麸炒白术化学成分的研究
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摘要
目的:研究麸炒白术的化学成分。方法:采用硅胶柱色谱方法进行分离纯化,通过质谱、核磁共振等谱学数据鉴定化合物结构。结果:从麸炒白术70%乙醇水提取物中鉴定了20个化合物,分别为苍术酮(1)、蒲公英萜醇乙酯(2)、白术内酯Ⅶ(3)、白术内酯Ⅰ(4)、双白术内酯(5)、双表白术内酯(6)、杜松脑(7)、白术内酯Ⅱ(8)、白术醚(9)、8-表白术内酯Ⅱ(10)、8-表白术内酯Ⅲ(11)、白术内酯Ⅲ(12)、4R,15-环氧白术内酯Ⅱ(13)、4R,15-环氧-8β-羟基白术内酯Ⅱ(14)、桉叶-4(15)、7-二烯-9α,11-二醇(15)、β-谷甾醇(16)、白术内酯Ⅳ(17)、豆甾醇(18)、葡萄糖(19)、蔗糖(20)。结论:化合物15为首次从中药白术中分离鉴定。本文首次报道麸炒白术的系统性化学成分研究。
Objective: To study the chemical constituents of Atractylodis Macrocephalae Rhizoma stir-fried with wheat bran. Methods: Repeated silica gel column chromatography was applied to the separation of compounds and their structures were determined by spectroscopic data analyses of MS and NMR. Results: Twenty compounds were obtained and identified as atractylon( 1),taraxerol acetate( 2),atractylenolide Ⅶ( 3),atractylenolide I( 4),biatractylenolide( 5),biepiatractylenolide( 6),juniper camphor( 7),atractylenolide Ⅱ( 8),atractylenother( 9),8-epiatractylenolide Ⅱ( 10),8-epiatractylenolide Ⅲ( 11),atractylenolide Ⅲ( 12),4 R,15-epoxylatractylenolide Ⅱ( 13),4 R,15-epoxy-8β-hydroxyatractylenolide Ⅱ( 14),eudesm-4( 15),7-diene-9α,11-diol( 15),β-sitosterol( 16),atractylenolide Ⅳ( 17),stigmasterol( 18),glucose( 19), and sucrose( 20), respectively. Conclusion: Compound 15 was isolated from the rhizomes of Atractylodis macrocephala for the first time. This article reports for the first time the systematic study of chemical constituents of Atractylodis Macrocephalae Rhizoma stir-fried with wheat bran.
Objective: To study the chemical constituents of Atractylodis Macrocephalae Rhizoma stir-fried with wheat bran. Methods: Repeated silica gel column chromatography was applied to the separation of compounds and their structures were determined by spectroscopic data analyses of MS and NMR. Results: Twenty compounds were obtained and identified as atractylon( 1),taraxerol acetate( 2),atractylenolide Ⅶ( 3),atractylenolide I( 4),biatractylenolide( 5),biepiatractylenolide( 6),juniper camphor( 7),atractylenolide Ⅱ( 8),atractylenother( 9),8-epiatractylenolide Ⅱ( 10),8-epiatractylenolide Ⅲ( 11),atractylenolide Ⅲ( 12),4 R,15-epoxylatractylenolide Ⅱ( 13),4 R,15-epoxy-8β-hydroxyatractylenolide Ⅱ( 14),eudesm-4( 15),7-diene-9α,11-diol( 15),β-sitosterol( 16),atractylenolide Ⅳ( 17),stigmasterol( 18),glucose( 19), and sucrose( 20), respectively. Conclusion: Compound 15 was isolated from the rhizomes of Atractylodis macrocephala for the first time. This article reports for the first time the systematic study of chemical constituents of Atractylodis Macrocephalae Rhizoma stir-fried with wheat bran.
引文
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[14]崔小兵,单晨啸,文红梅,等.基于UFLC/Q-TOF-MS分析麸炒白术的物质基础[J].中国中药杂志,2013,38(12):1929-1933.
[15]张金莲,谢日健,刘明贵,等.不同炮制方法对白术中白术内酯Ⅰ,Ⅱ,Ⅲ含量的影响[J].中国实验方剂学杂志,2016,22(21):15-18.
[16]赵文龙,吴慧,单国顺,等.麸炒白术“减酮减燥,增酯增效”炮制理论的再印证[J].中国中药杂志,2013,38(20):3493-3497.
[17]李伟,文红梅,崔小兵,等.白术的炮制机理及其倍半萜成分转化的研究[J].中国中药杂志,2006,31(19):1600-1603.
[18]宋丽艳,谷建梅.不同炮制方法对白术抗衰老作用影响的实验研究[J].中国现代医药杂志,2007,9(11):15-17.
[19] Zhang Y Q,Xu S B,Lin Y C,et al.Antagonistic effects of 3sesquiterpene lactones from Atractylodes macrocephala Koidz on rat uterine contraction in vitro[J]. Acta Pharmacol Sin,2000,21(1):91-96.
[20] Tsai C J,Liang J W,Lin H R,et al.Sesquiterpenoids from Atractylodes macrocephala act as farnesoid X receptor and progesterone receptor modulators[J]. Bioorg Med Chem Lett,2012,22:2326-2329.
[21] Jiang H,Shi J,Li Y Y.Screening for compounds with aromatase inhibiting activities from Atractylodes macrocephala Koidz[J].Molecules,2011,16(4):3146-3151.
[22] Li C Q,He L C,Jin J Q. Atractylenolide I and atractylenolideⅢinhibit lipopolysaccharide-induced TNF-αand NO production in macrophages[J]. Phytother Res,2007,21(4):347-353.
[23] Endo K,Taguchi T,Taguchi F,et al.Sesquiterpenoids.Part LV.Antiinflammatory principles of Atractylis rhizomes[J].Chem Pharml Bull,1979,27(12):2954-2958.
[2]李尧,李伟,王琳,等.麸炒白术研究述要[J].山东中医药大学学报,2018,42(2):182-185.
[3]杨秀伟.中药物质基础研究是中药继承、发展、创新的关键科学问题[J].中国中药杂志,2015,40(17):3429-3434.
[4]李滢,杨秀伟.生白术化学成分研究[J].中国现代中药,2018,20(4):382-386.
[5]杨秀伟,邹磊,吴琦,等.芙蓉菊化学成分研究[J].中国中药杂志,2008,33(8):905-908.
[6] Ding H Y,Liu M Y,Chang W L,et al.New sesquiterpenoids from the rhizomes of Atractylodes macrocephala[J]. Chin Pharm J(Taipei,Taiwan),2005,57(1):37-42.
[7]王保德,余亦华,膝宁宁,等.双表白术内酯的结构鉴定[J].化学学报,1999,57(9):1022-1025.
[8] Bagal S K,Adlington R M,Baldwin J E,et al.Biomimetic synthesis of biatractylolide and biepiasterolide[J].Org Lett,2003,5(17):3049-3052.
[9]夏郭平,冯煦,陈雨,等.北美盐角草(Salicornia bigelovii Torr.)化学成分的研究[J].天然产物研究与开发,2010,22(6):1012-1014.
[10] Li Y,Yang X W.New eudesmane-type sesquiterpenoids from the processed rhizomes of Atractylodes macrocephala[J]. J Asian Nat Prod Res,2014,16(2):123-128.
[11] Wang H X,Liu C M,Liu Q,et al.Three types of sesquiterpenes from rhizomes of Atractylodes lancea[J]. Phytochemistry,2008,69(10):2088-2094.
[12] Duan J A,Wang L Y,Qian S H,et al.A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC.[J].Arch Pharm Res,2008,31(8):965-969.
[13] Huang L Y,Cao Y Y,Xu H,et al. Separation and purification of ergosterol and stigmasterol in Anoectochilus roxburghii(wall)Lindl by high-speed counter-current chromatography[J].J Sep Sci,2011,34(4):385-392.
[14]崔小兵,单晨啸,文红梅,等.基于UFLC/Q-TOF-MS分析麸炒白术的物质基础[J].中国中药杂志,2013,38(12):1929-1933.
[15]张金莲,谢日健,刘明贵,等.不同炮制方法对白术中白术内酯Ⅰ,Ⅱ,Ⅲ含量的影响[J].中国实验方剂学杂志,2016,22(21):15-18.
[16]赵文龙,吴慧,单国顺,等.麸炒白术“减酮减燥,增酯增效”炮制理论的再印证[J].中国中药杂志,2013,38(20):3493-3497.
[17]李伟,文红梅,崔小兵,等.白术的炮制机理及其倍半萜成分转化的研究[J].中国中药杂志,2006,31(19):1600-1603.
[18]宋丽艳,谷建梅.不同炮制方法对白术抗衰老作用影响的实验研究[J].中国现代医药杂志,2007,9(11):15-17.
[19] Zhang Y Q,Xu S B,Lin Y C,et al.Antagonistic effects of 3sesquiterpene lactones from Atractylodes macrocephala Koidz on rat uterine contraction in vitro[J]. Acta Pharmacol Sin,2000,21(1):91-96.
[20] Tsai C J,Liang J W,Lin H R,et al.Sesquiterpenoids from Atractylodes macrocephala act as farnesoid X receptor and progesterone receptor modulators[J]. Bioorg Med Chem Lett,2012,22:2326-2329.
[21] Jiang H,Shi J,Li Y Y.Screening for compounds with aromatase inhibiting activities from Atractylodes macrocephala Koidz[J].Molecules,2011,16(4):3146-3151.
[22] Li C Q,He L C,Jin J Q. Atractylenolide I and atractylenolideⅢinhibit lipopolysaccharide-induced TNF-αand NO production in macrophages[J]. Phytother Res,2007,21(4):347-353.
[23] Endo K,Taguchi T,Taguchi F,et al.Sesquiterpenoids.Part LV.Antiinflammatory principles of Atractylis rhizomes[J].Chem Pharml Bull,1979,27(12):2954-2958.