Using UHPLC-MS Profiling for the Discovery of New Dihydro-β-Agarofurans from Australian Celastraceae Plant Extracts
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Materials
3.3. Preparation of Crude Plant Extracts for UHPLC-MS Analyses
3.4. UHPLC-MS Conditions
3.5. Large-scale Extraction and Isolation of the Fruits of D. celastroides
3.6. Denhaminol O (1)
3.7. Denhaminol P (2)
3.8. Denhaminol Q (3)
3.9. Denhaminol R (4)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Retention Time (tR, min) | [M + H]+ m/z | Molecular Weight | No. of SciFinder Scholar Hits a | No. of DNP Hits a | Compounds b |
---|---|---|---|---|---|
9.873 | 615 | 614 | 1 | 0 | Denhaminol O (1) |
10.097 | 657 | 656 | 0 | 0 | Denhaminol P (2) |
10.410 | 673 | 672 | 10 | 0 | Denhaminol G (5) |
11.087 | 631 | 630 | 4 | 0 | Denhaminol Q (3) |
11.513 | 653 | 652 | 17 | 0 | Denhaminol R (4) |
Position | δH, multiplicity (J in Hz) | |||
---|---|---|---|---|
1 | 2 | 3 | 4 | |
1 | 5.39, dd (12.1, 4.5) | 5.36, dd (12.1, 4.2) | 5.40, dd (12.1, 4.4) | 5.46, dd (12.1, 4.4) |
2α | 1.53, m | 1.51, m | 1.52, m | 1.54, m |
2β | 1.95, m | 1.91, m | 1.95, m | 1.98, m |
3α | 1.69, ddd (13.1, 3.4, 3.4) | 1.68, ddd (13.5, 3.3, 3.3) | 1.68, ddd (13.0, 3.2, 3.2) | 1.71, ddd (13.1, 3.4, 3.4) |
3β | 1.86, m | 1.86, m | 1.84, m | 1.88, m |
6 | 4.44, br s | 5.48, s | 4.37, br s | 4.42, br s |
7 | 2.37, br dd (3.5, 3.0) | 2.34, br dd (3.6, 3.0) | 2.64, br d (3.2) | 2.73, br d (3.3) |
8α | 2.26, ddd (16.6, 7.4, 3.5) | 2.46, ddd (16.6, 7.3, 3.6) | 4.30, dd (6.4, 3.2) | 4.35, dd (6.5, 3.3) |
8β | 2.03, dd (16.6, 3.0) | 2.12, m | - | - |
9 | 4.88, d (7.4) | 4.92, d (7.0) | 5.06, d (6.4) | 5.08, d (6.5) |
12 | 4.52, d (11.0) | 4.47, d (11.1) | 4.69, d (11.6) | 4.88, d (11.5) |
4.69, d (11.0) | 4.70, d (11.1) | 4.82, d (11.6) | 5.02, d (11.5) | |
13 | 1.63, s | 1.58, s | 1.65, s | 1.76, s |
14 | 1.59, s | 1.33, s | 1.57, s | 1.60, s |
15 | 1.33, s | 1.36, s | 1.32, s | 1.35, s |
17 | 4.31, d (15.9) | 4.33 (15.8) | 4.33, d (15.8) | 4.34, d (15.9) |
4.45, d (15.9) | 4.46 (15.8) | 4.47, d (15.8) | 4.47, d (15.9) | |
19 | 1.88, s | 1.91, s | 1.92, s | 1.91, s |
21 | 6.40, d (16.0) | 6.39, d (16.0) | 6.49, d (15.9) | 6.54, d (16.0) |
22 | 7.65, d (16.0) | 7.66, d (16.0) | 7.69, d (15.9) | 7.71, d (16.0) |
24 | 7.56, m | 7.56, m | 7.58, m | 7.54, m |
25 | 7.36, m | 7.37, m | 7.36, m | 7.33, m |
26 | 7.36, m | 7.37, m | 7.36, m | 7.36, m |
27 | 7.36, m | 7.37, m | 7.36, m | 7.33, m |
28 | 7.56, m | 7.56, m | 7.58, m | 7.54, m |
31 | 6.81, m | 6.81, m | 6.85, m | 8.03, m |
32 | 1.78, m | 1.78, m | 1.80, m | 7.45, m |
33 | 1.79, m | 1.78, m | 1.82, m | 7.57, m |
34 | - | - | - | 7.45, m |
35 | - | 2.15, s | - | 8.03, m |
Position | δH, Type | |||
---|---|---|---|---|
1 | 2 | 3 | 4 | |
1 | 73.2,* CH | 73.5, CH | 73.2,* CH | 73.2,* CH |
2 | 23.5, CH2 | 23.6, CH2 | 23.3, CH2 | 23.3, CH2 |
3 | 36.9, CH2 | 38.3, CH2 | 37.0, CH2 | 37.0, CH2 |
4 | 73.3,* C | 70.6, C | 73.3,* CH | 73.3,* CH |
5 | 92.4, C | 92.4, C | 91.8, C | 91.9, C |
6 | 79.4, CH | 79.4, CH | 78.0, CH | 78.0, CH |
7 | 49.0, CH | 48.0, CH | 56.0, CH | 55.9, CH |
8 | 31.7, CH2 | 31.8, CH2 | 70.3, CH | 70.5, CH |
9 | 72.1, CH | 72.0, CH | 74.4, CH | 74.6, CH |
10 | 50.3, C | 51.6, C | 48.7, C | 48.8, C |
11 | 84.9, C | 84.8, C | 85.5, C | 85.6, C |
12 | 69.4, CH2 | 68.8, CH2 | 69.8, CH2 | 70.3, CH2 |
13 | 25.1, CH3 | 24.7, CH3 | 24.9, CH3 | 24.9, CH3 |
14 | 23.8, CH3 | 24.2, CH3 | 23.8, CH3 | 23.8, CH3 |
15 | 20.0, CH3 | 19.8, CH3 | 20.1, CH3 | 20.2, CH3 |
16 | 167.1, C | 167.1, C | 167.1, C | 167.1, C |
17 | 60.8, CH2 | 60.8, CH2 | 60.8, CH2 | 60.8, CH2 |
18 | 170.2, C | 170.2, C | 170.2, C | 170.2, C |
19 | 20.3, CH3 | 20.4, CH3 | 20.3, CH3 | 20.3, CH3 |
20 | 165.9, C | 166.0, C | 167.6, C | 167.9, C |
21 | 117.7, CH | 117.0, CH | 117.5, CH | 117.3, CH |
22 | 146.2, CH | 146.3, CH | 146.9, CH | 147.1, CH |
23 | 134.6, C | 134.6, C | 134.6, C | 134.5, C |
24 | 128.6, CH | 128.7, CH | 128.7, CH | 128.76, CH |
25 | 128.8, CH | 128.8, CH | 128.9, CH | 128.83, CH |
26 | 130.4, CH | 130.5, CH | 130.5, CH | 130.6, CH |
27 | 128.8, CH | 128.8, CH | 128.9, CH | 128.83, CH |
28 | 128.6, CH | 128.7, CH | 128.7, CH | 128.76, CH |
29 | 167.6, C | 127.5, C | 167.9, C | 166.4, C |
30 | 128.5, C | 128.4, C | 128.8, C | 130.5, C |
31 | 137.7, CH | 137.9, CH | 137.5, CH | 129.8, CH |
32 | 14.5, CH3 | 14.6, CH3 | 14.5, CH3 | 128.5, CH |
33 | 12.2, CH3 | 12.2, CH3 | 12.2, CH3 | 133.1, CH |
34 | - | 170.6, C | - | 128.5, CH |
35 | - | 21.8, CH3 | - | 129.8, CH |
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Wibowo, M.; Forster, P.I.; Guymer, G.P.; Hofmann, A.; Davis, R.A. Using UHPLC-MS Profiling for the Discovery of New Dihydro-β-Agarofurans from Australian Celastraceae Plant Extracts. Molecules 2019, 24, 859. https://doi.org/10.3390/molecules24050859
Wibowo M, Forster PI, Guymer GP, Hofmann A, Davis RA. Using UHPLC-MS Profiling for the Discovery of New Dihydro-β-Agarofurans from Australian Celastraceae Plant Extracts. Molecules. 2019; 24(5):859. https://doi.org/10.3390/molecules24050859
Chicago/Turabian StyleWibowo, Mario, Paul I. Forster, Gordon P. Guymer, Andreas Hofmann, and Rohan A. Davis. 2019. "Using UHPLC-MS Profiling for the Discovery of New Dihydro-β-Agarofurans from Australian Celastraceae Plant Extracts" Molecules 24, no. 5: 859. https://doi.org/10.3390/molecules24050859