真菌中酚类生物合成的研究。烟曲霉I.M.I. 89353将[14C]苔黑酚酸和[14C]苔黑酚转化为烟熏醇。

Studies on the biosynthesis of phenols in fungi. Conversion of [14C]orsellinic acid and [14C]orcinol into fumigatol by Aspergillus fumigatus I.M.I. 89353.

Packter N M

Biochem J. 1966 Feb;98(2):353-9. doi: 10.1042/bj0980353.

Abstract

Sodium [1-(14)C]acetate was incorporated into orsellinic acid and fumigatol by Aspergillus fumigatus. 2. [(14)C]Orsellinic acid was prepared biosynthetically. It was converted almost entirely into fumigatol and fumigatin within 2 days of supplementation of the medium. The apparent decrease in incorporation after a longer period of growth was due to decomposition of radioactive fumigatol and the production of relatively unlabelled material. The addition of orcinol to these cultures decreased the conversion of [(14)C]orsellinic acid into fumigatol. [(14)C]Orsellinic acid was incorporated into 3,4-dihydroxytoluquinol in both sets of cultures. 3. [(14)C]Orcinol was prepared from [(14)C]orsellinic acid after acid hydrolysis. It was also very effective as a precursor of fumigatol (60% incorporation). 4. The specific activity of fumigatin was lower than that of fumigatol at early stages of growth (4-5 days after inoculation) with all the labelled substrates that were tested. This indicated that fumigatin arose from fumigatol after oxidation in the medium. 5. The presence of orcinol in the medium greatly stimulated the incorporation of radioactivity (presumably derived from the (14)CO(2)H of orsellinic acid) into the isoprenoid compounds, ergosterol and ubiquinone, in the mycelium.

摘要

烟曲霉将[1-(14)C]醋酸钠掺入苔色酸和烟曲霉醇中。2. [14)C]苔色酸通过生物合成制备。在培养基补充后2天内，它几乎完全转化为烟曲霉醇和烟曲霉毒素。生长较长时间后掺入量的明显下降是由于放射性烟曲霉醇的分解以及相对未标记物质的产生。向这些培养物中添加苔黑酚降低了[14)C]苔色酸向烟曲霉醇的转化。在两组培养物中，[14)C]苔色酸都掺入到3,4-二羟基甲苯醌中。3. [14)C]苔黑酚是在酸水解后由[14)C]苔色酸制备的。它作为烟曲霉醇的前体也非常有效（掺入率为60%）。4. 在生长早期（接种后4 - 5天），用所有测试的标记底物时，烟曲霉毒素的比活性低于烟曲霉醇。这表明烟曲霉毒素是在培养基中氧化后由烟曲霉醇产生的。5. 培养基中苔黑酚的存在极大地刺激了放射性（可能来自苔色酸的(14)CO(2)H）掺入菌丝体中的类异戊二烯化合物、麦角甾醇和泛醌中。