槐黄醇性质、用途与生产工艺
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。
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℃。
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。
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)
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.
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.
槐黄醇
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