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首页> 外文期刊>The Journal of Organic Chemistry >Bioactive Sesquiterpenes from the Edible Mushroom Flammulina velutipes and Their Biosynthetic Pathway Confirmed by Genome Analysis and Chemical Evidence
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Bioactive Sesquiterpenes from the Edible Mushroom Flammulina velutipes and Their Biosynthetic Pathway Confirmed by Genome Analysis and Chemical Evidence

机译：食用菌金针菇的生物活性倍半萜及其基因合成分析和化学证据的生物合成途径

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摘要

Twelve putative sesquiterpene synthases genes were found in clades along with enzymes with 1,6-, 1,10-, and 1,11-cyclase activities in the genome of Flammulina velutipes. Chemistry investigation of F. velutipes led to the identification of two seco-cuparane sesquiterpenes, flammufuranone A (1) and B (2); 13 new sesquiterpenes with nor-eudesmane, spiroaxane, cadinane, and cuparane skeletons (3-14, 16); as well as two new ergosterol derivatives (17 and 18). Sesquiterpenes (3-14) derived from 1,10-cyclizing enzyme were first reported from this mushroom. The absolute configurations in 1 (3R,7S) and 2 (3R,7R) were assigned by electronic circular dichroism (ECD) calculation. The absolute configuration in 3 was confirmed by X-ray diffraction analysis. The absolute configurations in the 1,2-diol moiety of 13, and in the 1,3-diol moiety of 17 and 18 were determined using Snatzke's method. Among these compounds, 3, 5, 13, and 14 were found to inhibit the HMG-CoA reductase with IC50 of 114.7, 77.6, 55.5, and 87.1 mu M, respectively. Compounds 5, 6, 7, 10, 13, and 14 showed DPP-4 inhibitory activity with IC50 of 75.9, 83.7, 70.9, 79.7, 80.5, and 74.8 mu M, respectively. The biosynthesis for sesquiterpenes in F. velutipes was also discussed.
机译：在金针菇的基因组中发现了十二个假定的倍半萜烯合酶基因以及具有1,6-，1,10-和1,11-环化酶活性的酶。天鹅绒假单胞菌的化学研究导致鉴定出两种癸二cu碱倍半萜烯，呋喃呋喃酮A（1）和B（2）。 13种新的倍半萜烯，具有正十二烷基，螺螺iro烷，正丁烷和铜烷骨架（3-14，16）;以及两种新的麦角固醇衍生物（17和18）。最早报道了从1,10-环化酶衍生出的倍半萜（3-14）。通过电子圆二色性（ECD）计算分配1（3R，7S）和2（3R，7R）中的绝对构型。通过X射线衍射分析确认3中的绝对构型。使用Snatzke方法确定13的1，2-二醇部分以及17和18的1，3-二醇部分中的绝对构型。在这些化合物中，发现3、5、13和14抑制HMG-CoA还原酶，IC50分别为114.7、77.6、55.5和87.1μM。化合物5、6、7、10、13和14表现出DPP-4抑制活性，IC50分别为75.9、83.7、70.9、79.7、80.5和74.8μM。还讨论了velutipes中倍半萜的生物合成。

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