Skip to main content
SpringerLink
Log in

Morinda Species: Biosynthesis of Quinones in Cell Cultures

  • Chapter
Medicinal and Aromatic Plants VIII

Part of the book series: Biotechnology in Agriculture and Forestry ((AGRICULTURE,volume 33))

Abstract

The genus Morinda belongs to the family Rubiaceae. Among the many species comprising this genus, six are of some pharmaceutical and technical importance (Kern et al. 1976). One of these is Morinda citrifolia which occurs in India and Southeast Asia. Its leaves and roots are used in the treatment of hypertension or as a diuretic and laxative. A more recent study (Younos et al. 1990) shows that extracts of the roots exhibit an analgesic and probably sedative effect on mice. Morinda lucida, another plant dealt with in this Chapter, grows in central Africa. Natives of central Africa use the plant as a diuretic, purgative and in the treatment of leprosy, fever, malaria, yellow fever, diarrhea and dysentery (Kern et al. 1976).

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 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover 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

  • Bauch HJ, Leistner E (1978a) Aromatic metabolites in cell suspension cultures of Galium mollugo L. Planta Med 33: 105–123

    Article  CAS  Google Scholar 

  • Bauch HJ, Leistner E (1978b) Attempts to demonstrate incorporation of labelled precursors into aromatic metabolites in cell suspension cultures of Galium mollugo L. Planta Med 33: 124–127

    Article  CAS  Google Scholar 

  • Breuer M, Igbavboa U, Kaiser A, Leistner E, Simantiras M, Weische A (1991) The o-succinylbenzoate synthase system in bacteria and plant cell suspension cultures. In: Bisswanger H, Ullrich J (eds) Biochemistry and physiology of thiamin diphosphate enzymes. VCH, Weinheim, pp 141–146

    Google Scholar 

  • Brickman TJ, Ozenberger BA, McIntosh MA (1990) Regulation of divergent transcription from the iron-responsive fepB-entC promoter-operator regions in Escherichia coli. J Mol Biol 212: 669–682

    Article  PubMed  CAS  Google Scholar 

  • Demagos GP, Baltus W, Höfle G (1981) New anthraquinones and anthraquinone glycosides from Morinda lucida. Z Naturforsch 36b: 1180–1184

    CAS  Google Scholar 

  • Elkins MF, Earhart CF (1988) An Escherichia coli enterobactin cluster gene with sequence homology to trpE and pabB. Microbiol Lett 56: 35–40

    Article  CAS  Google Scholar 

  • El-Shagi H, Schulte U, Zenk MH (1984) Specific inhibition of anthraquinone formation by amino compounds in Morinda cell cultures. Naturwissenschaften 71: 267

    Article  CAS  Google Scholar 

  • Emmons GT, Campbell IM, Bentley R (1985) Vitamin K (menaquinone) biosynthesis in bacteria: purification and probable structure of an intermediate prior to o-succinylbenzoate. Biochem Biophys Res Commun 131: 956–960

    Article  PubMed  CAS  Google Scholar 

  • Hawkins CF, Borges A, Perham RN (1989) A common structural motif in thiamine pyrophosphate binding enzymes. FEBS Lett 255: 77–82

    Article  PubMed  CAS  Google Scholar 

  • Heide L, Leistner E (1981) 2-Methoxycarbonyl-3-prenyl-1, 4-naphthoquinone, a metabolite related to the biosynthesis of mollugin and anthraquinones in Galium mollugo L. J Chem Soc Chem Commun 1981: 334–336

    Google Scholar 

  • Heide L, Leistner E (1982) Versuche zur Synthese natürlich vorkommender prenylierter Naphthalinderivate. Nachweis eines neuen Prenylnaphthochinonderivatives in Galium mollugo. Z Naturforsch 37c: 354–362

    CAS  Google Scholar 

  • Hubacek I (1991) Zur Frage der Substrataktivierung in den von Isocitrat-Lyase, bzw. 1,4-Dihydroxy2-naphothoat-Synthetase katalysierten Reaktionen. Dissertation, ETH, Zürich

    Google Scholar 

  • Hubacek I, Martinoni B, Arigoni D (1990) Zum Mechanismus der enzymatischen Bildung von 1,4-Dihydroxy-2-naphthosäure. Jahrestagung Schweiz Chem Ges, Bern, Kurzlassung der Vanträge und Poster, p 9

    Google Scholar 

  • Igbavboa U (1981) Anlage und Lipochinonbildung einer photoautotrophen Zellkultur von Morinda lucida Benth. Diplom-Arbeit, Universität Münster, Münster

    Google Scholar 

  • Igbavboa U, Leistner E (1990) Sequence of proton abstraction and stereochemistry of the reaction catalyzed by naphthoate synthase, an enzyme involved in menaquinone (vitamin K2) biosynthesis. Eur J Biochem 192: 441–449

    Article  PubMed  CAS  Google Scholar 

  • Igbavboa U, Sieweke HJ, Leistner E, Röwer I, Hüsemann W, Barz W (1985) Alternative formation of anthraquinones and lipoquinones in heterotrophic and photoautotrophic cell suspension cultures of Morinda lucida Benth. Planta 166: 537–544

    Article  CAS  Google Scholar 

  • Inoue K, Shiobara Y, Nayeshiro H, Inouye H, Wilson G, Zenk MH (1979) Site of prenylation in anthraquinone biosynthesis in cell cultures of Galium mollugo. J Chem Soc Chem Commun 1979: 957–959

    Article  Google Scholar 

  • Inoue K, Nayeshiro H, Inouye H, Zenk M (1981) Anthraquinones in cell suspension cultures of Morinda citrifolia. Phytochemistry 20: 1693–1700

    Article  CAS  Google Scholar 

  • Inoue K, Shiobara Y, Nayeshiro H, Inouye H, Wilson G, Zenk MH (1984) Biosynthesis of anthraquinones and related compounds in Galium mollugo cell suspension cultures. Phytochemistry 23: 307–311

    Article  CAS  Google Scholar 

  • Inouye H, Leistner E (1988) Biochemistry of quinones. In: Patai S, Rappoport Z (eds) The chemistry of quinonoid compounds, vol II. Wiley, New York, pp 1293–1349

    Chapter  Google Scholar 

  • Inouye H, Ueda S, Inoue K (1978) Biosynthesis of prenylnaphthoquinone congeners in callus cultures of Catalpa ovata. Tetrahedron Lett 46: 4551–4554

    Article  Google Scholar 

  • Kaiser A, Leistner E (1990) Role of the entC gene in enterobactin and menaquinone biosynthesis in Escherichia coli. Arch Biochem Biophys 276: 331–335

    Article  PubMed  CAS  Google Scholar 

  • Kaiser A, Leistner E (1992) The role of isochorismic acid in primary and secondary metabolism. World J Microbiol Biotechnol 8: 92–95

    Article  CAS  Google Scholar 

  • Kern W, Roth HJ, Schmid W, List PH, Hörhammer L (eds) (1976) Hager’s Handbuch der Pharmazeutischen Praxis, Band V. Springer, Berlin Heidelberg New York

    Google Scholar 

  • Kolkmann R, Leistner E (1987a) Synthesis, analysis and characterization of the coenzyme A esters of succinylbenzoic acid, an intermediate in vitamin K2 (menaquinone) biosynthesis. Z Naturforsch 42c: 542–552

    Google Scholar 

  • Kolkmann R, Leistner E (1987b) 4-(2′ -Carboxyphenyl)-4-oxo-butyryl coenzyme A ester, an intermediate in vitamin K2 (menaquinone) biosynthesis. Z Naturforsch 42c: 1207–1214

    Google Scholar 

  • Leduc C, Ruhnau P, Leistner E (1991) Isochorismate synthase from Rubiaceae cell suspension cultures. Plant Cell Rep 10: 334–337

    Article  Google Scholar 

  • Leistner E (1973) Mode of incorporation of precursors into alizarin (1,2-dihydroxy-9, 10-anthraquinone). Phytochemistry 12: 337–345

    Article  CAS  Google Scholar 

  • Leistner E (1975) Isolierung, Identifizierung und Biosynthese von Anthrachinonen in Zellsuspensionskulturen von Morinda citrifolia. Planta Med (Suppl) 214–224

    Google Scholar 

  • Leistner E (1985a) Biosynthesis of iso-chorismate-derived quinones. In: Conn EE (ed) The shikimic acid pathway. Plenum Press, New York, pp 243–261

    Google Scholar 

  • Leistner E (1985b) Occurrence and biosynthesis of quinones in woody plants. In: Higuchi T (ed) Biosynthesis and biodegradation of wood components. Academic Press, Orlando, pp 273–290

    Google Scholar 

  • Leistner E (1993) Die Bedeutung pflanzlicher Zellkulturen für das Verständnis von Biochemie und Physiologie des Sekundärstoffwechsels. ÖAZ 47: 203–205

    Google Scholar 

  • Liu J, Quinn N, Berchthold GA, Walsh CT (1990) Overexpression, purification and characterization of isochorismate synthase (EntC), the first enzyme involved in the biosynthesis of enterobactin from chorismate. Biochemistry 29: 1417–1425

    Article  PubMed  CAS  Google Scholar 

  • Luckner M, Nover L, Böhm H (1977) Secondary metabolism and cell differentiation. Springer, Berlin Heidelberg New York, p 80

    Book  Google Scholar 

  • Ozenberger BA, Brickman TJ, McIntosh MA (1989) Nucleotide sequence of Escherichia coli isochorismate synthetase gene entC and evolutionary relationship of isochorismate synthetase and other chorismate-utilizing enzymes. J Bacteriol 171: 775–783

    PubMed  CAS  Google Scholar 

  • Palaniappan C, Sharma V, Hudspeth MES, Meganathan R (1992) Menaquinone (Vitamin K2) biosynthesis: evidence that the Escherichia coli menD gene encodes both 2-succinyl-6-hydroxy-2, 4-cyclohexadiene-1-carboxylic acid synthase and a-ketoglutarate decarboxylase activities. J Bacteriol 174: 8111–8118

    PubMed  CAS  Google Scholar 

  • Poulsen C, Verpoorte R (1992) Activities of chorismate utilizing enzymes and of enzymes involved in indole alkaloid biosynthesis in cell suspension cultures. Plant Physiol Biochem 30: 105–113

    CAS  Google Scholar 

  • Poulsen C, van der Heijden R, Verpoorte R (1991) Assay of isochorismate synthase from plant cell cultures by high-performance liquid chromatography. Phytochemistry 30: 2873–2876

    Article  CAS  Google Scholar 

  • Robins RJ, Payne J, Rhodes MJC (1986) The production of anthraquinones by cell suspension cultures of Cinchona ledgeriana. Phytochemistry 25: 2327–2334

    Article  CAS  Google Scholar 

  • Ruyter CM, Stöckigt J (1989) Neue Naturstoffe aus pflanzlichen Zell- und Gewebekulturen. GIT 33: 283–293

    CAS  Google Scholar 

  • Schaaf PMM, Heide L, Tani Y, Karas M, Deutzmann R, Leistner E (1993) Properties of isochorismate hydroxymutase from Flavobacterium K3–15. J Nat Prod 56: 1294–1303

    Article  PubMed  CAS  Google Scholar 

  • Schulte U, El-Shagi H, Zenk MH (1984) Optimization of 19 Rubiaceae species in cell culture for the production of anthraquinones. Plant Cell Rep 3: 51–54

    Article  CAS  Google Scholar 

  • Sharma V, Meganathan R, Hudspeth MES (1993) Menaquinone (vitamin K2) biosynthesis: cloning, nucleotide sequence, and expression of the menC gene from Escherichia coli. J Bacteriol 175: 4917–4921

    PubMed  CAS  Google Scholar 

  • Sieweke HJ, Leistner E (1991) o-Succinylbenzoate: coenzyme A ligase, an enzyme involved in menaquinone (vitamin K2) biosynthesis, displays broad specificity. Z Naturforsch 46c: 585–590

    Google Scholar 

  • Sieweke HJ, Leistner E (1992) O-Succinylbenzoate: coenzyme A ligase from anthraquinone producing cell suspension cultures of Galium mollugo. Phytochemistry 31: 2329–2335

    Article  CAS  Google Scholar 

  • Simantiras M, Leistner E (1991) Cell free synthesis of o-succinylbenzoic acid in protein extracts from anthraquinone and phylloquinone (vitamin K1) producing plant cell suspension cultures. Occurrence of intermediates between isochorismic and o-succinylbenzoic acid. Z Naturforsch 46c 364–370

    Google Scholar 

  • Simantiras M, Schmidt K, Leistner E (1991) 4-(2′-Carboxyphenyl)-4-oxobutyrate: preparative isolation from anthraquinone producing cell suspension cultures of Galium mollugo. Phytochemistry 30: 823–824

    Article  CAS  Google Scholar 

  • Suzuki H, Matsumoto (1988) Anthraquinone: production by plant cell culture. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 4. Medicinal and aromatic plants I. Springer, Berlin Heidelberg New York, pp 237–250

    Chapter  Google Scholar 

  • Teuscher E (1973) Probleme der Prodkution sekundärer Pflanzenstoffe mit Hilfe von Zellkulturen. Pharmazie 28: 6–18

    PubMed  CAS  Google Scholar 

  • Thomson RH (1987) Naturally occurring quinones III: recent advances. Chapman and Hall, London

    Google Scholar 

  • Tiwari RD, Singh J (1977) Structural study of the anthraquinone glycoside from the flowers of Morinda citrifolia. J Indian Chem Soc 54: 429

    CAS  Google Scholar 

  • Tummuru MKR, Brickman TJ, McIntosh MA (1989) The in vitro conversion of chorismate to isochorismate catalyzed by the Escherichia coli entC gene product. J Biol Chem 264: 20547–20551

    PubMed  CAS  Google Scholar 

  • Uesato S, Ueda M, Inouye H, Kuwajima H, Yatsuzuka M, Takaishi K (1984) Iridoids from Galium mollugo. Phytochemistry 23: 2535–2537

    Article  CAS  Google Scholar 

  • Van den Berg AJJ, Labadie RP (1988) Rhamnus spp. In vitro production of anthraquinones, anthrones, and dianthrones. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 4. Medicinal and aromatic plants I. Springer, Berlin Heidelberg New York, pp 513–528

    Chapter  Google Scholar 

  • Van den Berg AJJ, Labadie RP (1989) Quinones. In: Harborne JB (ed) Methods in plant biochemistry, vol 1. Academic Press, Orlando, pp 451–491

    Google Scholar 

  • Weische A, Johanni M, Leistner E (1987a) Biosynthesis of o-succinylbenzoic acid I. Cell free synthesis of o-succinylbenzoic acid from isochorismic acid in enzyme preparations from vitamin K producing bacteria. Arch Biochem Biophys 256: 212–222

    Article  PubMed  CAS  Google Scholar 

  • Weische A, Garvert W, Leistner E (1987b) Biosynthesis of o-succinylbenzoic acid II. Properties of osuccinylbenzoic acid synthase, and enzyme involved in vitamin K2 biosynthesis. Arch Biochem Biophys 256: 223–231

    Article  PubMed  CAS  Google Scholar 

  • Wijnsma R, Verpoorte R (1986) Antraquinones in Rubiaceae. In: Zechmeister L, Herz W, Grisebach H, Kirby GW, Tamm Ch (eds) Progress in the chemistry of organic natural products. Springer, Vienna, pp 79–149

    Google Scholar 

  • Wijnsma R, Verpoorte R, Mulder-Krieger Th, Baerheim Svendsen A (1984) Anthraquinones in callus cultures of Cinchona ledgeriana. Phytochemistry 23: 2307–2311

    Article  CAS  Google Scholar 

  • Wijnsma R, Go JTKA, Harkes PAA, Verpoorte R, Baerheim Svendsen A (1986) Anthraquinones in callus cultures of Cinchona pubescens. Phytochemistry 25: 1123–1126

    Article  CAS  Google Scholar 

  • Yamamoto H, Tabata M, Leistner E (1987) Cytological changes associated with induction of anthraquinone synthesis in photoautotrophic cell suspension cultures of Morinda lucida. Plant Cell Rep 6: 187–190

    Article  CAS  Google Scholar 

  • Young IG, Batterham TJ, Gibson F (1969) The isolation, identification and properties of isochorismic acid. An intermediate in the biosynthesis of 2,3-dihydroxybenzoic acid. Biochem Biophys Acta 177: 389–400

    Article  PubMed  CAS  Google Scholar 

  • Younos C, Rolland A, Fleurentin J, Lanhers MC, Misslin R, Mortier F (1990) Analgesic and behavioural effects of Morinda citrifolia. Planta Med 56: 430–434

    Article  PubMed  CAS  Google Scholar 

  • Zenk MH (1991) Chasing the enzyme of secondary metabolism: plant cell culture as a pot of gold. Phytochemistry 30: 3861–3863

    Article  CAS  Google Scholar 

  • Zenk MH, El-Shagi H, Schulte U (1975) Anthraquinone production by cell suspension cultures of Morinda citrifolia. Planta Med (Suppl) 79–101

    Google Scholar 

  • Zenk MH, Schulte U, El-Shagi (1984) Regulation of anthraquinone formation by phenoxyacetic acids in Morinda cell cultures. Naturwissenschaften 71: 266

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Biologie, Rheinische Friedrich Wilhelms Universität, Nussallee 6, 53115, Bonn, Germany

    E. Leistner

Authors
  1. E. Leistner
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. A-137, New Friends Colony, New Delhi, 110 065, India

    Y. P. S. Bajaj

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Leistner, E. (1995). Morinda Species: Biosynthesis of Quinones in Cell Cultures. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants VIII. Biotechnology in Agriculture and Forestry, vol 33. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-08612-4_16

Download citation

  • DOI: https://doi.org/10.1007/978-3-662-08612-4_16

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-08201-6

  • Online ISBN: 978-3-662-08612-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation