Imamura N, Kakinuma K, Ikekawa N, Tanaka H, Omura S
J Antibiot (Tokyo). 1982 May;35(5):602-8. doi: 10.7164/antibiotics.35.602.
Biosynthetic studies of the antibacterial and antitumor antibiotics vineomycins A1 (1) and B2 (2), produced by Streptomyces matensis subsp. vineus, were carried out by labeling experiments with [1-13C]- and [1,2-18C2]sodium acetate followed by 18C NMR spectroscopy. The results show that the benz[a]anthraquinone chromophore of 1 is derived from a decacetate metabolite with decarboxylation at the carboxyl end and that 2 is formed via C-C bond cleavage of 1. Isolation of rabelomycin from the fermentation broth of the same strain suggests a close biosynthetic relationship among the simple benz[a]anthraquinone antibiotics such as rabelomycin, tetrangomycin, aquayamycin, a C-glycosylated benz[a]anthraquinone, and vineomycins. These biosynthetic data prompted us to reconsider the previously published structure of the antibiotic SS-228Y, which has not been revised.
对由马氏链霉菌葡萄亚种产生的抗菌和抗肿瘤抗生素维内霉素A1（1）和B2（2）进行了生物合成研究，采用[1-¹³C]-和[1,2-¹⁸C₂]醋酸钠进行标记实验，随后进行¹³C NMR光谱分析。结果表明，1的苯并[a]蒽醌发色团源自一种十醋酸代谢物，其羧基末端发生脱羧反应，且2是通过1的碳-碳键断裂形成的。从同一菌株的发酵液中分离出拉贝洛霉素，这表明在简单的苯并[a]蒽醌抗生素如拉贝洛霉素、四霉素、水霉素（一种C-糖基化苯并[a]蒽醌）和维内霉素之间存在密切的生物合成关系。这些生物合成数据促使我们重新考虑此前发表的尚未修订的抗生素SS-228Y的结构。
