Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance †
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of Compounds
2.2. Chemophenetic Significance
2.3. Biological Results
3. Experimental
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Kotschyanoside A (1)
3.5. Kotschyanoside B (2)
3.6. Kotschyanoside C (3)
3.7. Kotschyanoside D (4)
3.8. Cyclization of Compound 1
3.9. Bioassay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Position | 1 a | 2 b | 3 c | 4 c |
---|---|---|---|---|
δc | δc | δc | δc | |
1 | 36.7 | 36.1 | 37.1 | 37.6 |
2 | 32.1 | 30.8 | 35.3 | 37.5 |
3 | 70.7 | 69.3 | 78.6 | 78.7 |
4 | 39.1 | 33.4 | 47.0 | 30.6 |
5 | 47.5 | 53.7 | 46.7 | 55.2 |
6 | 46.8 | 74.6 | 30.1 | 76.5 |
7 | 212.2 | 211.7 | 214.4 | 212.3 |
8 | 50.1 | 46.8 | 50.6 | 48.4 |
9 | 55.9 | 54.6 | 48.2 | 56.7 |
10 | 36.9 | 35.8 | 37.3 | 49.6 |
11 | 22.1 | 21.0 | 22.5 | 22.6 |
12 | 39.1 | 38.3 | 40.1 | 40.0 |
13 | 43.1 | 41.7 | 43.5 | 43.4 |
14 | 47.8 | 46.3 | 48.2 | 48.0 |
15 | 37.4 | 35.9 | 37.2 | 36.8 |
16 | 72.3 | 70.6 | 73.0 | 73.0 |
17 | 62.0 | 60.2 | 62.1 | 62.0 |
18 | 13.8 | 12.9 | 13.5 | 13.4 |
19 | 12.2 | 12.7 | 12.0 | 13.3 |
20 | 28.1 | 26.5 | 28.3 | 28.3 |
21 | 20.7 | 19.5 | 20.4 | 20.3 |
22 | 40.9 | 38.3 | 40.6 | 40.5 |
23 | 69.7 | 67.5 | 69.4 | 69.5 |
24 | 69.3 | 67.7 | 70.0 | 70.0 |
25 | 30.8 | 29.4 | 31.2 | 31.1 |
26 | 19.0 | 18.1 | 18.5 | 18.5 |
27 | 19.6 | 18.8 | 19.1 | 19.1 |
28 | 57.2 | 55.5 | 58.0 | 58.0 |
29 | 14.2 | 13.3 | 13.7 | 13.7 |
1’ | - | - | 102.3 | 102.3 |
2’ | - | - | 75.2 | 75.1 |
3’ | - | - | 78.1 | 78.1 |
4’ | - | - | 77.9 | 77.9 |
5’ | - | - | 71.0 | 71.6 |
6’ | - | - | 62.8 | 62.7 |
Position | 1 a | 2 b | 3 c | 4 c |
---|---|---|---|---|
δH | δH | δH | δH | |
1 | 1.70, m | 0.92, m | 0.87, m | 1.07, m |
2 | 2.12, m 1.76, m | 1.63, m | 1.76, m | 1.80, m |
3 | 3.85, m | 3.27, m | 3.76, m | 3.76, m |
4 | 1.83, m 1.69, m | 1.99, m | 2.51 (t, 12.8) | 2.35, m |
5 | 1.47, m | 1.07, m | 2.58, m | 124, m |
6 | 2.10, m | 3.85, m | 1.95, m | 3.99 (d, 11.9) |
7 | - | - | - | - |
8 | 2.41 (t, 11.0) | 2.52, br s | 2.58 (t, 11.3) | 2.63 (t, 11.4) |
9 | 1.08, m | 0.95, m | 1.49, m | 1.11, m |
10 | - | - | - | - |
11 | 1.50, m | 1.46, m | 1.59, m | 1.61, m |
12 | 2.00, m | 1.86, m | 2.02, m 1.11, m | 2.03, m 1.11, m |
13 | - | - | - | - |
14 | 1.47, m | 1.18, m | 1.49, m | 1.38, m |
15 | 3.26, m | 2.80, m | 2.80, m 1.06, m | 2.81, m 1.09, m |
16 | 4.67 (td, 7.6, 4.3) | 4.23, m | 4.39, m | 4.39, m |
17 | 0.96, m | 0.90, m | 1.04, m | 2.82, m |
18 | 1.06, s | 0.80, s | 0.91, s | 0.92, s |
19 | 1.09, s | 1.04, s | 1.15, s | 1.20, s |
20 | 2.47, m | 1.89, m | 2.02, m | 2.03, m |
21 | 1.03 (d, 6.6) | 0.95 (d, 6.6) | 1.08 (d, 6.4) | 1.08 (d, 7.0) |
22 | 1.45, m | - | 1.58, m 1.12, m | 1.57, m 1.10, m |
23 | 4.28, br d | 3.73, m | 3.92 (dd, 11.2, 1.6) | 3.92 (dd, 11.2, 1.6) |
24 | - | - | - | - |
25 | 1.82, m | 1.64, m | 1.75, m | 1.74, m |
26 | 1.10 (d, 7.0) | 1.00 (d, 1.7) | 1.11 (d, 2.5) | 1.10 (d, 2.3) |
27 | 1.14 (d, 7.2) | 0.99 (d, 1.5) | 1.09 (d, 2.1) | 1.09 (d, 1.9) |
28 | 3.51 (q, 5.5) | 3.08 (q, 5.6) | 3.24 (q, 5.7) | 3.25 (q, 5.7) |
29 | 1.37 (d, 5.6) | 1.22 (d, 5.6) | 1.33 (d, 5.7) | 1.33 (d, 5.7) |
1’ | - | - | 4.40 (d, 7.8) | 4.40 (d, 7.8) |
2’ | - | - | 3.18, m | 3.35, m |
3’ | - | - | 3.36, m | 3.36, m |
4’ | - | - | 3.27, m | 3.27, m |
5’ | - | - | 3.29, m | 3.28, m |
6’ | - | - | 3.85, m 3.65 (d, 5.1) | 3.87 (dd, 11.9, 1.6) 3.65, m |
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Tseme Wandji, N.; Bitchagno, G.T.M.; Mawabo Kamga, I.; Tchamgoue, J.; Nkenfou, C.N.; Lenta, B.N.; Sewald, N.; Kouam, S.F. Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance. Molecules 2023, 28, 5278. https://doi.org/10.3390/molecules28135278
Tseme Wandji N, Bitchagno GTM, Mawabo Kamga I, Tchamgoue J, Nkenfou CN, Lenta BN, Sewald N, Kouam SF. Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance. Molecules. 2023; 28(13):5278. https://doi.org/10.3390/molecules28135278
Chicago/Turabian StyleTseme Wandji, Nadine, Gabin Thierry M. Bitchagno, Isabelle Mawabo Kamga, Joseph Tchamgoue, Celine Nguefeu Nkenfou, Bruno Ndjakou Lenta, Norbert Sewald, and Simeon Fogue Kouam. 2023. "Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance" Molecules 28, no. 13: 5278. https://doi.org/10.3390/molecules28135278