独一味中三个新的环烯醚萜苷类成分及其抗炎活性

doi:10.6023/cjoc202605008

摘要/Abstract

采用硅胶、凝胶等柱色谱及制备液相色谱, 从独一味中分离出三个新型的环烯醚萜苷类化合物. 通过高分辨质谱(HRESIMS)和核磁共振(NMR)等波谱技术解析了新化合物的结构, 并结合糖水解、衍生化、电子圆二色谱(ECD)计算, 进一步确认了三个化合物的绝对构型. 通过检测脂多糖(LPS)刺激的RAW 264.7巨噬细胞中一氧化氮(NO)的生成水平, 在7.5 μmol/L浓度下, (1S,4aS,7aS)-7-亚甲基-1-(((2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)-1,4a,7,7a-四氢环戊并[c]吡喃-4-甲酸甲酯(1)、(1S,4aR,5R,7aR)-4a,5-二羟基-7-亚甲基-1-(((2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)-1,4a,5,6,7,7a-六氢环戊并[c]吡喃-4-羧酸甲酯(2)、(1S,4aS,5R,7aS)-5-乙氧基-7-甲基-1-(((2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟甲基)四氢-2H-吡喃-2-基)氧基)-1,4a,5,7a-四氢环戊并[c]吡喃-4-甲酸甲酯(3)均显著抑制LPS诱导的NO生成.

关键词: 独一味, 环烯醚萜苷, 抗炎活性

Three new iridoid glycosides were isolated from Lamiophlomis rotata using silica gel, gel Sephadex LH-20 column chromatography, and preparative high-performance liquid chromatography. The structures of the new compounds were elucidated through analysis of spectroscopic evidence, including data obtained from high-resolution electrospray ionization mass spectrometry (HRESIMS) and nuclear magnetic resonance (NMR). The absolute configurations of the three compounds were confirmed by a combination of sugar hydrolysis, derivatization, and electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of methyl (1S,4aS,7aS)-7-methylene-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (1), methyl (1S,4aR,5R,7aR)-4a,5-dihy-droxy-7-methylene-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate (2), and methyl (1S,4aS,5R,7aS)-5-ethoxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (3) were evaluated by measuring nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. All these new findings showed significantly inhibited LPS-induced NO production at the concentration of 7.5 μmol/L.

Key words: Lamiophlomis rotata, iridoid glycosides, anti-inflammatory activity

引用此文

冉艳芳, 黄利, 李洁, 赵丽莲, 郭大乐. 独一味中三个新的环烯醚萜苷类成分及其抗炎活性[J]. 有机化学, 2026, 46(10): 4002-4007.

Yanfang Ran, Li Huang, Jie Li, Lilian Zhao, Dale Guo. Three Undescribed Iridoid Glycosides from Lamiophlomis rotata and Their Anti-inflammatory Activity[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 4002-4007.

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

分享此文

图/表 5

参考文献 15

[1]	Lu R.; Wang L.; Yang R. Chin. Wild Plant Resour. 2026, 45, 117 (in Chinese).
	(陆睿, 王莉, 杨荣, 中国野生植物资源, 2026, 45, 117.)
[2]	Qiao F.; Lu Y.; Geng G.; Zhou L.; Chen Z.; Wang L.; Xie H.; Qiu Q. S. J. Plant Physiol. 2023, 287, 154043. doi: 10.1016/j.jplph.2023.154043
[3]	Wang M.; Yue G.; Chen Y.; Li K.; Jiang G.; Zhuoma Z.; Zhang Y.; Liu X.; Wang F.; Ren Q.; Li C. J. Ethnopharmacol. 2026, 355, 120531. doi: 10.1016/j.jep.2025.120531
[4]	Geng X.; Wang Y.; Li H.; Song L.; Luo C.; Gu X.; Zhong H.; Chen H.; Chen X.; Wang J.; Pan Z. Chin. Med. 2024, 19, 53. doi: 10.1186/s13020-024-00921-1
[5]	Jiang Q.; Hu M.; Li X.; Zhang Q.; Zhang X.; Jiang M. Int. J. Biol. Macromol. 2025, 322, 146943. doi: 10.1016/j.ijbiomac.2025.146943
[6]	Xu Y.; Jiancuo S.; Luo X.; Ma Y. E.; Wu X.; Wu Z.; Yin H.; Zhang S.; Li W.; Sheng H. Biology (Basel) 2025, 14, 1554.
[7]	Zhong L.; Li T.; Zhang J.; Zhang J.; Zhang J.; Li L.; Chen G.; Zhong S.; Gu R. BMC Plant Biol. 2025, 25, 941. doi: 10.1186/s12870-025-06953-5
[8]	Wang W.; Liu T.; Ding Y.; Liu X.; Qingji R.; Zhang Y.; Zhang Z. Drug Des. Devel. Ther. 2026, 20, 591283.
[9]	Liu M. D.; Huang L. J.; Lei H. R.; Wang Y. J.; Hu Y. J.; Huo X. Y.; Li C. C.; Huang L.; Zhao L. L.; Zhang M. Z.; Gu Y. C.; Shyy M.; Sihota A.; Wang D.; Guo D. L.; Deng Y. Mar. Life Sci. Technol. 2026, 8, 1. doi: 10.1007/s42995-025-00336-3
[10]	Zhang C. Y.; Yang L. J.; Jiang L. S.; Mu Y. T.; Mao X. L.; Liu Q.; Deng F.; Guo D. L. Phytochem. Anal. 2026, 37, 85. doi: 10.1002/pca.v37.1
[11]	Roslund M. U.; Tahtinen P.; Niemitz M.; Sjoholm R. Carbohydr. Res. 2008, 343, 101. doi: 10.1016/j.carres.2007.10.008
[12]	Zuo Y.; Pu Y. R.; Liu J. A.; Chen H. Y.; Chen Y.; Li X. L.; Wang Y.; Zhang T. T.; Cheng H. B.; Liu J.; Deng Y.; Cong Z. T.; Wang M. L.; Lu J.; Chen S. L. Acta Pharm. Sin. B 2025, 16, 4083. doi: 10.1016/j.apsb.2025.11.011
[13]	Zhang C. Z.; Chen Y.; Shi X. K.; Liu Y.; Zhou J. W.; Leng L.; Zhang T. T.; Liu S. J.; Liu J.; Wang T. B.; Zheng C.; Zhang C. T.; Deng Y.; Guo J. L.; Lu J. J. Controlled Release 2026, 391, 114654. doi: 10.1016/j.jconrel.2026.114654
[14]	Hu S.; Zhao L. L.; Li X. Y.; Ye Y. B.; Deng Y.; Huang L. J.; Guo D. L. Chin. J. Org. Chem. 2026, 46, 300 (in Chinese). doi: 10.6023/cjoc202505002
	(胡苏, 赵丽莲, 李昕宇, 叶雨蓓, 邓赟, 黄莉钧, 郭大乐, 有机化学, 2026, 46, 300.)
[15]	Wu F.; Gu W. J.; Chen L.; Xia B.; Wang Y.; Huang L. J.; Wang K.; Gu Y. C.; Zhou Y. Phytochem. Anal. 2026, 37, 273. doi: 10.1002/pca.v37.2

No.	1^a		2^b		3^a
No.	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)
1	96.7	5.37, d (4.7)	94.9	5.83, d (2.2)	101.4	5.05, d (8.8)
3	153.0	7.45, d (1.5)	154.0	7.48, s	154.9	7.62, d (1.5)
4	111.8	—	110.1	—	108.5	—
5	41.1	3.70~3.73, m	72.9	—	42.0	3.07, ddd (7.6, 6.1, 1.6)
5-OH	—	—	—	4.70, s	—	—
6	140.7	6.29, dt (5.7, 2.0)	72.9	4.41, overlapped	84.1	4.42 ddd (6.2, 2.4, 1.1)
6-OH	—	—	—	4.54, dd (2.6, 1.5)	—	—
7	134.3	6.17, dd (5.6, 2.0)	37.5	2.13~2.21, m	129.5	5.85, t (2.3)
8	152.5	—	146.2	—	148.3	—
9	45.9	3.10, ddt (7.0, 4.4, 2.1)	49.2	2.97, overlapped	48.9	2.43, dd (8.8, 7.3)
10	107.5	5.11, d (2.3) 5.06, dq (1.8, 1.0)	109.7	5.02~5.09, m 4.92~5.01, m	17.4	1.95, dt (1.6, 0.8)
11	169.1	—	165.7	—	169.6	—
11-OMe	51.8	3.73, s	50.9	3.63, s	51.8	3.75, s
1'	99.8	4.69, d (7.9)	98.6	4.41, overlapped	100.2	4.77, d (7.9)
2'	74.7	3.23, dd (9.2, 7.9)	73.0	2.97 overlapped	75.0	3.26, dd (9.3, 7.9)
3'	78.0	3.39, dd (9.2, 8.4)	76.0	3.16, overlapped	78.0	3.40, d (19.3)
4'	78.4	3.30, d (2.0)	70.1	3.04, td (9.3, 5.1)	78.4	3.28~3.30, m
5'	71.6	3.30~3.26, m	77.4	3.16, overlapped	71.7	3.29~3.31, m
6'	62.8	3.89, dd (11.9, 2.0) 3.66, dd (12.0, 5.8)	61.1	3.45, ddd (11.8, 6.5, 5.1) 3.66~3.73, m	62.9	3.85, dd (12.1, 1.7) 3.65~3.69, m
1"	—	—	—	—	66.1	3.45~3.50, m 3.36, dd (9.5, 7.1)
2"	—	—	—	—	15.9	1.06, t (1.06)

No.	1^a		2^b		3^a
No.	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)	δ_C	δ_H (J in Hz)
1	96.7	5.37, d (4.7)	94.9	5.83, d (2.2)	101.4	5.05, d (8.8)
3	153.0	7.45, d (1.5)	154.0	7.48, s	154.9	7.62, d (1.5)
4	111.8	—	110.1	—	108.5	—
5	41.1	3.70~3.73, m	72.9	—	42.0	3.07, ddd (7.6, 6.1, 1.6)
5-OH	—	—	—	4.70, s	—	—
6	140.7	6.29, dt (5.7, 2.0)	72.9	4.41, overlapped	84.1	4.42 ddd (6.2, 2.4, 1.1)
6-OH	—	—	—	4.54, dd (2.6, 1.5)	—	—
7	134.3	6.17, dd (5.6, 2.0)	37.5	2.13~2.21, m	129.5	5.85, t (2.3)
8	152.5	—	146.2	—	148.3	—
9	45.9	3.10, ddt (7.0, 4.4, 2.1)	49.2	2.97, overlapped	48.9	2.43, dd (8.8, 7.3)
10	107.5	5.11, d (2.3) 5.06, dq (1.8, 1.0)	109.7	5.02~5.09, m 4.92~5.01, m	17.4	1.95, dt (1.6, 0.8)
11	169.1	—	165.7	—	169.6	—
11-OMe	51.8	3.73, s	50.9	3.63, s	51.8	3.75, s
1'	99.8	4.69, d (7.9)	98.6	4.41, overlapped	100.2	4.77, d (7.9)
2'	74.7	3.23, dd (9.2, 7.9)	73.0	2.97 overlapped	75.0	3.26, dd (9.3, 7.9)
3'	78.0	3.39, dd (9.2, 8.4)	76.0	3.16, overlapped	78.0	3.40, d (19.3)
4'	78.4	3.30, d (2.0)	70.1	3.04, td (9.3, 5.1)	78.4	3.28~3.30, m
5'	71.6	3.30~3.26, m	77.4	3.16, overlapped	71.7	3.29~3.31, m
6'	62.8	3.89, dd (11.9, 2.0) 3.66, dd (12.0, 5.8)	61.1	3.45, ddd (11.8, 6.5, 5.1) 3.66~3.73, m	62.9	3.85, dd (12.1, 1.7) 3.65~3.69, m
1"	—	—	—	—	66.1	3.45~3.50, m 3.36, dd (9.5, 7.1)
2"	—	—	—	—	15.9	1.06, t (1.06)