New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of Compounds
Position | 1a | 1b | 2a | 2b | 3b | 4 | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | |
2 | - | 164.5, C | - | 164.3, C | - | 164.3, C | - | 163.9, C | - | 164.4, C | - | 164.4, C |
3 | 6.81, s | 103.1, CH | 6.93, s | 103.9, CH | 6.93, s | 104.2, CH | 6.89, s | 103.7, CH | 6.87, s | 103.3, CH | 6.87, s | 103.3, CH |
4 | - | 182.5, C | - | 183.1, C | - | 182.6, C | - | 182.4, C | - | 182.5, C | - | 182.8, C |
5 | - | 157.5, C | - | 152.0, C | - | 161.0, C | - | 157.4, C | - | 157.5, C | - | 157.6, C |
6 | 6.29, s | 100.0, CH | 6.90, s | 104.1, CH | 6.60, d (1.8) | 102.1, CH | 6.30, s | 100.0, CH | 6.29, s | 99.9, CH | 6.53, s | 96.6, CH |
7 | - | 157.5, C | - | 148.3, C | - | 160.1, C | - | 157.5, C | - | 157.5, C | - | 159.7, C |
8 | - | 121.9, C | - | 129.5, C | 7.05, d (1.8) | 98.0, CH | - | 121.9, C | - | 121.1, C | - | 123.3, C |
9 | - | 150.2, C | - | 145.7, C | - | 156.9, C | - | 150.1, C | - | 151.9, C | - | 149.9, C |
10 | - | 104.4, C | - | 106.8, C | - | 106.2, C | - | 104.4, C | - | 104.4, C | - | 104.3, C |
1′ | - | 121.9, C | - | 123.5, C | - | 123.1, C | - | 123.4, C | - | 122.3, C | - | 123.7, C |
2′ | 8.03, d (8.7) | 129.0, CH | 8.11, d (8.9) | 129.3, CH | 8.07, d (8.7) | 129.0, CH | 8.14, d (8.9) | 129.1, CH | 7.64, dd (1.8, 8.5) | 121.1, CH | 8.28, d (8.7) | 129.7, CH |
3′ | 6.93, d (8.7) | 116.4, CH | 7.14, d (8.9) | 115.2, CH | 7.12, d (8.7) | 115.1, CH | 7.13, d (8.9) | 115.0, CH | 7.14, dd (0.7, 8.5) | 115.2, CH | 7.08, d (8.7) | 114.9, CH |
4′ | - | 161.8, C | - | 163.0, C | - | 162.9, C | - | 162.9, C | - | 151.2, C | - | 162.8, C |
5′ | 6.93, d (8.7) | 116.4, CH | 7.14, d (8.9) | 115.2, CH | 7.12, d (8.7) | 115.1, CH | 7.13, d (8.9) | 115.0, CH | - | 148.5, C | 7.08, d (8.7) | 114.9, CH |
6′ | 8.03, d (8.7) | 129.0, CH | 8.11, d (8.9) | 129.3, CH | 8.07, d (8.7) | 129.0, CH | 8.14, d (8.9) | 129.1, CH | 7.82, d (1.8) | 111.2, CH | 8.28, d (8.7) | 129.7, CH |
OCH3-4′ | - | - | 3.86, s | 56.1, CH3 | 3.86, s | 56.0, CH3 | 3.87, s | 56.0, CH3 | - | - | 3.86, s | 56.1, CH3 |
OCH3-7 | - | - | - | - | - | - | - | - | - | - | 3.85, s | 57.0, CH3 |
OCH3-5′ | - | - | - | - | - | - | - | - | 3.88, s | 56.4, CH3 | - | - |
OH-5 | 12.75, s | - | 12.16, s | - | 12.82, s | - | 12.70, s | - | 12.71, s | - | 12.87, s | - |
OH-8 | - | - | 8.98, s | - | - | - | - | - | - | - | - | - |
OH-7 | 9.96, s | - | - | - | - | - | - | - | - | - | - | - |
OH-4′ | 10.42, s | - | - | - | - | - | - | - | - | - | - | - |
2.2. Evaluation of Cytotoxicity
Treatment | IC50 (µg/mL) | |||
---|---|---|---|---|
Tumour Cell Lines | Normal Cell Lines | |||
UVW | PC-3M | PNT2A | Hs27 | |
acacetin | 27.37 ± 1.09 ab | 21.13 ± 1.16 ab | 51.33 ± 1.09 | >100 |
7,4′-di-O-methylisoscutellarein | 98.55 ± 1.13 ab | >100 | 88.73 ± 1.13 | NA |
tiliroside | >100 | 60.55 ± 1.12 ab | >100 | NA |
acacetin + apigenin (1.2:1) | >100 | 48.13 ± 1.09 ab | >100 | >100 |
2a + 2b (2:1) | >100 | 92.14 ± 1.09 ab | >100 | NA |
3. Experimental Section
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Compound Identification
3.5. Liquid Chromatography-Mass Spectrometry (LC-MS)
Time (min) | A% | B% |
---|---|---|
0 | 75 | 25 |
15 | 25 | 75 |
3.6. Cell lines and Cell Culture
3.7. Evaluation of Cytotoxicity
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Teles, Y.C.F.; Horta, C.C.R.; Agra, M.D.F.; Siheri, W.; Boyd, M.; Igoli, J.O.; Gray, A.I.; De Souza, M.D.F.V. New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). Molecules 2015, 20, 20161-20172. https://doi.org/10.3390/molecules201119685
Teles YCF, Horta CCR, Agra MDF, Siheri W, Boyd M, Igoli JO, Gray AI, De Souza MDFV. New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). Molecules. 2015; 20(11):20161-20172. https://doi.org/10.3390/molecules201119685
Chicago/Turabian StyleTeles, Yanna C. F., Carolina Campolina Rebello Horta, Maria De Fátima Agra, Weam Siheri, Marie Boyd, John O. Igoli, Alexander I. Gray, and Maria De Fátima Vanderlei De Souza. 2015. "New Sulphated Flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae)" Molecules 20, no. 11: 20161-20172. https://doi.org/10.3390/molecules201119685