Macrocyclic Trichothecene Mycotoxins from a Deadly Poisonous Mushroom, Podostroma cornu-damae,Journal of Natural Products

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Macrocyclic Trichothecene Mycotoxins from a Deadly Poisonous Mushroom, Podostroma cornu-damae
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-11-20 00:00:00 , DOI: 10.1021/acs.jnatprod.8b00823
Seoung Rak Lee ₁ , Soonja Seok ₂ , Rhim Ryoo ₃ , Sang Un Choi ₄ , Ki Hyun Kim ₁

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Three new macrocyclic trichothecenes (1–3) and five known related compounds (4–8) were isolated from the MeOH extract of a plate culture of the fungus Podostroma cornu-damae, a deadly poisonous mushroom. Miophytocen D (1) is a rearranged macrocyclic type D trichothecene, featuring a bicyclo-[6.5]dodecahydrocyclopenta[b]chromene scaffold, and the structures of new compounds (1–3) were delineated by the combination of 1D and 2D NMR spectroscopic experiments and HRESIMS, modified Mosher’s esterification, and quantum chemical ECD calculations. The isolated compounds (1–8) were evaluated for cytotoxicity against four human breast cancer cell lines (Bt549, HCC70, MDA-MB-231, and MDA-MB-468). Compounds 4, 6, and 8 exhibited significant cytotoxic effects against the breast cancer cell lines, with IC₅₀ values in the range of 0.02–80 nM, which is stronger than doxorubicin, the positive control, and a structure–activity relationship was suggested.

中文翻译：

从致命的有毒蘑菇，Podostroma cornu-damae的大环曲霉菌霉菌毒素

三个新的大环单端孢（1 - 3）和五个已知的相关化合物（4 - 8）从真菌的平板培养的甲醇提取物中分离火焰茸，致命毒蘑菇。Miophytocen d（1）是一个重排的大环型d单端孢，设有一个双环- [6.5]十二氢[ b ]色支架，和新的化合物（的结构1 - 3）通过的一维和二维NMR光谱的实验组合物划定和HRESIMS，改进的Mosher酯化和量子化学ECD计算。分离出的化合物（1 – 8评估了）对四种人类乳腺癌细胞系（Bt549，HCC70，MDA-MB-231和MDA-MB-468）的细胞毒性。化合物4，6，和8表现出对乳腺癌细胞系显著细胞毒性作用，与IC _50个在0.02-80纳米，这比多柔比星，阳性对照更强的范围内的值，并建议的结构-活性关系。

更新日期：2018-11-20

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