Min B S, Nakamura N, Miyashiro H, Kim Y H, Hattori M
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Japan.
Chem Pharm Bull (Tokyo). 2000 Feb;48(2):194-200. doi: 10.1248/cpb.48.194.
From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1,4,8-trihydroxynaphthalene 1-O-[alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside] (1) and 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (4), and two new alpha-tetralonyl glucopyranosides, 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (7) and 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",4",5"-trihydroxybenzoyl)]glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one alpha-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two galloyl glucopyranosides (13, 14). Amongst the isolated compounds, 1,2,6-trigalloylglucopyranose (13) and 1,2,3,6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 microM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 microM, comparable in potency to illimaquinone used as a positive control. 1,4,8-Trihydroxy-naphthalene 1-O-beta-D-glucopyranoside (2), 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)]glucopyranoside (3) and 8 showed moderate inhibition against both enzyme activities, and inhibitory potency of 2 against RNase H activity (IC50 = 156 microM) was slightly greater than that against the RT activity (IC50 = 290 microM). The inhibitory potencies of 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of > 500, 330 and 5.8 microM, respectively.
从胡桃楸的茎皮中分离得到两个新的萘基葡萄糖苷，即1,4,8 - 三羟基萘1 - O - [α - L - 阿拉伯呋喃糖基 - (1→6) - β - D - 葡萄糖苷]（1）和1,4,8 - 三羟基萘1 - O - β - D - [6'-O - (3",5"-二羟基 - 4"-甲氧基苯甲酰基)]葡萄糖苷（4），以及两个新的α - 四氢萘酮基葡萄糖苷，4α,5,8 - 三羟基 - α - 四氢萘酮5 - O - β - D - [6'-O - (3",5"-二羟基 - 4"-甲氧基苯甲酰基)]葡萄糖苷（7）和4α,5,8 - 三羟基 - α - 四氢萘酮5 - O - β - D - [6'-O - (3",4",5"-三羟基苯甲酰基)]葡萄糖苷（8），同时还分离得到三个已知的萘基葡萄糖苷（2、3和5）、一个α - 四氢萘酮基葡萄糖苷（6）、四个黄酮类化合物（9 - 12）以及两个没食子酰葡萄糖苷（13、14）。在分离得到的化合物中，1,2,6 - 三没食子酰葡萄糖（13）和1,2,3,6 - 四没食子酰葡萄糖（14）对逆转录酶（RT）活性表现出最强的抑制作用，IC50值分别为0.067和0.040微摩尔，而后者化合物对核糖核酸酶H（RNase H）活性也有抑制作用，IC50为39微摩尔，其效力与用作阳性对照的伊利马醌相当。1,4,8 - 三羟基萘1 - O - β - D - 葡萄糖苷（2）、1,4,8 - 三羟基萘1 - O - β - D - [6'-O - (4"-羟基 - 3",5"-二甲氧基苯甲酰基)]葡萄糖苷（3）和8对两种酶活性均表现出中等程度的抑制作用，2对RNase H活性的抑制效力（IC50 = 156微摩尔）略高于对RT活性的抑制效力（IC50 = 290微摩尔）。4α,5,8 - 三羟基 - α - 四氢萘酮5 - O - β - D - [6'-O - (4"-羟基 - 3",5"-二甲氧基苯甲酰基)]葡萄糖苷（6）、7和8对RT活性的抑制效力随着没食子酰残基上游离羟基数量的增加而增强，其IC50值分别为> 500微摩尔、330微摩尔和5.8微摩尔。
