厚朴中联苯型木脂素类成分及其生物活性研究

doi:10.6023/cjoc202512009

有机化学

厚朴中联苯型木脂素类成分及其生物活性研究

施冲煜, 陈家毅, 吕喆云, 舒积成, 张英琪, 刘建群^*

江西中医药大学现代中药制剂教育部重点实验室,江西南昌 330004

收稿日期:2025-12-09 修回日期:2026-02-06
基金资助:
国家自然科学基金项目（No. 82160731）; 江西中医药大学校级科技创新团队发展计划（No. CXTD22007）资助项目

Bioactive Biphenyl Lignans from Magnolia officinalis

SHI Chongyu, CHEN jiayi, LV zheyun, SHU jicheng, ZHANG yingqi, LIU Jianqun^*

Key Laboratory of Modern Preparation of Traditional Chinese Medicine, Ministry of Education, Jiangxi University of Chinese Medicine, Nanchang 330004, China

Received:2025-12-09 Revised:2026-02-06
Contact: ^*Email: liu5308@sina.com
Supported by:
National Natural Science Foundation of China ( No. 82160731 ) and Jiangxi University of Traditional Chinese Medicine Science and Technology Innovation Team Development Plan (No. CXTD22007 )

文章分享

1. 附件.pdf(1238KB)

摘要/Abstract

从中药厚朴皮中分离鉴定了12 个联苯型木脂素,其中薄荷基厚朴酚(menthylmagnolol, 1)为第二个报道的、罕见的薄荷基与厚朴酚通过六元环骈的单萜联苯型木脂素新化合物。它的结构通过高分辨质谱、一维/二维核磁共振谱和圆二色谱(ECD)等波谱技术得到确定。和厚朴酚4'-O-β-D-葡萄糖苷(honokiol 4′-O-β-D-glucoside, 9)为新的天然产物,其它联苯型木脂素2~12的结构通过与文献报道的核磁共振等波谱数据对比确定。首次发现化物3~6对蛋白酪氨酸磷酸酶1B(PTP1B)具有显著抑制活性,IC₅₀值分别为：9.20±1.95,9.23±1.12,8.71±0.54和6.90±0.70 μM。化合物4~6、10有显著的幽门螺旋杆菌抑制活性,最低抑菌浓度(MIC)均为500 mg/L。初步构效关系表明薄荷基等单萜基团的引入有利于提高联苯型木脂素的PTP1B酶和幽门螺旋杆菌抑制活性。结果表明单萜骈联苯型木脂素具有作为抗Ⅱ型糖尿病以及抗幽门螺旋杆菌药物的开发潜力。

关键词: 厚朴, 联苯型木脂素, 蛋白酪氨酸磷酸酶1B抑制活性, 抗幽门螺旋杆菌活性

Twelve biphenyl lignans including a new monoterpene biphenyl lignan (menthylmagnolol, 1) and a new natural product (honokiol 4′-O-β-D-glucoside, 9), along with ten known ones (2-12) were isolated from the cortex of Magnoliae officinalis. Their structures were elucidated by HR-MS and spectroscopic methods including 1D/2D NMR and ECD and so on. To the best of our knowledge, only one natural monoterpene biphenyl lignan in which the monoterpene unit and biphenyl lignan unit were fused via a six-membered ring was reported and compound 1 was the second reported natural product with this structural feature. Their in vitro inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and Helicobacter pylori were evaluated for the first time. Compounds 3~6 showed significant inhibitory activity against protein PTP1B, with IC₅₀ values of 9.20±1.95, 9.23±1.12, 8.71±0.54 and 6.90±0.70 μM, respectively. Compounds 4~6 and 10 showed significant anti-Helicobacter pylori activity with MIC all of 500 mg/L. The preliminary structure-activity relationship exhibited that the monoterpene units of biphenyl lignans were probably beneficial to improve the inhibitory activities against PTP1B and Helicobacter pylori. The research results indicate that monoterpene biphenyl lignans have development potential as drugs for treating type Ⅱdiabetes and Helicobacter pylori infections.

Key words: Magnolia officinalis, Biphenyl lignans, PTP1B inhibitory activity, anti-Helicobacter pylori activity

引用此文

施冲煜, 陈家毅, 吕喆云, 舒积成, 张英琪, 刘建群. 厚朴中联苯型木脂素类成分及其生物活性研究[J]. 有机化学, doi: 10.6023/cjoc202512009.

SHI Chongyu, CHEN jiayi, LV zheyun, SHU jicheng, ZHANG yingqi, LIU Jianqun. Bioactive Biphenyl Lignans from Magnolia officinalis[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202512009.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Editorial Board of the National Pharmacopoeia Chinese Pharmacopoeia, The Medicine Science and Technology Press of China, 2025 (in Chinese).
(国家药典编委会, 中华人民共和国药典, 中国医药科技出版社, 2025.)
[2] Zhang X.-J.;Zuo D.-D.;Hu N.-N.;Wang Y.-L. Inf. Tradit. Chin. Med. 2023, 40, 85(in Chinese).
(张晓娟,左冬冬,胡妮娜,王艳丽.中医药信息, 2023, 40, 85.)
[3] Wu J.-M.;Ying Y.-Q.;Yang Z.-H.;Jin Y.;Fang Y.-Y.J. Shenyang Pharm. Univ. 2023, 40, 1098(in Chinese).
(吴佳敏,应宇琦,杨尊华,金一,房元英.沈阳药科大学学报, 2023, 40, 1098.)
[4] Peng Y.;Liang J.-Q.;Duan Y.-Q.;Zhang Y.-Y.;Bai M.;Hu J.-R.;Song B.;Yuan X.-M.;Liu Z.-Y.Chin. Tradit. Pat. Med. 2025, 47, 641(in Chinese).
(彭月,梁建庆,段永强,张延英,白敏,虎峻瑞,宋冰,袁晓梅,刘自由.中成药, 2025, 47, 641.)
[5] Jiang H.-X.;Chen W.-J.;Xu W.-W.;Ma Q.-G.;Sun Q.;Chen S.;Liu J.-Q.Chin. Pharmacol. Bull. 2023, 39, 1764(in Chinese).
(蒋红霞,陈婉君,许炜炜,马勤阁,孙群,陈殊,刘建群.中国药理学通报, 2023, 39, 1764.)
[6] Jing W.-G.;Du J.;Wang J.-Y.;Sun X.-B.;Lan Q.-S. Mod. Chin. Med. 2018, 20, 764(in Chinese).
(荆文光,杜杰,王继永,孙晓波,兰青山.中国现代中药, 2018, 20, 764.)
[7] Chen J.-Y.;Shi C.-Y.;Shi X.-Y.; Liu J.-Q. Nat. Prod. Res. Dev. 2024, 36, 1625(in Chinese).
(陈家毅,施冲煜,石宣宜,刘建群. 天然产物研究与开发, 2024, 36, 1625)
[8] Li C.; Li C.-J.; Ma J.; Huang J.-W.; Wang X.-Y.; Wang X.-L.; Ye F.; Zhang D.-M.; Bioorganic Chemistry. 2018, 88, 102948.
[9] Li C.; Li C.-J.; Ma J.; Chen F.-Y.; Li L.; Wang X.-Y.; Ye F.; Zhang D.-M.; Org. Letters. 2018, 20, 3682.
[10] Luo H.-Y.; Wu H.-W.; Yu X.-K.; Zhang X.; Lu Y.-Q.; Fan J.-W.; Tang L.-Y.; Wang Z.-J.J. Ethnopharmacol. 2019, 236, 412.
[11] Thi P. N.; Thu T. C.H.; Huy, T. T.;Phuong, N. H.; Sinh, N. K.; Thi, N. D.; Thu, T. L. H.; Van, T. C.; Quynh, T. V. N.; The, N. A.; Quy, T. H.; Van, T. S.; Ngoc, H. A.; Phuong, T. T. T.Nat. Prod. Res. 2020, 35, 1.
[12] Wang Z.-J.; Chen Y.-C.; Zou F.-C.; Qin Y.; Zhu Y.-Y.; Xiao X.; Xie T.-Z.; He Y.-J.; Zhao Y.-L.; Luo X.-D.J. Agric. Food Chem. 2023, 71.
[13] Davis T. S.; Indrajit N. S.; Mrinalini K. D.; Remmei M.; Lhaineichong K.; Shanjukumar L. S.; Chandra N. B.; Ningombam S.; Brajakishor C. S.; Ramsing T. S. Molecules.2022, 27, 7288.
[14] Shih H.-C.; Kuo P.-C.; Wu S.-J.; Hwang T.-L.; Hung H.-Y.; Shen D.-Y.; Shieh P.-C.; Liao Y.-R.; Lee E.-J.; Gu Q.; Lee K.-H.; Wu T.-S.Bioorg. Med. Chem. 2016, 24, 1439.
[15] YAHARA S.; NISHIYORI T.; KOHDA A.; NOHARA T.; NISHIOKA I.Chem. Pharm. Bull. 1991, 39, 2024.
[16] Li J.; Zhang Y.-J.; Jin B.-F.; Su X.-J.; Tao Y.-W.; She Z.-G.; Lin Y.-C.Magn. Reson. Chem. 2008, 26, 497.
[17] Yang L.; Wang Z.-H.; Lei H.; Chen R.; Wang X.-L.; Peng Y.; Dai J.-G.Tetrahedron. 2014, 70, 8244.
[18] Ni H.-F.; Cai X.-Y.; Qiu X.; Liu L.; Ma X.; Wan L.;Ye H.-Y.; Chen L.-J.Fitoterapia. 2020, 147, 104769.
[19] Tang H.; Zhang Y.-G.; Li D.; Fu S.-H.; Tang M.-H.; Wan L.; Chen K.; Liu J.-W.; Xue L.-L.; Peng A.-H.; Ye H.-Y.; Chen L.-J.Eur. J. Med. Chem. 2018, 156, 190.
[20] Zhang B.-B.; Yu H.-T.; Lu W.; Yu B.; Liu L.; Jia W.-J.; Lin Z.-T.; Wang H.; Chen S.-Z.Phytochem. Lett. 2019, 29, 195.
[21] Zhao J.-N.; Yan Y.-F.; Zhang X.; Zhang M.-J.; Yan J.-J.; Liang, H.-H. Nat. Prod. Res. Dev.2024, 36, 1698(in Chinese).
(赵金诺,覃怡发,张轩,张梦娇,晏晶晶,梁皓皓. 天然产物研究与开发, 2024, 36, 1698)
[22] Geng C. M.S. Thesis, China Medical University, Shenyang, 2021(in Chinese).
(耿聪, 硕士论文, 中国医科大学, 沈阳, 2021.)