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Biosynthesis of the glucobrassicin aglycone from14C and15N labelled L-tryptophan precursors

Biosyntéza aglykonu glukobrasicinu z14C a15značných L-tryptofanových prekursorů

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Biologia Plantarum

Abstract

The formation of the isothiocyanate group of the aglycone of glucobrassicin (Glubr) an indole glucosinolate present in relatively large quantities in plants of the familyBrassicaceae, was studied. Labelled Glubr was synthesized from L-tryptophan-3-14C-amino15N in winter rape hypocotyl segments. After extraction it was finally isolated in a crystalline state by mixed crystallization with added inactive Glubr tetramethylammonium salt. The specific activity of14C and the atoms % excess15N were determined in both the precursor and the product. The ratio14C/15N as well as the values of dilution of14C and15N were in agreement in the precursor and in the final product. This shows,inter alie, that during the biosynthesis of Glubr, L-tryptophan is not deaminated. Thus the presumed isothiocyanate group of Glubr is synthesized on the α-carbon of the L-tryptophan alanine chain, the α-carbon together with the attached nitrogen pass directly from the precursor into the Glubr aglycone. This represents a type of glucosinolate aglycone biosynthesis where the carbon chain of the initial amino acid is not elongated. This finding is supported by the fact that L-tryptophan-l-14C does not yield labelled Glubr the C1 carbon being decarboxylated during Glubr synthesis.

Abstract

Byla studována tvorba isothiokyanátové skupiny předpokládaného aglykonu glukobrasicinu (Glubr), indolového glukosinalátu přítomného v relativné vyšších mnozstvích v rostlinách čeledi Brassicaceae.

Hypokotylární segmenty řepky syntetizovaly z L-tryptofanu-3-14C-amino15N isotopicky znaceny Glubr, který byl extrahován a konečnč isolován v krystaliekém stavu směsnou krystalizací s přidaným neaktivním Glubr ve formě tetramethylammoniové sole. U prekursoru a u produktu byly stanoveny s'pecifická aktivita14C a % obohacení15N. Jak poměry14C/15N, tak i hodnoty zředční14C a15N u prekursoru a u výsledného produktu si navzájem odpovídaly, což svědčí mj. o torn, že během biosyntézy Glubr z L-tryptofanu nedoohází k desaminaci aminokyseliny. Potenciální isothiokyanátová skupina Glubr se tak vytváří na α-uhlíku alaninového řetézce L-tryptofanu, α-uhlík včetně navázaného dusíku přeoházejí do aglykonu Glubr pří mo z prekursoru. Jde o typ biosyntézy aglykonu glukosinolátu v némž nedoohází k prodluzování uhlíkového řetězce výchozí aminokysoliny, Uvedený závěr dokládá zjištění, že L-tryptofan-l-14C neposkytuje značený Glubr, C1 uhlík je během syntézy Glubr dekarboxylován.

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  1. Institute of Experimental Botany, Czechoslovak Academy of Sciences, Ke dvoru 15, Praha, Praha 6 - Vokovice, Czechoslovakia

    M. Kutáček & Marie Králová

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  1. M. Kutáček
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Kutáček, M., Králová, M. Biosynthesis of the glucobrassicin aglycone from14C and15N labelled L-tryptophan precursors. Biol Plant 14, 279–285 (1972). https://doi.org/10.1007/BF02935853

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