Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Culturing and Isolation of Metabolites
3.4. Chemical Transformation
3.4.1. Formation of the (S)- and (R)-PGME Amides
3.4.2. Formation of Methyl Ester of 1
3.4.3. Methanolysis of 2–4
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Position | 1 | 2 | 3 | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
δHa | δC | δHa | δC | δHa | δC | ||||||||
1 | 177.5 | (s) | 173.5 | (s) | 174.3 | (s) | |||||||
2 | 3.27 | m | 44.9 | (d) | 3.28 | m | 45.4 | (d) | 3.28 | m | 44.9 | (d) | |
3 | 5.50 | d (10.2) | 127.0 | (d) | 5.49 | d (10.8) | 129.3 | (d) | 5.55 | d (9.6) | 129.3 | (d) | |
4 | 138.7 | (s) | 133.9 | (s) | 137.9 | (s) | |||||||
5A | 2.25 | m | 31.9 | (t) | 2.18 | m | 32.3 | (t) | 2.30 | ddd (14.4, 5.4, 5.4) | 27.7 | (t) | |
5B | 2.49 | m | 2.54 | m | 2.54 | ddd (14.4, 5.4, 5.4) | |||||||
6A | 3.68 | br s | 61.0 | (t) | 3.65 | br s | 61.4 | (t) | 4.20 | m | 63.5 | (t) | |
6B | 66.8 | (t) | 3.72 | br s | |||||||||
7A | 4.03 | br s | 4.05 | d (13.2) | 67.9 | (t) | 4.07 | m | 66.5 | (t) | |||
7B | d (13.2) | ||||||||||||
8A | 2.20 | m | 30.9 | (t) | 2.20 | m | 30.8 b5 | (t) | 2.20 | m | 31.4 | (t) | |
8B | 2.44 | m | 2.46 | m | 2.44 | m | |||||||
9 | 5.04 | dd | 120.2 | (d) | 5.03 | m | 120.2 b6 | (d) | 5.02 b1 | dd (7.2, 7.2) | 120.2 b2 | (d) | |
10 | 134.1 | (s) | 134.2 b7 | (s) | 134.3 | (s) | |||||||
11 | 1.67 | s | 25.7 | (q) | 1.67 | s | 25.7 | (q) | 1.67 | s | 25.7 | (q) | |
12 | 1.60 | s | 17.8 | (q) | 1.60 | s | 17.8 | (q) | 1.59 b3 | s | 17.8 b4 | (q) | |
1′ | 173.5 | (s) | 174.3 | (s) | |||||||||
2′ | 3.28 | m | 45.4 | (d) | 3.28 | m | 44.9 | (d) | |||||
3′ | 5.52 | d (10.8) | 127.2 | (d) | 5.51 | d (9.6) | 127.2 | (d) | |||||
4′ | 139.6 | (s) | 138.7 | (s) | |||||||||
5′A | 2.29 | m | 32.3 | (t) | 2.25 | m | 32.2 | (t) | |||||
5′B | 2.54 | m | 2.51 | m | |||||||||
6′A | 3.72 | br s | 60.5 | (t) | 3.65 | br s | 61.1 | (t) | |||||
6′B | 3.71 | br s | |||||||||||
7′ | 4.05 | br s | 67.5 | (t) | 4.02 | m | 67.4 | (t) | |||||
8′A | 2.20 | m | 30.6 b5 | (t) | 2.20 | m | 31.4 | (t) | |||||
8′B | 2.46 | m | 2.44 | m | |||||||||
9′ | 5.03 | m | 120.3 b6 | (d) | 5.06 b1 | dd (7.2, 7.2) | 120.3 b2 | (d) | |||||
10′ | 134.3 b7 | (s) | 134.3 | (s) | |||||||||
11′ | 1.67 | s | 25.7 | (q) | 1.67 | s | 25.7 | (q) | |||||
12′ | 1.60 | s | 17.8 | (q) | 1.61 b3 | s | 17.9 b4 | (q) |
Position | 4 | |||
---|---|---|---|---|
δHa | δC | |||
1 | 3.68 | m | 40.2 | (d) |
2 | 5.36 | br s | 121.2 | (d) |
3 | 139.2 | (s) | ||
4A | 2.45 | br d (19.2) | 30.3 | (t) |
4B | 2.59 | m | ||
5α | 4.68 | ddd (12.6, 12.6, 1.8) | 64.4 | (t) |
5β | 4.33 | ddd (12.6, 4.8, 2.4) | ||
6 | ||||
7 | 174.3 | (s) | ||
8A | 2.33 | ddd (14.4, 6.6, 6.6) | 30.1 | (t) |
8B | 2.52 | ddd (14.4, 6.6, 6.6) | ||
9 | 5.14 | dd (6.6, 6.6) | 120.9 | (d) |
10 | 134.6 | (s) | ||
11 | 1.72 | s | 25.8 | (q) |
12 | 1.67 | s | 18.0 | (q) |
13A | 3.99 | d (13.8) | 67.4 | (t) |
13B | 4.01 | d (13.8) |
Compounds | Cell Line P388 | Cell Line HL-60 | Cell Line L1210 |
---|---|---|---|
IC50 (μM) a | IC50 (μM) a | IC50 (μM) a | |
1 | >500 | >500 | >500 |
2 | >500 | 236.7 | >500 |
3 | >500 | 60.2 | 480.9 |
4 | >500 | 189.5 | >500 |
5-fluorouracil b | 6 | 4.9 | 4.5 |
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Yamada, T.; Matsuda, M.; Seki, M.; Hirose, M.; Kikuchi, T. Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus. Molecules 2018, 23, 1336. https://doi.org/10.3390/molecules23061336
Yamada T, Matsuda M, Seki M, Hirose M, Kikuchi T. Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus. Molecules. 2018; 23(6):1336. https://doi.org/10.3390/molecules23061336
Chicago/Turabian StyleYamada, Takeshi, Miwa Matsuda, Mayuko Seki, Megumi Hirose, and Takashi Kikuchi. 2018. "Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus" Molecules 23, no. 6: 1336. https://doi.org/10.3390/molecules23061336
APA StyleYamada, T., Matsuda, M., Seki, M., Hirose, M., & Kikuchi, T. (2018). Sterepinic Acids A–C, New Carboxylic Acids Produced by a Marine Alga-Derived Fungus. Molecules, 23(6), 1336. https://doi.org/10.3390/molecules23061336