Biomimetic Oxidation of Piperine and Piplartine Catalyzed by Iron(III) and Manganese(III) Porphyrins

Synthetic metalloporphyrins, in the presence of monooxygen donors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation of drugs and natural products. The oxidation of piperine and piplartine by iodosylbenzene using iron(III) and manganese(III) porphyrins yield...

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Published inBiological & Pharmaceutical Bulletin Vol. 33; no. 5; pp. 912 - 916
Main Authors Schaab, Estela Hanauer, Crotti, Antonio Eduardo Miller, Iamamoto, Yassuko, Kato, Massuo Jorge, Lotufo, Letícia Veras Costa, Lopes, Norberto Peporine
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 2010
Pharmaceutical Society of Japan
Japan Science and Technology Agency
Subjects
Alkaloids - metabolism
Benzodioxoles - metabolism
Biological Products
biomimetic oxidation
Biomimetics
Catalysis
Cytochrome P-450 Enzyme System - chemistry
Ferric Compounds - chemistry
Inactivation, Metabolic
Iodobenzenes - metabolism
Iron - chemistry
Manganese - chemistry
mass spectrometry
metalloporphyrin
Oxidation-Reduction
Piperidines - metabolism
Piperidones - metabolism
piperine
piplartine
Polyunsaturated Alkamides - metabolism
Porphyrins - chemical synthesis
Porphyrins - chemistry
Singlet Oxygen
Spectrometry, Mass, Electrospray Ionization
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Abstract Synthetic metalloporphyrins, in the presence of monooxygen donors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation of drugs and natural products. The oxidation of piperine and piplartine by iodosylbenzene using iron(III) and manganese(III) porphyrins yielded mono- and dihydroxylated products, respectively. Piplartine showed to be a more reactive substrate towards the catalysts tested. The structures of the oxidation products were proposed based on electrospray ionization tandem mass spectrometry.
AbstractList Synthetic metalloporphyrins, in the presence of monooxygen donors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation of drugs and natural products. The oxidation of piperine and piplartine by iodosylbenzene using iron(III) and manganese(III) porphyrins yielded mono- and dihydroxylated products, respectively. Piplartine showed to be a more reactive substrate towards the catalysts tested. The structures of the oxidation products were proposed based on electrospray ionization tandem mass spectrometry.
Synthetic metalloporphyrins, in the presence of monooxygen denors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation of drugs and natural products. The oxidation of piperine and piplartine by iodosylbenzene using iron(III) and manganese(III) porphyrins yielded mono- and dihydroxylated products, respectively. Piplartine showed to be a more reactive substrate towards the catalysts tested. The structures of the oxidation products were proposed based on electrospray ionization tandem mass spectrometry. Piperine and piplartine (Fig. 1) are naturally ocourring amides from Piper species (Piperaceae), which have been used in folk medicine of tropical and subtropical countries for treatment of asma, bronchitis, fever, hemorrhoidal afflictions, gastrointestinal diseases, rheumatism, and as food additive. 1-3) The amide piperine is the pungent principle of black pepper (P.nigrum) and can be extracted from dried fruits with a yield of 3-7%. 4) Several biological activities have been associated to piperine, including inhibition of liver metabolism, antioxidant, central nervous system depressant and antitumoral activities. 4-9)
Author Kato, Massuo Jorge
Lotufo, Letícia Veras Costa
Schaab, Estela Hanauer
Iamamoto, Yassuko
Lopes, Norberto Peporine
Crotti, Antonio Eduardo Miller
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Cites_doi 10.1002/(SICI)1099-1409(200006/07)4:4<350::AID-JPP249>3.0.CO;2-G
10.1111/j.1582-4934.2002.tb00186.x
10.1016/S0031-9422(97)00328-2
10.1016/0031-9422(90)85215-2
10.1016/0031-9422(81)85125-4
10.1007/s00216-007-1794-x
10.1016/1381-1169(94)00063-8
10.1055/s-2005-864155
10.1016/j.mrgentox.2009.04.007
10.1023/A:1020599814238
10.1016/j.molcata.2004.09.015
10.1111/j.1432-1033.1989.tb15017.x
10.1016/S0031-9422(00)00226-0
10.1016/j.tetlet.2005.07.012
10.1021/ja00498a040
10.1016/j.ejps.2005.04.014
10.1590/S0100-879X2006000600014
10.1023/A:1006877614411
10.1021/ja00272a011
10.1515/znc-2005-7-805
10.1016/j.molcata.2005.06.014
10.1002/jssc.200301511
10.1007/s11101-006-9058-5
10.1039/c39840000279
10.1590/S0100-40422008000400011
10.1016/j.molcata.2008.09.008
10.1016/j.bmc.2007.12.049
10.1016/j.crci.2006.11.001
10.1016/j.pupt.2005.04.002
10.1002/jat.1261
10.15227/orgsyn.043.0062
10.1016/j.phymed.2006.12.015
10.1016/j.cccn.2004.07.004
10.1016/j.ejphar.2007.07.056
10.1002/adsc.200303191
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References 31) Robaugh D. A., Stein S. E., J. Am. Chem. Soc., 108, 3224—3229 (1986).
11) Tsai I. L., Lee F. P., Wu C. C., Duh C. Y., Ishikawa T., Chen J. J., Chen Y. C., Seki H., Chen I. S., Planta Med., 71, 535—542 (2005).
15) Bezerra D. P., Vasconcellos M. C., Machado M. S., Villela I. V., Rosa R. M., Moura D. J., Pessoa C., Moraes M. O., Silveira E. R., Lima M. A., Aquino N. C., Henriques J. A., Saffi J., Costa-Lotufo L. V., Mutat. Res., 677, 8—13 (2009).
19) Zuber R., Anzenbacherová E., Anzenbacher P., J. Cell. Mol. Med., 6, 189—198 (2002).
25) Braz-Filho R., Souza M. P., Mattos M. E. O., Phytochemistry, 20, 345—346 (1981).
26) Sharefkin J. G., Saltzmann H., Org. Synth., 43, 62 (1963).
28) Silva Jr. L. F., Lopes N. P., Tetrahedron Lett., 46, 6023—6027 (2005).
7) Selvendiran K., Banu M., Sakthisekaran D., Clin. Chim. Acta, 350, 73—78 (2004).
29) Lohmann W., Karst U., Anal. Bioanal. Chem., 391, 79—96 (2008).
2) Kumar S., Singhal V., Roshnan R., Sharma A., Rembhotkar G. W., Ghosh B., Eur. J. Pharmacol., 575, 177—186 (2007).
20) Melo A. J. B., Iamamoto Y., Maestrin A. P. J., Smith J. R. L., Santos M. D., Lopes N. P., Bonato P. S., J. Mol. Catal. A: Chem., 226, 23—31 (2005).
33) Assis M. D., Melo A. J. B., Serra O. A., Iamamoto Y., J. Mol. Catal. A: Chem., 97, 41—47 (1995).
10) Felipe F. C. B., Filho J. T. S., Souza L. E. O., Silveira J. A., Uchoa D. E. A., Silveira E. R., Pessoa O. D. L., Viana G. S. B., Phytomedicine, 14, 605—612 (2007).
35) Groves J. T., Nemo T. E., Myers R. S., J. Am. Chem. Soc., 101, 1032— 1033 (1979).
5) Ferreira W. S., Lima M. E. F., Saraiva V. B., Alisson-Silva F., Mendonça-Previato L., Previato J. O., Echevarria A., Lima M. E. F., Bioorg. Med. Chem., 16, 2984—2991 (2008).
1) Scott I. M., Jensen H. R., Philogene B. J. R., Arnason J. T., Phytochem. Rev., 7, 65—75 (2008).
9) Bezerra D. P., Pessoa C., Moraes M. O., Silveira E. R., Lima M. A. S., Elmiro F. J. M., Lotufo L. V. C., Z. Naturforsch. [C], 60, 539—543 (2005).
18) Bernardou J., Meunier B., Top. Catal., 21, 47—54 (2002).
6) Selvendiran K., Singh J. P. V., Sakthisekaran D., Pulm. Pharmacol. Ther., 19, 107—111 (2006).
21) Mansuy D., Battioni P., Battioni J. P., Eur. J. Biochem., 184, 267—285 (1989).
14) Bezerra D. P., Castro F. O., Alves A. P. N. N., Pessoa C., Moraes M. O., Silveira E. R., Lima M. A. S., Elmiro F. J. M., Alencar N. M. N., Mesquita R. O., Lima M. W., Costa-Lotufo L. V., J. Appl. Toxicol., 28, 156—163 (2008).
8) Khajuria A., Thusu N., Zutshi U., Bedi K. L., Mol. Cell. Biochem., 189, 113—118 (1998).
4) Parmar V. S., Jain S. C., Bisht K. S., Jain R., Taneja P., Jha A., Tyagi O. D., Prasad A. K., Wengel J., Olsen C. E., Boll P. M., Phytochemistry, 46, 597—673 (1997).
24) Atal C. K., Dhar K. L., Singh J., Lloydia, 38, 256—264 (1975).
17) Bernardou J., Meunier B., Adv. Synth. Catal., 346, 171—184 (2004).
16) Mansuy D., Comptes Rendus Chimie, 10, 392—413 (2007).
32) Santos M. D., Martins P. R., Santos P. A., Bortocan R., Iamamoto Y., Lopes N. P., Eur. J. Pharm. Sci., 26, 62—70 (2005).
36) Bajad S., Khajuria R. K., Suri O. P., Bedi K. L., J. Sep. Sci., 26, 943— 946 (2003).
22) Santos M. D., Lopes N. P., Iamamoto Y., Quím. Nova, 31, 767—770 (2008).
27) Vinhado F. S., Gandini M. E. F., Iamamoto Y., Silva A. M. G., Simões M. M. Q., Neves M. G. P. M. S., Tomé A. C., Pereira A. M. V. M., Vol. 33, No. 5 Cavaleiro J. A. S., J. Mol. Cat. A: Chem., 239, 138—143 (2005).
13) Navickiene H. M. D., Alecio A. C., Kato M. J., Bolzani V. D., Young M. C., Cavalheiro A. J., Furlan M., Phytochemistry, 55, 621—626 (2000).
30) Groves J. T., J. Porphyr. Phtalocyan., 4, 350—352 (2000).
3) Bezerra D. P., Castro F. O., Alves A. P. N. N., Pessoa C., Moraes M. O., Silveira E. R., Lima M. A. S., Elmiro F. J. M., Lotufo L. V. C., Braz. J. Med. Biol. Res., 39, 801—807 (2006).
12) Duh C. Y., Wu Y. C., Wang S. K., Phytochemistry, 29, 2689—2691 (1990).
34) Traylor P. S., Dolphin D., Traylor T. G., J. Chem. Soc. Chem. Commun., 5, 279—280 (1984).
23) Mac Lead T. C. O., Faria A. L., Barros V. P., Queiroz M. E. C., Assis M. D., J. Mol. Catal. A: Chem., 296, 54—60 (2008).
22
23
24
Kumar S., Singhal V., Roshnan R., S (2) 2007; 575
25
Ferreira W. S., Lima M. E. F., Sara (5) 2008; 16
27
28
29
BEZERRA DANIEL P. (15) 2009; 677
Selvendiran K., Banu M., Sakthiseka (7) 2004; 350
30
31
10
32
11
33
12
34
Selvendiran K., Singh J. P. V., Sak (6) 2006; 19
13
35
14
36
16
17
19
Bernardou J., Meunier B. (18) 2002; 21
1
3
Sharefkin J. G., Saltzmann H. (26) 1963; 43
4
8
9
20
21
References_xml – ident: 30
  doi: 10.1002/(SICI)1099-1409(200006/07)4:4<350::AID-JPP249>3.0.CO;2-G
– ident: 19
  doi: 10.1111/j.1582-4934.2002.tb00186.x
– ident: 4
  doi: 10.1016/S0031-9422(97)00328-2
– ident: 12
  doi: 10.1016/0031-9422(90)85215-2
– ident: 25
  doi: 10.1016/0031-9422(81)85125-4
– ident: 29
  doi: 10.1007/s00216-007-1794-x
– ident: 33
  doi: 10.1016/1381-1169(94)00063-8
– ident: 11
  doi: 10.1055/s-2005-864155
– volume: 677
  start-page: 8
  issn: 0027-5107
  issue: 1-2
  year: 2009
  ident: 15
  publication-title: Mutat. Res.
  doi: 10.1016/j.mrgentox.2009.04.007
  contributor:
    fullname: BEZERRA DANIEL P.
– volume: 21
  start-page: 47
  issn: 1022-5528
  year: 2002
  ident: 18
  publication-title: Top. Catal.
  doi: 10.1023/A:1020599814238
  contributor:
    fullname: Bernardou J., Meunier B.
– ident: 20
  doi: 10.1016/j.molcata.2004.09.015
– ident: 21
  doi: 10.1111/j.1432-1033.1989.tb15017.x
– ident: 13
  doi: 10.1016/S0031-9422(00)00226-0
– ident: 24
– ident: 28
  doi: 10.1016/j.tetlet.2005.07.012
– ident: 35
  doi: 10.1021/ja00498a040
– ident: 32
  doi: 10.1016/j.ejps.2005.04.014
– ident: 3
  doi: 10.1590/S0100-879X2006000600014
– ident: 8
  doi: 10.1023/A:1006877614411
– ident: 31
  doi: 10.1021/ja00272a011
– ident: 9
  doi: 10.1515/znc-2005-7-805
– ident: 27
  doi: 10.1016/j.molcata.2005.06.014
– ident: 36
  doi: 10.1002/jssc.200301511
– ident: 1
  doi: 10.1007/s11101-006-9058-5
– ident: 34
  doi: 10.1039/c39840000279
– ident: 22
  doi: 10.1590/S0100-40422008000400011
– ident: 23
  doi: 10.1016/j.molcata.2008.09.008
– volume: 16
  start-page: 2984
  issn: 0968-0896
  year: 2008
  ident: 5
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/j.bmc.2007.12.049
  contributor:
    fullname: Ferreira W. S., Lima M. E. F., Sara
– ident: 16
  doi: 10.1016/j.crci.2006.11.001
– volume: 19
  start-page: 107
  issn: 1094-5539
  year: 2006
  ident: 6
  publication-title: Pulm. Pharmacol. Ther.
  doi: 10.1016/j.pupt.2005.04.002
  contributor:
    fullname: Selvendiran K., Singh J. P. V., Sak
– ident: 14
  doi: 10.1002/jat.1261
– volume: 43
  start-page: 62
  issn: 0078-6209
  year: 1963
  ident: 26
  publication-title: Org. Synth.
  doi: 10.15227/orgsyn.043.0062
  contributor:
    fullname: Sharefkin J. G., Saltzmann H.
– ident: 10
  doi: 10.1016/j.phymed.2006.12.015
– volume: 350
  start-page: 73
  issn: 0009-8981
  year: 2004
  ident: 7
  publication-title: Clin. Chim. Acta
  doi: 10.1016/j.cccn.2004.07.004
  contributor:
    fullname: Selvendiran K., Banu M., Sakthiseka
– volume: 575
  start-page: 177
  issn: 0014-2999
  year: 2007
  ident: 2
  publication-title: Eur. J. Pharmacol.
  doi: 10.1016/j.ejphar.2007.07.056
  contributor:
    fullname: Kumar S., Singhal V., Roshnan R., S
– ident: 17
  doi: 10.1002/adsc.200303191
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Snippet Synthetic metalloporphyrins, in the presence of monooxygen donors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation...
Synthetic metalloporphyrins, in the presence of monooxygen denors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation...
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SubjectTerms Alkaloids - metabolism
Benzodioxoles - metabolism
Biological Products
biomimetic oxidation
Biomimetics
Catalysis
Cytochrome P-450 Enzyme System - chemistry
Ferric Compounds - chemistry
Inactivation, Metabolic
Iodobenzenes - metabolism
Iron - chemistry
Manganese - chemistry
mass spectrometry
metalloporphyrin
Oxidation-Reduction
Piperidines - metabolism
Piperidones - metabolism
piperine
piplartine
Polyunsaturated Alkamides - metabolism
Porphyrins - chemical synthesis
Porphyrins - chemistry
Singlet Oxygen
Spectrometry, Mass, Electrospray Ionization
Title Biomimetic Oxidation of Piperine and Piplartine Catalyzed by Iron(III) and Manganese(III) Porphyrins
URI https://www.jstage.jst.go.jp/article/bpb/33/5/33_5_912/_article/-char/en
http://mol.medicalonline.jp/en/journal/download?GoodsID=cs7biolo/2010/003305/031&name=0912-0916e
https://www.ncbi.nlm.nih.gov/pubmed/20460777
https://www.proquest.com/docview/1449377842
Volume 33
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ispartofPNX Biological and Pharmaceutical Bulletin, 2010/05/01, Vol.33(5), pp.912-916
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