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2025年6月14日 16:52 星期六
首页 > 过刊浏览>2023年第54卷第12期 >2023,54(12):3759-3770. DOI:10.7501/j.issn.0253-2670.2023.12.002
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五味子中1个新的联苯环辛烯类木脂素

A new dibenzocyclooctadiene lignan from Schisandra chinensis

发布日期：2023-06-15
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    [关键词]
    [摘要]
    目的 研究中药五味子Schisandra chinensis的木脂素类化学成分。方法 采用硅胶柱色谱、中压反相柱色谱、半制备和制备液相对五味子中富含木脂素类成分的石油醚萃取部位进行分离、纯化，通过波谱数据鉴定化合物的结构。结果 从五味子中分离得到了26个化合物，分别鉴定为绿叶五味子素B（1）、sphaerandrin A（2）、sieverlignan E（3）、arisanschinin G（4）、widdaranal F（5）、戈米辛A（6）、戈米辛B（7）、戈米辛D（8）、戈米辛G（9）、(−)-戈米辛K1（10）、(＋)-戈米辛K2（11）、(−)-戈米辛L1（12）、(＋)-戈米辛M1（13）、戈米辛N（14）、当归酰戈米辛H（15）、当归酰戈米辛O（16）、当归酰戈米辛Q（17）、苯甲酰戈米辛Q（18）、五味子醇甲（19）、五味子甲素（20）、五味子乙素（21）、五味子丙素（22）、五味子酯丙（23）、neglschisandrin E（24）、7(18)-dehydroschisandro A（25）、安五脂素（26），其中24个为联苯环辛烯类木脂素（1～4、6～25）。结论 化合物1为新化合物，化合物2～5为首次从该植物中分离得到。
    [Key word]
    [Abstract]
    Objective To study the lignans in Schisandra chinensis. Methods The petroleum ether extract mainly contained lignans of S. chinensis was isolated and purified by silica gel column chromatography, medium pressure reversed phase column chromatography, semi-prepared and prepared liquid chromatography. The structures of compounds were identified by spectral data. Results Twenty-six compounds were obtained, in which 24 were dibenzocyclooctadiene lignans. They were identified as schiviridin B (1), sphaerandrin A (2), sieverlignan E (3), arisanschinin G (4), widdaranal F (5), gomisin A (6), gomisin B (7), gomisin D (8), gomisin G (9), (−)-gomisin K1 (10), (+)-gomisin K2 (11), (−)-gomisin L1 (12), (+)-gomisin M1 (13), gomisin N (14), angeloylgomisin H (15), angeloylgomisin O (16), angeloylgomisin Q (17), benzoylgomisin Q (18), schisandrin (19), schisandrin A (20), γ-schisandrin (21), schisandrin C (22), schisantherin C (23), neglschisandrin E (24), 7(18)-dehydroschisandro A (25), and anwulignan (26).Conclusion Compound 1 is new and compounds 2-5 are isolated from this plant for the first time.
    [中图分类号]
    R284.1
    [基金项目]
    国家自然科学基金项目（32070356）
    [1] 中国药典[S]. 一部. 2020:68.
    [2] Zhou Y, Men L H, Sun Y X, et al. Pharmacodynamic effects and molecular mechanisms of lignans from Schisandra chinensis Turcz. (Baill.), a current review[J]. Eur J Pharmacol, 2021, 892:173796-173807.
    [3] 陈丽华, 许智莹, 林程程, 等. 五味子木脂素舒张大鼠离体气管平滑肌的功能研究[J]. 西北农林科技大学学报:自然科学版, 2021, 49(10):24-29.
    [4] 孙靖辉, 吕希, 王春梅, 等. 五味子木脂素对哮喘模型小鼠Th2相关炎症因子的影响[J]. 北华大学学报:自然科学版, 2020, 21(3):325-328.
    [5] Zhong S, Nie Y C, Gan Z Y, et al. Effects of Schisandra chinensis extracts on cough and pulmonary inflammation in a cough hypersensitivity guinea pig model induced by cigarette smoke exposure[J]. J Ethnopharmacol, 2015, 165:73-82.
    [6] 林豪, 王阔, 曾钦成, 等. 基于网络药理学和分子对接技术探讨五味子治疗慢性咳嗽的机制研究[J]. 北华大学学报:自然科学版, 2022, 23(4):466-470.
    [7] 赵红舟, 龙杞, 刘肇恒, 等. 五味子乙素对博来霉素诱导小鼠肺纤维化的干预作用及机制研究[J]. 环球中医药, 2021, 14(4):556-561.
    [8] 魏菲, 刘斌, 肖娜, 等. 五味子乙素减轻博莱霉素诱导的肺纤维化[J]. 天津中医药大学学报, 2017, 36(3):200-204.
    [9] Zhong S, Bai L P, Liu X D, et al. Cough inhibition activity of Schisandra chinensis in guinea pigs[J]. J Med Food, 2021, 24(4):348-357.
    [10] Lv X, Xu Z Y, Xu G Y, et al. Investigation of the active components and mechanisms of Schisandra chinensis in the treatment of asthma based on a network pharmacology approach and experimental validation[J]. Food Funct, 2020, 11(4):3032-3042.
    [11] Kim H, Ahn Y T, Kim Y S, et al. Antiasthmatic effects of schizandrae fructus extract in mice with asthma[J]. Pharmacogn Mag, 2014, 10(Suppl 1):S80-S85.
    [12] 李舒丰, 刘芹燕, 刘文东, 等. 苏黄止咳胶囊及其挥发油中间体中挥发性成分的分析[J]. 中成药, 2017, 39(11):2329-2334.
    [13] 刘芹燕, 巫兴东, 陈东, 等. 苏黄止咳胶囊中非挥发性成分的LC-MS分析[J]. 中成药, 2019, 41(6):1434-1445.
    [14] Wu X D, Liu Q Y, Chen D, et al. Identification of quality control markers in Suhuang antitussive capsule based on HPLC-PDA fingerprint and anti-inflammatory screening[J]. J Pharm Biomed Anal, 2020, 180:113053-113061.
    [15] Tian T, Liu Y, Yu H Y, et al. Dibenzocyclooctadiene lignans from the fruits of Schisandra viridis[J]. Chem Nat Compd, 2015, 51(6):1046-1048.
    [16] Ying Y M, Yu H F, Rao G W, et al. Dibenzocyclooctadiene lignans from the stems of Schisandra sphaerandra[J]. Nat Prod Res, 2022, 36(1):287-294.
    [17] Zhou X D, Chen C X, Zheng X K, et al. Dibenzocyclooctadiene lignans from Artemisia sieversiana and their anti-inflammatory activities[J]. J Nat Med, 2021, 75(4):1014-1020.
    [18] Cheng Y B, Chang M T, Lo Y W, et al. Oxygenated lignans from the fruits of Schisandra arisanensis[J]. J Nat Prod, 2009, 72(9):1663-1668.
    [19] Amujuri D, Siva B, Bharathi K, et al. Bio-active constituents from Schisandra grandiflora:Isolation, semi-synthesis and evaluation of their anticancer activities[J]. Phytochem Lett, 2021, 45:184-189.
    [20] Choi S K, Lee Y G, Wang R B, et al. Dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis and their cytotoxicity on human cancer cell lines[J]. Appl Biol Chem, 2020, 63(1):1-8.
    [21] Ikeya Y, Taguchi H, Yosioka I, et al. The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin[J]. Chem Pharm Bull, 1979, 27(6):1383-1394.
    [22] 刘俊霞, 窦凤鸣, 王英平. 五味子藤茎中木脂素类化合物的杀虫活性成分研究[J]. 天然产物研究与开发, 2017, 29(7):1210-1217.
    [23] Ikeya Y, Taguchi H, Yosioka I. The constituents of Schizandra chinensis Baill. VII. The structures of three new lignans, (−)-gomisin K1 and (+)-gomisins K2 and K3[J]. Chem Pharm Bull, 1980, 28(8):2422-2427.
    [24] Ikeya Y, Taguchi H, Yosioka I. The Constituents of Schizandra chinensis Baill. X. The structures of GAMMA-schizandrin and four new lignans, (−)-gomisins L1 and L2, (±)-gomisin M1 and (+)-gomisin M2[J]. Chem Pharm Bull, 1982, 30(1):132-139.
    [25] Rui T, Lian-Niang L, Qicheng F. Studies on the chemical constituents of Kadsura longipedunculata:Isolation and structure elucidation of five new lignans[J]. Planta Med, 1984, 50(5):414-417.
    [26] Piao L Z, Lee Y J, PhamPhu T T, et al. Dibenzocyclooctene lignan compounds isolated from the fruits of Schisandra chinensis Baill[J]. Nat Prod Sci, 2005, 11(4):248-252.
    [27] Ikeya Y, Ookawa N, Taguchi H, et al. The constituents of Schizandra chinensis Baill. XI. The structures of three new lignans, angeloylgomisin O, and angeloyl- and benzoylisogomisin O[J]. Chem Pharm Bull, 1982, 30(9):3202-3206.
    [28] Ikeya Y, Miki E, Okada M, et al. Benzoylgomisin Q and benzoylgomisin P, two new lignans from Schisandra sphenanthera Rehd. et Wils[J]. Chem Pharm Bull, 1990, 38(5):1408-1411.
    [29] Ikeya Y, Taguchi H, Yosioka I. The constituents of Schizandra chinensis Baill. The cleavage of the methylenedioxy moiety with lead tetraacetate in benzene, and the structure of angeloylgomisin Q[J]. Chem Pharm Bull, 1979, 27(10):2536-2538.
    [30] Yan Z F, Guo J, Tian F H, et al. Active compounds from Schisandra chinensis exhibiting tyrosinase activity and melanin content inhibition in B16 melanoma cells[J]. Biotechnol Bioproc E, 2015, 20(4):814-823.
    [31] Smejkal K, Slapetová T, Krmenčík P, et al. Evaluation of cytotoxic activity of Schisandra chinensis lignans[J]. Planta Med, 2010, 76(15):1672-1677.
    [32] Chen M, Xu X M, Xu B, et al. Neglschisandrins E-F:Two new lignans and related cytotoxic lignans from Schisandra neglecta[J]. Molecules, 2013, 18(2):2297-2306.
    [33] Song Z H, Houa Y, Han N, et al. Research on the biotransformation of four Schisandra lignans[J]. J Tradit Chin Med, 2015, 10(6):129-133.
    [34] Baek N I, Lee Y G, Wang R B, et al. Anwulignan from the fruits of Schisandra chinensis and its cytotoxicity against human cancer cell lines[J]. Phcog Mag, 2020, 16(72):695-699.
    [35] 郭超, 童希洋, 秦伟伟, 等. 苏黄止咳胶囊改善哮喘豚鼠气道重塑的作用及其机制[J]. 中成药, 2021, 43(4):893-901.
    [36] Tong X Y, Liang R Y, Jia Y N, et al. Suhuang antitussive capsules-ameliorative effects on LPS-induced sputum obstruction in mice through promoting HGF secretion[J]. Front Pharmacol, 2019, 10:1422-1436.
    [37] Qin W W, Tong X Y, Liang R Y, et al. Preservation of mitochondrial homeostasis is responsible for the ameliorative effects of Suhuang antitussive capsule on non-resolving inflammation via inhibition of NF-κB signaling and NLRP3 inflammasome activation[J]. J Ethnopharmacol, 2021, 271:113827-113844.
    [38] Qin W W, Wu X D, Jia Y N, et al. Suhuang antitussive capsule inhibits NLRP3 inflammasome activation and ameliorates pulmonary dysfunction via suppression of endoplasmic reticulum stress in cough variant asthma[J]. Biomedecine Pharmacother, 2019, 118:109188-109202.
    [39] Jiang H, Bai Z Y, Ou Y Y, et al. β-Hydroxybutyric acid upregulated by Suhuang antitussive capsule ameliorates cough variant asthma through GSK3β/AMPK-Nrf2 signal axis[J]. J Ethnopharmacol, 2023, 307:116013-116025.
    [40] Liang R Y, Tong X Y, Dong Z K, et al. Suhuang antitussive capsule ameliorates post-infectious cough in mice through AhR-Nrf2 pathway[J]. J Ethnopharmacol, 2022, 283:114664-114676.
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