Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana
Abstract
:1. Introduction
2. Results and Discussion
Position | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δH (J in Hz) | δc | δH (J in Hz) | δc | δH (J in Hz) | δc | |
1 | 2.71 m | 41.8 | 2.72 dd (1.62, 5.1) | 41.8 | 2.41 m | 39.9 |
2 | 2.42 dt (8.5, 5.5) | 39.7 | 2.44 dt (9.3, 3.7) | 39.7 | 2.72 m | 41.8 |
3 | 1.73 m | 38.8 | 1.76 m | 38.9 | 1.74 m | 38.9 |
4 | 2.00 t (8.5) | 40.6 | 2.07 t (8.0) | 40.2 | 1.85 t (7.5) | 39.0 |
5 | 2.34 t (6.5) | 39.8 | 2.37 t (6.0) | 39.9 | 2.38 m | 39.8 |
6 | 1.55 d (13.0) 1.90 ddd (13.0, 7.5, 5.5) | 38.5 | 1.54 d (12.8) 1.90 ddd (13.0, 7.4, 5.4) | 38.4 | 1.58 d (12.8) 1.93 dt (7.1, 12.9) | 38.4 |
7 | 2.57 t (5.0) | 38.3 | 2.56 t (4.9) | 38.3 | 2.57 t (5.5) | 38.3 |
8 | 2.86 d (3.5) | 48.8 | 2.87 d (2.6) | 48.8 | 2.89 d (3.2) | 48.6 |
9 | 2.98 dt (7.0, 4.0) | 34.8 | 2.98 m | 34.8 | 3.05 t (3.6) | 34.8 |
10 | 6.22 t (4.0) | 131.3 | 6.22 m | 131.3 | 6.24 t (3.7) | 131.9 |
11 | 6.22 t (4.0) | 132.0 | 6.22 m | 132.0 | 6.24 t (3.7) | 132.3 |
1' | 2.72 m 2.78 m | 41.7 | 2.83 m 2.86 m | 41.9 | 2.35 m | 39.3 |
2' | - | 134.7 | - | 140.9 | 6.02 dt (6.9, 15.7) | 126.9 |
3' | 6.66 s | 109.1 | 7.15 d (7.1) | 128.7 | 6.29 d (15.7) | 130.5 |
4' | - | 147.5 | 7.28 t (7.6) | 128.3 | - | 131.4 |
5' | - | 145.7 | 7.19 t (7.3) | 125.8 | 6.90 d (1.2) | 108.4 |
6' | 6.72 d (8.0) | 108.1 | 7.28 t (7.6) | 128.4 | - | 148.0 |
7' | 6.60 d (8.0) | 121.5 | 7.15 d (7.1) | 128.6 | - | 146.7 |
8' | 5.92 s | 100.8 | 6.73 d (8.0) | 108.2 | ||
9' | 6.76 d (8.0) | 120.3 | ||||
10' | 5.94 s | 101.0 | ||||
C=O | - | 179.3 | - | 179.4 | - | 178.3 |
Position | 4 | 5 | ||
---|---|---|---|---|
δH (J in Hz) | δc | δH (J in Hz) | δc | |
1 | 2.73 m | 41.9 | 2.76 dd (5.1, 10.8) | 42.4 |
2 | 2.40 m | 39.8 | 2.46 m | 39.9 |
3 | 1.76 m | 39.0 | 2.62 m | 40.3 |
4 | 1.88 t (7.4) | 38.9 | 2.44 m | 35.3 |
5 | 2.36 t (7.4) | 39.9 | 2.37 t (6.6) | 40.2 |
6 | 1.61 d (12.7) 1.93 m | 38.4 | 1.74 d (12.6) 1.94 m | 39.3 |
7 | 2.58 t (5.1) | 38.3 | 2.31 t (4.6) | 43.1 |
8 | 2.90 d (3.8) | 48.6 | 3.25 d (2.5) | 47.9 |
9 | 3.06 t (3.8) | 34.8 | 2.72 m | 39.6 |
10 | 6.23 d (3.1) | 131.4 | 5.93 t (7.0) | 132.3 |
11 | 6.24 d (3.0) | 131.9 | 6.29 t (7.3) | 130.5 |
12 | 140.2 | |||
13 | 6.61 s | 109.5 | ||
14 | 146.9 | |||
15 | 145.2 | |||
16 | 6.67 d (8.0) | 107.4 | ||
17 | 6.54 d (8.0) | 121.6 | ||
18 | 5.89 s | 100.7 | ||
1' | 2.43 m | 39.4 | 2.64 m | 40.4 |
2' | 6.19 m | 128.7 | ||
3' | 6.38 d (15.8) | 131.0 | ||
4' | - | 137.7 | ||
5' | 7.35 d (7.2) | 126.0 | ||
6' | 7.30 t (7.6) | 128.5 | ||
7' | 7.20 t (7.3) | 127.0 | ||
8' | 7.30 t (7.6) | 128.5 | ||
9' | 7.35 d (7.2) | 126.0 | ||
10' | ||||
C=O | - | 177.5 | 176.9 |
Position | 6 | 7 | 10 | |||
---|---|---|---|---|---|---|
δH (J in Hz) | δc | δH (J in Hz) | δc | δH (J in Hz) | δc | |
1 | 2.45 m | 41.0 | 2.48 m | 40.9 | 2.42 m | 40.9 |
2 | 1.30 dt (6.3, 12.1) 1.53 dd (6.4, 11.9) | 34.7 | 1.29 m 1.79 m | 35.0 | 1.20 m 1.53 m | 37.0 |
3 | 2.55 m | 36.9 | 2.08 m | 44.1 | 2.04 m | 35.6 |
4 | 6.19 d (9.7) | 134.4 | 4.23 d (9.8) | 73.6 | 2.08 m, 2.47 m | 32.2 |
5 | 5.72 d (9.6) | 123.9 | 7.03 brs | 145.6 | 7.23 brs | 144.6 |
6 | 3.00 m | 49.0 | - | 134.3 | - | 134.6 |
7 | 2.84 m | 32.8 | 3.23 brs | 33.2 | 3.26 brs | 33.3 |
8 | 5.40 m | 129.8 | 5.43 d (10.5) | 127.7 | 5.39 d (10.0) | 127.1 |
9 | 5.42 m | 129.1 | 5.53 d (10.5) | 126.2 | 5.54 d (10.0) | 127.0 |
10 | 2.39 m | 34.5 | 2.42 m | 33.7 | 2.40 m | 33.2 |
11 | 1.82 m | 46.9 | 1.76 m | 46.8 | 1.74 m | 46.9 |
12 | 2.70 dd (7.7, 16.2) | 32.9 | 2.80 m | 33.6 | 2.77 m | 34.0 |
13 | 1.73 m | 42.0 | 1.86 m | 40.8 | 1.68 m | 42.2 |
1' | 2.81 m | 42.9 | 2.71 d (8.0) | 42.5 | 2.70 d (8.0) | 42.6 |
2' | - | 140.7 | - | 134.6 | - | 134.6 |
3' | 7.15 d (6.8) | 128.6 | 6.64 s | 108.9 | 6.65 s | 109.0 |
4' | 7.24 t (6.7) | 128.4 | - | 147.5 | - | 147.4 |
5' | 6.20 dt (2.1, 7.3) | 125.8 | - | 145.6 | - | 145.6 |
6' | 7.24 t (6.7) | 128.4 | 6.71 d (7.9) | 108.1 | 6.71 d (7.9) | 108.0 |
7' | 7.15 d (6.8) | 128.6 | 6.59 d (7.9) | 121.3 | 6.60 d (7.9) | 121.3 |
8' | 5.91 s | 100.7 | 5.91 s | 100.7 | ||
C=O | 179.4 | 170.3 | 178.0 |
Compounds | Bcl-xL/Bak binding affinity (%) | Mcl-1/Bid binding affinity (%) | Cytotoxicity (IC50 in µM,mean ± s.d., n = 3) | ||||
---|---|---|---|---|---|---|---|
20 μM | 100 μM | 20 μM | 100 μM | HT-29 | A549 | PC3 | |
1 | 3 ± 1.5 | 21 ± 1.8 | 3 ± 2.0 | 36 ± 2.3 | 35.0 ± 0.2 | 85.4 ± 0.2 | >100 |
3 | 9 ± 1.5 | 25 ± 1.7 | 30 ± 2.2 | 75 ± 1.1 | >100 | 85.3 ± 0.2 | >100 |
5 | 2 ± 1.4 | 1 ± 0.8 | 3 ± 1.3 | 8 ± 5.5 | 17.1 ± 0.1 | 15.4 ± 0.2 | 77.2 ± 0.2 |
6 | 4 ± 1.6 | 22 ± 2.9 | 28 ± 3.7 | 80 ± 0.7 | NT | NT | NT |
7 | 5 ± 1.3 | 19 ± 1.6 | 8 ± 1.1 | 47 ± 2.9 | NT | NT | NT |
8 | 0 | 10 ± 0.5 | 4 ± 0.8 | 39 ± 0.9 | >100 | >100 | >100 |
9 | 6 ± 1.5 | 26 ± 2.5 | 25 ± 2.1 | 81 ± 2.4 | >100 | 38.1 ± 0.1 | >100 |
U-Bak (Ki) | 12 ± 1 nM | ||||||
U-Bid (Ki) | 16 ± 2 nM | ||||||
ABT-737 (Ki) | 57 ± 10 nM | 47 ± 22 nM | |||||
Cisplatin | 70.3 ± 1.1 | 36.2 ± 1.4 | 44.5 ± 7.7 |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectral Data
3.5. Bcl-xL and Mcl-1 Binding Affinity Assays
3.6. Cell Viability Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Azmi, M.N.; Gény, C.; Leverrier, A.; Litaudon, M.; Dumontet, V.; Birlirakis, N.; Guéritte, F.; Leong, K.H.; Halim, S.N.A.; Mohamad, K.; et al. Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana. Molecules 2014, 19, 1732-1747. https://doi.org/10.3390/molecules19021732
Azmi MN, Gény C, Leverrier A, Litaudon M, Dumontet V, Birlirakis N, Guéritte F, Leong KH, Halim SNA, Mohamad K, et al. Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana. Molecules. 2014; 19(2):1732-1747. https://doi.org/10.3390/molecules19021732
Chicago/Turabian StyleAzmi, Mohamad Nurul, Charlotte Gény, Aurélie Leverrier, Marc Litaudon, Vincent Dumontet, Nicolas Birlirakis, Françoise Guéritte, Kok Hoong Leong, Siti Nadiah Abd. Halim, Khalit Mohamad, and et al. 2014. "Kingianic Acids A–G, Endiandric Acid Analogues from Endiandra kingiana" Molecules 19, no. 2: 1732-1747. https://doi.org/10.3390/molecules19021732