目的:从壮药拟草果中制备纯化3,5-二羟基-7,4'-二甲氧基黄酮候选化学对照品并建立其质量分析方法。方法:采用硅胶柱色谱、重结晶和高效制备液相色谱等,从拟草果中制备纯化得到高纯度的3,5-二羟基-7,4'-二甲氧基黄酮,通过红外、紫外、核磁共振等综合波谱解析方法及质谱确定其化学结构,采用薄层色谱法、高效液相色谱法检测色谱纯度,炽灼残渣法测定灰分,质量平衡法计算3,5-二羟基-7,4'-二甲氧基黄酮的含量。采用高效液相色谱法对建立的3,5-二羟基-7,4'-二甲氧基黄酮候选化学对照品质量分析方法进行方法学考察。结果:3,5-二羟基-7,4'-二甲氧基黄酮候选化学对照品用高效液相色谱法面积归一化法测定的含量均值为99.85%,炽灼残渣法测得灰分值为0.02%,以质量平衡法计算的含量为99.83%。建立的含量测定方法专属性强,精密度良好。结论:制备得到的3,5-二羟基-7,4'-二甲氧基黄酮候选化学对照品符合化学对照品的质量标准要求,可作为拟草果及其他含有此成分的药材与制剂质量控制的对照品。建立的质量分析方法准确、可靠,可为该对照品质量标准研究与制定提供科学依据。
Objective: To study the preparation and quality control of 3, 5-dihydroxy-7, 4'-dimethoxyflavone candidate chemical reference substance from Zhuang medicine Amomum paratsaoko S. Q. Tong & Y. M. Xia. Methods: 3, 5-dihydroxy-7, 4'-dimethoxyflavone was separated and purified consecutively by silica gel, recrystallization as well as preparative HPLC. The structure of 3, 5-dihydroxy-7, 4'-dimethoxyflavone was identified by IR, UV, NMR and other comprehensive spectrum analytical methods with MS spectrum. Its purity was determined by HPLC and TLC, the ash content was determined by incandescent residue method, and the content of 3, 5-dihydroxy-7, 4'-dimethoxyflavone was calculated by mass balance method. The method for quality analysis of 3, 5-dihydroxy-7, 4'-dimethoxyflavone candidate reference materials was investigated by HPLC. Results: The mean value determined by HPLC of 3, 5-dihydroxy-7, 4'-dimethoxyflavone was 98.85%, the ash value was 0.02%, and the content of 3, 5-dihydroxy-7, 4'-dimethoxyflavone calculated by mass balance method was 99.83%. The established analytical method was specific and precise. Conclusion: 3, 5-Dihydroxy-7, 4'-dimethoxyflavone which was prepared in this study met the quality standard requirements of chemical reference substance, and could be used as a reference substance for quality control of medicinal materials and their preparations such as Amomum paratsaoko S. Q. Tong & Y. M. Xia and others. The analysis method was accurate and reliable, which provided a scientific basis for the research and formulation of quality standard of this reference substance.
[1] 刘布鸣, 邱宏聪. 中药化学对照品研究与开发[J]. 广西科学, 2019, 26(5): 461
LIU BM, QIU HC. Research and development of traditional chinese medicine chemical reference substance[J]. Guangxi Sci, 2019, 26(5): 461
[2] BIAN QY, WANG SY, XU LJ, et al. Two new antioxidant diarylheptanoids from the fruits of Alpinia oxyphylla[J]. J Asian Nat Prod Res, 2013, 15(10): 1094
[3] CHAREONKLA A, POHMAKOTR M, REUTRAKUL V, et al. A new diarylheptanoid from the rhizomes of Zingiber mekongense[J]. Fitoterapia, 2011, 82(4): 534
[4] JASRII, MOOI LY, LAJIS NH, et al. Antioxidant and antitumor promoting activities of the flavonoids from Hedychium thyrsiforme[J]. Pharm Biol, 2003, 41(7): 506
[5] SUDSAI T, PRABPAI S, KONGSAEREE P, et al. Anti-inflammatory activity of compounds from Boesenbergia longiflora rhizomes[J]. J Ethnopharm, 2014, 154(2): 453
[6] SUDSAI T, WATTANAPIROMSAKUL C, TEWTRAKUL S. Wound healing property of isolated compounds from Boesenbergia kingii rhizomes[J]. J Ethnopharm, 2016, 184: 42
[7] SUN J, ZHOU W, WEI CX, et al. A new benzofuran from Artemisia halodendron Turcz. ex Bess[J]. Nat Prod Res, 2019, 33(2): 226
[8] 张丽坤, 罗都强, 冯玉龙, 等. 入侵植物飞机草的化学成分及其抗肿瘤活性[J]. 中成药, 2013, 35(3): 545
ZHANG LK, LUO DQ, FENG YL, et al. Chemical constituents of Chromolaena odorata and their anticancer activities[J]. Chin Tradit Pat Med, 2013, 35(3): 545
[9] RAHMAN MM, GIBBONS S. Antibacterial constituents of Neohyptis paniculata[J]. Fitoterapia, 2015, 105: 269
[10] VEDERNIKOV DN, ROSHCHIN VI. Extractive compounds of betulaceae family birch buds (Betula pendula Roth.): Ⅳ. Composition of sesquiterpene diols, triols, and flavonoids[J]. Russ J Bioorg Chem, 2012, 38(7): 753
[11] WOLLENWEBER E, DÖRR M. Flavonoid aglycones from the lipophilic exudates of some species of Rosaceae[J]. Biochem Syst Ecol, 2008, 36(5-6): 481
[12] ZHOU X, ZHANG Z, XU Y, et al. Flavone and isoflavone derivatives of terrestrial plants as larval settlement inhibitors of the barnacle Balanus amphitrite[J]. Biofouling, 2009, 25(1): 69
[13] CABANILLAS BJ, LE LAMER AC, OLAGNIER D, et al. Leishmanicidal compounds and potent PPAR gamma activators from Renealmia thyrsoidea (Ruiz & Pav.) Poepp. & Endl[J]. J Ethnopharm, 2014, 157: 149
[14] BENMERACHE A, BENTELDJOUNE M, ALABDUL MAGID A, et al. Chemical composition, antioxidant and antibacterial activities of Tamarix balansae J. Gay aerial parts[J]. Nat Prod Res, 2017, 31(24): 2828
[15] 柴玲, 陈明生, 袁健童, 等. 拟草果总黄酮制备纯化及抗炎活性研究[J]. 广西植物, 2020, 40(12): 1706
CHAI L, CHEN MS, YUAN JT, et al. Purification and anti-inflammatory activitiy of total flavonoids from Amomum psratasoko[J]. Guihaia, 2020, 40(12): 1706
[16] 柴玲, 林霄, 梁柏照, 等. 拟草果化学成分研究[J]. 中草药, 2018, 49(14): 3217
CHAI L, LIN X, LIANG BZ, et al. Chemical constituens from fruits of Amomum psratasoko[J]. Chin Tradit Herb Drug, 2018, 49(14): 3217
[17] 冯军, 柴玲, 陈明生, 等. 指纹图谱结合一测多评法评价拟草果质量的研究[J]. 中草药, 2021, 52(3): 852
FENG J, CHAI L, CHEN MS, et al. Application of fingerprint combined with QAMS in quality evaluation of Amomum paratsaoko[J]. Chin Tradit Herb Drug, 2021, 52(3): 852
[18] 张轶华, 田晓彤, 王柳, 等. 主成分自身对照法测定注射用奥美拉唑钠中的7个已知杂质[J]. 药物分析杂志, 2022, 42(7): 1201
ZHANG YH, TIAN XT, WANG L, et al. Determination of seven impurities in omeprazole sodium for injection by main component self-compare method[J]. Chin J Pharm Anal, 2022, 42(7): 1201
[19] 袁健童, 柴玲, 陈明生, 等. 棒柄花叶中胡椒酚-β-D-吡喃葡萄糖苷候选对照品的制备研究[J]. 药物分析杂志, 2023, 43(5): 889
YUAN JT, CHAI L, CHEN MS, et al. Preparation of candidate reference substance of chavicol-β-D-glucopyranoside from leaves of Cleidion brevipetiolatum [J]. Chin J Pharm Anal, 2023, 43(5): 889
[20] 国家药典委员会. 国家药品标准工作手册[M]. 北京: 中国医药科技出版社, 2015: 449
Chinese Pharmacopoeia Commission. National Drug Standard Working Manual[M]. Beijing: China Medical Science and Technology Press, 2015: 449
