STRUCTURE OF BRASSICICOLIN-A - A NOVEL ISOCYANIDE ANTIBIOTIC FROM THE PHYLLOPLANE FUNGUS ALTERNARIA-BRASSICICOLA
STRUCTURE OF BRASSICICOLIN-A - A NOVEL ISOCYANIDE ANTIBIOTIC FROM THE PHYLLOPLANE FUNGUS ALTERNARIA-BRASSICICOLA
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DOI：
10.1021/jo00251a017
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发表时间：
1988-08-05
影响因子：
3.6
通讯作者：
MCCLOSKEY, DV
中科院分区：
文献类型：
--
作者：
GLOER, JB;POCH, GK;MCCLOSKEY, DV
对植物病原性叶斑真菌芸苔链格孢菌（Alternaria brassicicicola（Schweinitz）Wiltshire）（NRRL 1299 = ATCC 6650）在培养物中产生的次级代谢产物的研究导致了芸苔素A（6）的分离，芸苔素A（6）是一种新的异氰化物抗生素，对革兰氏阳性细菌枯草芽孢杆菌和金黄色葡萄球菌具有有效的体外活性。阿曲西可林A是含有两个D-α-甘露醇的完全酰化的D-甘露醇衍生物。羟基异戊酰基单元、两个乙酰基和两个差向异构化的α-异氰基异戊酰基单元。通过对芸苔素A的化学降解研究以及对其脱异氰酸产物的核磁共振和质谱分析，初步确定芸苔素A的结构为6。该报告代表了第一份报告，异氰基异戊酰基作为天然存在的结构单元。
Studies of the secondary metabolites proudced in culture by the plant pathogenic phylloplane fungus Alternaria brassicicola (Schweinitz) Wiltshire (NRRL 1299 = ATCC 6650) have led to the isolation of brassiciolin A (6), a novel isocyanide antibiotic with potent in vitro activity against the gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Brassicicolin A is a fully acylated derivative of D-mannitol containing two D-.alpha.-hydroxyisovaleryl units, two acetyl groups, and two epimerized .alpha.-isocyanoisovaleryl units. The structure of brassicicolin A was assigned as 6 primarily through chemical degradation studies and by NMR and mass spectral analysis of its deisocyanation product. This account represents the first report of the .alpha.-isocyanoisovaleryl group as a naturally occurring structural unit.