Chien Shih-Chang, Chen Miaw-Ling, Kuo Hsiou-Ting, Tsai Yao-Ching, Lin Bi-Fong, Kuo Yueh-Hsiung
Tsuzuki Institute for Traditional Medicine, College of Pharmacy, China Medical University, Taichung, Taiwan.
J Agric Food Chem. 2008 Aug 27;56(16):7017-22. doi: 10.1021/jf801171x. Epub 2008 Jul 19.
Six new compounds, trans-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolidine-2,5-dione (1), trans-1-hydroxy-3-(4-hydroxyphenyl)-4-isobutylpyrrolidine-2,5-dione (2), cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione (3), 3-(4-hydroxyphenyl)-4-isobutyl-1H-pyrrole-2,5-dione (4), 3-(4-hydroxyphenyl)-4-isobutylfuran-2,5-dione (5), and dimethyl 2-(4-hydroxyphenyl)-3-isobutylmaleate (6), together with one known compound, 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]furan-2,5-dione (7), were isolated from the fruiting bodies of Antrodia camphorata. The structures of the compounds were elucidated by analysis of their spectroscopic data. To investigate the immunomodulatory potential of the compounds, RAW264.7 macrophage cells were treated with the compounds. Compound 1 significantly increased spontaneous TNF-alpha secretion from unstimulated RAW264.7 cells but suppressed IL-6 production [50% inhibition concentration value (IC50) = 10 microg/mL] in LPS-stimulated cells. Compounds 3, 4, and 6 also suppressed IL-6 production with IC50 values of 17, 18, and 25 microg/mL, respectively, suggesting that these four compounds may have an anti-inflammatory effect on macrophage-mediated responses. Of the six compounds, compound 1 was the most effective, exerting both immunostimulatory and anti-inflammatory effects.
从樟芝子实体中分离出6种新化合物，反式-3-异丁基-4-[4-(3-甲基-2-丁烯氧基)苯基]吡咯烷-2,5-二酮(1)、反式-1-羟基-3-(4-羟基苯基)-4-异丁基吡咯烷-2,5-二酮(2)、顺式-3-(4-羟基苯基)-4-异丁基二氢呋喃-2,5-二酮(3)、3-(4-羟基苯基)-4-异丁基-1H-吡咯-2,5-二酮(4)、3-(4-羟基苯基)-4-异丁基呋喃-2,5-二酮(5)和2-(4-羟基苯基)-3-异丁基马来酸二甲酯(6)，以及1种已知化合物3-异丁基-4-[4-(3-甲基-2-丁烯氧基)苯基]呋喃-2,5-二酮(7)。通过光谱数据分析阐明了这些化合物的结构。为了研究这些化合物的免疫调节潜力，用这些化合物处理RAW264.7巨噬细胞。化合物1显著增加未刺激的RAW264.7细胞的自发性肿瘤坏死因子-α分泌，但抑制脂多糖刺激细胞中白细胞介素-6的产生[50%抑制浓度值(IC50)=10μg/mL]。化合物3、4和6也抑制白细胞介素-6的产生，IC50值分别为17、18和25μg/mL，表明这四种化合物可能对巨噬细胞介导的反应具有抗炎作用。在这六种化合物中，化合物1最有效，具有免疫刺激和抗炎作用。
