摘要
目的 研究红花龙胆(Gentiana Rhodantha)的化学成分。方法 运用正相硅胶、十八烷基硅烷(ODS)反相硅胶、葡聚糖凝胶(Sephadex LH-20)以及半制备高效液相色谱等多种方法对红花龙胆中的化学成分进行系统分离纯化,并借助质谱法(MS)、一维和二维核磁共振(NMR)等现代波谱分析方法鉴定化合物结构,采用96孔板法测定所分离的化合物对青枯假单胞菌和产气荚膜梭菌的最小抑菌浓度。结果 从红花龙胆中分离得到15个萜类化合物化合物,分别鉴定为(2E, 6Z)-2,6-dimethyl-2,6-octadiene-1,8-dioic acid(1),(2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-dioic acid(2),(3S,6R)-dimethyloct-7-ene-2,3,6-triol(3),19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3-methyl ester(4),坡模酸(5),2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid(6),乌苏酸内酯(7),熊果醇(8),ilelatifol D(9),常春藤皂苷元(10),2α, 3β, 23-三羟基-12-烯-28-齐墩果酸(11),2α, 3β, 23-trihydroxyoleana-11, 13(18)-dien-28-oic acid(12),齐墩果酸(13),熊果醛(14),2α, 3β, 24-三羟基-12-烯-28-齐墩果酸(15)。结论 化合物1~5和7~10为首次从红花龙胆植物中分离得到,而化合物1~5和9为首次从龙胆属植物中分离鉴定。其中,化合物1为新化合物,化合物2和3为新天然产物,并首次对其1H-NMR和13C-NMR数据进行了归属。抗菌活性测试结果发现,3个化合物(4、5和6)对青枯假单胞菌(Pseudomonas solanacearum)具有明显抑制作用,此外,化合物5还对产气荚膜梭菌(Clostridium perfringens)表现出一定的抑菌活性。
Abstract
OBJECTIVE To study the chemical constituents of the Gentiana rhodantha. METHODS The chemical constituents from G. Rhodantha were investigated by using a series of separation materials and technologies, including silica gel column chromatography, reversed phase C-18 column chromatography, Sephadex LH-20 column chromatography, MCI column chromatography, semi-preparative HPLC and other separation materials and techniques. The 96-well plate method was used to determine antibacterial activity via minimum inhibitory concentration (MIC) for the isolates. RESULTS Fifteen compounds(1-15) were isolated from this plant, and their structures were identified as(2E, 6Z)-2,6-dimethyl-2,6-octadiene-1,8-dioic acid(1), (2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-dioic acid(2), (3S,6R)-dimethyloct-7-ene-2,3,6-triol(3), 19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3-methyl ester (4), pomolic acid (5), 2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid (6), ursolic acid lactone (7), uvaol (8), ilelatifol D (9), hederagenin (10), 2α, 3β, 23-trihydroxy-12-en-28-oleanic acid (11), 2α,3β, 23-trihydroxyoleana-11,13(18)-dien-28-oic acid (12), oleanic acid (13), ursolic aldehyde (14), 2α, 3β, 24-trihydroxy-12-en-28-oleanic acid (15). CONCLUSION Compound 1 is a new compound, 2 and 3 are new natural occurring products. Compounds 1-5 and 7-10 are isolated from G. Rhodantha for the first time. The antibacterical activity result show that compound 5 exhibits activity against C. perfringens, with the MIC value of 100 μmol·L-1. Moreover, compounds 4-6 shows potential activity on P. solanacearum .
关键词
红花龙胆 /
萜类 /
乌苏酸内酯 /
抑菌活性
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Key words
Gentiana rhodantha /
terpene /
ursolic acid lactone /
antibacterial activity
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周谣, 王苗苗, 刘翰飞, 王欢, 赵兴, 林开琴, 李金玉, 娄华勇, 潘卫东.
红花龙胆中萜类化学成分的研究[J]. 中国药学杂志, 2023, 58(17): 1540-1546 https://doi.org/10.11669/cpj.2023.17.002
ZHOU Yao, WANG Miaomiao, LIU Hanfei, WANG Huan, ZHAO Xing, LIN Kaiqin, LI Jinyu, LOU Huayong, PAN Weidong.
Terpenes from Gentiana rhodantha[J]. Chinese Pharmaceutical Journal, 2023, 58(17): 1540-1546 https://doi.org/10.11669/cpj.2023.17.002
中图分类号：
R282
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脚注
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基金
国家自然科学基金项目资助(U1812403, 32060100, 32100322);贵州省科技计划项目资助(黔科合基础-ZK一般534)
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