Advertisement

The Biosynthesis of Isoquinoline Alkaloids

  • R. B. Herbert
Part of the Proceedings in Life Sciences book series (LIFE SCIENCES)

Abstract

The tetrahydroisoquinoline skeleton occurs in numerous plant alkaloids. The simplest bearers of this structural unit are exemplified by anhalonidine (12) (Sect. 2). Slightly more elaborate are the benzylisoquinoline alkaloids exemplified at their simplest by reticuline (25) and papaverine (27) (Sect. 3).

Keywords

Cinnamic Acid Oxidative Coupling Mevalonic Acid Phenol Oxidation Isoquinoline Alkaloid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Barker AC, Battersby AR, McDonald E, Ramage R, Clements JH (1967) Biosynthesis of colchicine: Ring expansion and later stages. Structure of speciosine. J Chem Soc Chem Commun: 390–392Google Scholar
  2. Barton DHR, Cohen T (1957) In: Festschrift Dr A Stoll, Birkhäuser, Basel, p 117Google Scholar
  3. Barton DHR, Kirby GW, Taylor JB, Thomas GM (1963) Phenol oxidation and biosynthesis, part VI. The biogenesis of amaryllidaceae alkaloids. J Chem Soc:4545–4558Google Scholar
  4. Barton DHR, Hesse RH, Kirby GW (1965) Phenol oxidation and biosynthesis, part VIII. Investigations on the biosynthesis of berberine and protopine. J Chem Soc:6379–6389Google Scholar
  5. Barton DHR, Bracho RD, Potter CJ, Widdowson DA (1974) Phenol oxidation and biosynthesis, part XXIV. Origin-of chirality in the erythrinan system and derivation of the lactone rings of a-and (3.erythroidine. J Chem Soc Perkin Trans 1:2278–2283CrossRefGoogle Scholar
  6. Basmadjian GP, Paul AG (1971) The isolation of an 0-methyltransferase from peyote and its role in the biosynthesis of mescaline. Lloydia 34:91–93PubMedGoogle Scholar
  7. Basmadjian GP, Hussain SF, Paul AG (1978) Biosynthetic relationships between phenethylamine and tetrahydroisoquinoline alkaloids in peyote. Lloydia 41:375–380Google Scholar
  8. Battersby AR, Binks R, Francis RJ, McCaldin DJ, Ramuz H (1964) Alkaloid biosynthesis, part IV. 1-Benzylisoquinolines as precursors of thebaine, codeine and morphine. J Chem Soc: 3600–3610Google Scholar
  9. Battersby AR, Brown RT, Clements JH, Iverach GG (1965) On the biosynthesis of isothebaine. J Chem Soc Chem Commun:230–232Google Scholar
  10. Battersby AR, Brocksom TJ, Ramage R (1969) Further studies on the synthesis and biosynthesis of isothebaine. J Chem Soc Chem Commun:464–465Google Scholar
  11. Battersby AR, McHugh JL, Staunton J, Todd M (1971) Biosynthesis of the apparently “directly coupled” aporphine alkaloids. J Chem Soc Chem Commun:985–986Google Scholar
  12. Battersby AR, Herbert RB, Pijewska L, Santavy F, Sedmera P (1972a) Alkaloid biosynthesis, part XVII. The structure and chemistry of androcymbine. J Chem Soc Perkin Trans 1:17361740Google Scholar
  13. Battersby AR, Herbert RB, McDonald E, Ramage R, Clements JH (1972b) Alkaloid biosynthesis, part XVIII. Biosynthesis of colchicine from the 1-phenethylisoquinoline system. J Chem Soc Perkin Trans 1:1741–1746CrossRefGoogle Scholar
  14. Battersby AR, Sheldrake PW, Milner JA (1974) Biosynthesis of colchicine: Incorporation of a 13C-labelled precursor in a higher plant. Tetrahedron Lett:3315–3318Google Scholar
  15. Battersby AR, Francis RJ, Hirst M, Ruveda EA, Staunton J (1975) Biosynthesis, part XXI. Investigations on the biosynthesis of stylopine in Chelidonium majus. J Chem Soc Perkin Trans 1:1140–1147CrossRefGoogle Scholar
  16. Battersby AR, Staunton J, Summers MC, Southgate R (1979) Studies of enzyme-mediated reactions, part 9. Stereochemistry of oxidative ring cleavage adjacent to nitrogen during the biosynthesis of chelidonine. J Chem Soc Perkin Trans 1:45–52CrossRefGoogle Scholar
  17. Battersby AR, Jones RCF, Minta A, Ottridge AP, Staunton J (1981) Biosynthesis, part 25. Proof that hasubanonine and protostephanine are biosynthesised from the 1-benzylisoquinoline system. J Chem Soc Perkin Trans 1:2030–2039CrossRefGoogle Scholar
  18. Battersby AR, McDonald E, Stachulski AB (1983) Biosynthesis, part 26. Synthetic studies on structural modification of late biosynthetic precursors for colchicine. J Chem Soc Perkin Trans 1:3053–3063CrossRefGoogle Scholar
  19. Bhakuni DS, Jain S (1980) Late stages in the biosynthesis of abnormal Erythrina alkaloids. Tetrahedron 36:2153–2156CrossRefGoogle Scholar
  20. Bhakuni DS, Tewari S, Kapil RS (1977) Biosynthesis of boldine (1,10-dimethoxy-6-aa-aporphine2,9-diol). J Chem Soc Perkin Trans 1:706–709CrossRefGoogle Scholar
  21. Bhakuni DS, Labroo VM, Singh AN, Kapil RS (1978) Biosynthesis of the bisbenzylisoquinoline alkaloid cocsulin. J Chem Soc Perkin Trans 1:121–125CrossRefGoogle Scholar
  22. Blaschke G, Waldheim G, Schantz M von, Peura P (1974) Nachweis von Reticulin als Biosynthese Vorstufe in Corydalis cava. 4. Mitt. Untersuchungen zur Biosynthese von Alkaloiden. Arch Pharm 307:122–130CrossRefGoogle Scholar
  23. Brochmann-Hanssen E, Chen CH, Chiang H-C, Fu C-C, Nemoto H (1973) Opium alkaloids XIV: Biosynthesis of aporphines -detection of orientaline in opium poppy. J Pharm Sci 63:1291–1293CrossRefGoogle Scholar
  24. Brochmann-Hanssen E, Chen C, Chen CR, Chiang H, Leung AY, McMurtrey K (1975) Opium alkaloids, part XVI. The biosynthesis of 1-benzylisoquinolines in Papaver somniferum. Preferred and secondary pathways; stereo-chemical aspects. J Chem Soc Perkins Trans 1:1531–1537Google Scholar
  25. Haynes LI, Stuart KL, Barton DHR, Bhakuni DS, Kirby GW (1965) On the biosynthesis of crotonosine. J Chem Soc Chem Commun:141–142Google Scholar
  26. Hedges SH, Herbert RB, Wormald PC (1983) Biosynthesis of lythraceae alkaloids: Incorporation of DL-[4,5-13C2,6-14C] lysine and cis-and trans-4-(3,4-dihydroxyphenyl)quinolizidin-2one into vertine and lythrine. J Chem Soc Chem Commun:145–147Google Scholar
  27. Herbert RB (1980) In: Coffey S (ed) Rodd’s chemistry of carbon compounds, 2nd edn. Elsevier, Amsterdam, p 291Google Scholar
  28. Herbert RB, Mann J (1982) The biosynthesis of the ß-carboline alkaloids, harman and eleagnine. J Chem Soc Perkin Trans 1:1523–1525CrossRefGoogle Scholar
  29. Kapadia GJ, Rao GS, Leete E, Fayez MBE, Vaishnav YN, Fales HM (1970) On the origin of carbon 1 in tetrahydroisoquinoline alkaloids. J Am Chem Soc 92:6943–6951PubMedCrossRefGoogle Scholar
  30. Leete E, Ahmad A (1966) Biosynthesis of the Erythrina alkaloids. The incorporation of tyrosine-2-14C into the erythroidines. J Am Chem Soc 88:4722–4725PubMedCrossRefGoogle Scholar
  31. Lundström J (1971) Biosynthetic studies on mescaline and related cactus alkaloids. Acta Pharm Suec 8:275–302PubMedGoogle Scholar
  32. O’Donovan DG, Barry E (1974) Biosynthesis of lophocerine in Lophocereus schottii,part II. J Chem Soc Perkin Trans 1:2528–2529CrossRefGoogle Scholar
  33. Robinson R (1955) The structural relations of natural products. Oxford Univ Press, LondonGoogle Scholar
  34. Schumacher H-M, Riiffer M, Nagakura N, Zenk MH (1983) Partial purification and properties of (S)-norlaudanosoline synthase from Eschscholtzia tenuifolia cell cultures. Planta Med 48: 212–222PubMedCrossRefGoogle Scholar
  35. Takao N, Iwasa K, Kamigauchi M, Sugiura M (1976) Studies on the alkaloids of papaveraceous plants XXV. Biosynthesis of the alkaloids of Corydalis incisa Pers. and Chelidonium majus L. Incorporation of tetrahydroberberines, N-methosalts of tetrahydroprotoberberines and protopine. Chem Pharm Bull 24:2859–2868Google Scholar
  36. Takao N, Kamigauchi M, Okada M (1983) Biosynthesis of benzo[c]phenanthridine alkaloids sanguinarine, chelirubine and macarpine. Heiv Chim Acta 66:473–484CrossRefGoogle Scholar
  37. Uprety H, Bhakuni DS, Kapil RS (1975) Biosynthesis of papaverine. Phytochemistry 14:1535–1537CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1985

Authors and Affiliations

  • R. B. Herbert
    • 1
  1. 1.Department of Organic ChemistryUniversity of LeedsLeedsUK

Personalised recommendations