Essential oil biosynthesis and regulation in the genus Cymbopogon

Natural Product Communications

Volumn 5, Issue 1, 2010, Pages 163-172

  Ganjewala, Deepak ^a   Luthra, Rajesh ^b  

^a VIT UNIVERSITY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Acetate MVA pathway; Citral; Cymbopogon; Essential oil; Geraniol; Geranyl acetate; MEP pathway

Indexed keywords

2 METHYL DEXTRO ERYTHRITOL 4 PHOSPHATE; CITRAL; ESSENTIAL OIL; GERANIOL; GERANYL ACETATE; GERANYL ACETATE ESTERASE; GERANYL DIPHOSPHATE; ISOPENTENYL DIPHOSPHATE; TERPENE; TURPENTINE; UNCLASSIFIED DRUG; 2 C METHYLERYTHRITOL 4 PHOSPHATE; 2-C-METHYLERYTHRITOL 4-PHOSPHATE; DRUG DERIVATIVE; ERYTHRITOL; HEMITERPENE; ORGANOPHOSPHORUS COMPOUND; SUGAR PHOSPHATE;

ACETYLATION; ANTIFUNGAL ACTIVITY; BACTERICIDAL ACTIVITY; BIOSYNTHESIS; CYMBOPOGON; CYMBOPOGON CITRATUS; CYMBOPOGON FLEXUOSUS; CYMBOPOGON MARTINII; DRUG SYNTHESIS; HYDROLYSIS; NONHUMAN; OXIDATION; REVIEW; ECONOMICS; METABOLISM;

CITRUS LIMON; CYMBOPOGON; CYMBOPOGON FLEXUOSUS; CYMBOPOGON MARTINII; LAMIACEAE;

CYMBOPOGON; ERYTHRITOL; HEMITERPENES; MONOTERPENES; OILS, VOLATILE; ORGANOPHOSPHORUS COMPOUNDS; SUGAR PHOSPHATES; TERPENES;

EID: 77950464258     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1000500137     Document Type: Review

References (81)

1. Khanuja SPS, Shasany AK, Pawar A, Lal RK, Darokar MP, Naqvi AA, Rajkumar S, Sundaresan V, Lal N, Kumar S. (2005) Essential oil constituents and RAPD markers to establish species relationship in Cymbopogon Spreng. (Poaceae). Biochemical Systematics and Ecology, 33, 171-186. (Pubitemid 39645458)
2. Husain A. (1994) Palmarosa. In: Essential oil plants and their cultivation, Central Institute of Medicinal and Aromatic Plants (CIMAP), Lucknow, 58-66.
3. Ganjewala D, Kumari A, Khan KH. (2008) Ontogenic and developmental changes in essential oil content and compositions in Cymbopogon flexuosus cultivars: Recent Advance in Biotechnology, Excel India Publishers, New Delhi, 82-92.
4. Sidibe L, Chalchat JC, Garry RP, Lacombe L. (2001) Aromatic plants of Mali (IV): Chemical composition of essential oils of Cymbopogon citratus (DC) Stalf and C. giganteus (Hochst.) Chiov. Journal of Essential Oil Research, 13, 110-113.
5. Banthorpe DV, Charlwood BV. (1980) The Terpenoids. In Encyclopedia of Plant Physiology, New Series, Vol. 8: Secondary Plant Products. Bell EA, Charlwood BV. (Eds). Springer-Verlag, Berlin, 185-220.
6. Croteau R. (1987) Biosynthesis and catabolism of monoterpenoids. Chemical Reviews, 87, 929-954.
7. Rohmer M, Knani M, Simonin P, Sutter B, Sahm H. (1993) Isoprenoid biosynthesis in bacteria: A novel pathway for early steps leading to isopentenyl diphosphate. Biochemical Journal, 295, 517-524.
8. Mccaskill D, Croteau R. (1998) Some caveats for bioengineering terpenoid metabolism. Advances Biochemical Engineering Biotechnology, 55, 107-146.
9. Luthra R, Luthra PM, Kumar S. (1999) Redefined role of mevalonate-isoprenoid pathway in terpenoid biosynthesis in higher plants. Current Science, 76, 133-135. (Pubitemid 129558187)
10. Iijima Y, Gang DR, Ridman E, Lewinsohn E, Pichersky E. (2004) Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiology, 134, 370-379. (Pubitemid 38178709)
11. Yang T, Wang HX, Zeng Y. (2005) A geraniol synthase gene from Cinnamomum tenuipilum. Phytochemistry, 66, 285-293. (Pubitemid 40169988)
12. Ito M, Honda G. (2007) Geraniol synthases from Perilla and their taxonomical significance. Phytochemistry, 68, 446-453. (Pubitemid 46186439)
13. Singh N, Luthra R, Sangwan RS. (1990) Oxidative pathways and essential oil biosynthesis in the developing lemongrass (Cymbopogon flexuosus Stapf). Plant Physiology and Biochemistry, 28, 703-710.
14. Dubey VS, Bhalla R, Luthra R. (2003) An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants. Journal of Biosciences, 28, 637-646. (Pubitemid 37151106)
15. Ganjewala D, Luthra R. (2007) Essential oil biosynthesis and metabolism of geranyl acetate and geraniol in developing Cymbopogon flexuosus (Nees ex. Steud) Wats mutant cv. GRL-1 leaf. American Journal of Plant Physiology, 2, 269-275. (Pubitemid 47066535)
16. Luthra R, Srivastava AK, Ganjewala D. (2007) Histochemical localization of citral accumulating site in lemongrass (Cymbopogon flexuosus Nees Ex. Steud) Wats cultivar OD-19. Asian Journal of Plant Sciences, 6, 419-422. (Pubitemid 46408477)
17. Luthra R, Singh N, Sharma S. (1991) Changes in monoterpene content accompanying development of Cymbopogon winterianus Jowitt leaves. Journal of Essential Oil Research, 3, 349-354.
18. Singh N, Luthra R, Sangwan RS. (1991) Mobilization of starch and essential oil biogenesis during leaf ontogeny of lemongrass (Cymbopogon flexuosus Stapf). Plant Cell Physiology, 32, 803-811.
19. Dubey VS, Mallavarapu GR, Luthra R. (2000) Changes in the essential oil content and composition during palmarosa (Cymbopogon martini Roxb. Wats var. motia) inflorescence development. Flavour and Fragrance Journal, 15, 309-314.
20. Dawson FA. (1995) The amazing terpenes. Naval Stores Review, 6-12.
21. Rodov V, Ben-Yehoshua S, Fang DQ, Kim JJ, Ashkenazi R. (1995) Performed antifungal compounds of lemon fruit: citral and its relation to disease resistance. Journal of Agricultural and Food Chemistry, 43, 1057-1061.
22. Asthana A, Larson RA, Marley KA, Tuveson RW. (1992) Mechanisms of citral phototoxicity. Phytotoxicity and Photobiology, 56, 211-222.
23. Kim JK, Marshall MR, Cornel JA, Preston JF, Wei IC. (1995) Antibacterial activity of carvacrol, citral, and geraniol against Salmonella typhimurium in culture medium and on fresh cubes. Journal of Food Science, 60, 1364-1374.
24. Rice PJ, Coats JR. (1994) Insecticidal properties of several monoterpenoids to the house fly, red flour beetle and southern corn rootworm. Journal of Economic Entomology, 87, 1172-1179.
25. Ganjewala D, Luthra R. (2009) Geranyl acetate esterase controls and regulates the level of geraniol in lemongrass Cymbopogon flexuosus (Nees ex. Steud) Wats. mutant cv. GRL-1 leaves. Zeitschrift für Naturforschung C, 64, 251-259.
26. Singh N, Luthra R, Sangwan RS. (1989) Effect of leaf position and age on the essential quantity and quality in lemongrass (Cymbopogon flexusosus Stapf.). Planta Medica, 55, 254-256.
27. Bach TJ. (1995) Some aspects of isoprenoid biosynthesis in plants- a review. Lipids, 30, 191-202.
28. Chappel J. (1995) Biochemistry and molecular biology of the isoprenoid biosynthetic pathways in plants. Annual Review of Plant Physiology and Plant Molecular Biology, 46, 521-547.
29. Mccaskill D, Croteau R. (1995) Morphology and biosynthetic capabilities of secretory cell structures isolated from glandular trichomes of peppermint (Mentha piperita L). Planta, 187, 445-454.
30. Dubey VS, Bhalla R, Luthra R. (2003) An esterase is involved in geraniol production during palmarosa inflorescence development. Phytochemistry, 63, 257-264. (Pubitemid 36637352)
31. Luthra R, Sangwan RS, Sangwan NS. (1993) Utilization of exogenously supplied primary precursors for essential oil synthesis in Cymbopogon species. Biologia Plantarum, 35, 473-476.
32. Ganjewala D, Luthra R. (2007) Inhibitors of essential oil biosynthesis in Cymbopogon flexuosus (Nees ex. Steud) Wats mutant cv. GRL-1 leaves. American Journal of Plant Physiology, 2, 227-232. (Pubitemid 46997235)
33. Rohmer M, Knani M, Simonin P, Sutter B, Sahm H. (1993) Isoprenoid biosynthesis in bacteria: A novel pathway for early steps leading to isopentenyl diphosphate. Biochemical Journal, 295, 517-524. (Pubitemid 23315192)
34. Lichtenthaler HK, Schwender J, Disch A, Rohmer M. (1997) Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Letters, 400, 271-274.
35. Eisenrich W, Sanger S, Zenk MH, Bacher A. (1997) Monoterpenoid essential oils are not of mevalonate origin. Tetrahedron Letters, 38, 3889-3892.
36. Lichtenthaler HK. (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annual Review of Plant Physiology and Plant Molecular Biology, 50, 47-65.
37. Rohmer M. (2003) Mevalonate-independent methylerythritol phosphate pathway for isoprenoid biosynthesis. Elucidation and distribution. Pure Applied Chemistry, 75, 375-387.
38. Kleinig H. (1989) The role of plastids in isoprenoid biosynthesis. Annual Review of Plant Physiology and Plant Molecular Biology, 40, 39-59.
39. Rohdich F, Wungsintaweekul J, Eisenreich W, Richter G, Schuhr CA, Zenk MH, Bacher A. (2000) Biosynthesis of terpenoids: 4- diphosphocytidyl-2-C-methyl- D-erythritol synthase of Arabidopsis thaliana. Proceedings of the National Academy of Sciences USA, 97, 6451-6456.
40. Schwender J, Zeidler J, Groner R, Muller C, Focke M Braun S, Lichtenthaler FW, Lichtenthaler HK. (1997) Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Letters, 414, 129-134.
41. Eisenreich W, Rohdich F, Bacher A. (2001) Deoxyxylulose phosphate pathway to terpenoids. Trends in Plant Science, 6, 78-84.
42. Eisenreicha W, Bachera A, Arigonib D, Rohdicha F. (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cellular and Molecular Life Science, 61, 1401-1426.
43. Ganjewala D, Kumar S, Luthra R. (2009) An account of cloned genes of methyl-erythritol-4-phosphate pathway of isoprenoid biosynthesis in plants. Current Issues in Molecular Biology, S1, 35-45.
44. Sangwan RS, Sangwan NS, Luthra R. (1993) Metabolism of acyclic monoterpenes: Partial purification and properties of geraniol dehydrogenase from lemongrass (Cymbopogon flexuosus). Journal of Plant Physiology, 142, 129-134.
45. Banthorpe DV, Charlwood BV, Francis MJO. (1972) The biosynthesis of monoterpenes. Chemical Reviews, 72, 115-153.
46. Croteau R, Karp F. (1979) Biosynthesis of monoterpenes: Hydrolysis of bornyl pyrophosphate an essential step in camphor biosynthesis and hydrolysis of geranyl pyrophosphate the acyclic precursor of camphor by enzymes from sage (Salvia officinalis). Archive of Biochemistry and Biophysics, 198, 523-532.
47. Perez LM, Taucher G, Cori O. (1980) Hydrolysis of allylic phosphates by enzymes from flavedo of Citrus sinensis. Phytochemistry, 19, 183-187.
48. Nah J, Seon-Joo S, Kyoungwhan B. (2001) Partial characterization of farnesyl and geranylgeranyl diphosphatases induced in rice seedlings by UV-C irradiation. Plant Cell Physiology, 42, 864-867. (Pubitemid 32897209)
49. Croteau R, Hooper CL. (1978) Metabolism of monoterpenes: Acetylation of (-)-menthol by a soluble enzyme preparation from peppermint (Mentha piperita) leaves. Plant Physiology, 61, 737-742.
50. Shalit M, Guterman I, Volpin H, Bar E, Tamari T, Menda N, Adam Z, Zamir D, Vainstein A, Weiss D. (2003) Volatile ester formation in roses: identification of an acetyl-CoA: geraniol acetyltransferase in developing rose petals. Plant Physiology, 131, 1868-1876.
51. Dubey VS, Luthra R. (2001) Biotransformation of geranyl acetate to geraniol during palmarosa (Cymbopogon martini Roxb. Wats var. motia) inflorescence development. Phytochemistry, 57, 675-680.
52. Wermann U, Knoor D. (1993) Conversion of menthyl acetate or neomenthyl acetate into menthol or neomenthol by cell suspension cultures of Mentha candensis and Mentha piperita. Journal of Agriculture and Food Chemistry, 41, 517-520.
53. Gershenzon J, Croteau R. (1993) Terpenoid biosynthesis: the basic pathway and formation of monoterpenes, sesquiterpenes, and diterpenes. In: Lipid Metabolism in Plants. Moore TS. (Ed.) CRC Press, Boca Raton, FL, 339-388.
54. Duriyaprapan S, Briten EJ. (1982) The effect of age and location of leaf on quantity and quality of Japanese mint oil production. Journal of Experimental Botany, 33, 810-814.
55. Tyagi BR, Akhila A, Uniyal GC. (1983) Relationship of menthol biosynthesis in plant development in Mentha arvensis L. Pafai, 5, 28-31.
56. McConkey ME, Gershenzon J, Croteau R. (2000) Developmental regulation of monoterpene biosynthesis in the glandular trichomes of peppermint. Plant Physiology, 122, 215-223.
57. Saxena DB, Maheshwari ML. (1980) Terpenoids from palmarosa grass (Cymbopogon martinii var. matia). Indian Perfumer, 24, 115-120.
58. Banthorpe DV, Long DRS, Pink CR. (1983) Biosynthesis of geraniol and related monoterpenes in Pelargonium graveolens. Phytochemistry, 22, 2459-2463.
59. Malwatkar GM, Kokje BA, Kelkar GD. (1984) Seasonal variation in aldehyde content in oil: leaf yellowing and crinkling and leaf browning in jawa citronella (Cymbopogon winterianus Jowitt). Indian Perfumer, 28, 17-23.
60. Singh RS, Pathak MG, Singh KK. (1979) Dynamic and diurnal changes in oil of jawa citronella (Cymbopogon winterianus Jowitt). Indian Perfumer, 32, 116-120.
61. Oliveros-Belardo L, Aureus E. (1977) Essential oil from Cymbopogon citratus Stapf growing in the Philippines. International Congress on Essential Oil Japan, 7, 166-168.
62. Duhan SPS, Gulati BC, Garg SN. (1976) Essential oil of Cymbopogon pendulus Wats under Tarai climate of Utter Pradesh. Indian Journal of Pharmacy, 38, 79-82.
63. Lalitha R, Ramasarma T. (1986) Mevalonate phosphorylation in lemongrass leaves. Indian Journal of Biochemistry Biophysics, 23, 249-253.
64. Gulati BC, Gupta R, Duhan SPS. (1970) Trial cultivation of palmarosa (Cymbopogon martinii var. motia) in Tarai and Bhabar tract of Utter Pradesh. Indian Oil and Soap Journal, 36, 104-114.
65. Gupta R, Maheshwari ML, Singh RP, Mohan J, Gupta GK. (1978) Effects of fertilizers on yield oil content oil composition of palmarosa as influenced by seasonal variation. Indian Perfumer, 22, 79-87.
66. Hearth HMW, Ormrod D. (1979) Photosynthetic rates of citronella and lemongrass. Plant Physiology, 63, 406-408.
67. Croteau R. (1984) Development and essential oil content of secretory glands of sage (Salvia officinalis). Plant Physiology, 96, 148-150.
68. Pitarevic I, Kuftinec J, Blazevic N, Kustrak D. (1984) Seasonal variation of essential oil yield and composition of dalmation sage, Salvia officinalis. Journal of Natural Products, 47, 409-412.
69. Bouwmeester HJ, Kuijpers AM. (1993) Relationship between assimilate supply and essential oil accumulation in annual and biennial caraway (Carium carvi L). Journal of Essential Oil Research, 5, 143-152.
70. McGarvey DJ, Croteau R. (1995) Terpenoid metabolism. Plant Cell, 7, 1015-1026.
71. Lewinsohn E, Dudai N, Tadmor Y, Katzir I, Ravid U, Putievsky E, Joel DM. (1998) Histochemical localization of citral accumulation in lemongrass leaves (Cymbopogon citrtus (DC) Stapf., Poaceae). Annals of Botany, 81, 35-39.
72. Fahn A. (1988) Secretory tissues in plants. New Physiologist, 108, 229-257.
73. Werker E. (1993) Function of essential oil secreting glandular trichomes in aromatic plants of the Lamiaceae. A review. Flavour and Fragrance Journal, 8, 249-255.
74. Weiss EA. (1997) Essential oil crops: Wallingford, UK: CAB International, 59-137.
75. Bilkova J, Albrechtova J, Optama J. (1999) Histochemical detection and image analysis of non-specific esterase activity and the amount of polyphenols during annual bud development in Norway spruce. Journal of Experimental Botany, 50, 1129-1138.
76. Gersbach PV, Wyllie SG, Sarafis V. (2001) A new histochemical method for localization of the site of monoterpene phenol accumulation in plant secretory structures. Annals of Botany, 88, 521-525.
77. Gershenzon J, McCaskill D, Rajaonarivony JIM, Mihaliak C, Karp F, Croteau R. (1992) Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products. Annals of Biochemistry, 200, 130-138.
78. Werker E, Putievaky E, Ravid U, Dudai N, Katzir I. (1993) Glandular hairs and essential oil in developing of Ocimum basillicum L. (Lamiaceae). Annals of Botany, 71, 43-50.
79. Bohlman J, Mayer Gauen G, Croteau R. (1998) Plant terpenoid synthases: Molecular biology and phylogenetic analysis. Proceedings of Natural Academy of Sciences USA, 96, 4126-4133.
80. Gang DR, Wang JH, Dudareva N, Nam KH, Simon JE, Lewinsohn E, Pichersky E. (2001) An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiology, 125, 539-555.
81. Iruthayathas EE, Herath HMW. (1982) Microhairs of citronella leaves and their relationship to components of citronella oil. Tropical Agriculture, 59, 227-230.