Harunari Enjuro, Mae Shunsuke, Fukaya Keisuke, Tashiro Etsu, Urabe Daisuke, Igarashi Yasuhiro
Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.
Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan.
J Antibiot (Tokyo). 2022 Oct;75(10):542-551. doi: 10.1038/s41429-022-00559-x. Epub 2022 Sep 7.
A bisprenyl naphthoquinone, phytohabinone (1), and a calcimycin congener with unusual modifications, phytohabimicin (2), were isolated from the culture extract of Phytohabitans sp. RD003013. The structures of 1 and 2 were determined by NMR and MS analyses, and the absolute configuration of 2 was established by using electronic circular dichroism (ECD) calculation. The prenylation pattern of 1 was unprecedented among the known prenylated naphthoquinones. Compound 2 represents 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, 2 showed moderate antimicrobial activity against a Gram-negative bacterium Ralstonia solanacearum while calcimycin was inactive. Additionally, 2 inhibits the migration of EC17 cancer cells at noncytotoxic concentrations.
从植物栖居菌属（Phytohabitans sp.）RD003013的培养提取物中分离出一种双异戊烯基萘醌——植物栖居醌（1），以及一种具有不寻常修饰的钙离子载体A23187同类物——植物栖居霉素（2）。通过核磁共振（NMR）和质谱（MS）分析确定了1和2的结构，并利用电子圆二色光谱（ECD）计算确定了2的绝对构型。1的异戊烯基化模式在已知的异戊烯基化萘醌中是前所未有的。化合物2代表一个由聚酮化合物衍生而来的螺缩醛核心，被噻唑羧酸和二氯吡咯部分取代，这在已知的钙离子载体A23187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对革兰氏阴性细菌青枯雷尔氏菌（Ralstonia solanacearum）表现出中等抗菌活性，而钙离子载体A23187则无活性。此外，2在非细胞毒性浓度下可抑制EC17癌细胞的迁移。
