New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54
Abstract
:1. Introduction
2. Results
2.1. Structural Elucidation
2.2. The Bioactivities of Compounds 1–4 from Penicillium sp. J-54
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Fermentation and Extraction
3.4. Purification and Identification
3.5. Preparation of S-MTPA and R-MTPA Esters 1a, 1b, 2a, 2b, 3a, and 3b of Compounds 1, 2, and 3
3.6. Absolute Configuration of the 1, 2-Diol Moiety in 1
3.7. Bioassays
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Position | 1 | 2 | ||
---|---|---|---|---|
δC, Type | δH mult. (J in Hz) | δC, Type | δH, mult. (J in Hz) | |
1 | 83.9, CH | 2.74, dd, (9.2, 4.0) | 83.8, CH | 2.77, dd, (9.2, 3.9) |
2 | 66.7, CH | 3.54, m | 66.6, CH | 3.64, m |
3 | 40.5, CH2 | 1.79, m | 40.5, CH2 | 1.68, m |
1.43, m | 1.42, m | |||
4 | 33.7, CH | 1.71, m | 33.3, CH | 1.59, m |
5 | 45.7, CH | 1.31, m | 39.1, CH | 1.76, m |
6 | 31.3, CH2 | 1.41, m | 35.8, CH2 | 1.51, m |
1.25, m | 1.11, d, (13.0, 2.5) | |||
7 | 45.6, CH | 1.90, m | 72.7, qC | |
8 | 26.2, CH2 | 1.44, m | 30.4, CH2 | 1.54, m |
1.27, m | 1.33, m | |||
9 | 40.3, CH2 | 1.67, m | 35.9, CH2 | 1.66, m |
0.98, m | 1.35, m | |||
10 | 39.2, qC | 38.9, qC | ||
11 | 150.3, qC | 153.2, qC | ||
12 | 108.7, CH2 | 4.67, s | 108.5, CH2 | 4.96, d, (1.8) |
4.64, s | 4.68 d, (1.8) | |||
13 | 21.1, CH3 | 1.68, s | 19.2, CH3 | 1.74, s |
14 | 15.6, CH3 | 0.81, s | 14.6, CH3 | 0.79, s |
15 | 16.0, CH3 | 0.85, d, (7.6) | 15.9, CH3 | 0.86, d, (7.6) |
1-OH | 4.38, d, (3.7) | |||
2-OH | 4.41, d, overlap | 4.37, d, (3.7) | ||
5-OH | 4.41, d, overlap | |||
7-OH | 4.22, s |
Position | 3 | 4 | ||
---|---|---|---|---|
δC, Type | δH, mult. (J in Hz) | δC, Type | δH mult. (J in Hz) | |
1 | 77.8, CH | 3.45, dd, (9.1, 2.5) | 77.5, CH | 3.40, d, (9.2) |
2 | 67.7, CH | 3.66, m | 67.3, CH | 3.60, m |
3 | 35.9, CH2 | 2.06, m | 35.0, CH2 | 1.93, m |
1.48, m | 1.40, m | |||
4 | 41.2, CH | 1.71, m | 40.5, CH | 1.67, m |
5 | 75.3, qC | 76.7, qC | ||
6 | 37.1, CH2 | 1.79, m | 38.7, CH2 | 1.99, d, (14.0) |
1.25, dd, (13.3, 3.0) | 1.15, d, (14.0) | |||
7 | 39.2, CH | 2.53, m | 75.1, qC | |
8 | 25.4, CH2 | 1.49, m | 30.3, CH2 | 1.46, m |
1.34, m | ||||
9 | 33.3, CH2 | 1.76, m | 29.8, CH2 | 1.76, m |
1.43, m | 1.40, m | |||
10 | 41.9, qC | 42.1, qC | ||
11 | 150.7, qC | 151.6, qC | ||
12 | 108.7, CH2 | 4.73, d, (1.6) | 109.3, CH2 | 4.96, s |
4.75, d, (1.6) | 4.74, s | |||
13 | 21.3, CH3 | 1.67, s | 19.0, CH3 | 1.74, s |
14 | 17.8, CH3 | 0.96, d, (7.8) | 17.4, CH3 | 0.95, d, (7.8) |
15 | 16.9, CH3 | 0.86, s | 16.7, CH3 | 0.87, s |
1-OH | 4.29, d, (3.7) | 4.26, br s | ||
2-OH | 4.37, d, (2.8) | 4.20, br s | ||
5-OH | 3.74, s | 5.66, s | ||
7-OH | 5.63 s |
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Qiu, L.; Wang, P.; Liao, G.; Zeng, Y.; Cai, C.; Kong, F.; Guo, Z.; Proksch, P.; Dai, H.; Mei, W. New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54. Mar. Drugs 2018, 16, 108. https://doi.org/10.3390/md16040108
Qiu L, Wang P, Liao G, Zeng Y, Cai C, Kong F, Guo Z, Proksch P, Dai H, Mei W. New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54. Marine Drugs. 2018; 16(4):108. https://doi.org/10.3390/md16040108
Chicago/Turabian StyleQiu, Liuming, Pei Wang, Ge Liao, Yanbo Zeng, Caihong Cai, Fandong Kong, Zhikai Guo, Peter Proksch, Haofu Dai, and Wenli Mei. 2018. "New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54" Marine Drugs 16, no. 4: 108. https://doi.org/10.3390/md16040108
APA StyleQiu, L., Wang, P., Liao, G., Zeng, Y., Cai, C., Kong, F., Guo, Z., Proksch, P., Dai, H., & Mei, W. (2018). New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54. Marine Drugs, 16(4), 108. https://doi.org/10.3390/md16040108