目的 研究紫苏叶Perillae Folium的化学成分，化学模式识别法建立紫苏叶HPLC指纹图谱，并研究其抗流感病毒活性，为其进一步开发利用提供依据。方法 采用超高效液相色谱-三重四级杆飞行时间质谱联用（UPLC-Q-TOF-MS/MS）技术，鉴定紫苏叶的主要化学成分，建立HPLC指纹图谱，匹配共有峰并进行归属，通过对照品比对指认6种化学成分，使用SPSS 22.0、SIMCA 14.1软件进行聚类分析和主成分分析（principal component analysis，PCA），测定其抗流感病毒生物效价，并通过灰色关联分析（gray correlation analysis，GCA）建立其谱效关系。结果 从紫苏叶中鉴定出47个化合物；选取了19个色谱峰作为指纹图谱的共有峰，通过聚类分析可将15批紫苏叶分为2类，PCA与聚类分析结果基本一致；15批不同产地的紫苏叶样品均具有抗流感病毒活性，其生物效价为6.21、5.58、4.19、8.19、6.09、5.82、6.10、5.36、5.54、10.86、4.74、5.78、3.78、7.98、5.65 U/mg。19个共有峰与抗病毒活性存在一定的关联度（0.82～0.97），各共有峰代表的化学成分对其抗病毒活性贡献的大小顺序为峰6（咖啡酸）、19（木犀草素）＞2、8、9、12（阿魏酸）＞4、5、15（芹菜素-7-O-二葡萄糖醛酸苷）＞7、13＞11＞3、10、17＞1、16（野黄芩苷）＞14＞18（迷迭香酸）。结论 构建的紫苏叶抗流感病毒活性生物效价测定方法能关联其临床功效，而UPLC-Q-TOF-MS/MS法能快速鉴定紫苏叶的成分，结合指纹图谱和化学模式识别，发现紫苏叶抗病毒作用为“多成分”共同起效的结果，这将为其质量控制提供科学依据。

Objective To study the chemical components of Zisuye (Perillae Folium, PF), and establish the HPLC fingerprints of PF based on chemical pattern recognition, so as to provide basis for further development and utilization. Methods Qualitative analysis of the chemical components of PF was carried out by UPLC-Q-TOF-MS/MS, the HPLC fingerprints of PF were established to determine the common peaks. Six chemical components were identified and the content of the samples was determined by comparison with the reference materials. Cluster analysis and principal component analysis (PCA) were carried out by SPSS 22.0 and SIMCA 14.1 software. The antiviral activities were determined, and spectrum-effect relationship was established by gray correlation analysis (GCA). Results A total of 47 compounds were identified from PF. Nineteen chromatographic peaks were selected as the common peaks of the fingerprint, 15 bathes of PF could be divided into two categories by cluster analysis, and the results of PCA and cluster analysis were basically the same. Fifteen batches of samples from different producing areas all showed antiviral activities. The biological-potency were 6.21, 5.58, 4.19, 8.19, 6.09, 5.82, 6.10, 5.36, 5.54, 10.86, 4.74, 5.78, 3.78, 7.98 and 5.65 U/mg, respectively. The correlation between HPLC fingerprint and the antiviral activities was from 0.82 to 0.97. The contribution of chemical compositions represented by each characteristic peak to the antioxidant activity was in the order of peak 6 (caffeic acid), 19 (luteolin) > 2, 8, 9, 12 (ferulic acid) > 4, 5, 15 (apigenin-7-O-diglucuronoside) > 7, 13 > 11 > 3, 10, 17 > 1, 16 (scutellarin) > 14 > 18 (rosmarinic acid). Conclusion The UPLC-Q-TOF-MS/MS method can quickly identify the chemical components of PF, and the antiviral activities of PF may be the combined effect of a variety of chemical constituents. The establishment of HPLC fingerprint of PF and the application of chemical pattern recognition can provide scientific basis for quality control of PF.

国家自然科学基金资助项目（81860711）；广西高校中青年教师科研基础能力提升项目（2020KY07034）；2020年度广西壮瑶药重点实验室运行补助项目（桂科基[2019]32号）