Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans
Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans
复制标题
DOI：
10.1038/s41429-022-00559-x
复制
发表时间：
2022-09
期刊：
影响因子：
--
通讯作者：
Enjuro Harunari;Shunsuke Mae;K. Fukaya;E. Tashiro;D. Urabe;Y. Igarashi
中科院分区：
文献类型：
--
作者：
Enjuro Harunari;Shunsuke Mae;K. Fukaya;E. Tashiro;D. Urabe;Y. Igarashi
从植物栖息菌的培养提取液中分离得到一种双戊烯基萘醌类化合物，即植物抗菌素(1)和一种经过特殊修饰的钙霉素同系物--植物双菌素(2)。RD003013。1和2的结构经核磁共振和MS分析确定，并用电子圆二色谱(ECD)计算确定了2的绝对构型。1的预烯基化模式在已知的异戊二酚中是史无前例的。化合物2代表聚酮的螺缩醛核心，被噻唑羧酸和二氢吡咯部分取代，这在已知的钙霉素家族天然产物中是一种前所未有的修饰模式。值得注意的是，2对革兰氏阴性菌青枯拉氏菌表现出中等的抗菌活性，而钙霉素则不起作用。此外，在非细胞毒性浓度下，2可抑制EC17癌细胞的迁移。
A bisprenyl naphthoquinone, phytohabinone (1), and a calcimycin congener with unusual modifications, phytohabimicin (2), were isolated from the culture extract ofPhytohabitanssp. RD003013. The structures of1and2were determined by NMR and MS analyses, and the absolute configuration of2was established by using electronic circular dichroism (ECD) calculation. The prenylation pattern of1was unprecedented among the known prenylated naphthoquinones. Compound2represents a spiroacetal core of polyketide origin substituted with a thiazole carboxylic acid and a dichrolopyrrole moiety, which is an unprecedented modification pattern in the known calcimycin family natural products. Remarkably,2showed moderate antimicrobial activity against a Gram-negative bacteriumRalstonia solanacearumwhile calcimycin was inactive. Additionally,2inhibits the migration of EC17 cancer cells at noncytotoxic concentrations.