Yellow Pigments, Fomitellanols A and B, and Drimane Sesquiterpenoids, Cryptoporic Acids P and Q, from Fomitella fraxinea and Their Inhibitory Activity against COX and 5-LO
Abstract
:1. Introduction
2. Results and Discussion
Position | 1a | 2a | ||
---|---|---|---|---|
δC | δH (mult, J in Hz) | δC | δH (mult, J in Hz) | |
1 | 113.6 | 5.95 (s) | 113.4 | 5.93 (s) |
2a | 148.8 | 148.7 | ||
2b | 133.9 | 133.8 | ||
3 | 111.4 | 6.90 (d, J = 8.5) | 111.7 | 6.91 (d, J = 8.5) |
4 | 115.9 | 6.97 (d, J = 8.5) | 115.9 | 6.96 (d, J = 8.5) |
5 | 150.2 | 150.2 | ||
5a | 120.0 | 119.8 | ||
6 | 114.6 | 7.43 (d, J = 1.9) | 115.5 | 7.38 (d, J = 1.9) |
6a | 138.7 | 137.9 | ||
7 | 173.1 | 165.3 | ||
8 | 131.9 | 6.91 (t, J =1.4) | 133.2 | 6.54 (t, J =1.4) |
9 | 202.7 | 202.1 | ||
9a | 49.4 | 4.10 (br. d, J = 1.9) | 49.3 | 4.05 (br. s) |
9b | 46.2 | 46.2 | ||
10 | 58.9 | 4.94 (dt, J = 17.3, 1.4) | 60.4 | 5.27 (dt, J = 16.2, 1.4) |
5.07 (dt, J = 17.3, 1.4) | 5.38 (dt, J = 16.2, 1.4) | |||
11 | 16.5 | 1.13 (s) | 16.5 | 1.10 (s) |
1' | 72.1 | 4.26 (sept, J = 6.3) | 72.1 | 4.25 (sept, J = 6.3) |
2' | 22.2 | 1.24 (d, J = 6.3) | 22.2 | 1.24 (d, J = 6.3) |
3' | 23.5 | 1.31 (d, J = 6.3) | 23.5 | 1.31 (d, J = 6.3) |
Ac | 20.4 | 2.08 (s) | ||
170.2 |
Position | 3 | 4 | ||
---|---|---|---|---|
δC | δH (mult, J in Hz) | δC | δH (mult, J in Hz) | |
1 | 38.7 | 1.20 (m), 1.77 (m) | 38.6 | 1.15 (m), 1.72 (m) |
2 | 18.7 | 1.45 (m), 1.45 (m) | 18.6 | 1.45 (m), 1.45 (m) |
3 | 36.0 | 1.36 (m), 1.36 (m) | 35.9 | 1.34 (m), 1.34 (m) |
4 | 36.9 | 36.9 | ||
5 | 49.3 | 1.40 (dd, J = 12.6, 2.2) | 49.3 | 1.38 (m) |
6 | 24.0 | 1.27 (m), 1.51 (m) | 23.9 | 1.25 (m), 1.51 (m) |
7 | 37.6 | 2.01 (m), 2.32 (m) | 37.5 | 1.99 (m), 2.31 (m) |
8 | 147.1 | 147.0 | ||
9 | 56.2 | 2.21 (m) | 56.0 | 2.15 (m) |
10 | 38.9 | 38.8 | ||
11 | 68.2 | 3.81 (dd, J = 9.6, 3.3) | 68.6 | 3.70 (dd, J = 9.6, 3.3) |
4.33 (dd, J = 9.6, 8.2) | 4.14 (dd, J = 9.6, 8.0) | |||
12 | 108.9 | 5.02 (br. s) | 108.6 | 4.98 (br. s) |
5.31 (br. s) | 5.15 (br. s) | |||
13 | 15.9 | 0.79 (s) | 15.9 | 0.76 (s) |
14 | 17.5 | 0.75 (s) | 17.5 | 0.75 (s) |
15 | 73.0 | 3.74 (d, J = 10.7) | 73.0 | 3.73 (d, J = 11.0) |
3.94 (d, J = 10.7) | 3.93 (d, J = 11.0) | |||
1' | 80.1 | 4.70 (d, J = 4.7) | 79.5 | 4.57 (d, J = 4.4) |
2' | 45.7 | 4.14 (m) | 45.6 | 3.98 (m) |
3' | 33.4 | 3.26 (dd, J = 17.0, 4.1) | 33.6 | 3.09 (m) |
3.49 (dd, J = 17.0, 10.7) | 3.35 (dd, J = 17.3, 9.3) | |||
4' | 173.7 | 171.5 | ||
5' | 172.7 | 172.1 | ||
6' | 174.7 | 175.0 | ||
4'-OMe | 51.9 | 3.65 (s) | ||
5'-OMe | 51.9 | 3.73 (s) | 52.0 | 3.76 (s) |
Ac | 20.8 | 2.07 (s) | 20.8 | 2.08 (s) |
170.1 | 170.1 |
Compound | % Inhibition of at 10 μg/mL | IC50b,c | ||
---|---|---|---|---|
COX-1 | COX-2 | COX-1 | COX-2 | |
Extract a | 96.4 | 59.0 | ||
1a | 90.5 | 7.5 | 47.7 | ND d |
3 | 40.2 | 1.7 | ND | ND |
4 | 66.5 | 10.3 | 78.8 | ND |
6 | 35.8 | 19.0 | ND | ND |
aspirin | – | – | 79.0 | 150 |
Compound | % Inhibition of at 10 μg/mL | IC50b,c |
---|---|---|
Extract a | 69.5 | – |
1a | 84.7 | 15.1 |
3 | 14.9 | ND d |
4 | 50.1 | 203.5 |
6 | 28.9 | ND |
NDGA a | – | 0.4 |
3. Experimental
3.1. General
3.2. Materials
3.3. Extraction and Isolation
3.5. X-ray Crystallographic Data for 1b
3.6. Acetylations of 6 Giving 3 and of 5 Giving 4
3.7. COX-1 and COX-2-Catalyzed Prostaglandin Biosynthesis Assay in Vitro
3.8. Measurement of RBL-1 5-Lipoxygenase Activity
4. Conclusions
Supplementary Materials
Acknowledgments
References and Notes
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Yoshikawa, K.; Koso, K.; Shimomura, M.; Tanaka, M.; Yamamoto, H.; Imagawa, H.; Arihara, S.; Hashimoto, T. Yellow Pigments, Fomitellanols A and B, and Drimane Sesquiterpenoids, Cryptoporic Acids P and Q, from Fomitella fraxinea and Their Inhibitory Activity against COX and 5-LO. Molecules 2013, 18, 4181-4191. https://doi.org/10.3390/molecules18044181
Yoshikawa K, Koso K, Shimomura M, Tanaka M, Yamamoto H, Imagawa H, Arihara S, Hashimoto T. Yellow Pigments, Fomitellanols A and B, and Drimane Sesquiterpenoids, Cryptoporic Acids P and Q, from Fomitella fraxinea and Their Inhibitory Activity against COX and 5-LO. Molecules. 2013; 18(4):4181-4191. https://doi.org/10.3390/molecules18044181
Chicago/Turabian StyleYoshikawa, Kazuko, Kazuaki Koso, Masumi Shimomura, Masami Tanaka, Hirofumi Yamamoto, Hiroshi Imagawa, Shigenobu Arihara, and Toshihiro Hashimoto. 2013. "Yellow Pigments, Fomitellanols A and B, and Drimane Sesquiterpenoids, Cryptoporic Acids P and Q, from Fomitella fraxinea and Their Inhibitory Activity against COX and 5-LO" Molecules 18, no. 4: 4181-4191. https://doi.org/10.3390/molecules18044181