New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Preparation of (R)-and (S)-MTPA Esters
3.5. Cell Lines and Cell Culture
3.6. Cytotoxicity Assay (Nuclear Shrinkage)
3.7. Caspase 3/7-Activation Assay
3.8. MTT-Assay
3.9. Data Analysis
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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No. | 1 | 2 | ||||
---|---|---|---|---|---|---|
δC | Type | δH (J in Hz) | δC | Type | δH (J in Hz) | |
1 | 203.0 | C | - | 203.1 | C | |
2 | 32.9 | CH3 | 2.56 s | 32.9 | CH3 | 2.57 s |
1′ | 105.0 | C | - | 104.7 | C | - |
2′ | 163.1 | C | - | 162.3 | C | - |
3′ | 106.0 | C | - | 108.5 | C | - |
4′ | 164.1 | C | - | 163.3 | C | - |
5′ | 87.1 | CH | 6.21 s | 87.3 | CH | 6.23 s |
6′ | 161.8 | C | - | 161.8 | C | - |
1″ | 28.6 | CH2 | 2.62 dd (13.0/6.6) | 20.8 | CH2 | 3.13 d (7.2) |
2.71 dd (13.0/7.7) | ||||||
2″ | 73.5 | CH | 4.14 m | 122.6 | CH | 5.07 t (7.2/1) |
3″ | 148.1 | C | - | 130.3 | C | - |
4″ | 109.7 | CH2 | 4.51 m | 25.5 | CH3 | 1.59 s |
4.54 m | ||||||
5″ | 16.9 | CH3 | 1.69 s | 17.6 | CH3 | 1.68 s |
OCH3 at C-4′ | 55.8 | CH3 | 3.87 s | 56.0 | CH3 | 3.90 s |
OCH3 at C-6′ | 55.9 | CH3 | 3.92 s | 55.9 | CH3 | 3.92 s |
OH at C-2′ | - | 13.98 s | - | - | 13.95 s | |
OH at C-2″ | - | 4.63 d | - | - |
No. | 3 | 4 | ||||
---|---|---|---|---|---|---|
δC | Type | δH (J in Hz) | δC | Type | δH (J in Hz) | |
2 | 80.9 | C | - | 77.7 | C | - |
3 | 123.0 | CH | 5.38 d (10.1) | 69.3 | CH | 3.77 t (5.2/5.5) |
4a | 116.8 | CH | 6.59 d (10.1) | 26.2 | CH | 2.62 dd (17.1/5.5) |
4b | 2.84 dd (17.1/5.2) | |||||
5 | 161.2 | C | - | 159.7 | C | - |
6 | 91.9 | CH | 5.99 s | 88.1 | CH | 6.07 s |
7 | 166.7 | C | - | 156.8 | C | - |
8 | 106.0 | C | - | 113.8 | C | - |
9 | 156.7 | C | - | 151.5 | C | - |
10 | 102.7 | C | - | 100.9 | C | - |
11 | 202.9 | C | - | 201.6 | C | - |
12 | 33.1 | CH3 | 2.66 s | 32.7 | CH3 | 2.47 s |
13 a | 26.7 | CH3 | 1.43 s | 22.0 | CH3 | 1.33 s |
14 a | 41.7 | CH2 | 1.79 m | 24.8 | CH3 | 1.31 s |
1′ | 23.0 | CH2 | 2.10 m | - | - | - |
2′ | 123.6 | CH | 5.09 t (7.1/1.5) | - | - | - |
3′ | 132.9 | C | - | - | - | - |
4′ a | 25.9 | CH3 | 1.57 s | - | - | - |
5′ a | 17.3 | CH3 | 1.66 s | - | - | - |
OCH3 at C-5 | 55.7 | CH3 | 3.83 s | 55.7 | CH3 | 3.84 s |
OCH3 at C-7 | - | - | - | 56.2 | CH3 | 3.80 s |
OH at C-7 | - | - | 13.84 s | - | - | - |
Nuclear Shrinkage Assay | MTT Assay | |||
---|---|---|---|---|
IC50 [µM] | pIC50 ± SEM | IC50 [µM] | pIC50 ± SEM | |
Compound 2 | 30.0 | 4.52 ± 0.11 | >100 | <4 |
Cisplatin | 4.65 | 5.33 ± 0.07 | 6.42 | 5.19 ± 0.01 |
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Le, K.-T.; Bandolik, J.J.; Kassack, M.U.; Wood, K.R.; Paetzold, C.; Appelhans, M.S.; Passreiter, C.M. New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray. Molecules 2021, 26, 688. https://doi.org/10.3390/molecules26030688
Le K-T, Bandolik JJ, Kassack MU, Wood KR, Paetzold C, Appelhans MS, Passreiter CM. New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray. Molecules. 2021; 26(3):688. https://doi.org/10.3390/molecules26030688
Chicago/Turabian StyleLe, Kim-Thao, Jan J. Bandolik, Matthias U. Kassack, Kenneth R. Wood, Claudia Paetzold, Marc S. Appelhans, and Claus M. Passreiter. 2021. "New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray" Molecules 26, no. 3: 688. https://doi.org/10.3390/molecules26030688