Chemical Constituents of Kino Extract from Corymbia torelliana
Abstract
:1. Introduction
2. Results and Discussion
Compound | R1 | R2 | R3 | R4 | R5 |
---|---|---|---|---|---|
1 | H | OH | H | OH | H |
2 | H | OH | H | H | OH |
3 | H | OH | H | H | H |
4 | H | OMe | H | OH | H |
5 | H | OH | Me | H | H |
6 | Me | OH | Me | H | H |
7 | H | OMe | H | H | H |
Position | Compound 1 (d6 DMSO) | Compound 2 (CD3OD) | ||||
---|---|---|---|---|---|---|
13C | 1H | HMBC | 13C | 1H | HMBC | |
2 | 82.7 (CH) | 5.04 (d,11.4) | 3,4,8a,1',2' | 80.4 (CH) | 5.27 (dd, 12.6, 3.0) | 1',2',6' |
3 | 71.3 (CH) | 4.56 (d,11.4) | 2,4,1' | 44.1(CH2) | A 3.05 (dd,17.0, 12.6) | 2,4,1' |
B 2.69 (dd, 17.0, 3.0) | 4 | |||||
4 | 197.2 (C) | 197.2 (C) | ||||
4a | 100.1 (C) | 103.3 (C) | ||||
5 | 163.1 (C) | 165.1 (C) | ||||
5-OH | 11.9 br s | |||||
6 | 96.0 (CH) | 5.89 (d, 1.8 Hz) | 4a,5,7,8 | 97.6 (CH) | 5.88 (d, 1.7) | 4a,7 |
6-Me | ||||||
7 | 167.1 (C) | 169.0 (C) | ||||
7-Me | ||||||
8 | 95.0 (CH) | 5.83 (d,1.8 Hz) | 4a,6,7,8a | 96.5 (CH) | 5.86 (d, 1.7) | 4a,7,8a |
8a | 162.4 (C) | 164.6 (C) | ||||
1' | 127.5 (C) | 132.0 (C) | ||||
2' | 114.7 (CH) | 6.91 br s | 2,1',3',4',6' | |||
3' | 116.3 (CH) | 6.78 s | 1' | |||
4' | 157.6 (C) | 146.6 (C) | ||||
5' | 143.2 (C) | |||||
6' | 119.3 (CH) | 6.78 s | 2,2',4' | |||
2'/6' | 129.3 (CH) | 7.31 (d, 8.25) | 2,1',3'/5',4' | |||
3'/5' | 114.8 (CH) | 6.78 (d, 8.25) | 1',2'/6',4' |
Position | Compound 3 (d6 DMSO) | Compound 4 (CD3OD) | ||||
---|---|---|---|---|---|---|
13C | 1H | HMBC | 13C | 1H | HMBC | |
2 | 78.4 (CH) | 5.43 (dd, 12.9, 2.9) | 3,4,1',2' | 83.7 (CH) | 5.01 (d, 11.4) | 3,4,1',2' |
3 | 41.9 (CH2) | A 3.25 (dd, 17.2, 12.9) | 2,4,1' | 72.3 (CH) | 4.57 (d, 11.4) | 2,4,1' |
B 2.68 (dd, 17.2, 2.9) | 2,1' | |||||
4 | 196.8 (C) | 197.6 (C) | ||||
4a | 101.7 (C) | 101.2 (C) | ||||
5 | 162.9 (C) | 163.7 (C) | ||||
5-OH | 12.13 (br s) | 4a,5,6 | ||||
6 | 95.8 (CH) | 5.85 (br s) | 5,7,8,8a | 94.6 (CH) | 6.08 (d. 2.4) | 5,7,8,4a |
6-Me | ||||||
7 | 166.7 (C) | 168.4 (C) | ||||
7-Me | 54.9 (CH3) | 3.8 | 7 | |||
8 | 94.9 (CH) | 5.85 (br s) | 5,7,8,8a | 93.6 (CH) | 6.04 (d, 2.4) | 4a,6,7,8a |
8a | 163.4 (C) | 163.0 (C) | ||||
1' | 128.8 (C) | 127.7 (C) | ||||
2' | ||||||
3' | ||||||
4' | 157.6 (C) | 157.8 (C) | ||||
5' | 6.8 | |||||
6' | 7.35 | |||||
2'/6' | 128.3 (CH) | 7.31 (d, 8.5) | 2,1',3'/5',4' | 128.4 (CH) | 7.35 (d, 8.4) | 2,3',4' |
3'/5' | 115.1 (CH) | 6.79 (d,8.5) | 1',2'/6',4' | 114.7 (CH) | 6.80 (d, 8.4) | 1',2',4' |
Position | Compound 5 (d6 DMSO) | Compound 6 (CD3OD) | Compound 7 (CDCl3) | ||||||
---|---|---|---|---|---|---|---|---|---|
13C | 1H | HMBC | 13C | 1H | HMBC | 13C | 1H | HMBC | |
2 | 77.9 (CH) | 5.32 (dd,12.4,2.8) | 3,4,1',2' | 78.6 (CH) | 5.30 (dd, 12.9, 3.0) | 1',2' | 79.0 (CH) | 5.34 (dd, 13.0, 3.0) | 3,4,1',2' |
3 | 42.0 (CH2) | A 3.12(dd,17.0,12.4) B 2.60 (dd,17.0,2.8) | 2,4,1' 2,1' | 42.7(CH2) | A 3.05 (dd,16.8, 12.9) B 2.71 (dd, 16.8, 3.0) | 2,4,1' 4 | 43.2 ( CH2) | A 3.08 (dd,17.3, 13.0) B 2.78 (dd, 17.3, 3.0) | 2,4,1' 2,1' |
4 | 194.3 (C) | 196.7 (C) | 196.2 (C) | ||||||
4a | 100.6 (C) | 102.8 (C) | 103.9 (C) | ||||||
5 | 160.4 (C) | 157.9 (C) | 164.5 (C) | ||||||
5-OH | 12.47 (br s) | 4a,5,6 | |||||||
6 | 103.3 (C) | 103.5 (C) | 95.1 (CH) | 6.06 (d, 2.4) | 4a,5,7,8 | ||||
6-Me | 7.1 (CH3) | 1.83 (s) | 5,6,7 | 6.8 (CH3) | 1.99 (s) | 5,6,7 | |||
7 | 168.8 (C) | 163.6 | 168.1 (C) | ||||||
7-Me | 55.7 (CH3) | 3.79 (s) | 7 | ||||||
8 | 94.9 (CH) | 5.82 (s) | 6,7,8a | 101.6 (C) | 94.2 (CH) | 6.03 (d, 2.4) | 6,7,8a | ||
8-Me | 6.0 (CH3) | 1.98 (s) | 7,8,8a | ||||||
8a | 160.2 (C) | 158.8 (C) | 163.2 (C) | ||||||
1' | 129.2 (C) | 130.2 (C) | 127.7(C) | ||||||
2''/6'' | 128.0 (CH) | 7.29 (d, 8.3) | 2,1',3'/5',4' | 127.4 (CH) | 7.32 (d, 8.4) | 2,3',4' | 127.9 (CH) | 7.31 (d, 8.6) | 2,1',3'/5',4' |
3''/5' | 115.0 (CH) | 6.77 (d, 8.3) | 1',2'/6',4' | 114.9 (CH) | 6.81 (d, 8.4) | 1',2',4' | 115.7 (CH) | 6.88 (d, 8.6) | 1',2'/6',4' |
4' | 157.5 (C) | 157.4 (C) | 156.5 (C) |
Compound | Identification | Formula [M–H]− | Calculated Mass [M–H]− (m/z) | Found Mass |
---|---|---|---|---|
1 | 3,4',5,7-tetrahydroxyflavanone | C15H11O6 | 287.05553 | 287.0565 |
2 | 3',4',5,7-tetrahydroxyflavanone | C15H11O6 | 287.05553 | 287.0566 |
3 | 4',5,7-trihydroxyflavanone | C15H11O5 | 271.06063 | 271.0616 |
4 | 3,4',5 -trihydroxy-7-methoxyflavanone | C16H13O6 | 301.07119 | 301.0721 |
5 | (+)-(2S)-4',5,7-trihydroxy-6-methylflavanone | C16H13O5 | 285.07629 | 285.0773 |
6 | 4',5,7-trihydroxy-6,8-dimethylflavanone | C17H15O5 | 299.09695 | 299.0930 |
7 | 4',5-dihydroxy-7-methoxyflavanone | C16H13O5 | 285.07629 | 285.0771 |
3. Experimental Section
3.1. Plant Material
3.2. Extraction
3.3. Chromatography
3.3.1. Analytical HPLC-UV/DAD
3.3.2. Preparative HPLC
3.3.3. UPLC-HR-MS Analysis
3.3.4. Spectroscopic Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Nobakht, M.; Grkovic, T.; Trueman, S.J.; Wallace, H.M.; Katouli, M.; Quinn, R.J.; Brooks, P.R. Chemical Constituents of Kino Extract from Corymbia torelliana. Molecules 2014, 19, 17862-17871. https://doi.org/10.3390/molecules191117862
Nobakht M, Grkovic T, Trueman SJ, Wallace HM, Katouli M, Quinn RJ, Brooks PR. Chemical Constituents of Kino Extract from Corymbia torelliana. Molecules. 2014; 19(11):17862-17871. https://doi.org/10.3390/molecules191117862
Chicago/Turabian StyleNobakht, Motahareh, Tanja Grkovic, Stephen J. Trueman, Helen M. Wallace, Mohammad Katouli, Ronald J. Quinn, and Peter R. Brooks. 2014. "Chemical Constituents of Kino Extract from Corymbia torelliana" Molecules 19, no. 11: 17862-17871. https://doi.org/10.3390/molecules191117862