决明子中萘骈吡喃酮类衍生物的分离与鉴定
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摘要
目的研究决明子(Cassia obtusifolia L.)的化学成分。方法综合运用多种色谱学分离手段进行分离纯化,根据化合物波谱学数据对其结构进行鉴定。结果从决明子中共分离得到5个化合物,分别鉴定为2-甲基-5,10-二羟基-8-甲氧基-4H-萘[1,2-b]吡喃-4-酮-10-O-β-D-吡喃葡萄糖基-(1→3)-O-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖苷(1)、demethylflavasperone gentiobioside(2)、去甲基红镰霉素-6-O-β-D-吡喃葡萄糖苷(3)、去甲基红镰霉素-6-O-β-D-(6'-O-乙酰基)吡喃葡萄糖苷(4)、nor-rubrofusarin gentiobioside(5)。结论化合物1为新化合物。
Objective To investigate the chemical constituents from the seeds of Cassia obtusifolia L.Methods The chemical constituents were isolated by various modern chromatographic techniques. Their structures were identified by spectral analysis. Results Five compounds were isolated from the seeds of Cassia obtusifolia L. They were identified as 5,10-dihydroxy-8-methoxy-2-methyl-4H-naphtho [1,2-b]pyranone-10-O-β-D-glucopyranosyl-( 1 → 3)-O-β-D-glucopyranosyl-( 1 → 6)-O-β-D-glucopyranoside( 1),demethylflavasperone gentiobioside( 2),nor-rubrofusarin-6-O-β-D-glucophyranoside( 3),nor-rubrofusarin-6-O-β-D-( 6'-O-acetyl) glucopyranoside( 4),and nor-rubrofusarin gentiobioside( 5). Conclusions Compound 1 is a new compound.
Objective To investigate the chemical constituents from the seeds of Cassia obtusifolia L.Methods The chemical constituents were isolated by various modern chromatographic techniques. Their structures were identified by spectral analysis. Results Five compounds were isolated from the seeds of Cassia obtusifolia L. They were identified as 5,10-dihydroxy-8-methoxy-2-methyl-4H-naphtho [1,2-b]pyranone-10-O-β-D-glucopyranosyl-( 1 → 3)-O-β-D-glucopyranosyl-( 1 → 6)-O-β-D-glucopyranoside( 1),demethylflavasperone gentiobioside( 2),nor-rubrofusarin-6-O-β-D-glucophyranoside( 3),nor-rubrofusarin-6-O-β-D-( 6'-O-acetyl) glucopyranoside( 4),and nor-rubrofusarin gentiobioside( 5). Conclusions Compound 1 is a new compound.
引文
[1]国家药典委员会.中华人民共和国药典:一部[M].北京:中国医药科技出版社,2005:145.
[2]王艳霓,管养洪,彭飞,等. HPLC法测定决明子中橙黄决明素和大黄素的含量[J].中国中医药现代远程教育,2016,14(24):143-144.
[3]王祥,余炜,万毅.决明子炮制提取工艺及食品开发[J].中医药临床杂志,2016,28(4):590-592.
[4]耿丹丹,刘灵娣,欧阳燕飞,等.决明子中萘骈吡喃酮类化学成分及其生物活性研究进展[J].特产研究,2017(3):64-67.
[5]王杰.决明子的化学成分和医疗作用[J].山东中医学院,1989,8(6):33.
[6]王小华,邓斌,张晓军,等.决明子黄酮类化合物的提取工艺研究[J].现代农业科技,2008(24):7-8.
[7]刘娟,邓泽元.决明子在医药及食品应用中的进展[J].食品研究与开发,2001,22(5):7-12.
[8]吴远远,孟哲,孙汉文.超声波辅助提取决明子中脂溶性成分的GC-MS分析[J].河北大学学报,2011,31(3):258-261.
[9]杨美丽,张少杰,杨金蕊,等.决明子的特征图谱研究及质量分析[J].中国药业,2015,24(22):75-77.
[10]MEI L,TANG Y C,LI M,et al. Co-administration of cholesterol-lowering probiotics and anthraquinone from Cassia obtusifolia L. ameliorate non-alcoholic fatty liver[J]. PloS One,2015,10(9):e0138078.
[11]张喜,董慧.决明子及其主要成分治疗高血脂症的研究进展[J].现代中西医结合杂志,2014,23(35):3972-3974.
[12]卢金清,黎强,李肖爽,等.决明子研究进展[J].湖北中医药大学学报,2014,16(4):124-126.
[13]谭颖杰.决明子水提物对自发性高血压大鼠降压作用的实验研究[J].中外医学研究,2012,10(27):141.
[14]金雪梅,金光洙.天然蒽醌抗肿瘤作用机制研究进展[J].延边大学医学学报,2006,29(3):221-223.
[15]刘斌,巩鸿霞,肖学凤,等.决明子化学成分及药理作用研究进展[J].药物评价研究,2010,33(4):312-315.
[16]吴宿慧,刘亚敏,李寒冰,等.基于自由基学说研究决明子水煎液对小鼠静止代谢率和抗氧化活性的影响[J].中成药,2015,37(6):1343-1347.
[17]田大年,黄宇.决明子茶中游离蒽醌含量及抗氧化能力的研究[J].食品研究与开发,2014,35(12):54-57.
[18]PARK J H,LEE H S. Antimicrobial activities of 1,2-dihydroxyanthraquinone derivatives against food-borne bacteria[J]. Journal of the Korean Society for Applied Biological Chemistry,2015,58(1):121-125.
[19]陈艳玲,饶春恺.不同炮制方法对决明子抗菌作用的影响[J].药物研究,2001,10(4):7.
[20]项昭保,金光辉,王光利.决明子有效成分提取工艺和药理作用研究进展[J].食品工业科技,2013,34(2):387-391.
[21]吕翠婷,黎海彬,李续娥,等.中药决明子的研究进展[J].食品科技,2006,31(8):295-298.
[22]张加雄,万丽,胡轶娟,等.决明子提取物泻下作用研究[J].时珍国医国药,2005,16(6):467-468.
[23]李博萍,陈依雨,潘竞镪.决明子提取物对非酒精性脂肪肝大鼠的护肝、拮抗胰岛素抵抗和抗氧化糖基化作用[J].环球中医药,2015,8(10):1171-1175.
[24]李卉旭.中药治疗单纯型糖尿病视网膜病变64例分析[J].中国误诊学杂志,2008,8(15):3697-3698.
[25]TANAKA T,NAKASHIMA T,UEDA T,et al. Facile discrimination of aldose enantiomers by reversedphase HPLC[J]. Chemical&Pharmaceutical Bulletin,2007,55(6):899-901.
[26]LEE H J,JUNG J H,KANG S S,et al. A rubrofusarin gentiobioside isomer from roasted Cassia tora[J]. Archives of Pharmacal Research,1997,20(5):513-515.
[27]LI X C,DUNBAR D C,ELSOHLY H N,et al. A new naphthopyrone derivative from Cassia quinquangulata and structural revision of quinquangulin and its glycosides[J]. Journal of Natural Products,2001,64(9):1153-1156.
[28]李丽,张村肖,永庆,等.炒决明子的苷类成分研究[J].中国中药杂志,2010,35(12):1566-1568.
[29]HATANO T,UEBAYASHI H,ITO H,et al. Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillinresisrant Staphylococcus aureus[J]. Chemical&Pharmaceutical Bulletin,1999,47(8):1211-1127.
[2]王艳霓,管养洪,彭飞,等. HPLC法测定决明子中橙黄决明素和大黄素的含量[J].中国中医药现代远程教育,2016,14(24):143-144.
[3]王祥,余炜,万毅.决明子炮制提取工艺及食品开发[J].中医药临床杂志,2016,28(4):590-592.
[4]耿丹丹,刘灵娣,欧阳燕飞,等.决明子中萘骈吡喃酮类化学成分及其生物活性研究进展[J].特产研究,2017(3):64-67.
[5]王杰.决明子的化学成分和医疗作用[J].山东中医学院,1989,8(6):33.
[6]王小华,邓斌,张晓军,等.决明子黄酮类化合物的提取工艺研究[J].现代农业科技,2008(24):7-8.
[7]刘娟,邓泽元.决明子在医药及食品应用中的进展[J].食品研究与开发,2001,22(5):7-12.
[8]吴远远,孟哲,孙汉文.超声波辅助提取决明子中脂溶性成分的GC-MS分析[J].河北大学学报,2011,31(3):258-261.
[9]杨美丽,张少杰,杨金蕊,等.决明子的特征图谱研究及质量分析[J].中国药业,2015,24(22):75-77.
[10]MEI L,TANG Y C,LI M,et al. Co-administration of cholesterol-lowering probiotics and anthraquinone from Cassia obtusifolia L. ameliorate non-alcoholic fatty liver[J]. PloS One,2015,10(9):e0138078.
[11]张喜,董慧.决明子及其主要成分治疗高血脂症的研究进展[J].现代中西医结合杂志,2014,23(35):3972-3974.
[12]卢金清,黎强,李肖爽,等.决明子研究进展[J].湖北中医药大学学报,2014,16(4):124-126.
[13]谭颖杰.决明子水提物对自发性高血压大鼠降压作用的实验研究[J].中外医学研究,2012,10(27):141.
[14]金雪梅,金光洙.天然蒽醌抗肿瘤作用机制研究进展[J].延边大学医学学报,2006,29(3):221-223.
[15]刘斌,巩鸿霞,肖学凤,等.决明子化学成分及药理作用研究进展[J].药物评价研究,2010,33(4):312-315.
[16]吴宿慧,刘亚敏,李寒冰,等.基于自由基学说研究决明子水煎液对小鼠静止代谢率和抗氧化活性的影响[J].中成药,2015,37(6):1343-1347.
[17]田大年,黄宇.决明子茶中游离蒽醌含量及抗氧化能力的研究[J].食品研究与开发,2014,35(12):54-57.
[18]PARK J H,LEE H S. Antimicrobial activities of 1,2-dihydroxyanthraquinone derivatives against food-borne bacteria[J]. Journal of the Korean Society for Applied Biological Chemistry,2015,58(1):121-125.
[19]陈艳玲,饶春恺.不同炮制方法对决明子抗菌作用的影响[J].药物研究,2001,10(4):7.
[20]项昭保,金光辉,王光利.决明子有效成分提取工艺和药理作用研究进展[J].食品工业科技,2013,34(2):387-391.
[21]吕翠婷,黎海彬,李续娥,等.中药决明子的研究进展[J].食品科技,2006,31(8):295-298.
[22]张加雄,万丽,胡轶娟,等.决明子提取物泻下作用研究[J].时珍国医国药,2005,16(6):467-468.
[23]李博萍,陈依雨,潘竞镪.决明子提取物对非酒精性脂肪肝大鼠的护肝、拮抗胰岛素抵抗和抗氧化糖基化作用[J].环球中医药,2015,8(10):1171-1175.
[24]李卉旭.中药治疗单纯型糖尿病视网膜病变64例分析[J].中国误诊学杂志,2008,8(15):3697-3698.
[25]TANAKA T,NAKASHIMA T,UEDA T,et al. Facile discrimination of aldose enantiomers by reversedphase HPLC[J]. Chemical&Pharmaceutical Bulletin,2007,55(6):899-901.
[26]LEE H J,JUNG J H,KANG S S,et al. A rubrofusarin gentiobioside isomer from roasted Cassia tora[J]. Archives of Pharmacal Research,1997,20(5):513-515.
[27]LI X C,DUNBAR D C,ELSOHLY H N,et al. A new naphthopyrone derivative from Cassia quinquangulata and structural revision of quinquangulin and its glycosides[J]. Journal of Natural Products,2001,64(9):1153-1156.
[28]李丽,张村肖,永庆,等.炒决明子的苷类成分研究[J].中国中药杂志,2010,35(12):1566-1568.
[29]HATANO T,UEBAYASHI H,ITO H,et al. Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillinresisrant Staphylococcus aureus[J]. Chemical&Pharmaceutical Bulletin,1999,47(8):1211-1127.