The Center for Cell Signaling & Drug Discovery Research, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
J Nat Prod. 2011 Oct 28;74(10):2109-15. doi: 10.1021/np200355n. Epub 2011 Sep 26.
Seven new diarylheptanoids, (-)-(R)-4″-hydroxyyashabushiketol (1), (3S,5S)-alpinikatin (2), katsumain C (3), 7-epi-katsumain C (4), ent-alpinnanin B (5), ent-alpinnanin A (6), and ent-calyxin H (8), were isolated from the EtOAc extract of the seeds of Alpinia katsumadai together with three known compounds, alpinnanin B (7), epicalyxin H (9), and calyxin H (10). Each isomer mixture of 3 and 4, 5-7, and 8-10 was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (3 and 4, 5-7, 8-10) at 1 μM increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 μM. Compounds 1 and 2 did not affect the induction of HSF1 protein.
从高良姜种子的 EtOAc 提取物中分离得到了七种新的二芳基庚烷类化合物，包括(-)-(R)-4″-羟基雅沙宾酮（1）、（3S,5S）-阿朴新二氢黄酮（2）、卡苏马嗪 C（3）、7-表卡苏马嗪 C（4）、ent-阿尔皮那宁 B（5）、ent-阿尔皮那宁 A（6）和 ent-卡利辛 H（8），以及三种已知化合物，阿尔皮那宁 B（7）、表儿茶素 H（9）和卡利辛 H（10）。通过使用手性柱的制备 HPLC，成功地分离了 3 和 4、5-7 和 8-10 的每个异构体混合物。三种异构体混合物（3 和 4、5-7、8-10）在 1 μM 时均能增加热休克因子 1（HSF1）的表达，其倍数分别为 1.438、1.190 和 1.316，同时伴随着热休克蛋白（HSP）27（1.403-、1.250-和 1.270-倍）和 HSP70（1.373-、1.313-和 1.229-倍）的表达增加，而没有细胞毒性，这表明这些化合物可能作为 HSP 诱导剂应用。白藜芦醇作为 HSP 诱导的阳性对照，在 1 μM 时产生 1.066 倍（HSF1）、1.216 倍（HSP27）和 1.371 倍（HSP70）的增加。化合物 1 和 2 不影响 HSF1 蛋白的诱导。
