筒鞘蛇菰乙酸乙酯部位的化学成分研究
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摘要
目的:研究筒鞘蛇菰乙酸乙酯部位的化学成分,为进一步丰富该属植物的化学成分及筒鞘蛇菰的开发利用提供参考。方法:以75%乙醇提取筒鞘蛇菰全株得到醇提物,依次用石油醚、二氯甲烷、乙酸乙酯对提取物进行萃取得到相应部位萃取物。通过硅胶柱、凝胶柱、半制备柱对乙酸乙酯部位萃取物中化学成分进行分离纯化,然后结合波谱(质谱、氢谱、碳谱)数据和文献报道对分离得到的化学成分进行结构鉴定。结果:从筒鞘蛇菰乙酸乙酯部位共分离得到了13个化合物,分别鉴定为pyracanthoside(1)、5,7,3′,5′-四羟基二氢黄酮(2)、柚皮素(3)、高圣草酚(4)、橙皮素(5)、樱花亭(6)、圣草酚(7)、金鱼草素6-O-β-D-吡喃葡萄糖苷(8)、青霉酸(9)、二氢青霉酸(10)、2-甲基-3-呋喃甲酸(11)、5-hydroxymaltol(12)和5,7-二羟基色原酮(13),多为二氢黄酮类化合物。化合物2～13为首次从蛇菰属植物中分离得到。结论:本研究丰富了蛇菰属植物的化学成分,并为筒鞘蛇菰的质量评价奠定了一定基础。
OBJECTIVE:To study the chemical constituents in the ethyl acetate extract of Balanophora involucrate,and to provide reference for further enriching chemical constituent of the plant and the development and utilization of B. involucrate.METHODS:The whole plant of B. involucrate was extracted with 75% ethyl alcohol. The extraction was carried out by petroleum ether,dichloromethane,ethyl acetate and n-butyl alcohol in turn. The chemical compounds from ethyl acetate extract part were isolated and purified by silica gel column,gel column and semi-preparative HPLC. The structures were identified on the basis of spectral spectrum(mass spectrum,hydrogen spectrum and carbon spectrum) data and literature reports. RESULTS:Thirteen compounds were isolated from ethyl acetate extract part of B. involucrate,identified respectively as pyracanthoside(1),5,7,3′,5′-tetrahydroxyflavanone(2),naringenin(3),homoeriodictyol(4),hesperetin(5),sakuranetin(6),eriodyctiol(7),aureusidin-6-O-β-D-glucopyranoside(8),penicillic acid(9),dihydropenicillic acid(10),2-methyl-3-foroic acid(11),5-hydroxymaltol(12)and 5,7-dyhydroxy chromone(13). Most of them were dihydroflavones. Compounds 2 to 13 are isolated from Balanophora genus for the first time. CONCLUSIONS:The study enriched the chemical constituents of the Balanophora genus and lays foundation for quality evaluation of B. involucrate.
OBJECTIVE:To study the chemical constituents in the ethyl acetate extract of Balanophora involucrate,and to provide reference for further enriching chemical constituent of the plant and the development and utilization of B. involucrate.METHODS:The whole plant of B. involucrate was extracted with 75% ethyl alcohol. The extraction was carried out by petroleum ether,dichloromethane,ethyl acetate and n-butyl alcohol in turn. The chemical compounds from ethyl acetate extract part were isolated and purified by silica gel column,gel column and semi-preparative HPLC. The structures were identified on the basis of spectral spectrum(mass spectrum,hydrogen spectrum and carbon spectrum) data and literature reports. RESULTS:Thirteen compounds were isolated from ethyl acetate extract part of B. involucrate,identified respectively as pyracanthoside(1),5,7,3′,5′-tetrahydroxyflavanone(2),naringenin(3),homoeriodictyol(4),hesperetin(5),sakuranetin(6),eriodyctiol(7),aureusidin-6-O-β-D-glucopyranoside(8),penicillic acid(9),dihydropenicillic acid(10),2-methyl-3-foroic acid(11),5-hydroxymaltol(12)and 5,7-dyhydroxy chromone(13). Most of them were dihydroflavones. Compounds 2 to 13 are isolated from Balanophora genus for the first time. CONCLUSIONS:The study enriched the chemical constituents of the Balanophora genus and lays foundation for quality evaluation of B. involucrate.
引文
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[25]蒲首丞,郭远强,高文远.天胡荽化学成分的研究[J].中草药,2010,41(9):1440-1442.
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[2]阮汉利,张勇慧,皮慧芳,等.蛇菰的化学成分研究[J].天然产物研究与开发,2006,18(1):74-75.
[3]陈吉炎,李聪,王雪琴,等.蛇菰属药用植物的种类与研究进展[J].时珍国医国药,2010,21(8):2032-2034.
[4]阮汉利,张娟,赵晓亚,等.筒鞘蛇菰镇痛抗炎作用的研究[J].中医药学刊,2003,21(6):910-911.
[5]周卫华,石慧娟,杨梅松竹,等.蛇菰水提物对大鼠酒精性肝损伤的保护作用[J].中国老年学杂志,2012,32(20):4438-4440.
[6]张亚雄,涂璇,胡滨,等.蛇菰内生菌的抑菌作用及活性有效成分分析[J].时珍国医国药,2010,21(10):2509-2510.
[7]何玲,高辉,李春艳.筒鞘蛇菰多糖抗疲劳作用研究[J].怀化学院学报,2011,30(11):43-45.
[8]王慧,张红岐,邬昊洋,等.筒鞘蛇菰提取物及松柏苷的抗氧化作用研究[J].三峡大学学报,2009,31(3):99-101.
[9] PAN J,ZHANG S,YAN L,et al. Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18column[J]. J Chromatogr A,2008,1185(1):117-129.
[10] TAO J,ZHAO J,ZHAO Y,et al. BACE inhibitory flavanones from Balanophora involucrata Hook. f.[J]. Fitoterapia,2012,83(8):1386-1390.
[11]潘建宇,周媛,邹坤,等.筒鞘蛇菰的化学成分研究[J].中草药,2008,39(3):327-331.
[12]罗兵,邹坤,王慧,等.筒鞘蛇菰化学成分研究[J].时珍国医国药,2007,18(8):1929-1930.
[13] LUO B,ZOU K,GUO Z. Balanoinvolin,a new steroid derivative from Balanophora involucrate[J]. Chem Nat Comp,2009,45(3):371-373.
[14] OLENNIKOV DN,TANKHAEVA LM,PARTILKHAEV VV,et al. Chemical study of caragana spinosa seeds[J].Chemistry of Natural Compounds,2012,48(1):114-117.
[15]周学明,刘洪新,陈寿,等.桃金娘叶的化学成分研究[J].中草药,2016,47(15):2614-2620.
[16]李瑞玲,孙俊馥,杨森,等.白英正丁醇萃取部位的化学成分研究[J].中国药房,2016,27(30):4252-4254.
[17] LIU L,HO DK. CASSADY JM,et al. Isolation of potential cancer chemopreventive agents from Eriodictyon californicum[J]. J Nat Prod,1992,55(3):357-363.
[18]樊晓娜,林生,朱承根,等.小花异裂菊中的芳香化学成分及其活性[J].中国中药杂志,2011,36(1):48-56.
[19] VASCONCELOS JMJ,SILVA AMS,CAVALEIRO JAS.Chromones and flavanones from artemisia campestris subsp. maritime[J]. Phytochemistry,1998,49(5):1421-1424.
[20] MORETTI C,SAUVAIN M,LAVAUD C. A novel antiprotozoal aminosteroid from Saracha punctuate[J]. J Nat Prod,1998,61(11):1390-1393.
[21] SEABRA RM,ANDRADE PB,FERRERES F,et al. Methoxylated aurones from Cyperus capitatus[J]. Phytochemistry,1997,45(4):839-840.
[22]王立波,王健伟,甘春丽,等.沙生蜡菊花降脂活性部位的化学成分[J].沈阳药科大学学报,2011,28(11):868-870.
[23] SETO H,CARY LW,TANABE M. Letter:utilization of13C-13C coupling in structural and biosynthetic studies.Ⅳ.penicillic acid[J]. J Antibiot(Tokyo),1974,27(7):558-567.
[24]陈光英,朱峰,林永成.海洋放线菌Streptomyces sp.V5产生的一个新的八元环内酯[J].有机化学,2007,27(9):1159-1161.
[25]蒲首丞,郭远强,高文远.天胡荽化学成分的研究[J].中草药,2010,41(9):1440-1442.
[26]李占林,李丹毅,李铣,等.文冠果果壳中一个新生物碱[J].药学学报,2006,41(12):1197-1200.