Ma Min, Yu Shi-Shan
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica,Chinese Academy of Medical Sciences & Peking Union Medical College Beijing 100050, China.
Zhongguo Zhong Yao Za Zhi. 2023 Jan;48(2):415-420. doi: 10.19540/j.cnki.cjcmm.20220427.202.
Ten lignans were isolated from the ethanol extract of stems and branches of Rhododendron ovatum through column chromatography over silica gel, ODS, Sephadex LH-20, and MCI-gel resin and semi-preparative RP-HPLC. The structures of all compounds were elucidated by extensive spectroscopic data analysis(UV, IR, HR-ESI-MS, ECD and NMR) as(-)-4-epi-lyoniresinol-9'-O-α-L-rhamnopyranoside(1),(+)-lyoniresinol-3α-O-α-L-rhamnopyranoside(2),(+)-5'-methoxyisolariciresinol-9'-O-α-L-rhamnopyranoside(3),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(4),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(5),(-)-4-epi-lyoniresinol-9'-O-β-D-glucopyransoide(6), racemiside(7), neociwujiaphenol(8),(+)-syringaresinol(9), and homohesperitin(10). Among them, compound 1 was a new aryltetralin-type lignan. All the isolated lignans were tested for antioxidant activities in Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation in vitro, and compounds 8 and 9 showed antioxidant activities on the formation of malondiadehyde(MDA) in rat liver microsomes at 1×10(-5) mol·L~(-1), with significant inhibitory rates of 75.20% and 91.12%, respectively.
通过硅胶柱色谱、ODS柱色谱、葡聚糖凝胶LH-20柱色谱和MCI凝胶树脂柱色谱以及半制备型反相高效液相色谱,从满山红茎枝的乙醇提取物中分离得到10个木脂素。通过广泛的光谱数据分析(紫外光谱、红外光谱、高分辨电喷雾电离质谱、电子圆二色谱和核磁共振谱)确定了所有化合物的结构,分别为(-)-4-表-lyoniresinol-9'-O-α-L-鼠李糖苷(1)、(+)-lyoniresinol-3α-O-α-L-鼠李糖苷(2)、(+)-5'-甲氧基异落叶松脂醇-9'-O-α-L-鼠李糖苷(3)、(-)-lyoniresinol-3α-O-β-D-葡萄糖苷(4)、(+)-lyoniresinol-3α-O-β-D-葡萄糖苷(5)、(-)-4-表-lyoniresinol-9'-O-β-D-葡萄糖苷(6)、消旋糖苷(7)、新五味子酚(8)、(+)-丁香树脂醇(9)和高圣草素(10)。其中,化合物1是一种新的芳基四氢萘型木脂素。对所有分离得到的木脂素进行了体外Fe²⁺-半胱氨酸诱导的大鼠肝微粒体脂质过氧化反应中的抗氧化活性测试,化合物8和9在1×10⁻⁵ mol·L⁻¹浓度下对大鼠肝微粒体中丙二醛(MDA)的形成表现出抗氧化活性,抑制率分别为75.20%和91.12%,具有显著意义。