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 ›› 2026, Vol. 46 ›› Issue (6): 2337-2345.DOI: 10.6023/cjoc202512009 上一篇下一篇

研究论文

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南昌 330004

收稿日期:2025-12-09 修回日期:2026-02-06 发布日期:2026-04-27
通讯作者: 刘建群
基金资助:
国家自然科学基金(82160731); 江西中医药大学校级科技创新团队发展计划(CXTD22007)

Study on Biphonyl Lignans and Their Biological Activities from Magnolia officinalis

Chongyu Shi, Jiayi Chen, Zheyun Lü, Jicheng Shu, Yingqi Zhang, Jianqun Liu^*()

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

Received:2025-12-09 Revised:2026-02-06 Published:2026-04-27
Contact: Jianqun Liu
Supported by:
National Natural Science Foundation of China(82160731); Science and Technology Innovation Team Development Plan of Jiangxi University of Traditional Chinese Medicine(CXTD22007)

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摘要/Abstract

从中药厚朴皮中分离鉴定了12个联苯型木脂素, 其中包括一个新的单萜联苯型木脂素薄荷基厚朴酚(menthylmagnolol, 1)和一个新的天然产物和厚朴酚4'-O-β-D-葡萄糖苷(honokiol 4'-O-β-D-glucoside, 9), 此外还包括10个已知联苯型木脂素. 结构通过高分辨质谱及一维/二维核磁共振波谱及圆二色谱等波谱技术得以鉴定, 其中, 化合物1是第2个被报道的单萜单元与联苯单元通过六元环连接的单萜联苯型木脂素. 首次评估了它们对蛋白酪氨酸磷酸酶1B (PTP1B)和幽门螺杆菌的体外抑制活性, 发现化合物3~6对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) μmol/L. 化合物4~6和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, 结果证实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 were isolated from the bark of Magnoliae officinalis. Their structures were elucidated by HRMS and spectroscopic methods including 1D/2D NMR and electronic circular dichroism (ECD) and so on. Compound 1 was the second reported natural monoterpene biphenyl lignan in which the monoterpene unit and biphenyl lignan unit were fused via a six-membered ring. 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) μmol/L, respectively. Compounds 4~6 and 10 showed significant anti-Helicobacter pylori activity with minimum inhibitory concentration (MIC) 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 II diabetes and Helicobacter pylori infections.

Key words: Magnolia officinalis, biphenyl lignan, protein tyrosine phosphatase 1B (PTP1B) inhibitory activity, anti-Helico- bacter 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, 2026, 46(6): 2337-2345.

Chongyu Shi, Jiayi Chen, Zheyun Lü, Jicheng Shu, Yingqi Zhang, Jianqun Liu. Study on Biphonyl Lignans and Their Biological Activities from Magnolia officinalis[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2337-2345.

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参考文献 22

[1]	Editorial Board of the National Pharmacopoeia, Chinese Pharmacopoeia, The Medicine Science and Technology Press of China, Beijing, 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, 北京, 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. Bioorg. Chem. 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. Lett. 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.; Lhainei- chong, 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.; KohdaA, 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.)

No	δ_H^a	J/Hz	δ_C^a
1	—	—	126.30 (C)
2	6.89 (d)	8.1	130.99 (CH)
3	—	—	129.20 (C)
4	—	—	152.77 (C)
5	—	—	127.94 (C)
6	6.81 (d)	8.1	128.72 (CH)
7	3.32 (d)	6.7	40.48 (CH₂)
8	5.94~5.97 (m)	—	139.56 (CH)
9	5.05~5.09( m)	—	115.50 (CH₂)
10	—	—	76.90 (C)
11	1.99 d (13.2) 1.67~1.68 (m)	—	31.50 (CH₂)
12	3.12 (d)	—	36.27 (CH)
13	1.17~1.20 (m)	—	49.11 (CH)
14	1.53~1.54 (m)	—	20.93 (CH₂)
15	1.64~1.69 (m)	—	35.96 (CH₂)
16	1.88 (m)	—	27.37 (CH)
17	1.11 (d)	6.5	21.63 (CH₃)
18	0.98 (d)	6.5	22.43 (CH₃)
19	1.27 (s)	—	29.51 (CH₃)
1'	—	—	132.06 (C)
2'	7.01 (d)	8.1	132.70 (CH)
3'	—	—	132.52 (C)
4'	—	—	153.73 (C)
5'	6.79 (d)	2.2	117.44 (CH)
6'	6.99 (dd)	2.3, 8.1	129.40 (CH)
7'	3.32 (d)	6.7	40.48 (CH₂)
8'	5.98~6.01 (m)	—	139.50 (CH)
9'	5.00~5.03 (m)	—	115.44 (CH₂)

No	δ_H^a	J/Hz	δ_C^a
1	—	—	126.30 (C)
2	6.89 (d)	8.1	130.99 (CH)
3	—	—	129.20 (C)
4	—	—	152.77 (C)
5	—	—	127.94 (C)
6	6.81 (d)	8.1	128.72 (CH)
7	3.32 (d)	6.7	40.48 (CH₂)
8	5.94~5.97 (m)	—	139.56 (CH)
9	5.05~5.09( m)	—	115.50 (CH₂)
10	—	—	76.90 (C)
11	1.99 d (13.2) 1.67~1.68 (m)	—	31.50 (CH₂)
12	3.12 (d)	—	36.27 (CH)
13	1.17~1.20 (m)	—	49.11 (CH)
14	1.53~1.54 (m)	—	20.93 (CH₂)
15	1.64~1.69 (m)	—	35.96 (CH₂)
16	1.88 (m)	—	27.37 (CH)
17	1.11 (d)	6.5	21.63 (CH₃)
18	0.98 (d)	6.5	22.43 (CH₃)
19	1.27 (s)	—	29.51 (CH₃)
1'	—	—	132.06 (C)
2'	7.01 (d)	8.1	132.70 (CH)
3'	—	—	132.52 (C)
4'	—	—	153.73 (C)
5'	6.79 (d)	2.2	117.44 (CH)
6'	6.99 (dd)	2.3, 8.1	129.40 (CH)
7'	3.32 (d)	6.7	40.48 (CH₂)
8'	5.98~6.01 (m)	—	139.50 (CH)
9'	5.00~5.03 (m)	—	115.44 (CH₂)

Compound	MIC/(mg•L^–1)
1
2	1000
3	1000
4	500
5	500
6	500
7	>1000
8	>1000
9	>1000
10	500
11	>1000
12	>1000
Clarithromycin	31.3

Compound	MIC/(mg•L^–1)
1
2	1000
3	1000
4	500
5	500
6	500
7	>1000
8	>1000
9	>1000
10	500
11	>1000
12	>1000
Clarithromycin	31.3

厚朴中联苯型木脂素类成分及其生物活性研究

Study on Biphonyl Lignans and Their Biological Activities from Magnolia officinalis

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Compound	IC₅₀ value/(μmol•L^–1)
1	≈100
2	≈100
3	9.20±1.95
4	9.23±1.12
5	8.71±0.54
6	6.90±0.70
7	>100
8	>100
9	>100
10
11
12
Oleanolic acid	13.72±5.26

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