Three Undescribed Iridoid Glycosides from Lamiophlomis rotata and Their Anti-inflammatory Activity

doi:10.6023/cjoc202605008

Abstract

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

Cite this article

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.

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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)

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