Non-protein amino acids: A review of the biosynthesis and taxonomic significance

Natural Product Communications

Volumn 3, Issue 1, 2008, Pages 93-110

  Bell, E Arthur ^a   Watson, Alison A ^b   Nash, Robert J ^c  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b ABERYSTWYTH UNIVERSITY   (United Kingdom)

^c Summit (Wales) Limited   (United Kingdom)

Author keywords

Amino acid; Biosynthesis; Chemosystematics; Natural products; Non protein amino acid

Indexed keywords

ALANINE; ARGININE; AROMATIC AMINO ACID; ASPARAGINE DERIVATIVE; CANAVANINE; CARBOXYLIC ACID DERIVATIVE; CYSTEINE; GLUTAMIC ACID; GLYCINE DERIVATIVE; HOMOARGININE; PHENYLALANINE; PROPIONIC ACID DERIVATIVE; SERINE; TRANSFER RNA; TYROSINE;

ACETYLATION; ASTRAGALUS PLANT; AZADIRACHTA INDICA; BEAN; BEECH; BIOSYNTHESIS; BRYONIA; CAESALPINIA; CATALYSIS; CUCUMBER; DOLICHOS; GLEDITSIA; GRIFFONIA; HIPPOCASTANACEAE; LATHYRUS; LEGUME; OAK; PEA; PHASEOLUS VULGARIS; PLANT SEED; PLANT TAXONOMY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REVIEW; SANTALACEAE; TALUS; TOBACCO;

EID: 77953992376     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300117     Document Type: Review

References (94)

1. Krishna RG, Wold F. (1992) Post-translational modifications: unique amino acids in proteins. In Frontiers and New Horizons in Amino Acid Research, Takai K (Ed) Elsevier, New York, 183-195.
2. Allen AK, Neuberger A. (1973) The purification and properties of the lectin from potato tubers, a hydroxyproline-containing glycoprotein. Biochemical Journal, 135, 307-314.
3. Peterson PJ, Fowden L. (1963) Different species of proline-activating enzymes from some plant species. Nature, 200, 148-151.
4. Fowden L, Lea PJ, Bell EA. (1979) The non-protein amino acids of plants, in Advances in Enzymology. Meister A (Ed), Vol. 50, John Wiley, New York, 117-175.
5. Lea PJ, Wallsgrove RM, Miflin BJ. (1985) The biosynthesis of amino acids in plants. In The Chemistry and Biochemistry of Amino Acids, Barrett, GC(Ed). Chapman and Hall, London, 197-226.
6. Bryan JK. (1990). Advances in the biochemistry of amino acid biosynthesis, in The Biochemistry of Plants, Stump PK, Conn EE (Eds in chief) Vol. 16, Intermediary nitrogen metabolism. Miflin BJ, Lea, PJ. (Eds) 169-195.
7. Lea PJ, Forde BG. (1994) The use of mutants and transgenic plants to study amino acid metabolism Plant Cell and Environment, 17, 541-556.
8. Smith IK, Thompson JF. (1971) Purification and characterization of L-serine transacetylase and O-acetyl-L-serine sulfhydase from the kidney bean (Phaseolus vulgaris). Biochimica et Biophysica Acta, 227, 288-295.
9. Smith IK. (1977) Evidence for O-acetyl serine in Nicotiana tabacum. Phytochemistry, 16, 1293-1295.
10. Radhakrishnan AN, Gopalkrishnan KS, Giri KV. (1961) Distribution and seasonal variation of allo-hydroxy-L-proline in Santalum album L Biochemical Journal, 80, 378-384.
11. Kuttan R, Radhakrishnan AN. (1970) The biosynthesis of cis-4-hydroxyproline in sandal (Santalum album L). Biochemical Journal, 117, 1015-1017.
12. Bell EA, Janzen DH. (1971) Medical and ecological considerations of L-DOPA and 5-HTP in seeds. Nature, 229, 136-137.
13. Obata-Sasamoto H, Nishi N , Komamine A. (1981) Mechanism of suppression of DOPA accumulation in callus culture of Stizolobium hassjoo Plant and Cell Physiology, 22, 827-835.
14. Lea PJ, Wallsgrove RM, Miflin BJ. (1985) The biosynthesis of amino acids in plants. In The Chemistry and Biochemistry of Amino Acids, Barrett GC (Ed). Chapman and Hall, London, 197-226.
15. Frisch DM, Dunnill PM, Smith A, Fowden L. (1967) The specificity of amino acid biosynthesis in the Cucurbitaceae. Phytochemistry, 6, 921-931.
16. Peterson PJ, Fowden L. (1972) The biosynthesis of γ-substituted glutamic acids in Gleditsia triacanthos. Phytochemistry, 11, 663-673.
17. Murakoshi I, Kuramoto H, Haginiwa J, Fowden L. (1972) The enzymic synthesis of β-substituted alanines Phytochemistry, 11, 177-182.
18. Dunnill PM, Fowden L (1963) The biosynthesis of β-pyrazol-1- ylalanine Journal of Experimental Botany, 14, 237-248.
19. Frisch, DM, Dunnill, PM, Smith A, Fowden L. (1967) The specificity of amino acid biosynthesis in the Cucurbitaceae. Phytochemistry, 6, 921-931.
20. Ahmmad MAS, Maskall CS, Brown EG. (1984) Partial purification and properties of willardiine and isowillardiine synthase activity from Pisum sativum. Phytochemistry, 23, 265-270.
21. Giovanelli J, Mudd SH. (1967) Synthesis of homocysteine and cysteine by enzyme extracts of spinach. Biochemical and Biophysical Research Communications, 27, 150-156.
22. Ikegami F, Kaneko M, Lambein F, Kuo YH, Murakoshi I. (1987) Difference between uracilylalanine synthases and cysteine synthases in Pisum sativum. Phytochemistry, 26, 2699-2704.
23. Ikegami F, Murakoshi I. (1992) Biosynthesis of heterocyclic β-substituted alanines in higher plants. Thai Journal of Pharmaceutical Science, 16, 225-250.
24. Ashworth TS, Brown EG, Roberts FM. (1972) Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings. Biochemical Journal, 129, 897-905.
25. Brown EG, Flayeh KAM, Gallon JR. (1982) The biosynthetic origin of the pyrazole moiety of β-pyrazol-1-ylalanine. Phytochemistry, 21, 863-867.
26. Brown EG, Diffin FM. (1990) Biosynthesis and metabolism of pyrazole by Cucumis sativus: enzymic cyclization and dehydrogenation of 1,3-diaminopropane. Phytochemistry, 29, 469-478.
27. Brown EG. (1995) Biogenesis of N-heterocyclic amino acids by plants: mechanisms of biological significance. In Amino acids and their derivatives in higher plants. Wallsgrove, RM (Ed). Cambridge University Press, Cambridge, UK, 119-145.
28. Larsen PO, Onderka OF, Floss HG. (1975) Biosynthesis of phenylalanine, tyrosine,3-(3-carboxyphenyl)alanine and 3-(3-carboxyhydroxyphenyl) alanine in higher plants, Examples of the transformation possibilities for chorismic acid. Biochimica et Biophysica Acta, 381, 409-415.
29. Larsen PO, Wieczorkowska E. (1975) Intermediates in the metabolism of m-carboxysubstituted aromatic amino acids in plants. Phenylpyruvic acids, mandelic acids and phenylglyoxylic acids. Biochimica et Biophysica Acta, 381, 409-415.
30. Bell EA. (1964) Relevance of biochemical taxonomy to the problem of lathyrism. Nature, 203, 378-380.
31. Bell EA. (1963) A new amino acid, γ-hydroxyhomoarginine in Lathyrus. Nature, 199, 70-71.
32. Bell EA. (1964) The isolation of γ-hydroxyhomoarginine, as its lactone, from seeds of Lathyrus tingitanus: its biosynthesis and distribution. Biochemical Journal, 91, 358-361.
33. Bell EA, Przybylska J. (1965) The origin and site of synthesis of the pyrimidine ring in the amino acid lathyrine. Biochemical Journal, 94, 35.
34. Brown EG, Al-Baldawi NF. (1977) Biosynthesis of the pyrimidinyl amino acid lathyrine by Lathyrus tingitanus L. Biochemical Journal, 164, 589-594.
35. 14C] orotate by shoots of Pisum sativum, Phaseolus vulgaris and Lathyrus tingitanus. Phytochemistry, 22, 1925-1928.
36. Brown EG, Mohamad J. (1990) Biosynthesis of lathyrine; a novel synthase activity. Phytochemistry, 29, 3117-3121.
37. Brown EG, Turan Y. (1996) Lathyrine biosynthesis and the origin of the precursor 2-amino-4-carboxypyrimidine in Lathyrus tingitanus. Phytochemistry, 43, 1029-1031.
38. Malathi K, Padmanaban G, Sarma PS. (1970) The biosynthesis of β-N-oxalyl-L-α,β-diaminopropionic acid the Lathyrus sativus neurotoxin. Phytochemistry, 9, 1603-1610.
39. Lambein F, Schamp N, Vandendriessche L, Van Parijs R. (1969) A new UV-sensitive heterocyclic amino acid from pea seedlings: 2-alanyl-3-isoxazolin- 5-one. Biochemical and Biophysical Research Communications, 37, 375-382.
40. Lambein F, KuoYH, and Van Parijs R. (1976) Isoxazolin-5-ones. Chemistry and biology of a new class of plant products. Heterocycles, 4, 567-593.
41. Lambein F, De Bruyn A, Ikegami F, and Kuo YH. (1986) In Lathyrus and Lathyrism, Kaul AK, Combes D (Eds). Third World Medical Research Foundation, New York, 246-256.
42. Lambein F, Ongena G, Kuo YH. (1990) β-Isoxazolinone-alanine is involved in the biosynthesis of the neurotoxin β-N-oxalyl-L- α,β diaminopropionic acid. Phytochemistry, 29, 3793-3796.
43. Kuo YH, Lambein F. (1991) Biosynthesis of the neurotoxin β-N-oxalyl-α,β-diaminopropionic acid in callus tissue of Lathyrus sativus. Phytochemistry, 30, 3241-3244.
44. Kuo YH, Khan JK, Lambein F. (1994) Biosynthesis of the neurotoxin β-ODAP in the developing pods of Lathyrus sativus. Phytochemistry, 35, 911-913.
45. Kuo YH, Lambein F, Mellor LC, Adlington RA, Baldwin JE. (1994) Ring-nitrogen of â-isoxazolinone-alanine is incorporated into the neurotoxin α-N-oxalyl-L-α,β-diaminopropionic acid, in callus tissue of Lathyrus sativus. Phytochemistry, 37, 713-715.
46. Fowden L. (1956) Azetidine-2-carboxylic acid: a new cyclic imino acid occurring in plants. Biochemical Journal, 64, 323-332.
47. Sung ML, Fowden L. (1969) Azetidine-2-carboxylic acid from the legume Delonix regia. Phytochemistry, 8, 2095-2096.
48. Ikeda M, Naganuma Y, Ohta K, Sassa T, Miura Y. (1977) Isolation and identification of a plant growth inhibitor, azetidine-2-carboxylic acid from Clavaria miyabeana and its occurrence in the family Clavariaceae. Nippon Nogeikagaku Kaishi, 51, 519-522.
49. Fearon WR. (1946) The amidine-pentacyanoferrate reaction: a test for guanidines, urea and thiourea. Analyst, 71, 562-566.
50. Fearon WR, Bell EA. (1955) Canavanine: detection and occurrence in Colutea arborescens. Biochemical Journal, 59, 221-222.
51. Bell EA. (1960) Canavanine in the Leguminosae. Biochemical Journal, 75, 618-619.
52. Birdsong AA, Alston R, Turner BL. (1960) Distribution of canavanine in the family Leguminosae as related to phyletic groupings. Canadian Journal of Botany, 38, 499-505.
53. Bell EA, Lackey JA, Polhill RM. (1978) Systematic significance of canavanine in the Papilionoideae (Faboideae). Biochemical Systematics and Ecology, 6, 201-212.
54. Damodaran M, Ramaswamy R. (1937) Isolation of L-3,4- dihydroxyphenylalanine from the seeds of Mucuna pruriens. Biochemical Journal, 31B, 2149-2152.
55. Bell EA, Janzen DH. (1971) Medical and ecological considerations of L-Dopa and 5-HPT in seeds. Nature, 229, 136-137.
56. Udenfriend S, Titus E, Weissbach H, Petersen RE. (1956) Biogenesis and metabolism of 5-hydroxyindole compounds. Journal of Biological Chemistry, 219, 335-344.
57. Udenfriend S, Weissbach H, Bogdanski DF. (1957) Increase in tissue serotonin following administration of its precursor 5-hydroxytryptophan. Journal of Biological Chemistry, 224, 803-810.
58. Dannenburg WN, Liverman JL. (1957) Conversion of tryptophan-2-C14 indoleacetic acid by watermelon tissue slices Plant Physiology, 32, 263-269.
59. Mitoma C, Weissbach H, Undenfriend S. (1955) Formation of 5-hydroxytryptophan from tryptophan in Chromobacterium violaceum, Nature, 175, 994-995.
60. Bell EA, Fellows LE. (1966) Occurrence of 5-hydroxytryptophan as a free plant amino acid. Nature, 229, 529.
61. Irvine FR. (1961) Woody Plants of Ghana. Oxford University Press, London, 308-309.
62. Bell EA, Fellows LE, Qureshi MY. (1976) 5-Hydroxytryptophan: taxonomic character and chemical defence in Griffonia. Phytochemistry, 15, 823.
63. Fowden L, Steward FC. (1957) Nitrogenous compounds and nitrogen metabolism in the Liliaceae I. The occurrence of soluble nitogenous compounds Annals of Botany, 21, 53-67.
64. Sung ML, Fowden L. (1969) Azetidine-2-carboxylic acid from the legume Delonix regia Phytochemistry, 8, 2095-2096.
65. Watson R, Fowden L. (1973) Amino acids of Caesalpinia tinctoria and some allied species. Phytochemistry, 12, 617-622.
66. Bell EA, Evans CS. (1978) Uncommon amino acids in the seeds of 64 species of Caesalpinieae. Phytochemistry, 17, 1127-1129.
67. Bell EA. (1962) Associations of ninhydrin-reacting compounds in the seeds of 49 species of Lathyrus. Biochemical Journal, 83, 225-229.
68. Bell EA. (1971) Comparative biochemistry of non-protein amino acids. In Chemotaxonomy of the Leguminosae. Harborne JB, Boulter D, Turner BL (Eds). Academic Press, London and New York, 179-203.
69. Bell EA, Tirimanna ASL. (1965) Associations of amino acids and related compounds in seeds of forty-seven species of Vicia: their taxonomic and nutritional significance. Biochemical Journal, 97, 104-111.
70. Simola LK. (1967) The effect of some non-protein amino acids on pollen germination and pollen-tube growth in five species of the Vicieae Planta, 77, 287-97.
71. Lambein F, Van Parijs R. (1974) New isoxazolinone amino acids from Lathyrus odoratus seeds. Biochemical and Biophysical Research Communications, 61, 155-162.
72. Casimir J, Le Marchand G. (1966) Repartition et importance systematique des acides amines et des peptides libre des Phaseolinae. Bulletin de Jardin Botanique de Bruxelles, 36, 53-56.
73. Bell EA. (1966) Amino acids and related compounds in seeds of Vigna and Phaseolus species (Leguminosae: Papilionatae). Fourth International Symposium of Natural Products, Stockholm, Abstracts, p 186.
74. Bell EA Qureshi MY, Charlwood BV, Pilbeam DJ, Evans CS. (1977) The variability of free amino acids and related compounds in legume seeds. In Genetic Diversity in Plants Muhammed A, Aksel R, von Borstel RC (Eds) Vol. 8, Basic Life Sciences, Plenum Press, New York and London, 397-412.
75. Dunnill PM, Fowden L. (1967) The amino acids of the genus Astragalus. Phytochemistry, 6, 1659-1663.
76. Pilbeam DJ, Bell EA. (1979) Free amino acids of Crotalaria seeds. Phytochemistry, 18, 973-985.
77. Pilbeam DJ, Polhill RM, Bell EA. (1979) Free amino acids and alkaloids of South American, Asian and Australian Crotalaria species Botanical Journal of the Linnean Society, 79, 259-266.
78. Fellows LE, Polhill RM, Bell EA. (1978) 3-[2-Amino-2-imidazolin-4-yl] alanine, 2-[2-amino-2-imidazolin-4-yl] acetic acid, 2-aminoimidazole and other guanidino derivatives in the Tephrosieae. Biochemical Systematics and Ecology, 6, 213-215.
79. Evans SV, Fellows LE, Bell EA. (1985) Distribution and systematic significance of basic non-protein amino acids and amines in the Tephrosieae. Biochemical Systematics and Ecology, 13, 271-302.
80. Watson R, Fowden L (1973) Amino acids of Caesalpinia tinctoria and some allied species. Phytochemistry, 12, 617-622.
81. Evans CS, Bell EA. (1978) Uncommon amino acids in the seeds of 64 species of Caesalpinieae. Phytochemistry, 17, 1127-1129.
82. Evans SV, Shing TKM, Aplin RT, Fellows, LE, Fleet GWJ. (1985) Sulphate ester of trans-4-hydroxypipecolic acid in seeds of Peltophorum. Phytochemistry, 24, 2593-2596.
83. Krauss G-J, Reinbothe H. (1973) Die freien amino sauren in samen von Mimosaceae. Phytochemistry, 12, 125-142.
84. Seneviratne AS, Fowden L. (1968) The amino acids of the genus Acacia. Phytochemistry, 7, 1039-1045.
85. Evans CS, Qureshi MY, Bell EA. (1977) Free amino acids in the seeds of Acacia species. Phytochemistry, 16, 565-570.
86. Bell EA, Evans CS. (1978) Biochemical evidence of a former link between Australia and the Mascarene Islands Nature, 273, 295-296.
87. Guinet P, Vassal J. (1978) Hypotheses on the differentiation of the major groups in the genus Acacia (Leguminosae). Kew Bulletin, 32, 506-527.
88. Evans CS, Shah AJ, Adlard MW, Rico Arce ML. (1993) Non-protein amino acids in seeds of neotropical species of Acacia. Phytochemistry, 32, 123-126.
89. Dunnill PM, Fowden L. (1965) The amino acids of seeds of the Cucubitaceae. Phytochemistry, 4, 933-944.
90. Fowden L, Lea PJ, Bell EA. (1979). The non-protein amino acids of plants, in Advances in Enzymology, Meister A. (Ed), Volume 50, John Wiley, New York, 117-175.
91. Fowden L, Smith A. (1968) Newly characterized amino acids from Aesculus californica Phytochemistry, 7, 809-819.
92. Kasai T, Larsen PO, Sorensen H. (1978) Free amino acids and χ-glutamyl peptides in Fagaceae Phytochemistry, 17, 1911-1915.
93. Maeno K, Yoshii S, Mita K, Hamaguchi M, Yoshida T, Iinuma M, Nagai Y, Matsumoto T. (1979) Analysis of the inhibitory effect of canavanine on the replication of influenza RI/5+ virus. I. Inhibition of assembly of RNP. Virology, 94, 128-137.
94. Bence AK, Crooks PA. (2003) The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery. Journal of Enzyme Inhibition and Medicinal Chemistry, 18, 383-394.