Isolation, Biosynthetic Investigation, and Biological Evaluation of Maniwamycin G, an Azoxyalkene Compound from Streptomyces sp. TOHO-M025
Isolation, Biosynthetic Investigation, and Biological Evaluation of Maniwamycin G, an Azoxyalkene Compound from Streptomyces sp. TOHO-M025
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马尼瓦霉素 G（一种来自链霉菌属的氧化烯化合物）的分离、生物合成研究和生物学评价。
DOI：
10.1021/acs.jnatprod.2c00131
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发表时间：
2022
影响因子：
5.1
通讯作者：
Arakawa Kenji
中科院分区：
文献类型：
--
作者：
Tatsukawa Ayaka;Tanaka Yu;Nagano Haruka;Fukumoto Atsushi;Anzai Yojiro;Arakawa Kenji
从链霉菌中分离得到一个新的木兰素类似物--木兰素G。TOHO-M025为主打产品。甘尼瓦霉素G的分子式为C12H22N2O4，其核磁共振分析表明，甘尼瓦霉素G中含有甲氧基，而不是甘尼瓦霉素F中的酰胺。用圆二色谱和改进的Mosher方法分别确定其C-2和C-3构型为(2R，3R)。用同位素标记化合物研究了甘露霉素G的生物合成来源。甘露霉素G的碳源是四个乙酸酯单元(C-1‘，C-2’；C-3‘，C-4’；C-5‘，C-6’；以及C-4，C-5)和l-丝氨酸(C-1至C-3)。C-2(N-α)上的氮原子来自丝氨酸，而己烯-1-胺单元(N-β)的氮原子来自谷氨酸。甘露糖G的群体感应抑制活性比甘露糖F低2倍。
A new maniwamycin analogue, maniwamycin G, was isolated fromStreptomycessp. TOHO-M025 as a major product. Maniwamycin G has a molecular formula of C12H22N2O4, and its extensive NMR analysis revealed that maniwamycin G contains a methoxycarbonyl group instead of an amide as found in maniwamycin F. Its C-2 and C-3 configurations were determined to be (2R, 3R) by circular dichroism spectrum and a modified Mosher method, respectively. The biosynthetic origin of maniwamycin G was investigated using isotope-labeled compounds. The carbon source of maniwamycin G is four acetate units (C-1′, C-2′; C-3′, C-4′; C-5′, C-6′; and C-4, C-5) andl-serine (C-1 to C-3). The nitrogen atom attached at C-2 (Nα) originates from serine, whereas the nitrogen atom of a hexen-1-yl amine unit (Nβ) is derived from glutamic acid. The quorum-sensing inhibitory activity of maniwamycin G was 2-fold lower than that of maniwamycin F.