Abstract
The biosynthesis of prenylated indole alkaloids and related natural substances derived from tryptophan is reviewed. The families of compounds covered in this review include the brevianamides, austamides, paraherquamides, marcfortine, roquefortine, aszonalenin, echinulin, verruculogen, the fumitremorgins, a-cyclopiazonic acid, and the ergot alkaloids. Although other families of naturally occurring prenylated indole alkaloids exist, such as the iridoids, this review is intended to examine the biosynthesis of the groups selected based on their structural and biogenetic similarities. In addition, the biosynthesis of the families selected for this chapter have not, to the best of our knowledge, been previously reviewed.
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9 References
Birch AJ, Wright JJ (1969) J Chem Soc Chem Comm:644
Wilson BJ, Yang DTC, Harris TM (1973) Appl Microbiol:633
Robbers JE, Straus JW (1975) Lloydia 38:355
Coetzer J (1974) Acta Cryst B30:2254
Steyn P (1971) Tetrahedron Lett 3331
Steyn P (1973) Tetrahedron 29:107
Coetzer J, Steyn PS (1973) Acta Cryst B29:685
Birch AJ, Wright JJ (1970) Tetrahedron 26:2329
Birch AJ, Russell RA (1972) Tetrahedron 28:2999
Ritchie R, Saxton JE (1975) J Chem Soc Chem Comm 611
Ritchie R, Saxton JE (1981) Tetrahedron 37:4295
Kametani T, Kanaya N, Ihara M (1981) J Chem Soc Perkin Trans I:959
Baldas J, Birch AJ, Russell RA (1974) J Chem Soc Perkin Trans I:50
Porter AEA, Sammes PG (1970) J Chem Soc Chem Comm 1103
Birch AJ (1971) J Agr Food Chem 19:1088
Williams RM, Glinka T, Kwast E (1988) J Am Chem Soc 110:5927
Williams RM, Glinka T, Kwast E, Coffman H, Stille JK (1990) J Am Chem Soc 112:808
Williams RM, Kwast E, Coffman H, Glinka T (1989) J Am Chem Soc 111:3064
Sanz-Cervera JF, Glinka T, Williams RM (1993) Tetrahedron 49:8471
Domingo LR, Sanz-Cervera JF, Williams RM, Picher MT, Marco JA (1997) J Org Chem 62:1662
Williams RM, Kwast E (1989) Tetrahedron Lett 30:451
Williams RM (unpublished results)
Harrison DM (1981) Tetrahedron Lett 22:2501
Shoop WL, Egerton JR, Eary CH, Suhayda D (1990) J Parasitol 76:349
Ostlind DA, Mickle WG, Ewanciw DV, Andriuli WC, Campbell WC, Hernandez S, Mochales S, Munguira E (1990) Res Vet Sci 48:260
Shoop WL, Haines HW, Eary CH, Michael BF (1992) Am J Vet Res 53:2032
Shoop WL, Michael BF, Haines HW, Eary CH (1992) Vet Parasitol 43:259
Schaeffer JM, Blizzard TA, Ondeyka J, Goegelman R, Sinclair PJ, Mrozik H (1992) Biochem Pharmacol 43:679
Yamazaki M, Okuyama E (1981) Tetrahedron Lett 22:135
(a) Ondeyka JG, Goegelman RT, Schaeffer JM, Kelemen L, Zitano L (1990) J Antibiot 43:1375; (b) Liesch JM, Wichmann CF (1990) J Antibiot 43:1380; (c) Blizzard TA, Mrozik H, Fisher MH, Schaeffer SM (1990) J Org Chem. 55:2256; (d) Blizzard TA, Marino G, Mrozik H, Fisher MH, Hoogsteen K, Springer JP (1989) J Org Chem 54:2657; (e) Blizzard TA, Margiatto G, Mrozik H, Schaeffer JM, Fisher MH (1991) Tetrahedron Lett 32:2437; (f) Blizzard TA, Margiatto G, Mrozik H, Schaeffer JM, Fisher MH (1991) Tetrahedron Lett 32:2441; (g) Blizzard TA, Rosegay A, Mrozik H, Fisher MH (1989) J Labeled Compounds and Radiopharmaceuticals 28:461
(a) Blanchflower SE, Banks RM, Everett JR, Manger BR, Reading C (1991) J Antibiotics 44:492; (b) Blanchflower SE, Banks RM, Everett JR, Reading C (1993) J Antibiotics 46:1355
Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C (1997) J Antibiot 50:840
Hayashi H, Nishimoto Y, Nozaki H (1997) Tetrahedron Lett 38:5655
Whyte AC, Gloer JB (1996) J Nat Prod 59:1093
(a) Polonsky J, Merrien M-A, Prange T, Pacard C (1980) J Chem Soc Chem Comm 601; (b) Prange T, Billion M-A, Vuilhorgne M, Pascard C, Polonsky J, Moreau S (1981) Tetrahedron Lett 22:1977
Fuchser J (1995) PhD thesis of Jens Fuchser “Beeinflussung der Sekundarstoffbildung bei Aspergillus ochraceus durch Variation der Kulturbedingungen sowie Isolierung, Strukturaufklarung und Biosynthese der neuen Naturstoffe”, University of Goettingen. K. Bielefeld Verlag, Friedland (Prof. A. Zeeck).
(a) Kuo MS, Wiley VH, Cialdella JI, Yurek DA, Whaley HA, Marshall VP (1996) J Antibiot 49:1006; (b) Kuo MS, Yurek DA, Mizsak SA, Cialdella JI, Baczynskyj L, Marshall VP (1999) J Am Chem Soc 121:1763
Lee BH, Clothier MF (1997) J Org Chem 62:1795
Stocking EM, Sanz-Cervera JF, Williams RM, Unkefer CJ (1996) J Am Chem Soc 118:7008
Looser M (1989) PhD thesis. ETH (D.Arigoni)
Kellenberger JL (1997) PhD thesis. ETH (D.Arigoni)
Stocking E, Sanz-Cervera JF, Williams RM (1999) Angew Chem Int Ed Engl 38:786
Scott PM, Merrien M, Polonsky J (1976) Experientia 32:140
Barrow KD, Colley PW, Tribe DE (1979) J Chem Soc Chem Comm:225
Gorst-Allman CP, Steyn PS, Vleggaar R (1982) J Chem Soc Chem Comm 652
Bhat B, Harrison DM, Lamont HM (1990) J Chem Soc Chem Comm 1518
Bhat B, Harrison DM, Lamont HM (1993) Tetrahedron 49:10,663
Bycroft BW, Landon W (1970) J Chem Soc Chem Comm 967
Vleggaar R, Wessels PL (1980) J Chem Soc Chem Comm 160
Steyn PS, Vleggaar R (1983) J Chem Soc Chem Comm 560
(a) Mantle PG, Perera KPWC, Maishman NJ, Mundy GR (1983) Appl Environ Microbiol 45:1486; (b) For leading references on the biosynthesis of the penitrems and related metabolites, see Penn J, Mantle PG (1994) Phytochemistry 35:921
(a) Quilico A, Panizzi L (1943) Chem Ber 76:348; (b)Quilco A (1964) Res Progr Org Biol Medicin Chem 1:1964
(a) Birch AJ, Blance GE, David S, Smith H (1961) J Chem Soc 3128; (b) Birch AJ, Farrar KR (1963) J Chem Soc 4277
(a) MacDonald JC, Slater GP (1966) Can J Microbiol 12:455; (b) Slater GP, MacDonald JC, Nakashima R (1970) Biochemistry 9:2886
Marchelli R, Dossena A, Casnati G (1975) J Chem Soc Chem Comm 779
(a) Allen CM (1970) Biochemistry 11:2154; (b) Allen CM (1973) J Am Chem Soc 95:2386
Casnati G, Gardini GP, Palla G, Fuganti C (1974) J Chem Soc Chem Perkin Trans I:2397
Cardillo R, Fuganti C, Gatti G, Ghiringhelli D, Graselli P (1974) Tetrahedron Lett 3166
Cardillo R, Fuganti C, Ghiringhelli D, Graselli P (1975) J Chem Soc Chem Comm 778
Allen JK, Barrow KD, Jones AJ (1979) J Chem Soc Chem Comm 280
Grundon MF, Hamblin MR, Harrison DM, Derry Logue JN, Maguire M, McGrath JA (1980) J Chem Soc Chem Perkin Trans I:1294
Harrison DM, Quinn P (1983) J Chem Soc Chem Comm 879
Cardillo R, Fuganti C, Ghiringhelli D, Graselli P (1977) J Chem Soc Chem Comm 474
Fuganti C, Grasselli P, Pedrocchi-Fantoni G (1979) Tetrahedron Lett 2453
(a) Cole RJ, Kirksey JW, Moore JH, Blankenship BR, Diener UL, Davis NB (1972) Appl Microbiol 24:248; (b) Fayos J, Lokensgard D, Clardy J, Cole RJ, Kirksey JW (1974) J Am Chem Soc 96:6785; (c) Cole RJ, Kirksey JW, Cox RH, Clardy J (1975) J Agric Food Chem 23:1015; (d) Cole RJ, Kirksey JW, Dorner JW, Wilson DM, Johnson JC, Bedell DM, Springer JP, Chexal KK, Clardy JC, Cox RH (1977) J Agric Food Chem 25:826
(a) Yamazaki M, Suzuki S, Miyaki K (1971) Chem Pharm Bull 19:1739; (b) Yamazaki M, Sasago K, Miyaki K (1974) J Chem Soc Chem Comm 408; (c) Yamazaki M, Fujimoto H, Akiyama T, Sankawa U, Iitaka Y (1975) Tetrahedron Lett 27; (d) Yamazaki M, Fujimoto H, Kawasaki T (1975) Tetrahedron Lett 1241; (e) Yamazaki M, Suzuki K, Fujimoto H, Akiyama T, Sankawa U, Iitaka Y (1980) Chem Pharm Bull 28:861; (f) Yamazaki M, Fujimoto H, Kawasaki T (1980) Chem Pharm Bull 28:245; see also (g) Liu J, Yang Z-J, Meng Z-H (1996) Biomed Environ Sci 9:1
Day JB, Mantle PG (1982) Appl Environ Microbiol 43:514
Schroeder HW, Cole RJ, Hein H, Kirksey JW (1975) Appl Microbiol 29:857
(a) Cui C-B, Kakeya H, Okada G, Onose R, Ubukata M, Takahashi I, Isono K, Osada H (1995) J Antibiot 48:1382; (b) Cui C-B, Kakeya H, Okada G, Onose R, Osada H (1996) J Antibiot 49:527; (c) Cui C-B, Kakeya H, Osada H (1996) J Antibiot 49:534
(a) Cui C-B, Kakeya H, Osada H (1996) J Antibiot 49:832; (b) Cui C-B, Kakeya H, Osada H (1996) Tetrahedron 52:12, 651
(a) Cui C-B, Kakeya H, Osada H (1997) Tetrahedron 53:59; (b) Kondoh M, Usui T, Mayumi T, Osada H (1998) J Antibiot 51:801
Osada H (1998) J Antibiot 51:973
(a) Willingale J, Perera KPWC, Mantle PG (1983) Biochem J 214:991; (b) Mantle PG, Shipston NF (1987) Biochem Int 14:1115
Horak RM, Vleggaar R (1987) J Chem Soc Chem Comm 1568
Vleggaar R, Horak RM, Maharaj VJ (1993) J Chem Soc Chem Comm 274
Wilson BJ, Wilson CH, Hayes AW (1968) Nature 220:77
(a) Holzapfel CW, Wilkins DC (1971) Phytochemistry 10:351; (b) Holzapfel CW, Schabort J (1977) S Afr J Chem 30:233
de Jesus AE, Steyn PS, Vleggaar R, Kirby GW, Varley MJ, Ferreira NP (1981) J Chem Soc Perkin Trans I:3292
Chalmers AA, Gorst-Allman CP, Steyn PS (1982) J Chem Soc Chem Comm 1367
(a) Schabort JC, Potgieter JJ (1971) Biochem Biphys Acta 250:329; (b) Steenkamp DJ, Schabort JC, Holzapfel CW, Ferreira NP (1974) Biochem Biphys Acta 358:126; (c) Schabort JC, Marx M, Erasmus GL, Oosthuizen MJ, Pitout MJ, Ferreira NP (1978) Int J Biochem 9:427; (d) Schabort JC, Marx M, Erasmus GL, (1978) Int J Biochem 9:437; see also (e) Neethling DC, McGrath RM (1977) Can J Microbiol 23:856
Floss HG (1976) Tetrahedron 32:873
Shibuya M, Chou H-M, Fountoulakis M, Hassam S, Kim S-U, Kobayashi K, Otsuka H, Rogalska E, Cassady JM, Floss HG (1990) J Am Chem Soc 112:297
(a) Pachlatko P, Tabacik C, Acklin W, Arigoni D (1975) Chimia 29:526; (b) Pachlatko P (1975) PhD thesis. ETH, Zürich
(a) Gebler JC, Woodside AB, Poulter CD (1992) J Am Chem Soc 114:7354; (b) Tsai H-F, Wang H, Gebler JC, Poulter CD, Schardl CL (1995) Biochem Biophys Res Comm 216:119
Otsuka H, Anderson JA, Floss HG (1979) J Chem Soc Chem Chem 660
Kozikowski AP, Okita M, Kobayashi M, Floss HG (1988) J Org Chem 53:863
Kobayashi M, Floss HG (1987) J Org Chem 52:4350
Kozikowski AP, Wu J-P, Shibuya M, Floss HG (1988) J Am Chem Soc 110:1970
Robbers JE, Floss HG (1969) Tetrahedron Lett 1857
Robbers JE, Otsuka H, Floss HG (1980) J Org Chem 45:1117
Bajwa RS, Kohler R-D, Saini MS, Cheng M, Anderson JA (1975) Phytochemistry 14:735
Saini MS, Cheng M, Anderson JA (1976) Phytochemistry 15:1497
Herrmann KM, Somerville RL (1983) In: Amino acids biosynthesis and genetic regulation. Addison-Wesley, London, Chaps 18–20 and references cited therein
The crystal structure of tryptophan synthase was retrieved from the Brookhaven Protein data bank; see Schneider TR, Gerhardt E, Lee M, Liang P-H, Anderson KS, Schlichting I (1998) Biochem 37:5394
For reviews see: (a) Bloch K (1992) Steroids 57:378; (b) Banthorpe DV, Charlwood BV, Francis MJO (1972) Chem Rev 72:115; (c) Bach TJ (1995) Lipids 30:191
(a) Flesch G, Rohmer M (1988) Eur J Biochem 175:405–411; (b) Rohmer M, Sutter B, Sahm H (1989) J Chem Soc Chem Comm 1471; (c) Duvold T, Bravo J-M, Pale-Grosdemange C, Rohmer M (1997) Tetrahedron Lett 38:4679; (d) Putra SR, Charon L, Danielsen K, Pale-Grosdemange C, Lois L-M, Campos N, Boronat A, Rohmer M (1998) Tetrahedron Lett 39:6185
(a) Sagner S, Latzel C, Eisenreich W, Bacher A, Zenk MH (1998) J Chem Soc Chem Comm 221; (b) Arigoni D, Sagner S, Latzel C, Eisenreich W, Bacher A, Zenk MH (1997) Proc Natl Acad Sci USA 94:10, 600
Eisenreich W, Schwarz M, Cartayrade A, Arigoni D, Zenk MH, Bacher A (1998) Chem Biol 5:R221–R233
Kuzuyama T, Takahashi S, Watanabe S, Seto H (1998) Tetrahedron Lett 39:4509
Martin W, Muller M (1998) Nature 392:37
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Williams, R.M., Stocking, E.M., Sanz-Cervera, J.F. (2000). Biosynthesis of Prenylated Alkaloids Derived from Tryptophan. In: Leeper, F.J., Vederas, J.C. (eds) Biosynthesis. Topics in Current Chemistry, vol 209. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48146-X_3
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DOI: https://doi.org/10.1007/3-540-48146-X_3
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