天然产物研究与开发 ›› 2021, Vol. 33 ›› Issue (4): 598-606.doi: 10.16333/j.1001-6880.2021.4.009

• 研究简报 • 上一篇    下一篇

糙叶五加正丁醇萃取部位抗炎活性成分研究

唐思琪1,罗姣2,黄浩1,吴贤哲3,金伦喆3,刘向前2*,李小军1*   

  1. 1赣南医学院药学院 国家中药现代化工程技术研究中心客家中医药资源研究分中心,赣州 341000;2湖南中医药大学药学院,长沙 410208;3圆光大学药学院,韩国 益山 54538

  • 出版日期:2021-04-28 发布日期:2021-05-10
  • 基金资助:
    江西省自然科学基金(20202BABL216070);赣南医学院校级科研项目(ZD201911,YB201910);湖南省自然科学基金(2019JJ40223)

Study on anti-inflammatory active constituents from n-butanol extract of Acanthopanax henryi

TANG Si-qi1,LUO Jiao2,HUANG Hao1,OH Hyun-cheol3,KIM Youn-chul3,LIU Xiang-qian2*,LI Xiao-jun1*   

  1. 1National Engineering Research Center for Modernization of Traditional Chinese Medicine-Hakka Medical Resources Branch,School of Pharmacy,Gannan Medical University,Ganzhou 341000,China;2School of Pharmacy,Hunan University of Chinese Medicine,Changsha 410208,China;3School of Pharmacy,Wonkwang University,Iksan 54538,Korea

  • Online:2021-04-28 Published:2021-05-10

摘要: 本文对糙叶五加果实正丁醇萃取物的抗炎活性成分进行研究。采用硅胶柱色谱、C18柱色谱、LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20)柱色谱、半制备液相及重结晶等方法进行分离纯化,利用波谱分析结合理化性质鉴定化合物的结构。从糙叶五加果实正丁醇萃取部位中分离鉴定出17个化合物,分别为槲皮素-3-O-β-D-吡喃葡萄糖苷 (1)、槲皮素-3-O-β-D-吡喃半乳糖苷(2)、芦丁(3)、1,3-双咖啡酰奎宁酸(4)、1,4-双咖啡酰奎宁酸(5)、1,5-双咖啡酰奎宁酸(6)、3,4-双咖啡酰奎宁酸(7)、3,5-双咖啡酰奎宁酸(8)、4,5-双咖啡酰奎宁酸(9)、绿原酸甲酯(10)、(2E,6S)-1-羟基-2,6-二甲基-2,7-辛二烯-6-β-D-吡喃葡萄糖苷(11)、(2Z,6R)-6-羟基-2,6-二甲基-2,7-辛二烯-1-β-D-吡喃葡萄糖苷(12)、(2Z,6R)-1-羟基-2,6-二甲基-2,7-辛二烯-6-β-D-吡喃葡萄糖苷(13)、(2E,6R)-6-羟基-2,6-二甲基-2,7-辛二烯-1-β-D-吡喃葡萄糖苷(14)、(2E,6R)-1-羟基-2,6-二甲基-2,7-辛二烯-6-β-D-吡喃葡萄糖苷(15)、(-)-(3S,4S,6R)-3,6-二羟基-1-薄荷烯 6-O-β-D-吡喃葡萄糖苷(16)、(-)-(3S,4S,6R)-3,6-二羟基-1-薄荷烯3-O-β-D-吡喃葡萄糖苷(17)。化合物11、16、17为首次从五加科植物中分离得到;化合物13~15为首次从五加属植物中分离得到;除化合物1~9之外,其他化合物均为首次从该种植物中分离得到。其中,在0~80 μM的浓度范围内,被测试化合物均无明显的细胞毒性,化合物1016具有较好的NO抑制活性且呈剂量相关;化合物6和17表现出了适度的NO抑制活性;其它被测试化合物具有微弱的或者无NO抑制效果。


关键词: 糙叶五加, 黄酮苷, 咖啡酰奎宁酸, 单萜苷, 化学成分, 抗炎活性

Abstract:

The anti-inflammatory active ingredients from n-butanol extract of the fruits of A. henryi were studied in this paper.The compounds were isolated and purified by silica gel,C18 and Sephadex LH-20 column chromatography,as well as Prep-HPLC and recrystallization methods.Their structures were identified on the basis of their physicochemical properties and spectroscopic data.As a result,seventeen compounds were obtained from A. henryi  and the chemical structures were identified as quercetin-3-O-β-D-glucopyranoside (1),quercetin-3-O-β-D-galactopyranoside (2),rutin (3),1,3-di-O-caffeoyl quinic acid (4),1,4-di-O-caffeoyl quinic acid (5),1,5-di-O-caffeoyl quinic acid (6),3,4-di-O-caffeoyl quinic acid (7),3,5-di-O-caffeoyl quinic acid (8),4,5-di-O-caffeoyl quinic acid (9),methyl chlorogenate (10),(2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (11),(2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (12),(2Z,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (13),(2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (14),(2E,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (15),(-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 6-O-β-D-glucopyranoside (16),and (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-D-glucopyranoside (17),respectively.Among them,compounds 11,16,and 17 were isolated from Araliaceae for the first time.Compounds 13-15 were separated from Acanthopanax Miq.for the first time.Except compounds 1-9, all of the other compounds were obtained from this species for the first time.Moreover,compounds 10 and 16 showed significant inhibition of NO production with dose-dependent manner. Compounds 6 and 17 showed that the NO production were down-regulated moderately when the concentration was 80 μM.Other tested compounds showed weak or inactive inhibitory effects.

Key words: Acanthopanax henryi (Oliv.) Harms, flavonoid glycosides, caffeoyl quinic acid, monoterpenoid glycosides, chemical constituents, anti-inflammatory activity

中图分类号:  R284