Amavadine, a vanadium compound in amanita fungi

Vanadium: Biochemical and Molecular Biological Approaches

Volumn 9789400709133, Issue , 2012, Pages 35-49

  Da Silva, José A L ^a   Da Silva, João J R Fraústo ^a   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Amanita fungi; Amavadine; Catalase activity; Catalysis; Electrocatalysis; Non oxo vanadium(IV) complexes; Oxidation of alkanes; Oxidation of thiols; Peroxidase activity; Redox behavior; Vanadium accumulation

Indexed keywords

BIOLOGICAL SYSTEMS; CATALYSIS; ELECTROCATALYSIS; FUNGI; HALOGENATION; KETONES; MOLECULAR BIOLOGY; OXIDATION; SYNTHESIS (CHEMICAL);

AMAVADINE; CATALASE ACTIVITY; NON-OXO VANADIUM(IV) COMPLEXES; OXIDATION OF ALKANES; PEROXIDASE ACTIVITIES; REDOX BEHAVIOR;

VANADIUM COMPOUNDS;

EID: 84930899495     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-94-007-0913-3_2     Document Type: Chapter

References (74)

1. Henze M (1911) Testings on the blood of ascidians I announcement-the vanadium compound of the blood corpuscles. Z Physiol Chem 72:494-501
2. Geml J, Tulloss RE, Laursen GA, Sazanova NA, Taylor DL (2008) Evidence for strong inter-and intracontinental phylogeographic structure in Amanita muscaria, a wind-dispersed ectomycorrhizal basidiomycete. Mol Phylogenet Evol 48:694-701
3. Fraústo da Silva JJR (1989) Vanadium in biology-the case of the Amanita toadstools. Chem Spec Bioavailab 1:139-150
4. Bayer E (1995) Amavadin, the vanadium compound of Amanitae. In: Sigel H, Sigel A (eds) Vanadium and its role for life, metal ions in biological systems, vol 31. Marcel Dekker, New York, pp 407-421
5. Pombeiro AJL, Fraústo da Silva JJR, Fujiwara Y, Silva JAL, Reis PM, Palavra AMF Catalyst system and process for direct one-pot conversion of methane into acetic acid under relatively mild conditions, comprises vanadium complex, peroxodisulfate salt and trifluoroacetic acid. WO 2004/037416 A2. May 6, 2004
6. Ter Meulen H (1931) Regarding the distribution of the molybdene in nature. Rec Trav Chim Pays-Bas 50:491-504
7. Bertrand D (1943) Le vanadium chez les champignons et plus spécialement chez les amanite. Bull Soc Chim Biol 25:194-197
8. Meisch H-U, Reinle W, Schmitt JA (1979) High vanadium content in mushrooms is not restricted to the fly agaric (Amanita muscaria). Z Naturforsch 66:620-621
9. Matoso CMM, Pombeiro AJL, da Silva JJR Fraústo, da Silva MFCG, da Silva JAL, Baptista-Ferreira JL, Pinho-Almeida F 1998 A possible role for amavadine in some amanita fungi Tracey AS, Crans DC (eds) Vanadium compounds-chemistry, biochemistry and therapeutic applications, American chemical society symposium series no. 711. American Chemical Society Washington, DC,Chapter 18, and references therein 241-247.
10. Koch E, Kneifel H, Bayer E (1987) Occurrence of amavadin in mushrooms of the genus Amanita. Z Naturforsch 42c:873-878
11. Vetter J (2005) Mineral composition of basidiomes of Amanita species. Mycol Res 109: 746-750
12. Falandysz J, Kunito T, Kubota R, Lipka K, Mazur A, Falandysz JJ, Tanabe S (2007) Selected elements in fly agaric Amanita muscaria. J Environ Sci Health A 42:1615-1623, and references therein
13. Bayer E, Kneifel H (1972) Isolation of amavadin, a vanadium compound occurring in Amanita muscaria. Z Naturforsch 27b:207-207
14. Kneifel H, Bayer E (1973) Determination of the structure of the vanadium compound, amavadine, from fly agaric. Angew Chem Int Ed 12:508-508
15. Koch E, Kneifel H, Bayer E (1986) Synthesis of new complexons-N-hydroxy-alpha, alpha0-iminodipropionic-hydroxyiminodiacetic and N-hydroxyiminodiacetic acid. Z Naturforsch 41b:359-362
16. Kneifel H, Bayer E (1986) Stereochemistry and total synthesis of amavadin, the naturallyoccurring vanadium compound of Amanita-muscaria. J Am Chem Soc 108:3075-3077
17. Hubregtse T, Neeleman E, Maschmeyer T, Sheldon RA, Hanefeld U, Arends IWCE (2005) The first enantioselective synthesis of the amavadin ligand and its complexation to vanadium. J Inorg Biochem 99:1264-1267
18. Anderegg G, Koch E, Bayer E (1987) N-hydroxy-', '0-iminodipropionic and N-hydroxyiminodiacetic acid as complexing agents and an example for selective coordination of the vanadyl ion VO2C in amavadine. Inorg Chem Acta 127:183-188
19. Hubregtse T, Kooijman H, Spek AL, Maschmeyer T, Sheldon RA, Arends IWCE, Hanefeld U (2007) Study on the isomerism in meso-amavadin and an amavadin analogue. J Inorg Biochem 101:900-908
20. Smith PD, Berry RE, Harben SM, Beddoes RL, Helliwell M, Collison D, Garner CD (1997) New vanadium-(IV) and-(V) analogues of amavadin. J Chem Soc Dalton Trans 1997: 4509-4516
21. Hubregtse T, Hanefeld U, Arends IWCE (2007) Stabilizing factors for vanadium(IV) in amavadin. Eur J Org Chem 2007:2413-2422
22. Gillard RD, Lancashire RJ (1984) Electron-spin resonance of vanadium in Amanita muscaria. Phytochemistry 23:179-180
23. Felcman J, Fraústo da Silva JJR, Vaz MCTA (1984) Metal-complexes of N-hydroxy-imino-di-'-propionic acid and related ligands. Inorg Chim Acta 93:101-108
24. Bemski G, Felcman J, Fraústo da Silva JJR, Moura I, Moura JJG, Vaz MCTA, Vilas-Boas LF (1986) Amavadine, an oxovanadium(IV) complex of N-hydroxy-imino-', '0-dipropionic acid. In: Xavier AV (ed) Frontiers in bioinorganic chemistry. VCH Verlagsgesellaschaft, Weinheim, pp 97-105
25. Bayer E, Koch E, Anderegg G (1987) Amavadin, an example for selective binding of vanadium in nature-studies of its complexation chemistry and a new structural proposal. Angew Chem Int Engl 26:545-546
26. Carrondo MAAFdeCT, Duarte MTLS, Costa Pessoa J, Silva JAL, Fraústo da Silva JJR, Vaz MCTA, Vilas-Boas LF (1988) Bis-(N-hydroxy-iminodiacetate)vanadate(IV), a synthetic model of "amavadin". J Chem Soc Chem Commun 1988:1158-1159
27. Armstrong EM, Beddoes RL, Calviou LJ, Charnock JM, Collison D, Ertok N, Naismith JH, Garner CD (1993) The chemical nature of amavadin. J Am Chem Soc 115:807-808
28. Paine TK, Weyhermuller T, Slep LD, Neese F, Bill E, Bothe E, Wieghardt K, Chaudhuri P (2004) Nonoxovanadium(IV) and oxovanadium(V) complexes with mixed O, X, O-donor ligands (XDS, Se, P, or PO). Inorg Chem 43:7324-7338
29. Yadav HS, Armstrong EM, Beddoes RL, Collison D, Garner CD (1994) The molybdenum analog of amavadin. J Chem Soc Chem Commun 1994:605-606
30. Galvao AM, Levi E, Pombeiro AJL, Guedes da Silva MFC, Silva JAL, Fraústo da Silva JJR (1995) Modelos da amavadina-estudos com o complexo de crómio(III) com hida. In: 2nd conference on inorganic chemistry of the Portuguese Chemical Society, Monte Real-Portugal, CP22, pp 91-92
31. Harben SM, Smith PD, Beddoes RL, Collison D, Garner CD (1997) Eight-coordinate [bis(oxyiminodiacetate)titanium(IV)]2and nine-coordinate [bis(oxyiminodiacetate) aquazirconium( IV)]2-; variation in coordination mode in amavadin-like complexes. Angew Chem Int Engl 36:1897-1898
32. Harben SM, Smith PD, Helliwell M, Collison D, Garner CD (1997) The synthesis, structure and nuclear magnetic resonance properties of some titanium relatives of amavadin: [-Ti(R, R-hidpa)2]2-, [, -Ti(R, R-hidpa)2]2-and [, -Ti(hida)2]2-[H3hidpaD2,20-(hydroxyimino)dipropionic acid, H3hidaDN-hydroxyiminodiacetic acid]. J Chem Soc Dalton Trans 1997:4517-4523
33. Smith PD, Harben SM, Beddoes RL, Helliwell M, Collison D, Garner CD (1997) Synthesis and structures of niobium(V) and tantalum(V) analogues of amavadin: [M(hida)2]-(MDNb-V or Ta-V, H3hida equals hydroxyimino-diacetic acid) and [Nb(R, R-hidpa)2]-[H3hidpaD2,20-(hydroxyimino)-dipropionic acid]. J Chem Soc Dalton Trans 1997:685-691
34. Smith PD, Cooney JJA, McInnes EJL, Beddoes RL, Collison D, Harben SM, Helliwell M, Mabbs FE, Mandel A, Powell AK, Garner CD (2001) New molybdenum(V) analogues of amavadin and their redox properties. J Chem Soc Dalton Trans 2001:3108-3114
35. Carrondo MAAFD, Duarte MTLS, Silva JAL, daSilva JJRF (1991) The crystal and molecularstructure of N, N0-bipyridyl, N-methoxy iminodiacetate oxovanadium(IV). Polyhedron 10:73-77
36. Berry RE, Armstrong EM, Beddoes RL, Collison D, Ertok SN, HelliwellM, Garner CD (1999) The structural characterization of amavadin. Angew Chem Int Engl 38:795-797
37. Armstrong EM, Collison D, Ertok N, Garner CD (1999) NMR studies on natural and synthetic amavadin. Conference Information: XXXIst Colloquium Spectroscopicum Internationale, 05-10 Sept 1999 Ankara, Turkey Talanta 53 (2000) Spl. Issue SI 75-87
38. Armstrong EM, Collison D, Deeth RJ, Garner CD (1995) Discrete variational X' studies of the electronic-structure of amavadin. J Chem Soc Dalton Trans 1995:191-195
39. Remenyi C, Munzarova ML, Kaupp M (2005) Comparative density-functional study of the electron paramagnetic resonance parameters of amavadin. J Phys Chem B 109:4227-4233
40. Geethalakshmi KR, Waller MP, Buhl M (2007) The presumption of innocence? A DFTdirected verdict on oxidized amavadin and vanadium catecholate complexes. Inorg Chem 46: 11297-11307
41. Ooms KJ, Bolte SE, Baruah B, Choudhary MA, Crans DC, Polenova T (2009) 51V solid-state NMR and density functional theory studies of eight-coordinate non-oxo vanadium complexes: oxidized amavadin. Dalton Trans 2009:3262-3269
42. NawiMA, Riechel TL (1987) The electrochemistry of amavadine, a vanadium natural product. Inorg Chim Acta 136:33-39
43. Thackrey RD, Riechel TL (1988) Mediators for the oxidation of glutathione and other biological thiols. J Electroanal Chem 245:131-143
44. Fraústo da Silva JJR, Guedes da Silva MFC, Silva JAL, Pombeiro AJL (1993) Redox properties of the amavadine models [V(hida)2 ]2and [V(hidpa)2 ]2and their electroinduced reactivity toward activated-thiols and activated-phenols. In: Pombeiro AJL, McCleverty JA (eds) Molecular electrochemistry of inorganic, bioinorganic and organometallic compounds. Kluwer Academic, Dordrecht, pp 411-415
45. Guedes da Silva MFC, Silva JAL, Fraústo da Silva JJR, Pombeiro AJL, Amatore C, Verpeaux J-N (1996) Evidence for a Michaelis-Menten type mechanism in the electrocatalytic oxidation of mercaptopropionic acid by an amavadine model. J Am Chem Soc 118:7568-7573
46. Lenhardt JM, Baruah B, Crans DC, Johnson MD (2006) Self-exchange electron transfer in high oxidation state non-oxo metal complexes: amavadin. Chem Commun 44:4641-4643
47. Lenhardt JM, Baruah B, Crans DC, Johnson MD (2009) Electron transfer in nonoxovanadium( IV) and (V) complexes: kinetic studies of an amavadin model. Conference Information: 6th international symposium on chemistry and biological chemistry of vanadium, Lisbon, Portugal, 17-19 July 2009, Pure Appl Chem 81:1241-1249
48. Reis PM, Silva JAL, da Silva JJRF, Pombeiro AJL (2000) Amavadine as a catalyst for the peroxidative halogenation, hydroxylation and oxygenation of alkanes and benzene. Chem Commun 2000:1845-1856
49. Reis PM, Silva JAL, da Silva JJRF, Pombeiro AJL (2004) Peroxidative oxidation of benzene and mesitylene by vanadium catalysts. J Mol Catal A Chem 224:189-195
50. Reis PM, Silva JAL, Palavra AF, da Silva JJRF, Kitamura T, Fujiwara Y, Pombeiro AJL (2003) Single-pot conversion of methane into acetic acid in the absence of CO and with vanadium catalysts such as amavadine. Angew Chem Int Engl 42:821-823
51. Kirillova MV, Kuznetsov ML, Reis PM, da Silva JAL, da Silva JJRF, Pombeiro AJL (2007) Direct and remarkably efficient conversion of methane into acetic acid catalyzed by amavadine and related vanadium complexes. A synthetic and a theoretical DFT mechanistic study. J Am Chem Soc 129:10531-10545
52. Kirillova MV, Kuznetsov ML, da Silva JAL, da Silva MFC, da Silva JJRF, Pombeiro AJL (2008) Amavadin and other vanadium complexes as remarkably efficient catalysts for one-pot conversion of ethane to propionic and acetic acids. Chem Eur J 14:1828-1842
53. Kirillova MV, da Silva JAL, da Silva JJRF, Palavra AF, Pombeiro AJL (2007) Highly efficient direct carboxylation of propane into butyric acids catalyzed by vanadium complexes. Adv Synth Catal 349:1765-1774
54. Reis PM, Silva JAL, Palavra AF, da Silva JJRF, Pombeiro AJL (2005) Vanadium-catalyzed carboxylation of linear and cyclic C-5 and C-6 alkanes. J Catal 235:333-340
55. Pombeiro AJL, Kirillova MV, Kirillov AM, Silva JAL, Fraústo da Silva JJR method for the conversion, under mild conditions and in aqueous medium, of gaseous and liquid alkanes into carboxylic acids. WO/2008/088234-A1. July 24, 2008
56. Kirillova MV, Kirillov AM, Kuznetsov ML, Silva JAL, da Silva JJRF, Pombeiro AJL (2009) Alkanes to carboxylic acids in aqueous medium: metal-free and metal-promoted highly efficient and mild conversions. Chem Commun 2009:2353-2355
57. Kirillova MV, Kirillov AM, Pombeiro AJL (2009) Metal-free and copper-promoted single-pot hydrocarboxylation of cycloalkanes to carboxylic acids in aqueous medium. Adv Synth Catal 351:2936-2948
58. Kirillova MV, Kirillov AM, Pombeiro AJL (2010) Mild, single-pot hydrocarboxylation of gaseous alkanes to carboxylic acids in metal-free and copper-promoted aqueous systems. Chem Eur J 16:9485-9493
59. Hubregtse T (2007) Structural investigations of amavadin-based vanadium complexes. D Phil thesis, Technical University of Delft, The Netherlands
60. Carrondo MAAFD, Duarte MTLS, Silva JAL, Fraústo daSilva JJRF (1992) An X-ray study of the complex anion bis(N-hydroxy-iminodiacetate) vanadate(IV)-a model for vanadium containing biological compound. Struct Chem 3:113-119
61. Fraústo da Silva JJR, Williams RJP (2001) The biological chemistry of the elements-the inorganic chemistry of life, 2nd edn. Clarendon, Oxford
62. Crans DC, Smee JJ, Gaidamauskas E, Yang L (2004) The chemistry and biochemistry of vanadium and the biological activities exerted by vanadium compounds. Chem Rev 104: 8499-902
63. Durner J, Klessig DF (1995) Inhibition of ascorbate peroxidase by salicylic-acid and 2,6-dichloroisonicotinic acid, 2 inducers of plant defense responses. Proc Natl Acad Sci USA 92:11312-11316
64. Cotton FA, Wilkinson G (1966) Advanced inorganic chemistry-a comprehensive text, 2nd edn. Interscience, New York
65. Borovicka J, Randa Z (2007) Distribution of iron, cobalt, zinc and selenium in macrofungi. Mycol Prog 6:249-259
66. Williams RJP, Fraústo da Silva JJR (1996) The natural selection of the chemical elements. Oxford University Press, Oxford
67. Almeida M, Humanes M, Melo R, Silva JA, da Silva JJRF, Vilter H, Wever R (1998) Saccorhiza polyschides (phaeophyceae; phyllariaceae) a new source for vanadium-dependent haloperoxidases. Phytochemistry 48:229-239
68. Strack D, Vogt T, Schliemann W (2003) Recent advances in betalain research. Phytochemistry 62:247-269
69. Molina R, Trappe JM (1982) Patterns of ectomycorrhizal host specificity and potential among pacific northwest conifers and fungi. For Sci 28:423-458
70. Bertrand D (1950) The biochemistry of vanadium. Am Mus Nat Hist Bull 94:403-456
71. Watkinson JH (1964) Selenium-accumulating plant of humid regions-Amanita muscaria. Nature 202:1239-1240
72. Meisch H-U, Schmitt JA, Reinle W (1978) Heavy-metals in higher fungi. 3. vanadium and molybdenum. Z Naturforsch 33c:1-6
73. Stijve T (1977) Selenium content of mushrooms. Z Lebensm Unters Forsch 164:201-203
74. Drehmel D, Moncalvo JM, Vilgalys R (1999) Molecular phylogeny of Amanita based on large-subunit ribosomal DNA sequences: implications for taxonomy and character evolution. Mycologia 91:610-618