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一种来自铁皮石斛茎的新联苄衍生物

[A new bibenzyl derivative from stems of Dendrobium officinale].

作者信息

Meng Wei-Tong, Meng Xiao, Niu Li-Ting, Zhang Si-Si, Ouyang Chun-Jie, Ding Chun-Hua, Zhu Ling-Juan, Zhang Xue

机构信息

School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University Shenyang 110016, China.

Xiamen Eagledon Pharmaceutical Co., Ltd. Xiamen 361000, China.

出版信息

Zhongguo Zhong Yao Za Zhi. 2023 Feb;48(3):700-706. doi: 10.19540/j.cnki.cjcmm.20220517.201.

Abstract

Eleven compounds were isolated from the 95% ethanol extract of the stems of Dendrobium officinale after water extraction by various modern chromatographic techniques, such as silica gel column chromatography(CC), octadecyl-silica(ODS) CC, Sephadex LH-20 CC, preparative thin layer chromatography(PTLC) and preparative high performance liquid chromatography(PHPLC). According to spectroscopic analyses(MS, 1D-NMR, 2D-NMR) combined with optical rotation data and calculated electronic circular dichroism(ECD), their structures were identified as dendrocandin Y(1), 4,4'-dihydroxybibenzyl(2), 3-hydroxy-4',5-dimethoxybibenzyl(3), 3,3'-dihydroxy-5-methoxybibenzyl(4), 3-hydroxy-3',4',5-trimethoxybibenzyl(5), crepidatin(6), alternariol(7), 4-hydroxy-3-methoxypropiophenone(8), 3-hydroxy-4,5-dimethoxypropiophenone(9), auriculatum A(10) and hyperalcohol(11). Among them, compound 1 was a new bibenzyl derivative; compounds 2 and 7-11 have not been previously reported from Dendrobium plants; compound 6 was reported from D.officinale for the first time. Compounds 3-6 exhibited potent antioxidant activity with IC_(50) values of 3.11-9.05 μmol·L(-1) in ABTS radical scavenging assay. Compound 4 showed significant inhibitory effect on α-glucosidase, with IC_(50) value of 17.42 μmol·L(-1), indicating that it boasted hypoglycemic activity.

摘要

采用硅胶柱色谱(CC)、十八烷基硅胶(ODS)CC、葡聚糖凝胶LH-20 CC、制备型薄层色谱(PTLC)和制备型高效液相色谱(PHPLC)等多种现代色谱技术,对铁皮石斛茎的水提取物经水提取后的95%乙醇提取物进行分离,得到11种化合物。通过光谱分析(MS、一维NMR、二维NMR),结合旋光数据和计算电子圆二色光谱(ECD),确定它们的结构分别为石斛香豆素Y(1)、4,4'-二羟基联苄(2)、3-羟基-4',5-二甲氧基联苄(3)、3,3'-二羟基-5-甲氧基联苄(4)、3-羟基-3',4',5-三甲氧基联苄(5)、crepidatin(6)、链格孢酚(7)、4-羟基-3-甲氧基苯丙酮(8)、3-羟基-4,5-二甲氧基苯丙酮(9)、耳叶甲素A(10)和高醇(11)。其中,化合物1为新的联苄衍生物;化合物2和7-11此前未见从石斛属植物中报道;化合物6首次从铁皮石斛中报道。化合物3-6在ABTS自由基清除试验中表现出较强的抗氧化活性,IC50值为3.11-9.05 μmol·L-1。化合物4对α-葡萄糖苷酶有显著抑制作用,IC50值为17.42 μmol·L-1,表明其具有降血糖活性。

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