目的 利用分子拓扑结构探讨归肺和大肠经中药成分“印迹模板”的特征，并进行实验验证，确定归肺和大肠经可能的物质基础。方法 以普通高等教育“十三五”国家级规划教材《中药学》为基准，为排除其他经络如肝经、肾经等混合归经的影响，对443味中药（不包含附药）进行归纳且只确定归肺和大肠经中药，再通过查阅中国知网和中药系统药理学数据库与分析平台（Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform，TCMSP），归纳总结出归肺和大肠经中药化学成分，并对其中相同的化学成分进行整理、删减、合并，计算分子连接性指数（molecular connectivity index，MCI）；运用夹角余弦法计算出各成分MCI与总体平均MCI的相似度，确定成分部位和对照品；建立相似度与保留时间的关系，进行中药与对照品的HPLC指纹图谱的印迹性比较，从而确定归肺和大肠经可能表征的化学结构特征。结果 共获得11味中药的886种化学成分，黄酮、蒽醌、鞣质类成分的相似度较高，且在药材中分布集中，故选取其中相似度排名依次为5、8、10、16、40、44、49的7个成分：大黄素-1-O-β-D-葡萄糖苷、大黄酚-8-O-β-D-葡萄糖苷、大黄素-8-O-β-D-吡喃葡萄糖苷、3,3'-二甲基鞣花酸-4'-O-葡萄糖苷、山柰苷、芦丁、山柰酚-3-O-芸香糖苷，平均MCI的相似度为0.995 08～0.999 20，保留时间为39.63～60.14 min，基于定量结构-性质关系/定量结构-保留时间关系（quantitative structure-property relationship/quantitative structure-retention relationship，QSPR/QSRR）原理，对二者进行线性回归，相关系数R＝0.866 2（P＜0.01）；7个成分和9味药材的总量统计矩的一阶矩的15%范围分别为[44.46 min，46.50 min]、[39.70 min，47.08 min]，二者重叠，则有85%把握认为可用7个对照品成分表征归肺和大肠经的中药成分的“印迹模板”特征。结论 归肺和大肠经的中药成分可以用黄酮、蒽醌和鞣酸类成分进行“印迹模板”特征的表征。

Objective The molecular topological structures of “imprinted template” of traditional Chinese medicine (TCM) components attributed to lung and large intestine meridian tropism were explored, and the possible material bases were verified experimentally. Methods Based on the Traditional Chinese Pharmacology, as a textbook of the 13th Five-Year national planning for general higher education, 443 flavors of TCMs (excluding accompanying drugs) were investigated to screen out the TCMs attributed to lung and large intestine meridian tropism. By consulting CNKI and Traditional Chinese Medicine Systems Pharmacology Database and Analysis Platform (TCMSP) database, the chemical components of TCMs attributed to lung and large intestine meridian tropism were collected, and the same chemical components were deleted and integrated. Their molecular connectivity indexes (MCI) were calculated out in matrix, of which the similarity of each component versus total averages were calculated by the intersection angle cosine method. The components and their fraction were ranked according to the similarity, and from them selecting referent substances. The relationship between similarity and retention time was established to compare the imprinting of HPLC fingerprints of TCMs and referent substances, so as to determine the possible chemical structure characteristics attributed lung and large intestine meridian. Results A total of 886 chemical components were obtained from 11 flavors of TCMs. The flavonoids, anthraquinones and tannins were highly similar and concentrated in the medicinal materials, among which the seven components (emodin-1-O-β-D-glucoside, chrysophanol-8-O-β-D-glucoside, emodin-8-O-β-D-glucopyranoside, 3,3'-dimethyl ellagic acid-4'-O-glucoside, kaempferol, rutin, kaempferol-3-O-rutinoside) were selected with similarity ranking of 5, 8, 10, 16, 40, 44, 49, with the similarity to MCI in average as 0.995 08 to 0.999 20, were studied chromatographically, and their retentive times were from 39.63 min to 60.14 min. Based on the principle of quantitative structure-property relationship/ quantitative structure-retention relationship (QSPR/QSRR), the linear regression was conducted between the MCI and retentive times, as a result that there were a good correlation coefficient of R = 0.866 2 (P < 0.01). The first-order moments of the total statistical moments for the seven chemical components to the nine flavors of TCMs were in the interval of [44.46 min, 46.50 min] to [39.70 min, 47.08 min] in possibility of 15% correspondingly, and their intervals were overlapped. There was 85% confidence that seven reference components could be used to characterize the “imprinting template” characteristics of TCM components attributed to lung and large intestine meridian tropism. Conclusion Flavonoids, anthraquinone and tannic acid can be used to characterize the “imprinting template” characteristics of the TCM components of lung and large intestine meridian tropism.

R284；R285

国家自然科学基金资助项目（82274215）；湖南省大学生创新创业训练计划项目（S202110541027）；湖南省重点研发计划（2022SK2014）；湖南省自然科学基金和科药联合基金项目（2022JJ30453，2021JJ80058）