中国中药杂志

2020, v.45(12) 2907-2915

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苍耳子的化学成分研究
Chemical constituents from Xanthii Fructus

夏召;张海新;许天启;陈宜敏;周光雄;
XIA Zhao;ZHANG Hai-xin;XU Tian-qi;CHEN Yi-min;ZHOU Guang-xiong;Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research,Institute of Traditional Chinese Medicine and Natural Product, College of Pharmacy, Jinan University;

摘要(Abstract):

研究菊科植物苍耳Xanthium sibiricum的干燥成熟带总苞的果实(苍耳子)的化学成分。采用硅胶柱色谱,Sephadex LH-20,ODS和HPLC等色谱方法进行分离纯化,并结合HR-ESI-MS与现代波谱学技术鉴定化合物结构。采用脂多糖(LPS)诱导的巨噬细胞RAW264.7为筛选模型评价分离得到化合物的抗炎活性。从苍耳子95%乙醇提取物的乙酸乙酯萃取物中分离得到了21个化合物,分别鉴定为尿嘧啶(1),胸腺嘧啶(2),尿苷(3),吲哚-3-甲醛(4),吲哚-3-甲酸(5),2′-O-methyluridine(6),鸟苷(7),2,4(1H,3H)-quinazolinedione(8),3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9),nicotinamide(10),N-acetyl-L-phenylalaninol(11),heliolactam(12),terresoxazine(13),告达亭(14),qingyangshengenin(15),告达亭-3-O-β-D-夹竹桃吡喃糖基-(1→4)-β-D-加拿大麻吡喃糖基-(1→4)-β-D-加拿大麻吡喃糖苷(16),告达亭-3-O-β-D-加拿大麻吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖基-(1→4)-β-D-加拿大麻吡喃糖基-(1→4)-β-D-加拿大麻吡喃糖苷(17),caudatin-3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropy-ranoside(18),qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(19),qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside(20),rostratamine-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(21)。化合物5~21为首次从苍耳属植物中分离得到。对分离得到的21个化合物进行抗炎活性筛选,其中,化合物12~13具有抗炎活性,其IC_(50)分别为(15.45±0.56),(20.14±0.78)μmol·L~(-1)。
This study was carried out to investigate the chemical constituents from Xanthii Fructus(the fruits of Xanthium sibiricum). The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 and ODS chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR and other spectral data, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW264.7 as a screening model. A total of twenty-one compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as uracil(1), thymine(2), uridine(3), indole-3-carbaldehyde(4), indole-3-carboxylic acid(5), 2′-O-methyluridine(6), guanosine(7), 2,4(1H,3H)-quinazolinedione(8), 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9), nicotinamide(10), N-acetyl-L-phenylalaninol(11), heliolactam(12), terresoxazine(13), caudatin(14), qingyangshengenin(15), caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(16), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(17), caudatin-3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(18), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(19), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside(20), rostratamine-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(21). Compounds 5-21 are obtained from genus Xanthium for the first time. Compounds 12 and 13 indirectly exhibited anti-inflammatory activity by suppressing LPS-induced NO production in RAW264.7 cells with IC_(50) values of(15.45±0.56) and(20.14±0.78) μmol·L~(-1), respectively.

关键词(KeyWords): 苍耳子;菊科;nicotinamide;heliolactam;terresoxazine
Xanthii Fructus(fruits of Xanthium sibiricum);Compositae;nicotinamide;heliolactam;terresoxazine

Abstract:

Keywords:

基金项目(Foundation): 国家重点研发计划项目(2017YFC1703800);; 国家自然科学基金面上项目(81573578);; 广州市科技计划项目(201704030120)

作者(Author): 夏召;张海新;许天启;陈宜敏;周光雄;
XIA Zhao;ZHANG Hai-xin;XU Tian-qi;CHEN Yi-min;ZHOU Guang-xiong;Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research,Institute of Traditional Chinese Medicine and Natural Product, College of Pharmacy, Jinan University;

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