槐黄醇

作用制备生物活性靶点体外研究体内研究槐黄醇试剂级价格

槐黄醇

CAS号:216450-65-6
英文名:sophoflavescenol
中文名:槐黄醇
CBNumber:CB91390299
分子式:C21H20O6
分子量:368.38
MOL File:216450-65-6.mol

槐黄醇化学性质

熔点 :273-275 °C
沸点 :631.8±55.0 °C(Predicted)
密度 :1.359±0.06 g/cm3(Predicted)
储存条件 :4°C, away from moisture and light
溶解度 :Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
形态 :powder
酸度系数(pKa) :7.03±0.40(Predicted)
颜色 :Yellow

槐黄醇性质、用途与生产工艺

作用黄酮类化合物，包括抗肿瘤，抗炎和抗炎抗骨质疏松症活动，酶抑制和血管保护和雌激素调节活动。槐黄醇，一种C-8-异戊烯化的黄酮类化合物来自S.flavescens，是最有效和选择性的CGMP磷酸二酯酶5（PDE5;IC500.013μm）抑制剂，因此被认为是治疗的先导结构。槐黄醇也显示出对HL-60，LLC和A549肿瘤细胞的抑制活性。
制备 7,8-（2,2-二甲基-2H-吡喃）-5,4-二羟基黄酮醇（槐黄醇，12）:(CH3）2SO4（10.53mmol，1.0mL）滴加到搅拌的11（500mg，1.02mmol）的NaOH（5％水溶液;15mL）溶液中。将混合物在室温下搅拌，并保持在pH9-10，持续5小时。此后，将反应混合物调节至pH6使用HCl（2％水溶液），然后用混合物萃取。水无水Na2SO4干燥无，溶剂蒸发。将固体残余物从中重结晶EtOAc/石油醚，得到槐黄醇（181mg，96％），为黄色针状物，熔点熔点272-274℃。
生物活性 Sophoflavescenol 是一种异戊烯基黄酮类化合物，能够抑制 PDE5 的活性，IC50 值为 0.013 μM；同时抑制 RLAR，HRAR，BACE1，AChE 和 BChE，IC50 值分别为 0.30 µM，0.17 µM，10.98 µM，8.37 µM 和 8.21 µM。
靶点

IC50: 0.013 μM (PDE5), 0.30 µM (RLAR), 0.17 µM (HRAR), 17.89 µg/mL (AGE), 10.98 µM (BACE1), 8.37 µM (AChE), 8.21 µM (BChE)
体外研究

Sophoflavescenol shows cytotoxicity against human leukaemia (HL-60), Lewis lung carcinoma (LLC), and human lung adenocarcinoma epithelial (A549) cells. Sophoflavescenol exerts notable anti-inflammatory activity by inhibiting nitric oxide generation and tert-butylhydroperoxide-induced ROS generation rather than inhibiting nuclear factor kappa B activation in RAW 264.7 cells. Sophoflavescenol exhibits remarkable inhibition of RLAR activity with an IC ₅₀ value of 0.30 µM, compared with 0.07 µM for epalrestat, a well known ARI. Sophoflavescenol also shows potent inhibitory activity with an IC ₅₀ value of 0.17 µM, comparable to epalrestat (0.15 µM) in the HRAR assay. In the AGE assay, sophoflavescenol (IC ₅₀ 17.89 µg/mL) is a more potent inhibitor of AGE formation than aminoguanidine (IC ₅₀ 81.05 µg/mL). Sophoflavescenol exerts both potent AChE and BChE inhibitory effects with respective IC ₅₀ values of 8.37 and 8.21 µM. Sophoflavescenol also exhibits good BACE1 inhibition in a dose-dependent manner with an IC ₅₀ value of 10.98 µM. Sophoflavescenol is a mixed inhibitor (K _i =0.005 μM) against cGMP PDE5. Sophoflavescenol shows greatest selectivity toward PDE5, 31.5- and 196.2-fold over PDE3 and PDE4, respectively.
体内研究

Sophoflavescenol exerts potent in vivo antitumor activity by tumor growth inhibition in the LLC tumor model as well as apoptotic activity by caspase-3 activation in HL-60 cells.