NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, PR China.
J Antibiot (Tokyo). 2020 May;73(5):324-328. doi: 10.1038/s41429-020-0282-9. Epub 2020 Feb 12.
Lavanducyanin is a bioactive phenazine-containing secondary metabolite, and naphthomevalin is an antibacterial polyketide secondary metabolite. Herein, new analogues of lavanducyanin (2) and of naphthomevalin (4), together with lavanducyanin (1) and naphthomevalin (3), were identified from Streptomyces sp. CPCC 203577, an actinomycete soil isolate. The structures of 2 and 4 were elucidated as 1-hydroxy-7-oxolavanducyanin and Δ-6″-hydroxynaphthomevalin, respectively, by 1D and 2D NMR. Antibacterial assays revealed that 2 had significant but reduced anti-Gram-positive bacterial activity compared with 1, and 4 was devoid of anti-Gram-positive bacterial activity. This indicated that the phenazinone nucleus in lavanducyanin and the monoterpene side chain in naphthomevalin might be important for their anti-Gram-positive bacterial activity. Compounds 1-4 were all inactive against Gram-negative bacteria.
拉凡丁酮是一种含有苯并嗪的生物活性次生代谢物，萘甲羟戊酸是一种具有抗菌作用的聚酮类次生代谢物。本文从链霉菌 CPCC 203577 中鉴定出了拉凡丁酮（2）和萘甲羟戊酸（4）的新类似物，以及拉凡丁酮（1）和萘甲羟戊酸（3）。通过 1D 和 2D NMR，确定了 2 和 4 的结构分别为 1-羟基-7-氧代拉凡丁酮和 Δ-6″-羟基萘甲羟戊酸。抗菌试验表明，2 对革兰氏阳性菌的活性显著降低，但低于 1，而 4 对革兰氏阳性菌没有活性。这表明拉凡丁酮中的苯并嗪酮核和萘甲羟戊酸中的单萜侧链可能对其抗革兰氏阳性菌活性很重要。化合物 1-4 对革兰氏阴性菌均无活性。
