补骨脂的化学成分研究

doi:10.19803/j.1672-8629.2021.06.13

中国药物警戒 ›› 2021, Vol. 18 ›› Issue (6): 556-561.
DOI: 10.19803/j.1672-8629.2021.06.13

补骨脂的化学成分研究

高胡彤悦, 高盼盼, 臧应达, 马洁, 杨敬芝, 叶菲, 李创军^*, 张东明^#

中国医学科学院北京协和医学院药物研究所,天然药物生物活性物质和功能国家重点实验室,北京 100050

收稿日期:2021-03-04 出版日期:2021-06-15 发布日期:2021-07-02
通讯作者: ^*李创军,男,博士,副研究员,天然药物化学。E-mail: lichuangjun@imm.ac.cn;^#为共同通信作者。
作者简介:高胡彤悦,女,在读硕士,药物化学。
基金资助:
国家重点研发计划（2019YFC1711000）; 国家自然科学基金资助项目（21772234）; 中国医学科学院医学与健康科技创新工程（2016-I2M-2-003; 2019-I2M-1-005）

Chemical Constituents of Psoralea corylifolia L.

GAO Hutongyue, GAO Panpan, ZANG Yingda, MA Jie, YANG Jingzhi, YE Fei, LI Chuangjun^*, ZHANG Dongming^#

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Received:2021-03-04 Online:2021-06-15 Published:2021-07-02

摘要/Abstract

摘要： 目的研究补骨脂（Psoralea corylifolia L.）的化学成分。方法利用硅胶柱色谱,MCI柱色谱,ODS柱色谱以及高效液相色谱等分离手段,对补骨脂的95%乙醇提取物进行化学成分研究,并通过质谱和核磁共振等波谱数据对分离得到的化合物进行结构鉴定。结果从补骨脂的95%乙醇提取物中分离鉴定10个化合物,分别是seputhecarpan A（1）、补骨脂酚（2）、13-羟基异补骨脂酚（3）、12-羟基异补骨脂酚（4）、二聚补骨脂酚A（5）、二聚补骨脂酚B（6）、二聚补骨脂酚C（7）、4, 2′-二羟基-4′-甲氧基-5′-（3′′, 3′′-二甲基烯丙基）-查尔酮（8）、isobavachromene（9）、4-hydroxyisolonchocarpin（10）。结论化合物1首次从该植物中分离得到。蛋白质酪氨酸磷酸酶1B（PTP1B）抑制活性实验,结果显示化合物2和7具有PTP1B抑制活性。

关键词: 补骨脂, 单萜酚, 黄酮, PTP1B抑制活性

Abstract: Objective To analyze the chemical constituents of the fruit of Psoralea corylifolia L.. Methods 95% ethanol extract of Psoralea corylifolia L. was studied with silica gel, MCI, ODS column chromatography and high performance liquid chromatography. The structure was elucidated with MS and NMR. Results Ten compounds were isolated from 95% ethanol extract of Psoralea corylifolia L.. They were seputhecarpan A (1), bakuchiol (2), 13-hydroxyisobakuchiol (3), 12-hydroxyisobakuchiol (4), bisbakuchiol A (5), bisbakuchiol B (6), bisbakuchiol C (7), 4, 2'-dihydroxy-4'-methoxy-5′-(3'', 3''-dimethylallyl)-chalkone (8), isobavachromene (9) and 4-hydroxyisolonchocarpin (10). Conclusion Compound 1 was isolated from this plant for the first time. The results of evaluation of PTP1B inhibitory activities showed that compounds 2 and 7 displayed significant PTP1B inhibitory activities.

Key words: Psoralea corylifolia L., monoterpene phenols, flavonoids, PTP1B inhibitory activity

中图分类号:

R961

高胡彤悦, 高盼盼, 臧应达, 马洁, 杨敬芝, 叶菲, 李创军, 张东明. 补骨脂的化学成分研究[J]. 中国药物警戒, 2021, 18(6): 556-561.

GAO Hutongyue, GAO Panpan, ZANG Yingda, MA Jie, YANG Jingzhi, YE Fei, LI Chuangjun, ZHANG Dongming. Chemical Constituents of Psoralea corylifolia L.[J]. Chinese Journal of Pharmacovigilance, 2021, 18(6): 556-561.

参考文献

[1] Chinese Pharmacopoeia Commission.Pharmacopoeia of the people's Republic of China: Volume I, 2020 edition (中华人民共和国药典:一部,2020年版)[S]. Beijing: China Medical Science and Techno-logy Press, 2020.
[2] Jiang S, Tong HY, Hu YZ, et al.To observe the efficacy of the combination of Buguzhi tinctures and narrow-band ultraviolet B (NB-UVB) in the treatment of vitiligo[J]. Chin. Pharm.(中国药师), 2013, 16(7): 1051-1052.
[3] Li WD, Yan CP, Wu Y, et al.Osteoblasts proliferation and differe-ntiation stimulating activities of the main components of fructus Psoraleae corylifoliae[J]. Phytomedicine, 2014, 21(4): 400-405.
[4] Xu QX, Xu W, Yang XW, et al.Meroterpenoids from the fruits of Psoralea corylifolia[J]. Tetrahedron, 2020, 76(31-32): 131343-131350.
[5] Xu QX, Zhang YB, Liu XY.Cytotoxic heterodimers of meroterpene phenol from the fruits of Psoralea corylifolia[J]. Phytochemistry, 2020, 176: 112394-112340.
[6] Zhang X, Zhao W, Wang Y, et al.The chemical constituents and bioactivities of Psoralea corylifolia Linn.: a review[J]. Am J Chin Med, 2016, 44(1): 35-60.
[7] Yang T T, Qin M J.Isolation and structure identification of new isoflavones from Psoralea corylifolia[J]. Acta Pharmaceutica Sinica(药学学报), 2006, 41(1): 76-79.
[8] Wei YY, Zhang ZJ, Xu Y, et al.Estrogenic effect of Psoraleae Fructus in ovariectomized rats[J]. Chinese J Exp Formulas(中国实验方剂学杂志), 2011, 17(13): 158-161.
[9] Tan M, Sun J, Zhao H, et al.Comparative study of the effects of psoralen on breast cancer MCF-7 and MDA-MB-231 cells in vitro[J]. J. Guangzhou Univ Tradit. Chin. Med(广州中医药大学学报), 2009, 26(4): 359-362.
[10] Xiao GD, Li GW, Chen L, et al.Isolation of antioxidants from Psoralea corylifolia fruits using high-speed countercurrent chroma-tography guided by thin layer chromatography-antioxidant autog-raphic assay[J]. J. Chromatogr A, 2010, 1217(34): 5470-5476.
[11] Katsura H, Tsukiyama RI, Suzuki A, et al.In vitro antimicrobial activities of bakuchiol against oral microorganisms[J]. Antimicrob Agents Ch, 2001, 45(11): 3009-3013.
[12] Pae HO, Cho H, Oh GS, et al.Bakuchiol from Psoralea corylifolia inhibits the expression of inducible nitric oxide synthase gene via the inactivation of nuclear transcription factor-kappaB in RAW 264. 7 macrophages[J]. Int Immunopharmacol, 2001, 1(9-10): 1849-1855.
[13] Kong LD, Tan RX, Woo AY, et al.Inhibition of rat brain monoamine oxidas activities by psoralen and isopsoralen: implications for the treatment of affective disorders[J]. Pharmacol Toxicol, 2001, 88(2): 75-80.
[14] Cho H, Jun JY, Song EK, et al.Bakuchiol: A hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in HepG2 cells[J]. Planta Med, 2001, 67: 750-751.
[15] Park EJ, Zhao YZ, Kim YC, et al.Protective effect of (S)- bakuchiol from Psoralea corylifolia on rat liver injury in vitro and in vivo[J]. Planta Med, 2005, 71(6): 508-513.
[16] Don MJ, Lin LC, Chiou WF, et al.Neobavaisoflavone stimulates osteogenesis via p38-mediated up-regulation of transcription factors and osteoid genes expression in MC3T3-E1 cell[J]. Phytomedicine, 2012, 19(6): 551-561.
[17] Kim YC, Oh H, Kim BS, et al.In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia[J]. Planta Med, 2005, 71(1): 87-89.
[18] Li C, Li CJ, Xu KL, et al.Novel oligomeric neolignans with PTP1B inhibitory activity from the bark of Magnolia officinalis var. biloba[J]. Bioorganic Chemistry, 2020, 104: 104319-104326.
[19] Li C, Li C J, Ma J, et al.Magterpenoids A-C, three polycyclic meroterpenoids with ptp1b inhibitory activity from the bark of Magnolia officinalis var. biloba[J]. Org Lett, 2018, 20: 3682-3686.
[20] Ma YM, Tao RY, Liu Q, et al.PTP1B inhibitor improves both insulin resistance and lipid abnormalities in vivo and in vitro[J]. Molecular & Cellular Biochemistry, 2011, 357(1-2): 65-72.
[21] Fotso G W, Maher F A, Ngnintedo D, et al.Three new isoflavonoids with antioxidant properties from Ptycholobium contortum (NE Br.) Brummitt (Leguminosae)[J]. Phytochemistry Letters, 2015, 14: 254-259.
[22] Mehta G, Nayak UR, Dev S, et al.Meroterpenoids-I: Psoralea corylifolia Linn.-1. Bakuchiol, a novel monoterpene phenol[J]. Tetrahedron, 1973, 29(8): 1119-1125.
[23] Cecilia L, Francesca F, Joseph C, et al.Bakuchiol derivatives from the leaves of Psoralea glandulosa[J]. Phytochemistry, 1996, 42(5): 1299-1303.
[24] Wu CZ, Cai XF, Dat NT, et al.Bisbakuchiols A and B, novel dimeric meroterpenoids from Psoralea corylifolia[J]. Tetrahedron Letters, 2007, 48(50): 8861-8864.
[25] Wu CZ, Hong SS, Cai XF, et al.Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia[J]. Bioorganic Medicinal Chemistry Letters, 2008, 18(8): 2619-2623.
[26] Agarwal D, Garg SP, Sah P, et al.Isolation of Chalkones from the Seeds of Psoralea corylifolia Linn.[J]. ChemInform, 2010, 38(11): 2574-2579.
[27] Máximo P, Ana L, Feio SS, et al.Flavonoids from Ulex Species[J]. Ztschrift Fur Naturforschung C A Journal of Bioences, 2000, 55(7-8): 506-510.
[28] Ryu HW, Lee JH, Kang JE, et al.Inhibition of xanthine oxidase by phenolic phytochemicals from Broussonetia papyrifera[J]. Journal of the Korean Society for Applied Biological Chemistry, 2012, 55(5): 587-594.

补骨脂的化学成分研究

Chemical Constituents of Psoralea corylifolia L.

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