Skip to main content
SpringerLink
Log in

The Biosynthesis of Isoquinoline Alkaloids

  • Conference paper
The Chemistry and Biology of Isoquinoline Alkaloids

Part of the book series: Proceedings in Life Sciences ((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).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • 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: 390–392

    Google Scholar 

  • Barton DHR, Cohen T (1957) In: Festschrift Dr A Stoll, Birkhäuser, Basel, p 117

    Google Scholar 

  • Barton DHR, Kirby GW, Taylor JB, Thomas GM (1963) Phenol oxidation and biosynthesis, part VI. The biogenesis of amaryllidaceae alkaloids. J Chem Soc:4545–4558

    Google Scholar 

  • Barton DHR, Hesse RH, Kirby GW (1965) Phenol oxidation and biosynthesis, part VIII. Investigations on the biosynthesis of berberine and protopine. J Chem Soc:6379–6389

    Google Scholar 

  • 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 1:2278–2283

    Article  Google Scholar 

  • Basmadjian GP, Paul AG (1971) The isolation of an 0-methyltransferase from peyote and its role in the biosynthesis of mescaline. Lloydia 34:91–93

    PubMed  CAS  Google Scholar 

  • Basmadjian GP, Hussain SF, Paul AG (1978) Biosynthetic relationships between phenethylamine and tetrahydroisoquinoline alkaloids in peyote. Lloydia 41:375–380

    CAS  Google Scholar 

  • 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: 3600–3610

    Google Scholar 

  • Battersby AR, Brown RT, Clements JH, Iverach GG (1965) On the biosynthesis of isothebaine. J Chem Soc Chem Commun:230–232

    Google Scholar 

  • Battersby AR, Brocksom TJ, Ramage R (1969) Further studies on the synthesis and biosynthesis of isothebaine. J Chem Soc Chem Commun:464–465

    Google Scholar 

  • Battersby AR, McHugh JL, Staunton J, Todd M (1971) Biosynthesis of the apparently “directly coupled” aporphine alkaloids. J Chem Soc Chem Commun:985–986

    Google Scholar 

  • 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 1:17361740

    Google Scholar 

  • 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 1:1741–1746

    Article  Google Scholar 

  • Battersby AR, Sheldrake PW, Milner JA (1974) Biosynthesis of colchicine: Incorporation of a 13C-labelled precursor in a higher plant. Tetrahedron Lett:3315–3318

    Google Scholar 

  • 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 1:1140–1147

    Article  Google Scholar 

  • 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 1:45–52

    Article  Google Scholar 

  • 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 1:2030–2039

    Article  Google Scholar 

  • 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 1:3053–3063

    Article  Google Scholar 

  • Bhakuni DS, Jain S (1980) Late stages in the biosynthesis of abnormal Erythrina alkaloids. Tetrahedron 36:2153–2156

    Article  CAS  Google Scholar 

  • Bhakuni DS, Tewari S, Kapil RS (1977) Biosynthesis of boldine (1,10-dimethoxy-6-aa-aporphine2,9-diol). J Chem Soc Perkin Trans 1:706–709

    Article  Google Scholar 

  • Bhakuni DS, Labroo VM, Singh AN, Kapil RS (1978) Biosynthesis of the bisbenzylisoquinoline alkaloid cocsulin. J Chem Soc Perkin Trans 1:121–125

    Article  Google Scholar 

  • 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 307:122–130

    Article  CAS  Google Scholar 

  • 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 63:1291–1293

    Article  Google Scholar 

  • 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 1:1531–1537

    Google Scholar 

  • Haynes LI, Stuart KL, Barton DHR, Bhakuni DS, Kirby GW (1965) On the biosynthesis of crotonosine. J Chem Soc Chem Commun:141–142

    Google Scholar 

  • 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:145–147

    Google Scholar 

  • Herbert RB (1980) In: Coffey S (ed) Rodd’s chemistry of carbon compounds, 2nd edn. Elsevier, Amsterdam, p 291

    Google Scholar 

  • Herbert RB, Mann J (1982) The biosynthesis of the ß-carboline alkaloids, harman and eleagnine. J Chem Soc Perkin Trans 1:1523–1525

    Article  Google Scholar 

  • 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 92:6943–6951

    Article  PubMed  CAS  Google Scholar 

  • Leete E, Ahmad A (1966) Biosynthesis of the Erythrina alkaloids. The incorporation of tyrosine-2-14C into the erythroidines. J Am Chem Soc 88:4722–4725

    Article  PubMed  CAS  Google Scholar 

  • Lundström J (1971) Biosynthetic studies on mescaline and related cactus alkaloids. Acta Pharm Suec 8:275–302

    PubMed  Google Scholar 

  • O’Donovan DG, Barry E (1974) Biosynthesis of lophocerine in Lophocereus schottii,part II. J Chem Soc Perkin Trans 1:2528–2529

    Article  Google Scholar 

  • Robinson R (1955) The structural relations of natural products. Oxford Univ Press, London

    Google Scholar 

  • 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: 212–222

    Article  PubMed  CAS  Google Scholar 

  • 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 24:2859–2868

    CAS  Google Scholar 

  • Takao N, Kamigauchi M, Okada M (1983) Biosynthesis of benzo[c]phenanthridine alkaloids sanguinarine, chelirubine and macarpine. Heiv Chim Acta 66:473–484

    Article  CAS  Google Scholar 

  • Uprety H, Bhakuni DS, Kapil RS (1975) Biosynthesis of papaverine. Phytochemistry 14:1535–1537

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, University of Leeds, Leeds, LS2 9JT, UK

    R. B. Herbert

Authors
  1. R. B. Herbert
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Pharmacognosy, The School of Pharmacy, Brunswick Square, WC1N 1AX, London, UK

    J. David Phillipson  & Margaret F. Roberts  & 

  2. Pharmazeutische Biologie, Universität München, Karlstraße 29, 8000, München 2, Germany

    M. H. Zenk

Rights and permissions

Reprints and permissions

Copyright information

© 1985 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Herbert, R.B. (1985). The Biosynthesis of Isoquinoline Alkaloids. In: Phillipson, J.D., Roberts, M.F., Zenk, M.H. (eds) The Chemistry and Biology of Isoquinoline Alkaloids. Proceedings in Life Sciences. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-70128-3_14

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-70128-3_14

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-70130-6

  • Online ISBN: 978-3-642-70128-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation