Terpenoids from the Leaves of Turpinia arguta and Their Bioactivities

doi:10.6023/cjoc202507018

Abstract

A phytochemical investigation of the 90% MeOH extract of the leaves of Turpinia arguta led to the identification of 22 structurally diverse terpenoids, including two new ones: argutacid A (1, a 15-oxo-17-norabietane-type diterpenoid) and argutacid B (2, a labdane-type diterpenoid). Their structures were determined using spectroscopic techniques including mass spectrometry, one-dimensional/two-dimensional nuclear magnetic resonance (NMR) spectra, and electronic circular dichroism (ECD). (12Z)-Labd-8(17), 12,14-triene-18-al (4), oleanolic acid (7), arjunolic acid (8), maslinic acid (10)~betulinic acid (14), ursolic acid (16)~euscaphic acid J (20), and 3β-cis-p-coumaroyloxy-2α,23-dihydroxyolean acid (22), are reported from T. arguta for the first time. The isolated compounds were evaluated for their anti-inflammatory activity in lipopolysaccharide (LPS)-induced RAW 264.7 cells by suppressing nitric oxide (NO) production. Two oleanolic acid derivatives, pomolic acid (19) and 22, were found to have anti-inflammatory activities with IC₅₀ values of 11.3 and 19.1 μmol/L, respectively. Such an anti-inflammatory effect of 22 was reported for the first time. Furthermore, isoyarumic acid (9, a ursolic acid derivative) exhibited moderate cytotoxic effect against MDA-MB-231 cells with an IC₅₀ value of 17.6 μmol/L.

Key words: Turpinia arguta, diterpenes, argutacid A, argutacid B, triterpenoids, anti-inflammatory activity, cytotoxicity

Cite this article

Zhelu Jiang, Zeyu Zhao, Chunjing Chi, Jiangchuan Yu, Lihong Yan, Jinfeng Hu. Terpenoids from the Leaves of Turpinia arguta and Their Bioactivities[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 1087-1094.

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No.	1		2
No.	δ_H	δ_C	δ_H	δ_C
1α	1.20~1.16, m	38.0	1.76, dt (12.8, 5.2)	39.6
1β	1.92~1.88, m		1.05, dd (12.8, 11.3)
2α	1.75~1.71, m	17.9	1.88~1.83, m	18.9
2β	1.64, br d (12.5)		1.51~1.46, m
3α	1.81~1.77, m	37.1	2.17~2.14, m	37.7
3β	1.77~1.73, m		1.02~1.00, m
4		46.1		43.7
5	2.14, dd (12.3, 4.0)	44.5	1.21, dd (10.9, 5.4)	56.6
6α	2.19~2.15, m	26.5	1.93~1.88, m	21.9
6β	2.06~2.01, m		1.83~1.78, m
7α	5.96, br s	132.5	1.91~1.88, m	44.5
7β			1.36~1.33, m
8		135.6		74.0
9	1.99, dd (13.5, 7.0)	50.1	1.10, t (3.8)	60.9
10		34.4		39.8
11α	1.91~1.87, m	21.4	1.62~1.57, m	24.6
11β	1.18~1.13, m		1.43~1.38, m
12α	2.72, dq (17.7, 2.2)	23.6	2.38~2.34, m	35.0
12β	1.90, dd (17.0, 13.4)		2.27~2.21, m
13		136.9		147.3
14	6.96, br s	140.3	6.35, dd (17.6, 11.4)	138.7
15a		199.1	5.30, d (17.6)	113.5
15b			5.07, d (11.4)
16	2.32, s	25.2	5.01, s	115.7
17		—	1.18, s	23.6
18		183.2	1.26, s	28.9
19	1.29, s	16.7		182.3
20	0.83, s	13.9	0.72, s	13.0

No.	1		2
No.	δ_H	δ_C	δ_H	δ_C
1α	1.20~1.16, m	38.0	1.76, dt (12.8, 5.2)	39.6
1β	1.92~1.88, m		1.05, dd (12.8, 11.3)
2α	1.75~1.71, m	17.9	1.88~1.83, m	18.9
2β	1.64, br d (12.5)		1.51~1.46, m
3α	1.81~1.77, m	37.1	2.17~2.14, m	37.7
3β	1.77~1.73, m		1.02~1.00, m
4		46.1		43.7
5	2.14, dd (12.3, 4.0)	44.5	1.21, dd (10.9, 5.4)	56.6
6α	2.19~2.15, m	26.5	1.93~1.88, m	21.9
6β	2.06~2.01, m		1.83~1.78, m
7α	5.96, br s	132.5	1.91~1.88, m	44.5
7β			1.36~1.33, m
8		135.6		74.0
9	1.99, dd (13.5, 7.0)	50.1	1.10, t (3.8)	60.9
10		34.4		39.8
11α	1.91~1.87, m	21.4	1.62~1.57, m	24.6
11β	1.18~1.13, m		1.43~1.38, m
12α	2.72, dq (17.7, 2.2)	23.6	2.38~2.34, m	35.0
12β	1.90, dd (17.0, 13.4)		2.27~2.21, m
13		136.9		147.3
14	6.96, br s	140.3	6.35, dd (17.6, 11.4)	138.7
15a		199.1	5.30, d (17.6)	113.5
15b			5.07, d (11.4)
16	2.32, s	25.2	5.01, s	115.7
17		—	1.18, s	23.6
18		183.2	1.26, s	28.9
19	1.29, s	16.7		182.3
20	0.83, s	13.9	0.72, s	13.0

Compd.	NO inhibition/%	IC₅₀^b/(μmol•L^－1)
1	14.9±1.6	>50
2	2.1±2.9	>50
3	25.4±2.9	>50
4	27.5±15.1	>50
5	58.8±4.1	>20
6	0.5±3.1	>50
7	N.T.^d	N.T.^d
8	N.T.^d	N.T.^d
9	76.9±2.3	>20
10	23.8±1.9	>50
11	9.5±8.0	>50
12	26.2±2.2	>50
13	12.6±3.1	>50
14	35.9±19.6	>50
15	27.5±3.8	>50
16	N.T.^d	N.T.^d
17	24.4±9.3	>50
18	N.T.^d	N.T.^d
19	69.5±2.2	11.3±2.0
20	24.4±9.3	>50
21	20.9±1.7	>50
22	81.1±1.0	19.1±0.8
1400W^c	86.9±1.8	0.4±0.01

Compd.	NO inhibition/%	IC₅₀^b/(μmol•L^－1)
1	14.9±1.6	>50
2	2.1±2.9	>50
3	25.4±2.9	>50
4	27.5±15.1	>50
5	58.8±4.1	>20
6	0.5±3.1	>50
7	N.T.^d	N.T.^d
8	N.T.^d	N.T.^d
9	76.9±2.3	>20
10	23.8±1.9	>50
11	9.5±8.0	>50
12	26.2±2.2	>50
13	12.6±3.1	>50
14	35.9±19.6	>50
15	27.5±3.8	>50
16	N.T.^d	N.T.^d
17	24.4±9.3	>50
18	N.T.^d	N.T.^d
19	69.5±2.2	11.3±2.0
20	24.4±9.3	>50
21	20.9±1.7	>50
22	81.1±1.0	19.1±0.8
1400W^c	86.9±1.8	0.4±0.01

山香圆叶中萜类成分及其生物活性研究