, London, pp 81–90.

    Google Scholar 

  • West CA, Lois AF, Wickham KA, Ren YY (1990) In: Towers GHN, Stafford HA (eds) Biochemistry of the mevalonic acid pathway to terpenoids. Plenum Press, New York, pp 219–248.

    Google Scholar 

  • Wheeler NC, Jech K, Masters S, Brobst SW, Alvarado AB, Hoover AJ, Snader KM (1992) J Nat Prod 55: 432–440.

    PubMed  CAS  Google Scholar 

  • Wickham KA, West CA (1992) Arch Biochem Biophys 293: 320–332.

    PubMed  CAS  Google Scholar 

  • Witherup KM, Look SA, Stasko MW, Ghiorzi TJ, Muschik GM, Cragg GM (1990) J Nat Prod 53: 1249–1255.

    PubMed  CAS  Google Scholar 

  • Wong BL, Berryman AA (1977) Can J Bot 55: 2358–2365.

    Google Scholar 

  • Wright LC, Berryman AA, Gurusiddaiah S (1979) Can Entomol 111: 1255–1262.

    CAS  Google Scholar 

  • Yamada T (1992) In: Blanchette RA, Biggs AR (eds) Defense mechanisms of woody plants against fungi. Springer, Berlin Heidelberg New York, pp 147–184.

    Google Scholar 

  • Zamir LO, Nedea ME, Garneau FX (1992) Tetrahedron Lett 33: 5235–5236.

    CAS  Google Scholar 

  • Zeevaart JAD (1971) Plant Physiol 47: 821–827.

    PubMed  CAS  Google Scholar 

  • Zeevaart JAD (1974) In: Tamura S (ed) Plant growth substances. Hirokawa, Tokio, pp 1175–1181.

    Google Scholar 

  • Zeevaart JAD (1985) Planta 166: 276–279.

    CAS  Google Scholar 

  • Zeevaart JAD, Gage DA (1993) Plant Physiol 101: 25–29.

    PubMed  CAS  Google Scholar 

  • Zeevaart JAD, Talon M, Wilson TM (1990) In: Takahashi N, Phinney BO, MacMillan J (eds) Gibberellins. Springer, Berlin Heidelberg New York, pp 273–279.

    Google Scholar 

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Schütte, H.R. (1997). Secondary Plant Substances. Diterpenes. In: Behnke, HD., Lüttge, U., Esser, K., Kadereit, J.W., Runge, M. (eds) Progress in Botany. Progress in Botany/Fortschritte der Botanik, vol 58. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-60458-4_10

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