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Lanostane Triterpenoids with Glucose-Uptake-Stimulatory Activity from Peels of the Cultivated Edible Mushroom Wolfiporia cocos
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-06-10 00:00:00 , DOI: 10.1021/acs.jafc.9b02606 Baosong Chen 1, 2 , Jinjin Zhang 1, 2 , Junjie Han 1 , Ruilin Zhao 1 , Li Bao 1 , Ying Huang 3 , Hongwei Liu 1, 2
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-06-10 00:00:00 , DOI: 10.1021/acs.jafc.9b02606 Baosong Chen 1, 2 , Jinjin Zhang 1, 2 , Junjie Han 1 , Ruilin Zhao 1 , Li Bao 1 , Ying Huang 3 , Hongwei Liu 1, 2
Affiliation
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A chemical study on the peels of the cultivated edible mushroom Wolfiporia cocos led to the isolation and identification of 47 lanostane triterpenoids including 16 new compounds (1–16). The structures of the new compounds were determined by analysis of the NMR, MS, and electronic circular dichroism (ECD) data. Compounds 1 and 2 represent new members of the family of 4,5-secolanostane triterpenes. Compound 3 is a new aromatic lanostane triterpene with an unusual methyl rearrangement from C-10 to C-6. The absolute configurations of 1 and 8 were assigned by ECD spectra calculation. All compounds were evaluated for cytotoxicity (K562, SW480, and HepG2) and glucose-uptake-stimulating effects. Compounds 23, 25, 29, and 31 showed weak inhibition on the K562 cells with IC50 in the range of 25.7 to 68.2 μM, respectively. Compounds 21, 28, and 30 increased the glucose uptake in 3T3-L1 cells by 25%, 14%, and 50% at 5 μM, respectively. In addition, compounds 14, 23, 29, 35, and 43 showed insulin-sensitizing activity by increasing the insulin-stimulated glucose uptake at 2.5 μM in 3T3-L1 adipocytes. A preliminary structure–activity relationship analysis indicates that the 6/6/6/5 ring skeleton and the double bond between C-8 and C-9 are beneficial for the glucose-uptake-stimulating and insulin-sensitizing activities. Furthermore, the alkaline-insoluble fraction mainly containing compounds 22, 24, 28, and 31 were confirmed to have hypoglycemic and hypolipidemic activity on high-fat-diet-induced obese mice. This work confirms the potential of the peels’ extracts of W. cocos as a functional food or dietary supplements.
中文翻译：
从培养的可食用蘑菇Wolfiporia cocos的果皮中具有葡萄糖摄取刺激活性的羊毛脂三萜类化合物
对栽培食用蘑菇枸杞果皮的化学研究导致分离和鉴定了47种羊毛甾烷三萜类化合物，其中包括16种新化合物（1 – 16）。通过分析NMR，MS和电子圆二色性（ECD）数据确定了新化合物的结构。化合物1和2代表4,5-secolanostane triterpenes家族的新成员。化合物3是一种新的芳香族羊毛甾烷三萜，具有从C-10到C-6的不寻常的甲基重排。1和8的绝对配置通过ECD光谱计算分配。评价所有化合物的细胞毒性（K562，SW480和HepG2）和葡萄糖摄取刺激作用。化合物23，25，29，和31显示对K562细胞与IC弱抑制50在25.7至68.2微米，分别。化合物21，28和30由25％，14％和50％在5μM分别增加在3T3-L1细胞的葡萄糖摄取。另外，化合物14，23，29，35，和43通过增加3T3-L1脂肪细胞中2.5μM胰岛素刺激的葡萄糖摄取来显示胰岛素敏化活性。初步的结构-活性关系分析表明，6/6/6/5环骨架以及C-8和C-9之间的双键有利于葡萄糖摄取刺激和胰岛素敏化活性。此外，所述不溶性碱性级分主要含有化合物22，24，28，和31被证实具有对高脂饮食诱导的肥胖小鼠中的降血糖和降血脂活性。这项工作证实了W. cocos的果皮提取物具有作为功能性食品或膳食补充剂的潜力。
更新日期：2019-06-10
中文翻译：
从培养的可食用蘑菇Wolfiporia cocos的果皮中具有葡萄糖摄取刺激活性的羊毛脂三萜类化合物
对栽培食用蘑菇枸杞果皮的化学研究导致分离和鉴定了47种羊毛甾烷三萜类化合物，其中包括16种新化合物（1 – 16）。通过分析NMR，MS和电子圆二色性（ECD）数据确定了新化合物的结构。化合物1和2代表4,5-secolanostane triterpenes家族的新成员。化合物3是一种新的芳香族羊毛甾烷三萜，具有从C-10到C-6的不寻常的甲基重排。1和8的绝对配置通过ECD光谱计算分配。评价所有化合物的细胞毒性（K562，SW480和HepG2）和葡萄糖摄取刺激作用。化合物23，25，29，和31显示对K562细胞与IC弱抑制50在25.7至68.2微米，分别。化合物21，28和30由25％，14％和50％在5μM分别增加在3T3-L1细胞的葡萄糖摄取。另外，化合物14，23，29，35，和43通过增加3T3-L1脂肪细胞中2.5μM胰岛素刺激的葡萄糖摄取来显示胰岛素敏化活性。初步的结构-活性关系分析表明，6/6/6/5环骨架以及C-8和C-9之间的双键有利于葡萄糖摄取刺激和胰岛素敏化活性。此外，所述不溶性碱性级分主要含有化合物22，24，28，和31被证实具有对高脂饮食诱导的肥胖小鼠中的降血糖和降血脂活性。这项工作证实了W. cocos的果皮提取物具有作为功能性食品或膳食补充剂的潜力。
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