荨麻青霉S11R59合成大环内酯类抗生素帕特洛内酯：通过¹³C核磁共振光谱法鉴定碳原子来源

Biosynthesis of the macrolide antibiotic patulolides by Penicillium urticae S11R59: identification of the origin of carbon atoms by 13C NMR spectroscopy.

作者信息

Rodphaya D, Nihira T, Sakuda S, Yamada Y

机构信息

Department of Fermentation Technology, Faculty of Engineering, Osaka University, Japan.

出版信息

J Antibiot (Tokyo). 1988 Nov;41(11):1649-58. doi: 10.7164/antibiotics.41.1649.

DOI:10.7164/antibiotics.41.1649

PMID:3198497

Abstract

Patulolides are 12-membered macrolides produced by Penicillium urticae S11R59, and they are the simplest macrolide antibiotics. All carbon signals, including six methylene signals of patulolides A (1), B (2), and C (3), were completely assigned by use of the 13C two-dimensional INADEQUATE. The biosynthesis of patulolides was investigated with 13C labeled acetate. Feeding of [1-13C]acetate to a culture of P. urticae S11R59 gave patulolides A (1), B (2), C (3), each of which showed enrichment at carbons 1, 3, 5, 7, 9, and 11; enrichment at carbons 2, 4, 6, 8, 10, and 12 was observed upon feeding of [2-13C]acetate. These results showed that patulolides A (1), B (2), and C (3) are pure acetogenic hexaketides derived from six acetate units coupled in head-to-tail fashion.

摘要

棒曲霉素是由荨麻青霉S11R59产生的12元大环内酯类化合物，它们是最简单的大环内酯类抗生素。通过使用13C二维INADEQUATE，所有碳信号，包括棒曲霉素A（1）、B（2）和C（3）的六个亚甲基信号，都被完全归属。用13C标记的乙酸盐研究了棒曲霉素的生物合成。将[1-13C]乙酸盐加入到荨麻青霉S11R59的培养物中，得到棒曲霉素A（1）、B（2）、C（3），它们在碳1、3、5、7、9和11处均显示出富集；在加入[2-13C]乙酸盐后，观察到碳2、4、6、8、10和12处有富集。这些结果表明，棒曲霉素A（1）、B（2）和C（3）是由六个乙酸盐单元以头对尾方式偶联而成的纯乙酸源六酮化合物。