Ling-Xia Xu, Xin-Xin Huang, Ji-Cheng Shu, Ting Tan, Yun Luo
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A total of 15 compounds were isolated and identified as 5-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(1), 3,5-di(hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(2), protocatechualdehyde(3), protocatechuic acid(4), 3,4-dihydroxyacetophenone(5), syringic acid(6), vanillic acid(7), p-hydroxybenzoic acid(8),(2S)-4'-hydroxy-7-methoxyflavan(9), 2,4,6-trimethoxyacetophenone(10), N-trans-ferulic acid p-hydroxyphenylethylamine(11), N-cis-p-coumaroyltyramine(12), N-trans-p-coumaroyltyramine(13), piscidic acid(14), 5-hydroxymethylfurfural(15). Compounds 1 and 2 are new compounds with similar structure that have not been reported yet, named narcissus A and narcissus B. Compounds 8-13 were isolated and identified from the genus Narcissus for the first time, and compounds 14 and 15 were isolated from BNTC for the first time. Compounds 1 and 2 inhibited the release of NO from RAW264.7 cells induced by lipopolysaccharide(LPS)(P<0.001), with compound 1 having an IC_(50) value of(72.76±2.97) μmol·L~(-1) and compound 2 having an IC_(50) value of(63.59±0.96) μmol·L~(-1).</p>","PeriodicalId":52437,"journal":{"name":"Zhongguo Zhongyao Zazhi","volume":"50 9","pages":"2404-2410"},"PeriodicalIF":0.0000,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"[Chemical constituents of bulbs of Narcissus tazetta var. chinensis].\",\"authors\":\"Ling-Xia Xu, Xin-Xin Huang, Ji-Cheng Shu, Ting Tan, Yun Luo\",\"doi\":\"10.19540/j.cnki.cjcmm.20250131.202\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The 95% ethanol extract from bulbs of Narcissus tazetta var. chinensis(BNTC) was eluted with 30%, 60%, and pure methanol on D-101 macroporous resin. The elution fractions were isolated and purified by silica gel column chromatography, thin layer chromatography, D-101 macroporous resin, semi-preparative high performance liquid chromatography(HPLC), and HPLC. The purified compounds were identified using one-dimensional and two-dimensional spectroscopy, high-resolution mass spectrometry, and other techniques. A total of 15 compounds were isolated and identified as 5-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(1), 3,5-di(hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(2), protocatechualdehyde(3), protocatechuic acid(4), 3,4-dihydroxyacetophenone(5), syringic acid(6), vanillic acid(7), p-hydroxybenzoic acid(8),(2S)-4'-hydroxy-7-methoxyflavan(9), 2,4,6-trimethoxyacetophenone(10), N-trans-ferulic acid p-hydroxyphenylethylamine(11), N-cis-p-coumaroyltyramine(12), N-trans-p-coumaroyltyramine(13), piscidic acid(14), 5-hydroxymethylfurfural(15). Compounds 1 and 2 are new compounds with similar structure that have not been reported yet, named narcissus A and narcissus B. Compounds 8-13 were isolated and identified from the genus Narcissus for the first time, and compounds 14 and 15 were isolated from BNTC for the first time. 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引用次数: 0
摘要
以水仙(Narcissus tazetta var. chinensis, BNTC)球茎95%乙醇提取物为溶剂,分别用30%、60%和纯甲醇在D-101大孔树脂上进行洗脱。采用硅胶柱层析、薄层色谱、D-101大孔树脂、半制备高效液相色谱和高效液相色谱对洗脱组分进行分离纯化。纯化的化合物通过一维和二维光谱、高分辨率质谱和其他技术进行鉴定。共分离得到15个化合物,鉴定为5-(4-羟基-3-甲氧基苯基)-3-(4-羟基苯基)- n -甲基-3,6-二氢吡啶-2(1H)- 1(1)、3,5-二(羟基苯基)- n -甲基-3,6-二氢吡啶-2(1H)- 1(2)、原儿茶醛(3)、原儿茶酸(4)、3,4-二羟基苯乙酮(5)、丁香酸(6)、香草酸(7)、对羟基苯甲酸(8)、(2S)-4'-羟基-7-甲氧基黄烷(9)、2,4,6-三甲氧基苯乙酮(10)、n -反式阿卫酸对羟基苯乙胺(11)、n -顺-对-香豆酰乙胺(12),n -反-对-香豆酰乙胺(13),鱼酸(14),5-羟甲基糠醛(15)。其中化合物1和2为结构相似的新化合物,命名为narcissus A和narcissus b。化合物8 ~ 13为首次从水仙属植物中分离鉴定,化合物14和15为首次从BNTC中分离得到。化合物1和2抑制脂多糖(LPS)诱导RAW264.7细胞释放NO (P<0.001),其中化合物1的ic50值为(72.76±2.97)μmol·L~(-1),化合物2的ic50值为(63.59±0.96)μmol·L~(-1)。
[Chemical constituents of bulbs of Narcissus tazetta var. chinensis].
The 95% ethanol extract from bulbs of Narcissus tazetta var. chinensis(BNTC) was eluted with 30%, 60%, and pure methanol on D-101 macroporous resin. The elution fractions were isolated and purified by silica gel column chromatography, thin layer chromatography, D-101 macroporous resin, semi-preparative high performance liquid chromatography(HPLC), and HPLC. The purified compounds were identified using one-dimensional and two-dimensional spectroscopy, high-resolution mass spectrometry, and other techniques. A total of 15 compounds were isolated and identified as 5-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(1), 3,5-di(hydroxyphenyl)-N-methyl-3,6-dihydropyridine-2(1H)-one(2), protocatechualdehyde(3), protocatechuic acid(4), 3,4-dihydroxyacetophenone(5), syringic acid(6), vanillic acid(7), p-hydroxybenzoic acid(8),(2S)-4'-hydroxy-7-methoxyflavan(9), 2,4,6-trimethoxyacetophenone(10), N-trans-ferulic acid p-hydroxyphenylethylamine(11), N-cis-p-coumaroyltyramine(12), N-trans-p-coumaroyltyramine(13), piscidic acid(14), 5-hydroxymethylfurfural(15). Compounds 1 and 2 are new compounds with similar structure that have not been reported yet, named narcissus A and narcissus B. Compounds 8-13 were isolated and identified from the genus Narcissus for the first time, and compounds 14 and 15 were isolated from BNTC for the first time. Compounds 1 and 2 inhibited the release of NO from RAW264.7 cells induced by lipopolysaccharide(LPS)(P<0.001), with compound 1 having an IC_(50) value of(72.76±2.97) μmol·L~(-1) and compound 2 having an IC_(50) value of(63.59±0.96) μmol·L~(-1).