Skip to main content
SpringerLink
Log in

Biosynthesis of Limonoids in Citrus

  • Chapter
Secondary-Metabolite Biosynthesis and Metabolism

Part of the book series: Environmental Science Research ((ESRH,volume 44))

Abstract

Limonoids represent a group of chemically related triterpenes found in the Rutaceae and Meliaceae. Bitterness due to limonoids in a variety of citrus juices is a major problem in the citrus industry. Among 38 limonoids isolated from Citrus and its hybrids, limonin, a bitter member of the group, occurs widely in citrus juices and is the major cause of the bitterness. Recently, limonoids have been shown to be present as glucoside derivatives in the Rutaceae1–6. These glucosides are one of the major secondary metabolites present in Citrus 7–9. Limonoids have also been found to possess biological activities, such as anticarcinogenic activity in laboratory animals10–12 and antifeedant activity against insects13–19. Recently, the biochemistry of limonoids in Citrus 20–21 and the removal of bitter limonoids from citrus juices by adsorption22–24 and biological means24–25 have been reviewed. This review summarizes the biosynthetic pathways of the major limonoids in Citrus and the alternative pathways occurring in Ichang Chie (C. ichangensis), sour orange (C. aurantium) and calamondin (C. reticulata x Fortunella sp). Also included is a review of the sites of biosynthesis in citrus tissues and information on when limonoids are biosynthesized during fruit growth and maturation.

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 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
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

  1. S. Hasegawa, R.D. Bennett, Z. Herman, C. H. Fong and P.Ou Limonoid glucosides in Citrus, Phytochemistry 28:1717 (1989) .

    Article  CAS  Google Scholar 

  2. R.D. Bennett, S. Hasegawa and Z. Herman, Glucosides of acidic limonoids in Citrus ,Phytochemistry 28:2777 (1989).

    Article  CAS  Google Scholar 

  3. H. Maeda, Y. Ozaki, M. Miyake, Y. Ifuku and S. Hasegawa, Limonoid glucosides in Hassaku (Citrus hassaku Hort.ex Tanaka), Nippon Nogeikagaku Kaishi 64:1231 (1990).

    Article  CAS  Google Scholar 

  4. Y. Ozaki, M. Miyake, H. Maeda, Y. Ifuku, R.D. Bennett, Z.Herman, C.H. Fong and S. Hasegawa, Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa ,Phytochemistry 30: 2659 (1991).

    Article  CAS  Google Scholar 

  5. Y. Ozaki, M. Miyake, Y. Ifuku, R.D. Bennett and S Hasegawa, Limonoid glucosides in Tetradium rutaecarpa ,Phytochemistry 30: 2365.

    Google Scholar 

  6. R.D. Bennett, M. Miyake, Y. Ozaki and S. Hasegawa, Limonoid glucosides in sour orange, Phytochemistry (in press).

    Google Scholar 

  7. C.H. Fong, S. Hasegawa, Z. Herman and P. Ou, Limonoid glucosides in commercial citrus juices, J. Food Sci. 54:1505 (1989).

    Article  CAS  Google Scholar 

  8. Z. Herman, C.H. Fong, P. Ou and S. Hasegawa, Limonoid glucosides in orange juices by HPLC, J. Agric. Food Chem. 38:1860 (1990) .

    Article  CAS  Google Scholar 

  9. Y. Ozaki, C.H. Fong, Z. Herman, H. Maeda, M. Miyake, Y.Ifuku and S. Hasegawa, Limonoid glucosides in citrus seeds, Agric. Biol.Chem. 55:137 (1991).

    Article  CAS  Google Scholar 

  10. L.K.T. Lam and S. Hasegawa, Inhibition of benzo(a)pyrene-induced forestomach neoplasia in mice by citrus limonoids, Nutrition and Cancer. 12:43 (1989).

    Article  PubMed  CAS  Google Scholar 

  11. L.K.T. Lam, Y. Li and S. Hasegawa, Effects of citrus limonoids on glutathione S-transferase activity in mice, J. Agrjg. Food Chem. 37:878 (1989).

    Article  CAS  Google Scholar 

  12. E.G. Miller, R. Fanous, F. Rivera-Hidalgo, W.H. Binnie,S. Hasegawa and L.K.T. Lam, The effect of citrus limonoids on hamster buccal pouch carcinogensis, Carcinogenesis 10:1535 (1989).

    Article  PubMed  CAS  Google Scholar 

  13. J.A. Klocke and I. Kubo, Citrus limonoid by-products as insect control agents, Ent. Exp. & Appl. 32:299 (1982).

    Article  CAS  Google Scholar 

  14. A.R. Alford and M.D. Bentley, Citrus limonoids as potential antifeedants for the spruce budworm (Lepidoptera tortricidae), J. Econ. Entomol. 79:35 (1986).

    CAS  Google Scholar 

  15. A.R. Alford, J.A. Cullen, R.H. Storch and M.D. Bentley, Antifeedant activity of limonin against the Colorado potato beetle, J. Econ.Entomol., 80:575 (1987).

    CAS  Google Scholar 

  16. J.T. Arnason, B.J.R. Philogene, D. Donskov and I. Kubo,Limonoids from the Meliaceae and Rutaceae reduce feeding, growth and development of Ostrinia nubilalis ,Ent. Exp. & Appl. 43:221 (1987).

    Article  Google Scholar 

  17. M.D. Bentley, M.S. Rajab, A.R. Alford, M.J. Mendel and A.Hassanali, Structure-activity studies of modified citrus limonoids as antifeedants for Colorado potato beetle larvae (Leptinotarsa decemlineata) , Ent. Exp. & Appl. 49:189 (1989).

    Article  Google Scholar 

  18. M.D. Bentley, M.S. Rajab, M.J. Mendel and A.R. Alford, Limonoid model insect antifeedants, J. Agric. Food Cheιt? 38:1400 (1990).

    Article  CAS  Google Scholar 

  19. Y.B. Liu, A.R. Alford, M.S. Rajab and M.D. Bentley, Effects of and modes of action of citrus limonoids against Leptinotarsa decemlineata ,Physiol. Entomol. 15:37 (1990).

    Article  CAS  Google Scholar 

  20. S. Hasegawa, Biochemistry and biological removal of limonoid bitterness in citrus juices, in: “Quality Factors of Fruits and Vegetables: Chemistry and Technology,” J.J. Jen, ed., ACS Symposium Series 405, American Chemical Society, Washington, D.C. (1989).

    Google Scholar 

  21. S. Hasegawa and V.P. Maier, Biochemistry of limonoid citrus juice bitterness principles and biochemical debittering processes in: “Bitterness in Food and Beverages,” R.L. Rouseff, ed., Elsevier, Amsterdam (1990).

    Google Scholar 

  22. A. Puri, Removal of bitter compounds from citrus products by adsorption techniques, iß: “Bitterness in Foods and Beverages,” R.L. Rouseff, ed., Elsevier, Amsterdam (1990).

    Google Scholar 

  23. P.E. Shaw, Cyclodextrin polymers in the removal of bittercomponents from citrus juice, in: “Bitterness in Foods and Beverages,” R.L. Rouseff, ed., Elsevier, Amsterdam (1990).

    Google Scholar 

  24. R.F.H. Dekker, De-bittering of citrus fruit juices:Specific removal of limonin and other bitter principles, AUS. J. Biotechnol. 2:65 (1988).

    CAS  Google Scholar 

  25. S. Hasegawa, Limonoid debittering of citrus juices using immobilized bacterial cell systems, Food Biotechnol. 1:249 (1987).

    Article  CAS  Google Scholar 

  26. S. Hasegawa, R.D. Bennett and Z. Herman, A limonoid from young calamondin seedlings, Phytochemistry 25:1984 (1986).

    Article  CAS  Google Scholar 

  27. Z. Herman, R.D. Bennett, P. Ou, C.H. Fong and S. Hasegawa, Metabolism of limonoids in the Citrus hybrid calamondin. Phytochemistry 26:2247 (1987).

    Article  CAS  Google Scholar 

  28. S. Hasegawa, Z. Herman, P. Ou and C.H. Fong, Metabolism of limonoids in calamondin: conversion of calamin to cyclocalamin, Phytochemistry 27:1349 (1988).

    Article  CAS  Google Scholar 

  29. R.D. Bennett, Z. Herman and S. Hasegawa, Ichangensin: a new citrus limonoid, Phytochemistry 27:1543 (1988).

    Article  CAS  Google Scholar 

  30. Z. Herman, S. Hasegawa, C.H. Fong and P. Ou, Limonoids in Citrus ichangensis ,J. Agric. Food Chem. 37:850 (1989).

    Article  CAS  Google Scholar 

  31. S. Hasegawa, P. Ou, C.H. Fong, Z. Herman, C.W. Coggins,Jr. and D.R. Atkin, Changes in the limonoate A-ring lactone and limonin 17-ß-D-glucopyranoside content of navel oranges during fruit growth and maturation, J. Agric. Food Chem. 39:262 (1991).

    Article  CAS  Google Scholar 

  32. S. Hasegawa and Z. Herman, Biosynthesis of obacunone from nomilin in Citrus limon ,Phytochemistry 24:1973 (1985).

    Article  CAS  Google Scholar 

  33. Z. Herman and S. Hasegawa, Limonin biosynthesis from obacunone via obacunoate in Citrus limon, Phytochemistry 24: 2911 (1985).

    Article  CAS  Google Scholar 

  34. Z. Herman, S. Hasegawa and P. Ou, Nomilin acetyl-lyase, a bacterial enzyme for nomilin debittering of citrus juices, J. Food Sci.50:118 (1985).

    Article  CAS  Google Scholar 

  35. S. Hasegawa and Z. Herman, Biosynthesis of limonoids: conversion of deacetylnomilinate to nomilin in Citrus limon ,Phytochemistry 25:2523 (1986).

    Article  CAS  Google Scholar 

  36. S. Hasegawa, Z. Herman and P. Ou, Metabolism of limonoids: nomilin to nomilinate in Citrus limon ,Phytochemistry 25:542 (1986).

    Article  CAS  Google Scholar 

  37. S. Hasegawa, R.D. Bennett and C.P. Verdon, Metabolism of limonoids via a deoxylimonoid pathway in Citrus ,PhytQChemiStry 19:1445 (1980).

    CAS  Google Scholar 

  38. S. Hasegawa, V.P. Maier and R.D. Bennett, Detection of limonoate dehydrogenase activity in albedo tissues of Citrus sinensis ,Phytochemistry 13:103 (1974).

    Article  CAS  Google Scholar 

  39. S. Hasegawa, R.D. Bennett, V.P. Maier and A.D. King, Jr.Limonoate dehydrogenase from Arthrobacter globiformis J. Agric. Food Chem. 20:1031 (1972).

    Article  PubMed  CAS  Google Scholar 

  40. F. Hashinaga and S. Hasegawa, Limonoids in seeds of Sudachi (Citrus sudachi Hort. ex Shirai), J. Japan Soc. Hort. Sci. 58:227 (1989).

    Article  CAS  Google Scholar 

  41. F. Hashinaga, C.H. Fong and S. Hasegawa, Biosynthesis of limonoids in Citrus sudachi ,Agric. Biol. Chem. 54:3019 (1990).

    Article  CAS  Google Scholar 

  42. F. Hashinaga, Z. Herman and S. Hasegawa, Limonoids in seeds of Yuzu (Citrus junos Sieb. ex Tanaka), Nippon Shokuhin Kogyo Gakkaishi 37:380 (1990).

    Article  CAS  Google Scholar 

  43. R.D. Bennett and S. Hasegawa, Isolimonic acid, a new citrus limonoid, Phytochemistry 19:2417 (1980).

    Article  CAS  Google Scholar 

  44. R.D. Bennett and S. Hasegawa, Limonoids of calamondin seeds, Tetrahedron 37:17 (1981).

    Article  CAS  Google Scholar 

  45. C.H. Fong, S. Hasegawa, Z. Herman and P. Ou, Biosynthesis of limonoid glucosides in lemon (Citrus limon), J. Sci. Food Agric. 54:393 (1991).

    Article  CAS  Google Scholar 

  46. Z. Herman, C.H. Fong and S. Hasegawa, Biosynthesis of limonoids in citrus fruit tissues, Abstract, Citrus Research Conference, Pasadena, CA (1990).

    Google Scholar 

  47. S. Hasegawa, Z. Herman, E.D. Orme and P. Ou, Biosynthesis of limonoids in Citrus: sites and translocation, Phytochemistry 25:2783 (1986).

    Article  CAS  Google Scholar 

  48. P. Ou, S. Hasegawa, Z. Herman and C.H. Fong, Limonoid biosynthesis in the stem of Citrus limon ,Phytochemistry 27:115 (1988).

    Article  CAS  Google Scholar 

  49. S. Hasegawa, R.D. Bennett and V.P. Maier, Biosynthesis of limonoids in Citrus seedlings, Phytochemistry 23:1601 (1984).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Agricultural Research Service Fruit and Vegetable Chemistry Laboratory, USDA, 263 South Chester Avenue, Pasadena, CA, 91106, USA

    Shin Hasegawa & Zareb Herman

Authors
  1. Shin Hasegawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zareb Herman
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Agricultural Research Service, United States Department of Agriculture, Peoria, Illinois, 61604, USA

    Richard J. Petroski  & Susan P. McCormick  & 

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer Science+Business Media New York

About this chapter

Cite this chapter

Hasegawa, S., Herman, Z. (1992). Biosynthesis of Limonoids in Citrus . In: Petroski, R.J., McCormick, S.P. (eds) Secondary-Metabolite Biosynthesis and Metabolism. Environmental Science Research, vol 44. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3012-1_21

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-3012-1_21

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6312-5

  • Online ISBN: 978-1-4615-3012-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation