光叶兔儿风中一个新的愈创木烷型倍半萜及其抗炎活性

doi:10.6023/cjoc202501020

有机化学 ›› 2025, Vol. 45 ›› Issue (8): 3028-3032.DOI: 10.6023/cjoc202501020 上一篇下一篇

研究简报

光叶兔儿风中一个新的愈创木烷型倍半萜及其抗炎活性

邱雄^a^,^b^,^d^,^†, 李慧娟^a^,^c^,^†, 唐艳玲^a^,^c^,^†, 许耀军^a^,^c, 李娜^a^,^c, 李晓莉^a^,^c^,^*(), 张兴杰^a^,^c^,^*(), 肖伟烈^a^,^b^,^c^,^d^,^*()

^a 云南大学药学院教育部自然资源药物化学重点实验室云南省特色植物提取实验室有限公司昆明 650500
^b 云南大学国际河流与生态安全研究院昆明 650500
^c 云南大学化学科学与工程学院昆明 650500
^d 西南联合研究生院昆明 650092

收稿日期:2025-01-21 修回日期:2025-03-10 发布日期:2025-03-31
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(U24A20805); 国家自然科学基金(22477108); 国家自然科学基金(82260682); 国家自然科学基金(22467022); 国家自然科学基金(22167021); 云岭学者计划资助项目及云南特色植物筛选与研发服务CXO平台(2022YKZY001); 云南大学第四届专业学位研究生实践创新(ZC-24248956); 云南省基础应用研究基金(202401AT070444); 植物化学研发共享平台KIB资助项目.

One New Guaianolide Sesquiterpenoid with Potential Anti-inflammatory Activity from Ainsliaea glabra.

Xiong Qiu^a^,^b^,^d, Huijuan Li^a^,^c, Yanling Tang^a^,^c, Yaojun Xu^a^,^c, Na Li^a^,^c, Xiaoli Li^a^,^c^,^*(), Xingjie Zhang^a^,^c^,^*(), Weilie Xiao^a^,^b^,^c^,^d^,^*()

^a Yunnan Characteristic Plant Extraction Laboratory Co. Ltd., Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education), School of Pharmacy, Yunnan University, Kunming 650500
^b Institute of International Rivers and Eco-Security, Yunnan University, Kunming 650500
^c School of Chemical Science and Technology, Yunnan University, Kunming 650500
^d Southwest United Graduate School, Kunming 650092

Received:2025-01-21 Revised:2025-03-10 Published:2025-03-31
Contact: *E-mail:lixiaoli@ynu.edu.cn;zhangxj@ynu.edu.cn;xiaoweilie@ynu.edu.cn
About author:
†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(U24A20805); National Natural Science Foundation of China(22477108); National Natural Science Foundation of China(82260682); National Natural Science Foundation of China(22467022); National Natural Science Foundation of China(22167021); Yun Ling Scholar Project and the Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(2022YKZY001); Fourth Professional Degree Graduate Practice Innovation Project of Yunnan University(ZC-24248956); Applied Basic Research Foundation of Yunnan Province(202401AT070444); and the Sharing Platform of Phytochemistry R&D, KIB.

文章分享

1. cjoc202501020辅助材料.pdf(1127KB)

摘要/Abstract

从光叶兔儿风中分离得到8个倍半萜化合物, 其中包括1个新的愈创木内酯倍半萜, 命名为ainglaolide A (1), 7个已知的倍半萜2~8. 化合物1是一种新型愈创木内酯倍半萜, 其特征是在C-4和C-15之间形成了一个罕见的六元内酯环. 通过高分辨质谱及核磁共振确定了新化合物的结构, 同时通过电子圆二色谱(ECD)计算确定了化合物1的绝对构型. 对分离得到的化合物进行抗炎活性试验, 表明化合物1对NLRP3炎性小体具有显著的抑制作用, IC₅₀值为1.86 μmol/L.

关键词: 光叶兔儿风, 倍半萜, 抗炎活性

Eight sesquiterpenes were isolated from Ainsliaea glabra. Among them, a new guaianolide sesquiterpenoid, named ainsglaolide A (1), and seven known sesquiterpenoids 2~8 were identified. Compound 1 was a novel guaianolide sesquiterpenoid featuring a rare six-membered lactone ring formed between C-4 and C-15. The new compound structure was elucidated by HRESI-MS and NMR spectroscopy, as well as electrostatic circular dichroism (ECD) calculations were used to further confirm the absolute of 1. Anti-inflammatory activity tests were conducted on the separated compounds, indicating that compound 1 had significant inhibitory effect on NLRP3 inflammasome with an IC₅₀ value of 1.86 μmol/L.

Key words: Ainsliaea glabra, sesquiterpenes, anti-inflammatory activity

引用此文

邱雄, 李慧娟, 唐艳玲, 许耀军, 李娜, 李晓莉, 张兴杰, 肖伟烈. 光叶兔儿风中一个新的愈创木烷型倍半萜及其抗炎活性[J]. 有机化学, 2025, 45(8): 3028-3032.

Xiong Qiu, Huijuan Li, Yanling Tang, Yaojun Xu, Na Li, Xiaoli Li, Xingjie Zhang, Weilie Xiao. One New Guaianolide Sesquiterpenoid with Potential Anti-inflammatory Activity from Ainsliaea glabra.[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 3028-3032.

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

分享此文

图/表 5

Figure 1. Chemical structures of compounds 1~8

Position	δ_H, mult. (J/HZ)	δ_C
1	2.62, t (5.7)	40.8
2	2.10, overlap; 1.63, overlap	30.7
3	1.97~1.89, m; 2.24, overlap	37.7
4		90.0
5	2.28, t (5.7)	50.8
6	4.08, ddd (10.4, 5.7, 1.6)	81.0
7	2.94, td (10.4, 1.6)	44.8
8	2.16, overlap; 1.46~1.35, m	26.8
9	2.46~2.38, m; 1.69, overlap	31.8
10	2.67, br s	47.9
11		139.0
12		170.0
13	6.21, dd (3.1, 1.6); 5.50, dd (3.1, 1.6)	120.6
14	1.49, s	21.8
15		173.0

Table 1. 1H NMR (400 MHz) and 13C NMR (100 MHz) data of compound 1 in CDCl3

Figure 2. Key 1H-1H COSY (), HMBC () and NOESY () correlations of compound 1

Figure 3. Experimental and calculated ECD curves of compound 1

Figure 4. Screening of anti-inflammatory compounds from Alisliaea glabra at LDH and elisa level (A) Primary evaluation of the impact of compounds 1 through 8 on lactate dehydrogenase (LDH) release was conducted (n=3), MCC950 served as the positive control in this assay. Compounds with lower LDH release were identified with a red arrow (B, C). Calculate IC50 for compounds with good anti-inflammatory activity. The LDH release inhibition rate of compound 1 (1.25, 2.5, 5, 10 μmol/L) was evaluated in J774A.1 cells of NLRP3 inflammasome-activated. (D) IL-1β level (ELISA). The data of are represented by mean±SD. The LPS＋Nigericin group served as A control (A), *P<0.05, **P<0.01, ***P<0.001. n.s.=not significant (P>0.05).

参考文献 19

[1]	Editorial Committee of Flora of China Flora of China, Vol. 79, Science Press, Beijing, 2004, p. 68.
[2]	Hisanori, J. Yakugaku Zasshi 1982, 102, 911.
[3]	Li, X.; Wang, W.; Jaeger, F.; Kreyenschmidt, J. Nat. Prod. Res. 2014, 2, 115.
[4]	Wang, H.; Wu, T.; Yan, M.; Liu, G.; Li, P.; Zhang, X. Q.; Ye, W. C.; Zhang, L. Y. Chem. Pharm. Bull. 2009, 6, 597.
[5]	Wu, Z. J.; Xu, X. K.; Zeng, H. W.; Shen, Y. H. Planta Med. 2011, 13, 1545.
[6]	Zeng, R. T.; Dong, X. Y.; Fang, X.; Yang, N.; Shi, Z. R.; Zhuo, Z. G.; Shen, Y. H.; Zhang, W. D. Chem. Biodiversity 2017, 12, e1600210.
[7]	Lone, S. H.; Bhat, K. A.; Khuroo, M. A. Chem. Biodiversity 2015, 240, 180.
[8]	Chu, H.; Smith, J. M.; Felding, J.; Baran, P. S. ACS Cent. Sci. 2017, 1, 47.
[9]	Wu, Z. J; Xu, X. K.; Shen, Y. H.; Su, J.; Tian, J. M.; Liang, S.; Li, H. L.; Liu, R. H.; Zhang, W. D. Org. Lett. 2008, 12, 2397.
[10]	Wang, Y.; Shen, Y. H.; Jin, H. Z.; Fu, J. J.; Hu, X. J.; Qin, J. J.; Liu, J. H.; Chen, M.; Yan, S. K.; Zhang, W. D. Org. Lett. 2008, 24, 5517.
[11]	Pelin, T.; Zsuzsanna, H.; Norbert, K.; István, Z.; Izabella, S.; Bijen, K.; Judit, H. Molecules 2019, 17, 3165.
[12]	Tae, J. H.; Ki, H. P.; Dae, S. J.; Jong, R. L.; Ki, M. P.; Min, S. Y. Heterocycles 2003, 60, 623.
[13]	Tasqiah, J.; Yoshie, H.; Stefanie, Z.; Marcel, K.; Matthias, H.; Michael, A. Fitoterapia 2011, 7, 955.
[14]	Klaudia, M.; Jolanta, M.; Wanda, K. Fitoterapia 2010, 5, 434.
[15]	Chen, Y. P.; Tong, C.; Lu, W. Q.; Shen, Y. H.; Wu, Z. J.; Chen, W. S. Nat. Prod. Res. 2019, 2, 274.
[16]	Zidorna, C.; Ellmerer, E. P.; Stuppner, H. Phytochemistry 1999, 51, 991.
[17]	Zidorn, C.; Ellmerer, E. P.; Stuppner, H. Phytochem. Anal. 2001, 4, 281.
[18]	Stephens, P. J.; Harada, N. Chirality 2009, 22, 229.
[19]	Bruhn, T.; Schaumlöffel, A.; Hemberger, Y.; Bringmann, G. Chirality 2013, 25, 243.

光叶兔儿风中一个新的愈创木烷型倍半萜及其抗炎活性

One New Guaianolide Sesquiterpenoid with Potential Anti-inflammatory Activity from Ainsliaea glabra.

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 5

参考文献 19

相关文章 15

编辑推荐

相关统计

本文评价

[1]	小红, 覃玉月, 陈烁, 岑福凌, 高转生, 黎婉珊, 陈光英. 海洋来源真菌Phellinus sp. HN-22倍半萜类化合物及其抗炎活性研究[J]. 有机化学, 2025, 45(8): 3033-3038.
[2]	张晶晶, 李慧琼, 张兴杰, 王永朋, 周学梅, 肖伟烈, 程立君, 李晓莉. 高卢蜜环菌中一个新的甾体类化合物[J]. 有机化学, 2025, 45(4): 1411-1416.
[3]	魏琴芝, 余章昕, 徐盟, 徐伟, 岑福凌, 张雅琦, 李小宝, 陈光英. 诺丽种子的化学成分及其抗炎活性研究[J]. 有机化学, 2024, 44(4): 1357-1362.
[4]	魏艳梅, 余章昕, 杜怡益, 王平淑, 岑福凌, 李小宝, 陈光英. 土坛树中高度氧化的杜松烷型倍半萜及其生物活性研究[J]. 有机化学, 2024, 44(4): 1363-1367.
[5]	肖梦佳, 高希珂. 含苯并咪唑结构的薁类衍生物的设计合成及抗炎活性研究[J]. 有机化学, 2023, 43(9): 3246-3256.
[6]	吴秀蓉, 肖朝江, 沈怡, 汤红霞, 朱俊逸, 姜北. 植物来源抗疟倍半萜类天然产物研究(1972~2022)[J]. 有机化学, 2023, 43(8): 2764-2789.
[7]	余章昕, 蒙玉琴, 薛萌琳, 李小宝, 陈光英, 韩长日. 裸花紫珠叶中两个新的半日花烷型二萜[J]. 有机化学, 2023, 43(7): 2567-2571.
[8]	孙泽人, 翟冰新, 何光超, 沈慧, 陈琳雅, 张杉, 邹毅, 朱启华, 徐云根. 新型1,2,3-三氮唑类衍生物的合成及抗炎活性研究[J]. 有机化学, 2023, 43(6): 2143-2155.
[9]	余章昕, 宋鑫明, 姚远, 杨俊, 杨硕, 李小宝. 长叶暗罗中克罗烷型二萜及其抗炎作用[J]. 有机化学, 2023, 43(2): 751-755.
[10]	荀稳, 蒋丽清, 陈晓蕾, 吴静纯, 梁飞燕, 邓懿楠, 许波. 具有avarane骨架结构的Dysidea属海绵来源的倍半萜醌/氢醌类天然产物的合成研究进展[J]. 有机化学, 2023, 43(12): 4188-4212.
[11]	刘绪, 苏盼杰, 崔文博, 张宗萍, 陈晓涵, 王儒月, 费冬青, 张占欣. 栗色鼠尾草中一个新的吉马烷型倍半萜内酯类化合物[J]. 有机化学, 2022, 42(7): 2243-2247.
[12]	李敏欣, 邹秋萍, 杜文绒, 高金春, 李艳平, 毛泽伟. Dorsmerunin A的全合成及其抗炎活性研究[J]. 有机化学, 2021, 41(8): 3292-3296.
[13]	刘文琪, 佘嘉祎, 杨英, 朱世明, 熊校勤, 谭芬, 张洪权, 杨新洲, 曾国平. 毛华菊中倍半萜内酯类化学成分研究[J]. 有机化学, 2021, 41(7): 2898-2904.
[14]	肖检, 彭羽, 李卫东. 倍半萜生物碱Dendrobine的全合成研究进展[J]. 有机化学, 2021, 41(7): 2636-2649.
[15]	张旭, 邵思远, 冯子明, 姜建双, 杨桠楠, 张培成. 连翘果实中的三个新化合物[J]. 有机化学, 2021, 41(6): 2496-2501.