Cyclic tetrapeptides from the marine strain Streptomyces sp. PNM-161a with activity against rice and yam phytopathogens
Cyclic tetrapeptides from the marine strain Streptomyces sp. PNM-161a with activity against rice and yam phytopathogens
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DOI：
10.1038/s41429-019-0201-0
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发表时间：
2019-10-01
影响因子：
3.3
通讯作者：
Ramos, Freddy A.
中科院分区：
文献类型：
--
作者：
Betancur, Luz A.;Forero, Abel M.;Ramos, Freddy A.
从海洋链霉菌161 a的液体培养物中分离到两个环四肽，以下命名为前肽A（1）和B（2），沿着的还有五个已知的二酮哌嗪（3-7）。环四肽和二酮哌嗪（DKP）的结构通过1D和2D NMR数据、MS以及与文献数据的比较来确定。用Marvet法确定了化合物cyclo-（L-Pro-L-Leu-D-Pro-L-Phe）1和cyclo-（-Pro-Ile-Pro-Phe）2的绝对立体化学。化合物1对水稻病原菌颖壳伯克霍尔德氏菌（MIC = 1.1 mM）和唐菖蒲伯克霍尔德氏菌（MIC = 0.068 mM）具有抗菌活性，化合物2仅对B具有抗菌活性。DKP cyclo-[L-Pro-L-Leu] 5对B有活性。唐菖蒲（MIC = 0.3 mM）和B.（MIC = 2.4mM）。化合物1和2在1.1 mM浓度下对胶孢炭疽菌（山药病原体）分生孢子萌发的抑制率分别为65%和50%。
Two cyclotetrapeptides, henceforth named Provipeptides A (1) and B (2), along with five known diketopiperazines (3-7) were isolated from the liquid culture of marine Streptomyces sp. 161a recovered from a sample of sea grass Bryopsis sp. The structures of cyclotetrapeptides and diketopiperazines (DKPs) were established by 1D and 2D NMR data, MS, and by comparison with literature data. The absolute stereochemistry of compounds cyclo-(L-Pro-L-Leu-D-Pro-L-Phe) 1 and cyclo-(-Pro-Ile-Pro-Phe) 2 was established by the Marfey's method. Compound 1 showed antibacterial activity against rice phytopathogenic strains Burkholderia glumae (MIC = 1.1 mM) and Burkholderia gladioli (MIC = 0.068 mM), compound 2 was active only against B. glumae (MIC = 1.1 mM), and DKP cyclo-[L-Pro-L-Leu] 5 showed to be active against B. gladioli (MIC = 0.3 mM) and B. glumae (MIC = 2.4 mM). Compounds 1 and 2 showed 65% and 50% inhibition of Colletotrichum gloeosporioides (yam pathogen) conidia germination, respectively at a concentration of 1.1 mM.