A Saprophytic Fungus Tubeufia rubra Produces Novel Rubracin D and E Reversing Multidrug Resistance in Cancer Cells
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Fungus Materials
2.3. Fermentation, Extraction and Isolation
2.4. Spectral Data
2.5. Cytotoxicity Assays
2.6. Reversed MDR Assays
2.7. Western Blot (WB) Assay
2.8. Data Analysis
3. Results
3.1. Structure Identification of Compounds 1–18
3.2. Results of Bioactivity Assays
3.2.1. Cytotoxicity Evaluation In Vitro
3.2.2. MDR Reversal Effects of Compound 1 and 2 In Vitro
4. Discussion
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Position | 1 | Position | 2 | ||
---|---|---|---|---|---|
δC | δH, mult (J in Hz) | δC | δH, mult (J in Hz) | ||
1 | 64.0, CH2 | 4.44, dd, (12.1, 2.9) 4.22, dd, (12.0, 6.6) | 1 | 63.9, CH2 | 4.44, dd, (12.0, 2.9) 4.22, overlap |
2 | 71.7, CH | 5.25, m | 2 | 71.7, CH | 5.24, m |
3 | 68.7, CH2 | 3.91, dd, (10.9, 5.4) 3.74, overlap | 3 | 68.7, CH2 | 3.91, dd, (10.9, 5.4) 3.74, overlap |
1′ | 105.4, CH | 4.24, d, (7.4) | 1′ | 105.4, CH | 4.24, d, (7.3) |
2′ | 72.3, CH | 3.51, dd, (9.7, 7.2) | 2′ | 72.3, CH | 3.51, dd, (9.7, 7.3) |
3′ | 74.7, CH | 3.47, dd, (9.7, 3.2) | 3′ | 74.7, CH | 3.47, dd, (9.7, 3.2) |
4′ | 70.1, CH | 3.85, dd, (3.1, 0.6) | 4′ | 70.1, CH | 3.85, dd, (3.1, 0.6) |
5′ | 74.8, CH | 3.70, overlap | 5′ | 74.8, CH | 3.70, overlap |
6′ | 68.2, CH2 | 3.89, overlap 3.64, dd, (10.0, 5.5) | 6′ | 68.2, CH2 | 3.89, overlap 3.64, dd, (10.0, 5.5) |
1″ | 100.5, CH | 4.85, br s | 1″ | 100.5, CH | 4.85, br s |
2″ | 70.2, CH | 3.76, overlap | 2″ | 70.2, CH | 3.76, overlap |
3″ | 70.9, CH | 3.72, overlap | 3″ | 70.9, CH | 3.72, overlap |
4″ | 71.2, CH | 3.87, overlap | 4″ | 71.2, CH | 3.87, overlap |
5″ | 70.0, CH | 4.04, br t, (6.7) | 5″ | 70.0, CH | 4.04, br t, (6.7) |
6″ | 65.0, CH2 | 4.20, d (6.4) | 6″ | 65.0, CH2 | 4.20, d (6.4) |
1′″″ | 172.7, C | 1′″″ | 172.7, C | ||
2′″″ | 20.9, CH3 | 2.06, s | 2′″″ | 20.9, CH3 | 2.06, s |
1′″ | 175.0, C | 1′″ | 175.0, C | ||
2′″ | 35.1, CH2 | 2.32, t, (7.3) | 2′″ | 35.1, CH2 | 2.32, t, (7.3) |
3′″, 3″″ | 26.0, CH2 | 1.60, m | 3′″, 3″″ | 26.0, CH2 | 1.60, m |
4′″, 4″″-7′″, 7″″ | 30.2–30.8, CH2 | 1.28–1.36, m | 4′″-13′″ | 30.2–30.8, CH2 | 1.28–1.36, m |
8′″, 8″″, 14′″, 14″″ | 28.2, CH2 | 2.05, m | 14′″, 16″″ | 32.7, CH2 | 1.28–1.36, m |
9′″, 9″″ | 131.0 a, CH | 5.34, m | 15′″, 17″″ | 23.6, CH2 | 1.28–1.36, m |
10′″, 10″″ | 129.2 b, CH | 5.32, m | 16′″, 18″″ | 14.5, CH3 | 0.90, t, (6.9) |
11′″, 11″″ | 26.6, CH2 | 2.77, t, (6.6) | 1″″ | 174.6, C | |
12′″, 12″″ | 129.1 b, CH | 5.32, m | 2″″ | 35.0, CH2 | 2.31, t, (7.3) |
13′″, 13″″ | 130.9 a, CH | 5.34, m | 4″″-7″″ | 30.2–30.8, CH2 | 1.28–1.36, m |
15′″, 15″″ | 30.2–30.8, CH2 | 1.28–1.36, m | 8″″, 14″″ | 28.2, CH2 | 2.05, m |
16′″, 16″″ | 32.7, CH2 | 1.28–1.36, m | 9″″ | 131.0 a, CH | 5.34, m |
17′″, 17″″ | 23.7, CH2 | 1.28–1.36, m | 10″″ | 129.1 b, CH | 5.32, m |
18′″, 18″″ | 14.5, CH3 | 0.90, t, (6.9) | 11″″ | 26.6, CH2 | 2.77, t, (6.4) |
1′″″ | 174.6, C | 12″″ | 129.0 b, CH | 5.32, m | |
2′″″ | 35.0, CH2 | 2.31, t, (7.3) | 13″″ | 130.8 a, CH | 5.34, m |
15″″ | 30.2–30.8, CH2 | 1.28–1.36, m |
Samples | IC50 (μg/mL) | |||
---|---|---|---|---|
MCF-7/ADM | K562/ADM | A549/ADM | ||
1 | 5 μg/mL | 54.958 ± 7.595 | 3.813 ± 0.123 | 2.897 ± 0.072 |
10 μg/mL | 50.456 ± 4.071 | 3.182 ± 0.157 | 2.358 ± 0.133 | |
20 μg/mL | 41.726 ± 2.585 | 2.360 ± 0.208 | 1.841 ± 0.079 | |
2 | 5 μg/mL | 54.487 ± 3.538 | 3.764 ± 0.297 | 3.480 ± 0.129 |
10 μg/mL | 46.289 ± 0.825 | 3.195 ± 0.347 | 3.155 ± 0.338 | |
20 μg/mL | 40.567 ± 9.532 | 2.448 ± 0.225 | 2.755 ± 0.263 | |
Vrp | 5 μg/mL | 44.371 ± 5.746 | 4.038 ± 0.514 | 2.927 ± 0.226 |
10 μg/mL | 38.471 ± 1.397 | 3.452 ± 0.401 | 2.051 ± 0.107 | |
20 μg/mL | 31.799 ± 0.875 | 2.554 ± 0.197 | 1.848 ± 0.015 | |
ADM | 63.031 ± 2.616 | 4.797 ± 0.093 | 3.630 ± 0.207 |
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Qian, S.; Zeng, X.; Qian, Y.; Lu, Y.; He, Z.; Kang, J. A Saprophytic Fungus Tubeufia rubra Produces Novel Rubracin D and E Reversing Multidrug Resistance in Cancer Cells. J. Fungi 2023, 9, 309. https://doi.org/10.3390/jof9030309
Qian S, Zeng X, Qian Y, Lu Y, He Z, Kang J. A Saprophytic Fungus Tubeufia rubra Produces Novel Rubracin D and E Reversing Multidrug Resistance in Cancer Cells. Journal of Fungi. 2023; 9(3):309. https://doi.org/10.3390/jof9030309
Chicago/Turabian StyleQian, Shengyan, Xuebo Zeng, Yixin Qian, Yongzhong Lu, Zhangjiang He, and Jichuan Kang. 2023. "A Saprophytic Fungus Tubeufia rubra Produces Novel Rubracin D and E Reversing Multidrug Resistance in Cancer Cells" Journal of Fungi 9, no. 3: 309. https://doi.org/10.3390/jof9030309