VZL 2010, 79(3):114-118

Beta-Amino Acids and Their Natural Biologically Active Derivatives. III. Derivatives of Beta-Phenylalanine and Beta-Tyrosine

Jiří Patočka ORCID...
Jihočeská univerzita v Českých Budějovicích, Zdravotně sociální fakulta, katedra radiologie a toxikologie, České Budějovice
Vysoká škola aplikovaných ekonomických studií, s. r. o., Praha

Na rozdíl od proteinogenních α-aminokyselin, které jsou součástí všech proteinů a enzymů kontrolujících metabolismus živé materie, β-aminokyseliny jsou méně hojné než jejich α-isomery. Většinou je nacházíme jako součást různých přírodních produktů, jako jsou peptidy, cyklopeptidy, depsipeptidy, glykopeptidy, alkaloidy či terpenoidy. Zejména bakterie, cyanobakterie, houby a rostliny často inkorporují β-aminokyseliny do svých sekundárních metabolitů. Ty pak slouží jako obranné nástroje jejich přežití v konkurenci s jinými organismy. Tyto látky proto často charakterizuje výrazná biologická aktivita, která je často založena právě na přítomnosti β-aminokyselin.
Nejvýznamnějšími β-aminokyselinami jsou β-alanin, β-leucin, β-lysin, β-arginin, β-glutamát, β-fenylalanin a β-tyrosin. Předmětem zájmu tohoto článku jsou deriváty β-fenylalaninu a β-tyrosinu.

Keywords: β-aminokyseliny; β-fenylalanin; β-tyrosin; Taxany; Pyloricidiny; Cyclochlorotin; Makrocyklické sperminové alkaloidy

Unlike proteinogenic α-amino acids that are constituents of all proteins and enzymes, which control the metabolism in living matter, β-amino acids are less abundant than their α-isomers. Mostly they occur as constituents of distinct natural products, such as peptides, cyclopeptides, depsipeptides, glycopeptides, alkaloids or terpenoids. Especially, bacteria, cyanobacteria, fungi, and plants often incorporate β-amino acids into their secondary metabolites. These serve as tools to secure their survival in competition with other organisms. Therefore, these compounds are often characterized by potent biological activities which are often based on their β-amino acid substructures.The most important β-amino acids are β-alanine, β-leucine, β-lysine, β-arginine, β-glutamate, β-phenylalanine and β-tyrosine. Natural derivatives of β-phenylalanine and β-tyrosine are the aim of this article.

Keywords: β-Amino acids; β-Phenylalanine; β-Tyrosine; Taxanes; Pyloricdines; Cyclochlorotin; Macrocyclic spermine alkaloid

Received: September 30, 2009; Published: September 1, 2010  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Patočka, J. (2010). Beta-Amino Acids and Their Natural Biologically Active Derivatives. III. Derivatives of Beta-Phenylalanine and Beta-Tyrosine. Vojenské Zdravotnické Listy, 79(3), 114-118
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. AHMAD, VU. - SULTANA, V. Spermine alkaloids from Schweinfurthia papilionacea. J. Nat. Prod., 1990, vol. 53, no. 5, p. 1162-1167. Go to original source... Go to PubMed...
    2. ANDEREGG, RJ. - BIEMANN, K. - MANMADE, A., et al. Mass spectrometric peptide sequencing: cyclochlorotine. Biomed. Mass Spectrom., 1979, vol. 6, no. 3, p. 129-134. Go to original source... Go to PubMed...
    3. BIENZ, S. - BISEGGER, P. - GUGGISBERG, A., et al. Polyamine alkaloids. Nat. Prod. Rep., 2005, vol. 22, p. 647-658. Go to original source... Go to PubMed...
    4. CAMPO, SM. - ZULLO, A. - HASSAN, C., et al. Antibiotic treatment strategies for Helicobacter pylori infection. Recent Pat. Antiinfect. Drug Discov., 2007, vol. 2, no. 1, p. 11-17. Go to original source... Go to PubMed...
    5. DRANDAROV, K. Verballoscenine, the Z isomer of verbascenine from Verbascum phoeniceum. Phytochemistry, 1997, vol. 44, no. 5, p. 971-973. Go to original source...
    6. FREITAS, VM. - RANGEL, M. - BISSON, LF., et al. The geodiamolide H, derived from Brazilian sponge Geodia corticostylifera, regulates actin cytoskeleton, migration and invasion of breast cancer cells cultured in three-dimensional environment. J. Cell. Physiol., 2008, vol. 216, no. 3, p. 583-594. Go to original source... Go to PubMed...
    7. GALA, F. - D'URIA, CD. - DE MARINO, S., et al. Jaspamides M-P: new tryptophyn modified jaspamide derivatives from sponge Jaspis splendans. Tetrahedron, 2009, vol. 65, no. 1, p. 51-56. Go to original source...
    8. GHOSH, AC. - MANMADE, A. - TOWNSEND, JM., et al. Production of cyclochlorotine and a new metabolite, simatoxin, by Penicillium islandicum Sopp. Appl. Environ. Microbiol., 1978, vol. 35, no. 6, p. 1074-1078. Go to original source... Go to PubMed...
    9. HOLZINGER, A. Jasplakinolide. An actin-specific reagent that promotes actin polymerization. Methods Mol. Biol., 2001, vol. 161. p. 109-120. Go to original source... Go to PubMed...
    10. HUIZING, MT. - MISSER, VH. - PIETERS, RC., et al Taxanes: a new class of antitumor agents. Cancer Invest., 1995, vol. 13, no. 4, p. 381-404. Go to original source... Go to PubMed...
    11. CHMARA, H. - BOROWSKI, E. Antibiotic edeine. I. Isolation of induced high activity mutant of Bacillus brevis Vm4. Acta Microbiol. Pol., 1966, vol. 15, no. 3, p. 223-234. Go to PubMed...
    12. KRUG, D. - MÜLLER, R. Discovery of additional members of the tyrosine aminomutase enzyme family and the mutational analysis of CmdF. Chembiochem., 2009, vol. 10, no. 4, p. 741-750. Go to original source... Go to PubMed...
    13. KUNZE, B. - JANSEN, R. - SASSE, F., et al. Chondramides A-D, new antifungal and cytostatic depsipeptides from Chondromyces crocatus (myxobacteria). Production, physico-chemical and biological properties. J. Antibiot. (Tokyo), 1995, vol. 48, no. 11, p. 1262-1266. Go to original source... Go to PubMed...
    14. NAGANO, Y. - IKEDO, K. - FUJISHIMA, A., et al. Pyloricidins, novel anti-Helicobacter pylori antibiotics produced by bacillus sp. II. Isolation and structure elucidation. J. Antibiot. (Tokyo), 2001, vol. 54, no. 11, p. 934-947. Go to original source... Go to PubMed...
    15. NEZBEDOVÁ, L. - HESSE, M. - DRANDAROV, K., et al. Phenol oxidative coupling in the biogenesis of the macrocyclic spermine alkaloids aphelandrine and orantine in Aphelandra sp. Planta, 2001, vol. 213, no. 3, p. 411-417. Go to original source... Go to PubMed...
    16. PAPAZOGLOU, G. - SIERRA. J. - HOMBERGER, K., et al. Biosynthesis of the Spermine Alkaloid Aphelandrine. Helv. Chim. Acta, 1991, vol. 74, no. 3, p. 565-571. Go to original source...
    17. PATOČKA, J. Hemiasterlin - tripeptid s antimitotickou aktivitou. Toxicology [online]. 8. 12. 2007 [cit. 2009-7-30]. Dostupné z: http://www.toxicology.cz/modules.php?name=News&file=article&sid=145
    18. PATOČKA, J. - KUEHN GD. Natural polyamines and their biological cinsequence in mammals. Acta Medica (Hradec Kralove), 2000, vol. 43, no. 4, p. 119-124. Go to original source...
    19. PATOČKA, J. - STRUNECKÁ, A. The most important microtubule natural inhibitors. Acta Medica (Hradec Kralove), 1999, vol. 4, no. 1, p. 3-8. Go to original source...
    20. PATOČKA, J. VacA toxin a vředová choroba žaludku. Toxicology [online]. 28. 7. 2009 [cit. 2009-7-30]. Dostupné z: http://www.toxicology.cz/modules.php?name=News&file=article&sid=245
    21. PIOLETTI, M. - SCHLÜNZEN, F. - HARMS, J., et al. Crystal structures of complexes of the small ribosomal subunit with tetracycline, edeine and IF3. EMBO J., 2001, vol. 20, no. 8, p.1829-1839. Go to original source... Go to PubMed...
    22. RACHID, S. - KRUG, D. - WEISSMAN, KJ., et al. Biosynthesis of (R)-beta-tyrosine and its incorporation into the highly cytotoxic chondramides produced by Chondromyces crocatus. J. Biol. Chem., 2007, vol. 282, no. 30, p. 21810-21817. Go to original source... Go to PubMed...
    23. RANGEL, M. - PRADO, MP. - KONNO, K., et al. Cytoskeleton alterations induced by Geodia corticostylifera depsipeptides in breast cancer cells. Peptides, 2006, vol. 27, no. 9, p. 2047-2057. Go to original source... Go to PubMed...
    24. SAMOYLENKO, V. - JACOB, MR. - KHAN, SI., et al. Antimicrobial, antiparasitic and cytotoxic spermine alkaloids from Albizia schimperiana. Nat. Prod. Commun., 2009, vol. 4, no. 6, p. 791-796. Go to original source... Go to PubMed...
    25. SASSE, F. - KUNZE, B. - GRONEWOLD, TM., et al. The chondramides: cytostatic agents from myxobacteria acting on the actin cytoskeleton. J. Natl. Cancer Inst., 1998, vol. 90, no. 20, p. 1559-1563. Go to original source... Go to PubMed...
    26. SEIFERT, K. - JOHNE, S. - HESSE, M. Verbascenin, ein macrocyclisches Spermin-Alkaloid aus verbascum 184. Mitteilung über organische Naturstoffe. Helv. Chim. Acta, 1982, vol. 65, no. 8, p. 2540-2547. Go to original source...
    27. SPITELLER, P. - NUSSBAUM, F., von. β-Amino acids in natural products. In JUARISTI, E. - SOLOSHONOK, VA. (Eds.). Enatioselective Synthesis of β-Amino Acids. 2nd Ed. John Wiley and Sons, 2005. 634 p. Go to original source...
    28. STEELE, CL. - CHEN, Y. - DOUGHERTY, BA., et al. Purification, cloning, and functional expression of phenylalanine aminomutase: the first committed step in Taxol side-chain biosynthesis. Arch. Biochem. Biophys., 2005, vol. 438, no. 1, p. 1-10. Go to original source... Go to PubMed...
    29. TABUDRAVU, JN. - MORRIS, LA. - MILNE, BF., et al. Conformational studies of free and Li+ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens. Org. Biomol. Chem., 2005, vol. 3, no. 5, p. 745-749. Go to original source... Go to PubMed...
    30. TALPIR, R. - BENAYAHU, Y. - KASHMAN, Y., et al. Hemiasterlin and geodiamolide TA; two new cytotoxic peptides from the marine sponge Hemiasterella minor (Kirkpatrick). Tetrahedron Lett., 1994, vol. 35, no. 25, p. 4453-4456. Go to original source...
    31. TERAO, K. - ITO, E. - TATSUNO, T. Liver injuries induced by cyclochlorotine isolated from Penicillium islandicum. Arch. Toxicol., 1984, vol. 55, no. 1, p. 39-46. Go to original source... Go to PubMed...
    32. UDAGAWA, S. - TATSUNO, T. Safety of rice grains and mycotoxins - a historical review of yellow rice mycotoxicoses. [Article in Japanese]. Yakushigaku Zasshi, 2004, vol. 39, no. 2, p. 321-342.
    33. UENO, Y. - TANAKA, Y. - SATO, K., et al. Similarity of chloropeptide to phalloidin in toxicity to isolated hepatocytes. J. Toxicol. Sci., 1984, vol. 9, no. 2, p. 117-130. Go to original source... Go to PubMed...
    34. WU, B. - SZAMANSKI, W. - WIETZES, P., et al. Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivatives. Chembiochem., 2009, vol. 10, no. 2, p. 338-344. Go to original source... Go to PubMed...
    35. ZHU, J. - HESSE, M. The spermine alkaloids of Chaenorhinum minus. Planta Med., 1988, vol. 54, no. 5, p. 430-433. Go to original source... Go to PubMed...

    Return to the content