Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation of Garcinamines F–H (1–3)
2.2. Biological Activity
3. Materials and Methods
3.1. General
3.2. Plant Material, Extraction and Isolation
3.3. Biological Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Positions | Garcinamine F (1) | Garcinamine G (2) | Garcinamine H (3) |
---|---|---|---|
δH, type | δH, type | δH, type | |
1 | 35.4, CH | 35.4, CH | 136.2, C |
2 | 26.0, CH2 | 25.6, CH2 | 33.0, CH2 |
3 | 41.4, CH2 | 41.4, CH2 | 39.2, CH2 |
4 | 79.5, C | 79.6, C | 80.3, C |
5 | 55.1, CH | 54.9, CH | 56.6, CH |
6 | 84.1, CH | 84.6, CH | 83.3, CH |
7 | 43.0, CH | 41.4, CH | 47.0, CH |
8 | 39.5, CH2 | 38.5, CH2 | 35.7, CH2 |
9 | 74.6, CH | 73.2, CH | 71.4, CH |
10 | 152.6, C | 150.8, C | 131.3, C |
11 | 41.8, CH | 41.6, CH | 41.6, CH |
12 | 177.0, C | 177.1, C | 177.0, C |
13 | 53.0, CH2 | 53.1, CH2 | 52.5, CH2 |
14 | 108.5, CH2 | 111.1, CH2 | 15.0, CH3 |
15 | 22.5, CH3 | 22.5, CH3 | 21.8, CH3 |
1′ | 171.9, C | 171.9, C | 172.0, C |
2′ | 70.8, CH | 70.6, CH | 70.6, CH |
3′ | 28.6, CH2 | 28.6, CH2 | 28.6, CH2 |
4′ | 23.5, CH2 | 23.4, CH2 | 23.4, CH2 |
5′ | 54.1, CH2 | 54.1, CH2 | 54.2, CH2 |
Positions | Garcinamine F (1) | Garcinamine G (2) | Garcinamine H (3) |
---|---|---|---|
δH (multiplicity, J in Hz) | δH (multiplicity, J in Hz) | δH (multiplicity, J in Hz) | |
1 | 3.04 (dd, 4.0, 11.0) | 3.56 m | - |
2a | 1.92 (m) | 1.90 (m) | 2.12 (m) |
2b | 1.83, overlapped | 1.78 (m) | 1.70 (m) |
3 | 1.83–1.85 (m) | 1.82 (m) | 1.76 (m) |
5 | 2.30 (t, 11.0) | 2.28 (t, 11.0) | 2.70 (d, 10.5) |
6 | 4.23 (d, 11.0) | 4.26 (d, 11.0) | 4.02 (bd, 10.5) |
7 | 2.30 (m) | 2.52 (m) | 2.31 (dd, 3.0, 13.0) |
8α | 2.39 (dd, 4.0, 9.0) | 2.24 (m) | 2.06 (d, 11.5) |
8β | 1.42 (m) | 1.65 (m) | 1.65 (d, 11.5) |
9 | 3.99 (dd, 4.0, 7.0) | 4.56 (bs) | 4.23 (bs) |
11 | 3.0 (m) | 3.07 (dd, 4.0, 11.5) | 3.13 (dd, 3.5, 12.5) |
13a | 3.63 (dd, 11.0, 12.5) | 3.60 (dd, 11.0, 12.5) | 3.65 (dd, 10.5, 12.5) |
13b | 3.53 (dd, 4.0, 12.5) | 3.45 (dd, 4.0, 12.5) | 3.57 (dd, 3.5, 10.5) |
14a | 5.51 (bs) | 5.15 (bs) | 1.77 (s) |
14b | 5.17 (bs) | 5.05 (bs) | - |
15 | 1.33 (s) | 1.30 (s) | 1.36 (s) |
2′ | 4.02 (dd, 5.0, 9.5) | 4.02 (dd, 5.0, 9.5) | 4.06 (dd, 6.0, 10.0) |
3′a | 2.46 (dd, 3.5, 9.5) | 2.45 (dd, 3.5, 9.5) | 2.46 (dd, 3.5, 10.0) |
3′b | 2.26 (dd, 5.0, 3.5) | 2.24 (dd, 5.0, 3.5) | 2.26 (m) |
4′a | 2.17 (m) | 2.15 (m) | 2.17 (m) |
4′b | 1.98 (m) | 1.97 (m) | 1.99 (m) |
5′a | 3.86 (dd, 4.0, 7.5) | 3.85 (dd, 4.0, 7.5) | 3.88 (dd, 4.0, 7.5) |
5′b | 3.25 (dd, 7.5, 10.5) | 3.24 (dd, 7.5, 10.5) | 3.27 (dd, 7.5, 10.5) |
Compound | Cell Lines and IC50 (µM) | ||
---|---|---|---|
A549 | LoVo | MCF-7 | |
1 | NA | NA | NA |
2 | NA | NA | NA |
3 | NA | NA | NA |
4 | NA | NA | NA |
5 | 83.7 ± 0.3 | 121.4 ± 3.2 | 75.0 ± 5.3 |
6 | NA | NA | NA |
7 | 31.5 ± 3.1 | 39.2 ± 3.0 | 36.0 ± 3.4 |
8 | 75.8 ± 1.4 | 38.8 ± 2.1 | 71.6 ± 5.2 |
Doxorubicin | 0.98 ± 0.02 | 5.5 ± 0.5 | 2.3 ± 0.1 |
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Aati, H.Y.; Perveen, S.; Orfali, R.; Al-Taweel, A.M.; Peng, J.; Tabassum, S.; Abdel-Kader, M.S.; Yusufoglu, H.S.; Taglialatela-Scafati, O. Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities. Plants 2021, 10, 1130. https://doi.org/10.3390/plants10061130
Aati HY, Perveen S, Orfali R, Al-Taweel AM, Peng J, Tabassum S, Abdel-Kader MS, Yusufoglu HS, Taglialatela-Scafati O. Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities. Plants. 2021; 10(6):1130. https://doi.org/10.3390/plants10061130
Chicago/Turabian StyleAati, Hanan Y., Shagufta Perveen, Raha Orfali, Areej M. Al-Taweel, Jiangnan Peng, Sobia Tabassum, Maged S. Abdel-Kader, Hasan Soliman Yusufoglu, and Orazio Taglialatela-Scafati. 2021. "Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities" Plants 10, no. 6: 1130. https://doi.org/10.3390/plants10061130