Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production
Abstract
:1. Introduction
2. Results
2.1. Structure Elucidation of New Compounds 1–3
2.2. Inhibitory Effects of Compounds on LPS-Induced PGE2 Production in RAW 264.7 Macrophages
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. General Experimental Procedures
4.3. Extraction and Isolation
4.3.1. Campanulalignan A (1)
4.3.2. Campanulalignan B (2)
4.3.3. Campanulalignan C (3)
4.4. Enzymatic Hydrolysis of Compound 1
4.5. Absolute Configurations of β-glucose in Compound 1
4.6. Cell Culture
4.7. Cell Viability Test
4.8. Measurement of PGE2 Production
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Position a | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δC | δHb | δC | δHb | δC | δHb | |
1 | 134.9 | 135.4 | 140.0 | |||
2 | 119.5 | 123.9 | 119.0 | |||
3 | 152.4 | 153.0 | 150.1 | |||
4 | 134.9 | 139.3 | 134.6 | |||
5 | 150.1 | 150.8 | 152.5 | |||
6 | 102.5 | 6.71 s | 110.8 | 6.87 s | 102.9 | 6.71 s |
7 | 129.3 | 6.86 d (15.5) | 128.9 | 6.81 d (15.5) | 72.1 | 5.40 d (5.5) |
8 | 132.0 | 6.24 dt (15.0, 5.0) | 130.0 | 6.17 dt (15.5, 6.0) | 141.7 | 6.01 ddd (16.5, 10.0, 5.0) |
9 | 62.2 | 4.24 dd (5.5, 2.0) | 63.9 | 4.21 dd (5.5, 2.0) | 115.2 | 5.26 d (17.0) |
5.12 d (10.5) | ||||||
1′ | 136.9 | 136.6 | 136.9 | |||
2′ | 108.2 | 6.48 d (2.0) | 108.2 | 6.49 d (2.0) | 103.1 | 6.47 d (1.5) |
3′ | 151.9 | 152.0 | 152.5 | |||
4′ | 134.5 | 134.6 | 134.6 | |||
5′ | 154.1 | 154.3 | 154.3 | |||
6′ | 103.0 | 6.47 d (2.0) | 103.1 | 6.48 d (2.0) | 108.4 | 6.48 d (1.5) |
7′ | 130.9 | 6.14 (15.5) | 130.4 | 6.13 d (15.5) | 131.0 | 6.18 d (16.0) |
8′ | 129.9 | 6.20 dt (15.0, 5.0) | 131.4 | 6.24 dt (15.5, 5.5) | 130.1 | 6.24 dt (15.5, 6.0) |
9′ | 29.9 | 3.55 d (5.5) | 30.2 | 3.55 d (5.5) | 29.5 | 3.62 d (7.0) |
3.54 d (6.0) | ||||||
Glc-1 | 107.3 | 4.67 d (8.0) | 107.3 | 4.81 d (8.0) | 107.3 | 4.67 d (8.0) |
Glc-2 | 71.0 | 3.45 overlap | 71.0 | 3.49 m | 71.0 | 3.51 overlap |
Glc-3 | 77.8 | 3.40 overlap | 78.0 | 3.43 overlap | 77.8 | 3.45 overlap |
Glc-4 | 75.5 | 3.49 overlap | 75.5 | 3.43 overlap | 75.5 | 3.42 overlap |
Glc-5 | 78.5 | 3.22 m | 78.6 | 3.22 overlap | 78.7 | 3.23 overlap |
Glc-6 | 62.0 | 3.68/3.82 overlap | 62.4 | 3.82 overlap | 62.3 | 3.86 m |
Glc-1′ | 107.0 | 4.63 d (8.0) | 107.0 | 4.64 d (8.0) | 107.1 | 4.63 d (7.5) |
Glc-2′ | 71.0 | 3.47 overlap | 71.0 | 3.47 m | 71.0 | 3.51 overlap |
Glc-3′ | 77.8 | 3.43 overlap | 77.9 | 3.84 overlap | 77.8 | 3.45 overlap |
Glc-4′ | 75.5 | 3.51 m | 75.5 | 3.44 m | 75.5 | 3.42 overlap |
Glc-5′ | 78.5 | 3.30 m | 78.5 | 3.29 m | 78.7 | 3.23 overlap |
Glc-6′ | 62.0 | 3.68/3.82 overlap | 62.2 | 3.22 overlap | 62.3 | 3.78 m |
OCH3-5 | 56.8 | 3.86 s | 62.7 | 3.87s | 56.8 | 3.84 s |
OCH3-5′ | 56.8 | 3.81 s | 56.8 | 3.81s | 56.7 | 3.81 s |
Compound | IC80 (μM) Cytotoxicitiy | Inhibition Rate (%) a | Compound | IC80 (μM) Cytotoxicitiy | Inhibition Rate (%) a |
---|---|---|---|---|---|
1 | >50 | 23.92 | 10 | >50 | 62.53 |
2 | 33.66 | 33.07 | 11 | >50 | 85.17 |
3 | - | - | 12 | >50 | 31.07 |
4 | 30.69 | 7.89 | 13 | >50 | 33.12 |
5 | >50 | 69.35 | 14 | >50 | 23.55 |
6 | >50 | 20.01 | 15 | >50 | 43.49 |
7 | >50 | 60.01 | 16 | >50 | 36.73 |
8 | >50 | 58.08 | 17 | >50 | 34.51 |
9 | >50 | 37.44 | 18 | >50 | 97.01 |
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Qi, Y.; Choi, S.-I.; Son, S.-R.; Han, H.-S.; Ahn, H.S.; Shin, Y.-K.; Lee, S.H.; Lee, K.-T.; Kwon, H.C.; Jang, D.S. Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production. Plants 2020, 9, 1232. https://doi.org/10.3390/plants9091232
Qi Y, Choi S-I, Son S-R, Han H-S, Ahn HS, Shin Y-K, Lee SH, Lee K-T, Kwon HC, Jang DS. Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production. Plants. 2020; 9(9):1232. https://doi.org/10.3390/plants9091232
Chicago/Turabian StyleQi, Yutong, Se-In Choi, So-Ri Son, Hee-Soo Han, Hye Shin Ahn, Yu-Kyong Shin, Sun Hee Lee, Kyung-Tae Lee, Hak Cheol Kwon, and Dae Sik Jang. 2020. "Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production" Plants 9, no. 9: 1232. https://doi.org/10.3390/plants9091232