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丹参根中分离得到的咖啡酸衍生物的抗炎活性。

Anti-inflammatory activity of caffeic acid derivatives isolated from the roots of Salvia miltiorrhiza Bunge.

机构信息

College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Taegu, 41566, Republic of Korea.

College of Natural Sciences, Kangwon National University, Chuncheon, 24341, Republic of Korea.

出版信息

Arch Pharm Res. 2018 Jan;41(1):64-70. doi: 10.1007/s12272-017-0983-1. Epub 2017 Nov 9.

Abstract

Ten caffeic acid derivatives (1-10) were isolated from the roots of Salvia miltiorrhiza by using various chromatographic methods and their chemical structures were spectroscopically elucidated. The absolute configurations of chiral centers were determined by comparison with reported coupling constants, optical rotation values, and CD techniques. Anti-inflammatory activities were evaluated using nitric oxide (NO), inducible nitric oxide synthase (iNOS), cyclooxygenase (COX)-2 inhibition assays, and by determining the expression of heme oxygenase (HO)-1. Two new caffeic acid derivatives, 8-epiblechnic acid 9-methyl ester (4) and 8-epiblechnic acid 9'-methyl ester (5), and eight known derivatives, caffeic acid methyl ester (1), shimobashiric acid B (2), rosmarinic acid methyl ester (3), salvianolic acid C (6), methyl salvianolate C (7), lithospermic acid monomethyl ester (8), lithospermic acid dimethyl ester (9), and dimethyl lithospermate B (10), were isolated from the ethyl acetate fraction of S. miltiorrhiza. All caffeic acid derivatives were evaluated for their inhibitory effect on NO production. Compounds 2 and 3 inhibited NO production with IC values of 1.4 and 0.6 μM, respectively. These compounds also strongly inhibited the production of iNOS and COX-2. In addition, compound 3 induced the expression HO-1 in a concentration-dependent manner at 0.1, 0.3, and 1.0 μM.

摘要

从丹参根部分离得到 10 个咖啡酸衍生物(1-10),采用各种色谱方法进行分离,并通过光谱解析其化学结构。通过与报道的偶合常数、旋光值和 CD 技术比较,确定了手性中心的绝对构型。采用一氧化氮(NO)、诱导型一氧化氮合酶(iNOS)、环氧化酶(COX)-2 抑制测定法和血红素加氧酶(HO)-1 的表达来评价抗炎活性。从丹参的乙酸乙酯部分分离得到两个新的咖啡酸衍生物,8-epiblechnic 酸 9-甲酯(4)和 8-epiblechnic 酸 9'-甲酯(5),以及 8 个已知衍生物,咖啡酸甲酯(1),shimobashiric 酸 B(2),迷迭香酸甲酯(3),丹酚酸 C(6),甲基丹酚酸 C(7),虎杖苷单甲酯(8),虎杖苷二甲酯(9)和二甲基虎杖苷 B(10)。所有咖啡酸衍生物均评价了其对 NO 生成的抑制作用。化合物 2 和 3 的 IC 值分别为 1.4 和 0.6 μM,抑制 NO 生成的作用较强。这些化合物还强烈抑制 iNOS 和 COX-2 的产生。此外,化合物 3 在 0.1、0.3 和 1.0 μM 时以浓度依赖性方式诱导 HO-1 的表达。

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