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. 1972 Jul;50(1):43–50. doi: 10.1104/pp.50.1.43

An Intermediate in the Synthesis of Glucobrassicins from 3-Indoleacetaldoxime by Woad Leaves 1

S Mahadevan a,2, Bruce B Stowe a
PMCID: PMC367313  PMID: 16658130

Abstract

Leaves of woad (Isatis tinctoria L.) were found to incorporate efficiently tritiated indoleacetaldoxime and 35S from 35S-l-cystine into glucobrassicin and sulfoglucobrassicin. Time course of incorporation of 35S from 35S-cystine into the glucosinolates indicated that glucobrassicin was formed first and then sulfoglucobrassicin. Simultaneous administration of tritiated indoleacetaldoxime and 35S-cystine gave doubly labeled glucobrassicin and sulfoglucobrassicin. About twice as much 35S was present in sulfoglucobrassicin as compared to glucobrassicin per unit of 3H incorporated, indicating that a second, probably oxidized, atom of 35S was later introduced into sulfoglucobrassicin. However, the 35S incorporated from cystine into both glucosinolates during the first 8 hours of metabolism was almost exclusively in the divalent sulfur moiety. The incorporation patterns of 35S and titritated indoleacetaldoxime into the glucosinolates suggested a fast turnover of glucobrassicin in the metabolizing leaves.

A new indolic, sulfur-containing neutral compound X was found to accumulate in woad leaves when administered 3H-3-indoleacetaldoxime and cold cystine or 35S-cystine and cold 3-indoleacetaldoxime. This accumulation was enhanced about 2- to 2.5-fold by the simultaneous administration of postassium selenate, an inhibitor of biological sulfation processes. Selenate also appeared to inhibit the conversion of glucobrassicin to 1-sulfoglucobrassicin. Partially purified compound X was efficiently converted (56-60%) to glucobrassicin and 1-sulfoglucobrassicin on readministration to woad leaves, indicating it to be a precursor of the glucosinolates. Compound X, on treatment with myrosinase, slowly yielded a less polar, indolic, sulfur containing compound Y and glucose. Compound Y decomposed with time into indoleacetonitrile suggesting that it may be indoleacetothiohydroximate. Compound X has been tentatively assigned the structure of desthioglucobrassicin, the nonsulfated form of glucobrassicin.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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