Skip to main content
SpringerLink
Log in

Tagetes spp. (Marigolds): In Vitro Culture and the Production of Thiophenes

  • Chapter
Medicinal and Aromatic Plants IV

Part of the book series: Biotechnology in Agriculture and Forestry ((AGRICULTURE,volume 21))

Abstract

Tagetes species were used by ancient civilizations like the Aztecs for various purposes (Neher 1968). The pigments of the flowers were used as a dye and in chicken feed, oil was extracted from the leaves and used as an ingredient of perfumes, and the roots were also assumed to have interesting properties. Field tests in the USA in the 1930s showed that larvae of a root-knot nematode entered the roots of marigolds, but usually failed to develop and neither reached the adult stage nor produced eggs (Steiner 1941). In 1953, a Dutch bulb breeder (Van de Berg-Smit 1953) reported the biological activity of common garden marigolds (Tagetes patula) against root rot in Narcissus caused by free-living nematodes. The latter finding was an incentive for a scientific analysis of the effect of Tagetes plants by the crop protection industry and the academic world. A few years after the initial report by Van de Berg-Smit (1953), Uhlenbroek and Bijloo (1958, 1959, 1960) isolated and described some active principles from Tagetes plants. These chemicals belonged to a group of heterocyclic sulphur-containing compounds, the thiophenes. The thiophene α-terthienyl, which occurs in Tagetes and related species, was first synthesized in 1941 (Steinkopf et al. 1941) and isolated from plants in 1947 (Zechmeister and Sease 1947).

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 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
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

  • Adamse P (1990) Selection of high-yielding cell lines of Tagetes using flow cytometry. In: Nijkamp HJJ, Plas LHW van der, Aartrijk J van (eds) Progress in plant cellular and molecular biology. Kluwer, Dordrecht, pp 726–731

    Chapter  Google Scholar 

  • Arroo RRJ, Kenkel H, Meijers H, Croes AF, Wullems GJ (1990) Cellular aspects of thiophene accumulation in relation to root differentiation. In: Nijkamp HJJ, Plas LHW van dm, Aartrijk J van (eds) Progress in plant cellular and molecular biology. Kluwer, Dordrecht, pp 587–591

    Chapter  Google Scholar 

  • Bakker J, Gommers FJ, Nieuwenhuis J, Wijnberg H (1979) Photoactivation of the nematicidal compound a-terthienyl from roots of marigolds (Tagetes species). J Biol Chem 254: 1841–1844

    PubMed  CAS  Google Scholar 

  • Berg-Smit J van de (1953) Over het wortelrot bij Narcissen. Weekbl Bollencultuur 93/94: 437

    Google Scholar 

  • Birot AM, Bouchez D, Casse-Delbart F, Durand-Tardif M, Jouanin L, Pautot V, Robaglia C, Tepfer D, Tepfer M, Tourneur J, Vilaine F (1987) Studies and uses of the Ri plasmids of Agrobacterium rhizogenes. Plant Physiol Biochem 25: 323–335

    CAS  Google Scholar 

  • Bohlmann F, Zdero C (1985) Naturally occurring thiophenes. In: Weissberger A, Taylor EC (eds) Chemistry of heterocyclic compounds, part 1. Gronowitz S (ed) Thiophene and its derivatives. Wiley & Sons, New York, pp 221–323

    Google Scholar 

  • Bohlmann F, Burkhardt T, Zdero C (1973) Naturally occurring acetylenes. Academic Press, London

    Google Scholar 

  • Brown S (1984) Analysis and sorting of plant material by flow cytometry. Physiol Veg 22: 341–349

    Google Scholar 

  • Burkill JH (1966) A dictionary of the economic products of the Malay peninsula. Ministry of Agriculture and Cooperation, Kuala Lumpur, Malaysia, 2444 pp

    Google Scholar 

  • Cleene M de, Ley J de (1981) The host range of infectious hairy-root. Bot Rev 47: 147–194

    Article  Google Scholar 

  • Constabel F (1965) Phenolics in tissue cultures derived from Juniperus communis L.: studies on tannin synthesis. In: White PR, Grove AR (eds) Proc Int Conf Plant tissue Culture, Berkeley McCutcham, Berkeley, pp 183–190

    Google Scholar 

  • Croes AF, Aarts AM, Bosveld M, Breteler H, Wullems GJ (1989a) Control of thiophene accumulation in calli of two Tagetes species. Physiol Plant 76: 205–210

    Article  CAS  Google Scholar 

  • Croes AF, Berg AJR van den, Bosveld M, Breteler H, Wullems GJ (1989b) Thiophene accumulation in relation to morphology in roots of Tagetes patula; effects of auxin and transformation by Agrobacterium. Planta 179: 43–50

    Article  CAS  Google Scholar 

  • Drawert F, Berger RG (1982) Uber die Biogenese von Aromastoffen bei Pflanzen und Früchten. XIX Mitt: Vergleich der Biosynthese von Aromastoffen in Segment-, Kallus- und Suspensionskulturen von Citrusarten. Chem Mikrobiol Technol Lebensm 7: 143–147

    CAS  Google Scholar 

  • Duke J, Ayensu ES (1985) Medicinal plants öf China, vol 1. Reference Publications, Michigan

    Google Scholar 

  • Evans, PK, Cocking, EC (1977) Isolated plant protoplasts. In: Street HE (ed) Plant tissue and cell culture. Botanical monographs, vol 11, 2nd edn. Black well, Oxford, pp 103–135

    Google Scholar 

  • Flores HE (1987) Use of plant cell and organ cultures in the production of biological chemicals. In: Mumma RO, Lebaron H, Honeycutt RC, Duesing JH (eds) Application of biotechnology to agricultural chemistry. Am Chem Soc Symp Ser Washington DC 334: 67–86

    Google Scholar 

  • Flores HE, Hoy MW, Pickard J J (1987) Secondary metabolites from root cultures. Trends Biotechnol 5: 64–69

    Article  CAS  Google Scholar 

  • Flores HE, Pickard JJ, Hoy MW (1988) Production of polyacetylenes and thiophenes in heterotrophic and photosynthetic root cultures of Asteraceae. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally-occurring acetylenes and related compounds (NOARC), Elsevier, Amsterdam, pp 233–254

    Google Scholar 

  • Gommers FJ, Bakker J, Smits L (1980) Effects of singlet oxygen generated by the nematicidal compound a-terthienyl from Tagetes on the nematodeAphelenchus avenae. Nematologica 26: 369–375

    Article  CAS  Google Scholar 

  • Gommers FJ, Bakker J, Wijnberg H (1982) Dithiophenes as singlet oxygen sensitizers. Photochem Photobiol 35: 615–619

    Article  CAS  Google Scholar 

  • Groneman AF, Posthumus MA, Tuinstra LGM Th, Traag WA (1984) Identification and determination of metabolites in plant cell biotechnology by gas chromatography and gas chromatography/mass spectrometry: application to nonpolar products ofChrysanthemum cinerariaefolium and Tagetes species. Anal Chim Acta 163: 43–54

    Article  CAS  Google Scholar 

  • Helsper JPFG, Prins T, Lütke Willink D, Breteler H (1988a) 5-(4-Acetoxy-l-butinyl)-2,2-bithiophene (BBTOAc): acetate esterase in intact plants, calli and cell cultures of Tagetes patula, cv. Nana Furia. Plant Physiol 86 (Suppl): 143

    Article  Google Scholar 

  • Helsper JPFG, Ketel DH, Hülst AC, Breteler H (1988b) Production and secretion of thiophenes by differentiated cell cultures of Tagetes. In: Lam J. Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally-occurring acetylenes and related compounds (NOARC). Elsevier, Amsterdam, pp 279–286

    Google Scholar 

  • Hulst AC, Verlaan P, Breteler H, Ketel DH (1987) Thiophene production by Tagetes patula in a pilot plant airlift-loopreactor (ALR). In: Neyssel OM, Meer RR van der, Luyben KCAM (eds) Proc 4th Eur Congr Biotechnol. Elsevier, Amsterdam, pp 401–404

    Google Scholar 

  • Hulst AC, Meyer MMT, Breteler H, Tramper J (1989) Effect of aggregate size in cell cultures of T. patula on thiophene production and cell growth. Appl Microbiol Biotechnol 30: 18–25

    Article  CAS  Google Scholar 

  • Jente R, Olatunji GA, Bosold F (1981) Formation of natural thiophene derivatives from acetylenes by Tagetes patula. Phytochemistry 20: 2169–2175

    Article  CAS  Google Scholar 

  • Ketel DH (1986) Morphological differentiation and occurrence of thiophenes in leaf callus cultures from Tagetes species: relation to the growth medium of the plants. Physiol Plant 66: 392–396

    Article  CAS  Google Scholar 

  • Ketel DH (1987a) Distribution and accumulation of thiophenes in plants and calli of different Tagetes species. J Exp Bot 38: 322–330

    Article  CAS  Google Scholar 

  • Ketel DH (1987b) Callus and cell culture of Tagetes species in relation to production of thiophenes. Thesis, Agric Univ Wageningen, The Netherlands

    Google Scholar 

  • Ketel DH (1988) Selection of thiophene-producing calli of Tagetes patula in relation to the production of thiophenes in liquid cultures. In: Robins RJ, Rhodes MJC (eds) Manipulating secondary metabolism in culture. Cambridge Univ Press, Cambridge, pp 225–232

    Google Scholar 

  • Ketel DH, Breteler H, Groot B de (1985) Effect of explant origin on growth and differentiation of calli from Tagetes species. J Plant Physiol 118: 327–333

    Google Scholar 

  • Ketel DH, Hulst AC, Gruppen H, Breteler H, Tramper J (1987) Effects of immobilization and environmental stress on growth and production of non-polar metabolites ofTagetes minuta cells. Enzyme Microb Technol 9: 303–307

    Article  CAS  Google Scholar 

  • Ketel DH, Breteler H (1988) Morphogenesis and thiophene production in cell cultures of Tagetes species. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally- occurring acetylenes and related compounds (NOARQ. Elsevier, Amsterdam, pp 267–278

    Google Scholar 

  • Kothari SL, Chandra N (1985) Plant regeneration in callus and suspension cultures of Tagetes erecta L. (African marigold) J Plant Physiol 122: 235–241

    Google Scholar 

  • Lam J, Thomasen T (1988) Complexing agents for protection of highly conjugated compounds against photodegradation. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally-occurring acetylenes and related compounds (NOARC). Elsevier, Amsterdam, pp 47–60

    Google Scholar 

  • Lam J, Breteler H, Arnason T, Hansen L (1988) Chemistry and biology of naturally occurring acetylenes and related compounds (NOARC). Proc NOARC-Conf Aarhus-Denmark. Elsevier, Amsterdam, 366 pp

    Google Scholar 

  • Metschulat G, Siitfeld R (1988) Acetyl-CoA: 4-hydroxy butinyl bithiophene o-acetyltransferase isoenzymes from Tagetes patula seedlings. Z Naturforsch 42c: 885–890

    Google Scholar 

  • Mihalik GJ (1978/79) Guyanese ethnomedical botany. A folk pharmacopoeia. Ethnomedicine 1/2: 83–96

    Google Scholar 

  • Muir WH, Hildebrandt AC, Riker AJ (1954) Plant tissue cultures produced from single isolated cells. Science 119: 877–878

    Article  Google Scholar 

  • Mulder-Krieger T, Verpoorte R, Water A de, Gekel M van, Oeveren BCJA van, Baerheim Svendsen A (1982) Identification of the alkaloids and anthraquinones in Cinchona ledgeriana callus cultures. Planta Med 46: 19–24

    Article  PubMed  CAS  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco cultures. Physiol Plant 15: 473–497

    Article  CAS  Google Scholar 

  • Neher RT (1968) The ethnobotany ofTagetes. Econ Bot 22: 317–325

    Article  Google Scholar 

  • Nester EW, Gordon MP, Amasino RM, Yanofsky MF (1984) Crown gall: a molecular and physiological analysis. Annu Rev Plant Physiol 35: 387–413

    Article  CAS  Google Scholar 

  • Norton RA, Finlayson AJ, Towers GHN (1985) Thiophene production by crown galls and callus tissues of Tagetes patula. Phytochemistry 24: 719–722

    Article  CAS  Google Scholar 

  • Offringa JA, Melchers LS, Regenburg-Tuink AJG, Constantino P, Schilperoort RA, Hooykaas PJJ (1986) Complementation of Agrobacterium tumefaciens tumor-inducing aux mutants by genes from the Tr-region of the Ri plasmid of Agrobacterium rhizogenes. Proc Natl Acad Sci 83: 6935–6939

    Article  PubMed  CAS  Google Scholar 

  • Otten LABM, Schilperoort RA (1978) A rapid microscale method for the detection of lysopine andnopaline dehydrogenase activities. Biochim Biophys Acta 527: 497–500

    PubMed  CAS  Google Scholar 

  • Pensl R, Siitfeld R (1985) Occurrence of 3,4-diacetoxybutinylbithiophene in Tagetes patula and its enzymatic conversion. Z Naturforsch 40c: 3–7

    CAS  Google Scholar 

  • Petit A, David C, Dahl GA, Ellis JG, Guyon P, Casse-Delbart F, Tempe J (1983) Further extension of the opine concept: plasmids in Agrobacterium rhizogenes cooperate for opine degradation. Mol Gen Genet 190: 204–214

    Article  CAS  Google Scholar 

  • Philogene BJR, Arnason JT, Berg CW, Duval F, Champagne D, Taylor RG, Leitch LC, Morand P (1985) Synthesis and evaluation of the naturally occurring phototoxin, Alpha-terthienyl as a control agent for larvae ofAedes intrudens, Aedes atropalpus (Diptera: Culicidae) and Simulium verecundum (Diptera: Simuliidae). J Econ Entomol 78: 121–126

    PubMed  CAS  Google Scholar 

  • Quisumbing E (1951) Medicinal plants of the Philippines. Bureau of printing, Manila, 100 pp

    Google Scholar 

  • Reis Altschul S von (1973) Drugs and foods from little-known plants. Harvard Univ Press, Cambridge, MA, 366 pp

    Google Scholar 

  • Rhodes MJC, Robins RJ, Kamill JD, Parr A J, Walton NJ (1987) Secondary product formation using Agrobacterium rhizogenes transformed “hairy root” cultures. IAPTC Newslett 53: 2–15

    Google Scholar 

  • Sahai OP, Shuler ML (1984) Environmental parameters influencing phenolics production by batchcultures of Nicotiana tabacum. Biotech Bioeng 26: 111–120

    Article  CAS  Google Scholar 

  • Sanchez de Jimenez E, Fernandez L (1983) Biochemical parameters to assess cell differentiation of Bouvardia termifolia Schecht callus. Planta 158: 377–383

    Article  Google Scholar 

  • Slogteren GMS van, Hoge JHC, Hooykaas PJJ, Schilperoort RA (1983) Clonal analysis of heterogeneous crown gall tumor tissues induced by wild-type and shooter mutant strains of Agrobacterium tumefaciens expression of T-DNA genes. Plant Mol Biol 2: 321–333

    Article  Google Scholar 

  • Steiner G (1941) Nematodes parasitic on and associated with roots of marigolds (Tagetes hybrids). Proc Biol Soc Wash 54: 31–34

    Google Scholar 

  • Steinkopf W, Leitsmann R, Hofmann KH (1941) Studien in der Thiophenreihe. LVII. Uber a-Polythienyle. Liebigs Ann Chem 546: 180–199

    Article  CAS  Google Scholar 

  • Street HE, Henshaw GG, Buiatti MC (1965) The culture of isolated plant cells. Chem Ind 2 (January): 27–33

    Google Scholar 

  • Sütfeld R (1982) Distribution of thiophene derivatives in different organs of Tagetes patula seedlings grown under various conditions. Planta 156: 536–540

    Article  Google Scholar 

  • Sütfeld R (1987) HPLC of thiophenes for phytochemical and biochemical research. In: Linskens HF, Jackson JF (eds) High performance liquid chromatography in plant sciences. Springer, Berlin Heidelberg New York, pp 104–113

    Google Scholar 

  • Sütfeld R (1988) Enzymological investigations into the metabolism of bithiophene derivatives. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally occurring acetylenes and related compounds (NOARC), vol 7. Elsevier, Amsterdam, pp 201–208

    Google Scholar 

  • Sütfeld R (1989) Preparative liquid chromatography with analytical separation quality. Interval injection/displacement reversed-phase high performance liquid chromatography. J Chromatogr 464: 103–115

    Article  Google Scholar 

  • Sütfeld R, Breteler H (1988) Effects of plant material and extract treatment on the yield of natural products from Tagetes. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally occurring acetylenes and related compounds (NOARC). Elesevier, Amsterdam, pp 101–106

    Google Scholar 

  • Sütfeld R, Towers GHN (1982) 5-(4-Acetoxy-l-butinyl)-2,2’-bithiopheneacetate esterase from Tagetespatula. Phytochemistry 21: 277–279

    Article  Google Scholar 

  • Tang CS, Wat CK, Towers GHN (1987) Thiophenes and benzofurans in the undisturbed rhizosphere of Tagetes patula L. Plant Soil 98: 93–97

    Article  CAS  Google Scholar 

  • Thellier M, Desbiez MO, Champagnat P, Kergosien Y (1982) Do memory processes occur also in plants? Physiol Plant 56: 281–284

    Article  Google Scholar 

  • Thorpe A (1978) Regulation of organogenesis in vitro. In: Hughes KW, Henke R, Constantin M (eds) Propagation of higher plants through tissue culture. A bridge between research and application. Univ Tennessee Symp Proc Conf 7804111, 16–19 April, USD of Energy, Washington

    Google Scholar 

  • Uhlenbroek JH, Bijloo JD (1958) Investigations on nematicides I. Isolation and structure of a nematicidal principle occurring in Tagetes roots. Rec Trav Chim 77: 1004–1009

    Article  CAS  Google Scholar 

  • Uhlenbroek JH, Bijloo JD (1959) Investigations on nematicides II. Structure of a second nematicidal rinciple isolated from Tagetes roots. Rec Trav Chim 78: 382–390

    Article  CAS  Google Scholar 

  • Uhlenbroek JH, Bijloo JD (1960) Investigations on nematicides III. Polythienyls and related compounds. Rec Trav Chim 79: 1181–1198

    Article  CAS  Google Scholar 

  • Watt G (1889–1896) A dictionary of the economic products of India, 7 Volumes. Periodical Experts, Delhi, India

    Google Scholar 

  • Wiermann R (1981) Secondary plant products and cell and tissue differentiation. In: Stumpf PK, Conn EE (eds) The biochemistry of plants. A comprehensive treatise, vol 7. Academic Press, New York, pp 86–116

    Google Scholar 

  • Wijnberg H (1988) The chemistry of a-terthienyl. In: Lam J, Breteler H, Arnason T, Hansen L (eds) Chemistry and biology of naturally-occurring acetylenes and related compounds (NOARC). Elsevier, Amsterdam, pp 21–28

    Google Scholar 

  • Yeoman MM, Miedzybrodzka MB, Lindsey K, McLauchlan WR (1979) The synthetic potential of cultured plant cells. In: Sala F, Parasi B, Cella R, Ciferri O (eds) Plant cell cultures: results and perspectives. Developments in plant biology, vol 5. Elsevier, Amsterdam, pp 327–348

    Google Scholar 

  • Zechmeister L, Sease JW (1947) A blue-fluorescing compound, terthienyl, isolated from marigolds. J Am Chem Soc 69: 273–275

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centre for Agrobiological Research (CABO), P.O. Box 14, 6700 AA, Wageningen, The Netherlands

    D. H. Ketel

Authors
  1. H. Breteler
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. H. Ketel
    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, 110065, New Delhi, India

    Y. P. S. Bajaj

Rights and permissions

Reprints and permissions

Copyright information

© 1993 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Breteler, H., Ketel, D.H. (1993). Tagetes spp. (Marigolds): In Vitro Culture and the Production of Thiophenes. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants IV. Biotechnology in Agriculture and Forestry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-77004-3_26

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-77004-3_26

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-77006-7

  • Online ISBN: 978-3-642-77004-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation