Skip to main content

Citrus paradisi Macf. (Grapefruit): In Vitro Culture and the Bioproduction of Sesquiterpenes Nootkatone, Valencene, and Other Secondary Metabolites

  • Chapter
Medicinal and Aromatic Plants VII

Part of the book series: Biotechnology in Agriculture and Forestry ((AGRICULTURE,volume 28))

Abstract

The genus Citrus (family Rutaceae), produces coumarins, flavanones, flavones, and flavonols which occur in the free form and/or as glycosides (Maier and Metzler 1967; Horowitz and Gentili 1977), in addition to an extremely complex group of compounds which are volatile and are responsible for determining the characteristic aroma of each Citrus variety (Ting and Rouseff 1986).

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

Access this chapter

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

  • Albach RF, Wutscher HK (1988) Flavanone content of whole grapefruit and juice as influenced by fruit development. J Rio Grande Valley Hortic Soc 41:89–96

    CAS  Google Scholar 

  • Albach RF, Redman GH, Cruse RR (1981) Annual and seasonal changes in naringin concentration of Ruby Red grapefruit juice. J Agric Food Chem 29:808–811

    Article  CAS  Google Scholar 

  • Anon (1982) Naringin, a bitter flavouring, available in high-purity grades. Food Dev 16:29–29

    Google Scholar 

  • Bär A, Borrego F, Benavente O, Castillo J, Del Río JA (1990) Neohesperidin dihydrochalcone: properties and applications. Food Sci Technol 23:371–376

    Google Scholar 

  • Barrett HC, Rhodes AM (1976) A numerical taxonomic study of affinity relationship in cultivated Citrus and its close relatives. Syst Bot 1:105–136

    Article  Google Scholar 

  • Barthe GA, Jourdan PS, McIntosh CA, Mansell RL (1987) Naringin and limonin production in callus cultures and regenerated shoots from Citrus sp. J Plant Physiol 127:55–65

    Article  CAS  Google Scholar 

  • Berhow MA, Vandercook CE (1989) Biosynthesis of naringin and prunin in detached grapefruit. Phytochemistry 28:1627–1630

    Article  CAS  Google Scholar 

  • Berhow MA, Vandercook CE (1991) Sites of naringin biosynthesis in grapefruit seedlings. J Plant Physiol 138:176–179

    Article  CAS  Google Scholar 

  • Borrego F, Castillo J, Benavente-Garcia O, Del Río JA (1991) Application potential of the citrus origin sweetener neohesperidin dihydrochalcone. Int Food Ingredients 2:23–26

    Google Scholar 

  • Bosabalidis A, Tsekos I (1982) Ultrastructural studies on the secretory cavities of Citrus deliciosa Ten. II. Development of the essential oil-accumulating central space of the gland and process of active secretion. Protoplasma 112:63–70

    Article  Google Scholar 

  • Bricout J, Paupardin C (1974) Sur la composition de l’huile essentielle de tissus de péricarpe de Citron (Citrus limonia Obseck) cultivés in vitro. C R Acad Sci Paris Ser D 278:719–722

    CAS  Google Scholar 

  • Brown JT, Charlwood BV (1986) The accumulation of essential oils by tissue cultures of Pelargonium fragrans (Willd.). FEBS Lett 204:117–120

    Article  CAS  Google Scholar 

  • Bruckner V, Szent-Györgyi A (1936) Chemical nature of citrin. Nature (Lond) 138:1057–1057

    Article  CAS  Google Scholar 

  • Castillo J, Benavente O, Del Río JA (1992) Naringin and neohesperidin levels during development of leaves, flower buds, and fruits of Citrus aurantium. Plant Physiol 99:67–73.

    Article  PubMed  CAS  Google Scholar 

  • Chen YT, Zheng RL, Jia ZJ, Ju Y (1990) Flavonoids as Superoxide scavengers and antioxidants. Free Radical Biol Med 9:19–21

    Article  Google Scholar 

  • De Billy F, Paupardin C (1971) Sur l’évolution des huiles essentielles dans les tissus de péricarpe de Citron (Citrus limonia Obseck) cultivés in vitro. C R Acad Sci Paris Ser D 273:1690–1693

    Google Scholar 

  • Del Río JA, Ortuño A, García Puig D, Iborra JL, Sabater F (1991) Accumulation of the sesquiterpenes nootkatone and valencene by callus cultures of Citrus paradisi, Citrus limonia and Citrus aurantium. Plant Cell Rep 10:410–413

    Article  Google Scholar 

  • Del Río JA, Ortuño A, Garcia Puig D, Porras I, Garcia-Lidón A, Sabater F (1992a) Variations of nootkatone and valencene levels during the development of grapefruit. J Agric Food Chem 40:1488–1490

    Article  Google Scholar 

  • Del Río JA, Ortuño A, Marin FR, Garcia Puig D, Sabater F (1992b) Bioproduction of neohesperidin and naringin in callus cultures of Citrus aurantium. Plant Cell Rep 11:592–596

    Article  Google Scholar 

  • Del Río JA, García Puig D, Ortuño A, Sabater F, García-Lidón A, Porras I (1992c) Sesquiterpene nootkatone as an indicator of ripening in Citrus paradisi Macf. Proc VII Int Soc Citricult 420-422

    Google Scholar 

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

    CAS  Google Scholar 

  • Drawert F, Berger RG, Godelmann R (1984) Regioselective biotransformation of valencene in cell suspension cultures of Citrus sp. Plant Cell Rep 3:37–40

    Article  CAS  Google Scholar 

  • FAO (1991) Citrus fruit fresh and processed. FAO, Rome.

    Google Scholar 

  • Francis AR, Shetty TK, Bhattacharya RK (1989) Modulating effect of plant flavonoids on the mutagenicity of N-methyl-N′-nitro-N-nitrosoguanidine. Carcinogenesis 10:1953–1955

    Article  PubMed  CAS  Google Scholar 

  • Furia TE, Bellanca N (1975) Fenarolis handbook of flavor ingredients vol 2, 3rd edn. CRC Press, Cleveland, 438 pp

    Google Scholar 

  • Gábor M (1988) Szent-Györgyi and the bioflavonoids: new results and perspectives of pharmacological research into benzo-pyrone derivatives. In: Cody V, Middleton E Jr, Harborne JB, Beretz A (eds) Plant flavonoids in biology and medicine. II. Biochemical, cellular, and medicinal properties. Alan R Liss, New York, pp 1–15

    Google Scholar 

  • García Puig D, Ortuño A, Sabater F, Pérez ML, Porras I, García-Lidón A, Del Río JA (1993) Effect of ethylene on sesquiterpene nootkatone production during the maturation-senescence stage in grapefruit (Citrus paradisi Macf.). In: Pech JC, Latché A, Balagué C (eds) Cellular and molecular aspects of the plant hormone ethylene. Kluwer Academic, Dordrecht, pp 146–147

    Chapter  Google Scholar 

  • Gavish H, Lewinsohn E, Vardi A, Fluhr R (1989) Production of flavanone-neohesperidosides in Citrus embryos. Plant Cell Rep 8:391–394

    Article  CAS  Google Scholar 

  • Guengerich FP, Kim DM (1990) In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis 11:2275–2279

    Article  PubMed  CAS  Google Scholar 

  • Hasegawa S, Maier VP (1981) Some aspects of Citrus biochemistry and juice quality. Proc Int Soc Citricult 2:914–918

    CAS  Google Scholar 

  • Horowitz RM (1986) Taste effects of flavonoids. In: Cody V, Middleton E Jr, Harborne JB (eds) Plant flavonoids in biology and medicine: biochemical, pharmacological, and structure-activity relationships. Alan R Liss, New York, pp 163–175

    Google Scholar 

  • Horowitz RM, Gentili B (1963) Dyhydrochalcone derivatives and their use as sweetening agents. USA Patent 3,087,821

    Google Scholar 

  • Horowitz RM. Gentili B (1977) Flavonoid constituents of Citrus. In: Nagy S, Shaw PE, Veldhuis MK (eds) Citrus science and technology, vol 1. AVI, Westport, pp 397–426

    Google Scholar 

  • Jourdan PS, McIntosh CA, Mansell RL (1985) Naringin levels in citrus tissues. II. Quantitative distribution of naringin in Citrus paradisi Macfad. Plant Physiol 77:903–908

    Article  PubMed  CAS  Google Scholar 

  • Keterson JW, Hendrickson R, Braddock RJ (1971) Florida citrus oils. Univ Florida, Agric Exp Stn Bull 749, Gainesville

    Google Scholar 

  • Krbechek L, Inglett G, Holik M, Dowling B, Wagner R, Ritter R (1968) Dihydrochalcones. Synthesis of potential sweetening agents. J Agric Food Chem 16:108–112

    Article  CAS  Google Scholar 

  • Kunitake H, Mii M (1995) Somatic embryogenesis in Citrus species. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 30. Somatic embryogenesis and synthetic seed I. Springer Berlin Heidelberg New York (in press)

    Google Scholar 

  • Lewinsohn E, Berman E, Mazur Y, Gressel J (1986) Glucosylation of exogenous flavonones by grapefruit (Citrus paradisi) cell cultures. Phytochemistry 25:2531–2535

    Article  CAS  Google Scholar 

  • Lewinsohn E, Berman E, Mazur Y, Gressel J (1989) (7) Glucosylation and (1–6) rhamnosylation of exogenous flavonones by undifferentiated Citrus cell cultures. Plant Sci 61:23–28

    Article  CAS  Google Scholar 

  • Linsmaier EM, Skoog F (1965) Organic growth factor requirements of tobacco tissue cultures. Physiol Plant 18:100–127

    Article  CAS  Google Scholar 

  • Louzada ES, Grosser JW (1994) Somatic hybridization of Citrus with sexually incompatible wild relatives. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 27. Somatic hybridization in crop improvement I. Springer, Berlin Heidelberg New York, pp 427–438

    Google Scholar 

  • MacLeod WD, Buigues N (1964) Sesquiterpenes I. Nootkatone, a new grapefruit flavor constituent. J Food Sci 29:565–568

    Article  CAS  Google Scholar 

  • Maier VP, Metzler DM (1967) Grapefruit phenolics. II. Principal aglycons of endocarp and peel and their possible biosynthetic relationship. Phytochemistry 6:1127–1135

    Article  CAS  Google Scholar 

  • Mansell RL, Mclntosh CA (1991) Citrus spp.: In vitro culture and the production of naringin and limonin. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 15. Medicinal and aromatic plants III. Springer Berlin Heidelberg New York, pp 193-210

    Google Scholar 

  • Moore GA, Jacoco CC, Neidigh JL, Lawrence SD, Cline K (1993) Transformation in Citrus. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 23. Plant protoplasts and genetic engineering IV. Springer, Berlin Heidelberg New York, pp 194–208

    Google Scholar 

  • Moshonas MGH (1971) Analysis of carbonyl flavor constituents from grapefruit oil. J Agric Food Chem 19:769–770

    Article  CAS  Google Scholar 

  • Murashige T, Tucker DPH (1969) Growth factor requirements of citrus tissue culture. In: Chapman HD (ed) Proc 1st Int Citrus Symp, vol III. Univ California, Riverside, pp 1155–1161

    Google Scholar 

  • Navarro L (1992) Citrus shoot-tip grafting in vitro. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 18. High-Tech and micropropagation II. Springer, Berlin Heidelberg New York, pp 327–338

    Google Scholar 

  • Nishina A, Kihara H, Uchibori T, Takashi O (1991) Antimicrobial substances in “DF-100” extract of grapefruit seeds. J Antibact Antifung Agents 19:401–404

    CAS  Google Scholar 

  • Ortuño A, Sanchez-Bravo J, Moral JR, Acosta M, Sabater F (1990) Changes in the concentration of indole-3-acetic acid during the growth of etiolated lupin hypocotyls. Physiol Plant 78:211–217

    Article  Google Scholar 

  • Ortuño A, Garcia Puig D, Sabater F, Porras I, Garcia-Lidón A, Del Río JA (1993) Influence of ethylene and ethephon on the sesquiterpene nootkatone production in Citrus paradisi. J Agric Food Chem 41:1566–1569

    Article  Google Scholar 

  • Paupardin C (1974) Sur l’evolution de l’huile essentielle dans des tissus de fruits de Citron (Citrus limonia Osbeck) cultivés in vitro dans diverses conditions. Rev Gén Bot 81:223–241

    Google Scholar 

  • Paupardin C (1976) Sur la différenciation d’un tissu sécréteur et la formation d’huile essentielle par des tissus végétaux cultivés in vitro. C R Congr Natl Soc Sav Sect Sci 101:619–628

    CAS  Google Scholar 

  • Robertson GL, Nisperos MO (1983) Changes in the chemical constituents of New Zealand grapefruit during maturation. Food Chem 11:167–174

    Article  CAS  Google Scholar 

  • Rouseff RL, Martin SF, Youtsey CO (1987) Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in Citrus. J Agric Food Chem 35:1027–1030

    Article  CAS  Google Scholar 

  • Salvayre R, Nègre A, Affany A, Lenoble M, Douste-Blazy L (1988) Protective effect of plant flavonoids, analogs, and vitamin E against lipid peroxidation of membranes. In: Cody V, Middleton E Jr. Harborne JB, Beretz A (eds) Plant flavonoids in biology and medicine. II. Biochemical, cellular, and medicinal properties. Alan R Liss, New York, pp 313–316

    Google Scholar 

  • Shaw PE, Wilson CW III (1981) Importance of nootkatone to the aroma of grapefruit oil and the flavor of grapefruit juice. J Agric Food Chem 29:677–679

    Article  CAS  Google Scholar 

  • Shaw PE, Calkins CO, McDonald RE, Greany PD, Webb JC, Nisperos-Carriedo MO, Barros SM (1991) Changes in limonin and naringin levels in grapefruit albedo with maturity and the effects of gibberellic acid on these changes. Phytochemistry 30:3215–3219

    Article  CAS  Google Scholar 

  • Sinclair WB (1972) The grapefruit: its composition, physiology and products. Univ California, Div Agric Sciences

    Google Scholar 

  • Thorpe TA, Maier VP, Hassegawa S (1971) Phenylalanine amonio-lyase activity in Citrus fruit tissue cultured in vitro. Phytochemistry 10:711–718

    Article  CAS  Google Scholar 

  • Ting SV, Rouseff RL (1986) Chemical constituents affecting quality characteristics of Citrus products. In: Citrus fruits and their products. Marcel Dekker, New York, pp 105–106

    Google Scholar 

  • Vandercook CE, Tisserat B (1989) Flavonoid changes in developing lemons grown in vivo and in vitro. Phytochemistry 28:799–803

    Article  CAS  Google Scholar 

  • Webber HJ (1943) Cultivated varieties of citrus. In: Webber HJ, Batchelor LD (eds) The Citrus industry I. Univ California Press, Berkeley, pp 475–668

    Google Scholar 

  • Wilson CW III, Shaw PE (1980) Glass capillary gas chromatography for quantitative determination of volatile constituents in cold-pressed grapefruit oil. J Agric Food Chem 28:919–922

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1994 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Del Río, J.A., Ortuño, A. (1994). Citrus paradisi Macf. (Grapefruit): In Vitro Culture and the Bioproduction of Sesquiterpenes Nootkatone, Valencene, and Other Secondary Metabolites. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants VII. Biotechnology in Agriculture and Forestry, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-30369-6_9

Download citation

  • DOI: https://doi.org/10.1007/978-3-662-30369-6_9

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-30371-9

  • Online ISBN: 978-3-662-30369-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics