Anti-Inflammatory Activities of Constituents from Cinnamomum insularimontanum Hayata Leaves and Their Mechanisms
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Composition Analysis and Its Anti-Inflammatory Activity of C. insularimontanum Leaves Essential Oil (CILE)
2.2. Anti-Inflammatory Activity of Ethanolic Extract and Its Bioactive Compounds Isolation
2.3. Anti-Inflammatory Activity of Isoburmanol (F1) and Burmanol (F2)
2.3.1. NO Production and PGE2 Synthesis Inhibitory Activity
2.3.2. Effects of F1 and F2 on iNOS Expression in LPS-Induced Macrophages
2.3.3. Effects of F1 and F2 on Upstream Transcription Factors NF-κB and AP-1 Expression in LPS-Induced Macrophages
2.3.4. Effects of Isoburmanol and Burmanol on MAPK
2.4. Molecular Docking Simulation Analysis
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Preparation of C. insularimontanum Leaves Essential Oil (CILE) and GC/MS Analysis
3.4. Extraction and Isolation
3.5. Cell Culture and Cell Survival Assay
3.6. Anti-Inflammatory Assay
3.7. Protein Extraction and Immunoblotting
3.8. Molecular Docking
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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RT (min) | Name | Concentration% | KI a | Identification b |
---|---|---|---|---|
15.97 | α-Pinene | 7.55 | 934 | KI/MS/ST |
17.12 | Camphene | 2.44 | 950 | KI/MS/ST |
18.97 | Sabinene | 5.06 | 974 | KI/MS/ST |
19.12 | β-Pinene | 3.14 | 976 | KI/MS/ST |
21.93 | α-Terpinene | 0.53 | 1014 | KI/MS/ST |
22.44 | m-Cymene | 0.74 | 1023 | KI/MS |
22.69 | Limonene | 4.14 | 1028 | KI/MS/ST |
22.85 | 1,8-Cineole | 35.94 | 1030 | KI/MS/ST |
24.51 | γ-Terpinene | 2.46 | 1059 | KI/MS/ST |
31.21 | 4-Terpeneol | 1.54 | 1180 | KI/MS/ST |
32.02 | α-Terpineol | 3.61 | 1194 | KI/MS/ST |
36.29 | Isobornyl acetate | 4.81 | 1283 | KI/MS/ST |
40.27 | α-Cubebene | 0.46 | 1371 | KI/MS |
42.13 | Caryophyllene | 0.93 | 1413 | KI/MS/ST |
45.06 | (+)-Valencene | 0.85 | 1483 | KI/MS |
45.36 | β-Guaiene | 0.37 | 1490 | KI/MS |
46.32 | Cubebol | 0.61 | 1514 | KI/MS/ST |
47.21 | α-Calacorene | 0.55 | 1537 | KI/MS |
47.57 | β-Elemol | 0.93 | 1546 | KI/MS/ST |
48.77 | Nerolidol | 0.87 | 1576 | KI/MS/ST |
50.79 | Guaiol | 0.83 | 1628 | KI/MS |
51.61 | α-Eudesmol | 6.17 | 1650 | KI/MS/ST |
64.95 | Kaurene | 1.47 | 2034 | KI/MS/ST |
Fractions | A | B | C | D | E | F | G | H | I | J | CUR a |
---|---|---|---|---|---|---|---|---|---|---|---|
Weight (g) | 0.1 | 0.3 | 0.7 | 1.5 | 5.0 | 4.2 | 2.4 | 3.2 | 1.8 | 3.4 | - |
IC50 b (μg/mL) | >40 | >20 | 19.0 | 25.5 | 37.2 | 15.8 | 23.5 | 25.1 | 33.9 | 38.0 | 2.6 |
Positions | 13C | 1H | HMBC |
---|---|---|---|
1 | 131.5 | 7.26 (d, J = 8.3 Hz, 1H) | H-1/C-2, H-1/C-3, H-1/C-11a, H-1/C-11b |
2 | 114.1 | 6.70 (dd, J = 8.3, 2.5 Hz, 1H) | H2/C-1, H-2/C-3, H-2/C-4 |
3 | 158.1 | ||
4 | 114.0 | 6.65 (d, J = 2.5 Hz, 1H) | H-4/C-2, H-4/C-3, H-4/C-4a, H-4/C-5 |
4a | 131.8 | ||
5 | 34.1 | Ha: 2.72 (dd, J = 12.6, 6.3 Hz, 1H) | H-5/C-4, H-5/C-4a, H-5/C-6, H-5/C-7, H-5/C-11b |
Hb: 3.03 (dd, J = 12.6, 8.2 Hz, 1H) | |||
6 | 128.0 | 6.13 (t, J = 7.4 Hz, 1H) | H-6/C-5, H-6/C-7a, H-6/C-12 |
7 | 139.1 | ||
7a | 129.6 | ||
8 | 110.8 | 7.18 (s, 1H) | H-8/C-7, H-8/C-9, H-8/C-10 |
9 | 147.8 | ||
10 | 146.5 | ||
11 | 117.2 | 7.03 (s, 1H) | H-11/C-7a, H-11/C-9, H-11/C-11a |
11a | 135.6 | ||
11b | 145.1 | ||
12 | 66.4 | Ha: 4.33 (d, J = 13.0 Hz, 1H) | H-12/C-6, H-12/C-7, H-12/C-7a |
Hb: 4.45 (d, J = 13.0 Hz, 1H) | |||
OMe | 56.6 | 3.92 (s, 3H) | OMe/C-9 |
Positions | 13C | 1H | HMBC |
---|---|---|---|
1 | 131.4 | 7.32 (d, J = 8.4 Hz, 1H) | H-1/C-3, H-1/C-11a, H-1/C-11b |
2 | 114.3 | 6.71 (dd, J = 8.4, 2.6 Hz, 1H) | H-2/C-3, H-2/C-4 |
3 | 158.3 | ||
4 | 114.1 | 6.64 (d, J = 2.6 Hz, 1H) | H-4/C-2, H-4/C-3, H-4/C-4a, H-4/C-5 |
4a | 132.0 | ||
5 | 34.1 | Ha: 2.72 (dd, J = 12.6, 6.3 Hz, 1H) | H-5/C-4, H-5/C-4a, H-5/C-6, H-5/C-7, H-5/C-11b |
Hb: 3.03 (dd, J = 12.6, 8.2 Hz, 1H) | |||
6 | 127.9 | 6.13 (t, J = 7.6 Hz, 1H) | H-6/C-5, H-6/C-7, H-6/C-12 |
7 | 138.9 | ||
7a | 130.8 | ||
8 | 114.1 | 7.06 (s, 1H) | H-8/C-7, H-8/C-9, H-8/C-10 |
9 | 146.5 | ||
10 | 148.1 | ||
11 | 113.7 | 7.08 (s, 1H) | H-11/C-7a, H-11/C-9, H-11/C-10, H-11/C-11a |
11a | 134.2 | ||
11b | 145.2 | ||
12 | 66.1 | Ha: 4.30 (d, J = 13.0 Hz, 1H) | H-12/C-6, H-12/C-7, H-12/C-7a |
Hb: 4.39 (d, J = 13.0 Hz, 1H) | |||
OMe | 56.5 | 3.93 (s, 3H) | OMe/C-10 |
Compound | Protein | PDB Code | IC50 (μM) | Minimum Binding Energy |
---|---|---|---|---|
Isoburmanol | AP-1 | 5VPA | 14.0 | −103.53 |
AP-1 (oxidized form) | 5VPB | −95.50 | ||
AP-1 (bound to DNA) | 1FOS | −85.33 | ||
JNK1 (MYU binding sites) | 3V3V | −96.61 | ||
IKKβ (KSA binding sites) | 4KIK | −94.71 | ||
NF-κB | 1BFT | −86.78 | ||
Burmanol | AP-1 | 5VPA | 43.8 | −98.88 |
AP-1 (oxidized form) | 5VPB | −87.82 | ||
AP-1 (bound to DNA) | 1FOS | −88.51 | ||
JNK1 (MYU binding sites) | 3V3V | −91.95 | ||
IKKβ (KSA binding sites) | 4KIK | −90.82 | ||
NF-κB | 1BFT | −89.70 | ||
Curcumin | AP-1 | 5VPA | 9.4 | −113.54 |
AP-1 (oxidized form) | 5VPB | −113.95 | ||
AP-1 (bound to DNA) | 1FOS | −103.62 | ||
JNK1 (MYU binding sites) | 3V3V | −114.44 | ||
IKKβ (KSA binding sites) | 4KIK | −122.01 | ||
NF-κB | 1BFT | −120.81 | ||
Ethyl p-coumarate | AP-1 | 5VPA | 58.0 | −89.43 |
AP-1 (oxidized form) | 5VPB | −82.96 | ||
AP-1 (bound to DNA | 1FOS | −72.42 | ||
JNK1 (MYU binding sites) | 3V3V | −77.13 | ||
IKKβ (KSA binding sites) | 4KIK | −73.09 | ||
NF-κB | 1BFT | −74.87 |
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Chen, C.-Y.; Wu, P.-C.; Tsao, N.-W.; Tseng, Y.-H.; Chu, F.-H.; Wang, S.-Y. Anti-Inflammatory Activities of Constituents from Cinnamomum insularimontanum Hayata Leaves and Their Mechanisms. Plants 2022, 11, 3252. https://doi.org/10.3390/plants11233252
Chen C-Y, Wu P-C, Tsao N-W, Tseng Y-H, Chu F-H, Wang S-Y. Anti-Inflammatory Activities of Constituents from Cinnamomum insularimontanum Hayata Leaves and Their Mechanisms. Plants. 2022; 11(23):3252. https://doi.org/10.3390/plants11233252
Chicago/Turabian StyleChen, Chieh-Yin, Pei-Chen Wu, Nai-Wen Tsao, Yen-Hsueh Tseng, Fang-Hua Chu, and Sheng-Yang Wang. 2022. "Anti-Inflammatory Activities of Constituents from Cinnamomum insularimontanum Hayata Leaves and Their Mechanisms" Plants 11, no. 23: 3252. https://doi.org/10.3390/plants11233252