Anti-Inflammatory, Neurotrophic, and Cytotoxic Oxylipins Isolated from Chaenomeles sinensis Twigs
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Plant Material
2.3. Compounds Extraction and Isolation
Pos. | 1 | 2 | 3 | 4 | ||||
---|---|---|---|---|---|---|---|---|
δC | δH, multi., (J in Hz) | δC | δH, multi., (J in Hz) | δC | δH, multi., (J in Hz) | δC | δH, multi., (J in Hz) | |
1 | 175.8 | 175.8 | 174.1 | 174.1 | ||||
2 | 34.7 | 2.35, t (7.4) | 34.7 | 2.35, t (7.4) | 34.4 | 2.28, t (7.4) | 34.4 | 2.28, t (7.4) |
3 | 22.1 | 1.66, m; 1.71, m | 22.2 | 1.66, m; 1.72, m | 25.0 | 1.61, quin (7.4) | 25.0 | 1.61, m |
4 | 37.6 | 1.54, m | 37.6 | 1.53, m | 29.2 | 1.30 * | 29.2 | 1.30 * |
5 | 72.7 | 4.07, m | 72.6 | 4.06, m | 29.3 | 1.30 * | 29.3 | 1.30 * |
6 | 136.3 | 5.72, dd (15.5, 5.4) | 136.2 | 5.72 * | 29.1 | 1.30 * | 29.1 | 1.30 * |
7 | 131.4 | 5.69, dd (15.5, 5.5) | 131.4 | 5.72 * | 25.3 | 1.32 *; 1.39 * | 25.3 | 1.32 *; 1.39 * |
8 | 75.8 | 3.90, t (5.5) | 75.7 | 3.95, m | 37.3 | 1.53 * | 37.3 | 1.54 * |
9 | 76.5 | 3.41, m | 75.9 | 3.45, m | 72.2 | 4.15, q (5.9) | 72.2 | 4.15, q (5.8) |
10 | 33.6 | 1.35 *; 1.53 * | 31.6 | 2.12, m; 2.35 * | 136.4 | 5.82, dd (15.6, 5.9) | 136.4 | 5.84, dd (15.5, 5.8) |
11 | 26.7 | 1.34 *; 1.52 * | 126.4 | 5.44, m | 129.8 | 5.71, dd (15.6, 6.2) | 129.7 | 5.73, dd (15.5, 6.0) |
12 | 33.1 | 1.53 * | 134.4 | 5.46, m | 75.4 | 3.92, m | 74.7 | 4.01, t (6.0) |
13 | 23.8 | 1.33 * | 21.7 | 2.06, quin (7.5) | 74.7 | 3.47, m | 74.2 | 3.53, m |
14 | 14.5 | 0.91, t (7.1) | 14.6 | 0.96, t (7.5) | 33.1 | 1.42 *; 1.51 * | 31.1 | 2.30, t (7.5) |
15 | 52.0 | 3.65, s | 52.0 | 3.65, s | 25.4 | 1.38 *; 1.50 * | 123.9 | 5.40, m |
16 | 31.9 | 1.29 * | 135.5 | 5.58, m | ||||
17 | 22.7 | 1.31 * | 20.8 | 2.07, quin (7.5) | ||||
18 | 14.2 | 0.89, t (7.0) | 14.3 | 0.97, t (7.5) | ||||
19 | 60.3 | 4.12, q (7.1) | 60.3 | 4.12, q (7.1) | ||||
20 | 14.4 | 1.25, t (7.1) | 14.4 | 1.25, t (7.1) |
2.4. Nitric Oxide (NO) Assay
2.5. Nerve Growth Factor (NGF) Assay
2.6. Cytotoxicity Assignment
3. Results and Discussion
3.1. Structure Elucidation of Compounds 1–5
3.2. Biosynthetic Proposal
3.3. Anti-Neuroinflammatory Activity of the Isolated Compounds (1–5)
3.4. Neurotrophic Activity of the Isolated Compounds (1–5)
3.5. Cytotoxic Activity of the Isolated Compounds (1–5)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | Normalized NO production (µM) 1 | Cell viability (%) 2 |
---|---|---|
DMSO | 2.33 ± 0.58 | 117.52 ± 1.04 |
LPS-treated | 39.95 ± 1.17 ### | 100.00 ± 0.88 |
1 | 38.56 ± 1.61 | 105.36 ± 3.55 |
2 | 38.69 ± 1.41 | 97.39 ± 7.89 |
3 | 30.70 ± 1.38 *** | 121.17 ± 8.80 |
4 | 8.46 ± 0.68 *** | 97.77 ± 1.23 |
5 | 24.09 ± 1.11 *** | 109.15 ± 1.81 |
L-NMMA 3 | 22.37 ± 0.69 *** | 104.56 ± 4.21 |
Compound | Normalized NGF secretion (%) 1 | Cell viability (%) 2 |
---|---|---|
DMSO | 100.0 ± 0.6 | 100.0 ± 1.1 |
1 | 79.6 ± 3.4 | 98.5 ± 0.8 |
2 | 86.0 ± 4.4 | 109.9 ± 9.3 |
3 | 126.7 ± 2.4 * | 105.3 ± 1.6 |
4 | 157.7 ± 2.4 *** | 107.7 ± 11.2 |
5 | 123.8 ± 11.0 * | 101.6 ± 1.4 |
6-shogaol 3 | 154.0 ± 5.6 ** | 97.1 ± 0.2 |
Compound | IC50 (μM) 1 | |||
---|---|---|---|---|
A549 | SK-OV-3 | SK-MEL-2 | MKN-1 | |
1 | >30 | >30 | >30 | >30 |
2 | >30 | >30 | >30 | >30 |
3 | >30 | >30 | >30 | >30 |
4 | 27.4 | >30 | >30 | >30 |
5 | 17.5 | 18.9 | 15.1 | 26.6 |
Etoposide 2 | 1.0 | 2.2 | 1.8 | 3.5 |
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Lee, D.Y.; Park, K.J.; Subedi, L.; Lee, G.S.; Lee, J.-H.; Lee, W.-M.; Choi, S.U.; Hong, S.-M.; Kim, S.Y.; Kim, C.S. Anti-Inflammatory, Neurotrophic, and Cytotoxic Oxylipins Isolated from Chaenomeles sinensis Twigs. Antioxidants 2023, 12, 284. https://doi.org/10.3390/antiox12020284
Lee DY, Park KJ, Subedi L, Lee GS, Lee J-H, Lee W-M, Choi SU, Hong S-M, Kim SY, Kim CS. Anti-Inflammatory, Neurotrophic, and Cytotoxic Oxylipins Isolated from Chaenomeles sinensis Twigs. Antioxidants. 2023; 12(2):284. https://doi.org/10.3390/antiox12020284
Chicago/Turabian StyleLee, Da Yeong, Kyoung Jin Park, Lalita Subedi, Gyu Sung Lee, Ji-Hyeok Lee, Won-Min Lee, Sang Un Choi, Seong-Min Hong, Sun Yeou Kim, and Chung Sub Kim. 2023. "Anti-Inflammatory, Neurotrophic, and Cytotoxic Oxylipins Isolated from Chaenomeles sinensis Twigs" Antioxidants 12, no. 2: 284. https://doi.org/10.3390/antiox12020284