Citation: Chen Lingling, Zhu Tonghan, Zhu Guoliang, Liu Yunlong, Wang Cong, Piyachaturawat Pawinee, Chairoungdua Arthit, Zhu Weiming. Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2752-2762. doi: 10.6023/cjoc201705002 shu

Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920

a.
Key Laboratory of Marine Drugs of Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003
b.
Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400

Corresponding author: Zhu Weiming, weimingzhu@ouc.edu.cn
Received Date: 2 May 2017
Revised Date: 30 May 2017
Available Online: 2 October 2017
Fund Project: the National Natural Science Foundation of Chi-na-Guangdong Fund Joint Project U1501221Project supported by the National Natural Science Foundation of China (Nos.81561148012,41376148) and the National Natural Science Foundation of Chi-na-Guangdong Fund Joint Project (No.U1501221)the National Natural Science Foundation of China 41376148the National Natural Science Foundation of China 81561148012

Figures(4)

A mycophenolic acid producing strain OUCMDZ-4920, identified as Penicillium brevicompactum, was isolated from a marine sediment (-68 m) collected in South China Sea by means of intergrated chemical and bioactive screening method. Eleven compounds including mycophenolic acid (3) and its seven analogues (1, 2 and 4~8) were isolated from a nutrient-poor fermentation broth of P. brevicompactum OUCMDZ-4920, among which (±)-brevicolides A (1) and B (2) were new compounds. On the bases of spectroscopic and electronic circular dichroism (ECD) analyses, chemical transformation, chiral separation and Mosher's method, new compounds (-)-brevicolide A (1a), (+)-brevicolide A (1b), (-)-brevicolide B (2a) and (+)-brevicolide B (2b) were identified as 7-hydroxy-6-((S)-2-hydroxy-2-((R)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzofuran-1(3H)-one, 7-hydroxy-6-((R)-2-hydroxy-2-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzofuran-1(3H)-one, 7-hydroxy-6-((S)-2-hydroxy-2-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzo-furan-1(3H)-one and 7-hydroxy-6-((R)-2-hydroxy-2-((R)-2-methyl-5-oxotetrahydro-furan-2-yl)ethyl)-5-methoxy-4-methylisobenzo-furan-1(3H)-one, respectively. And the known compounds were identified as mycophenolic acid (3), 3-hydroxymycophenolic acid (4), (S)-4-(5-hydroxy-7-methoxy-4-methyl-1-oxo-1, 3-dihydroisobenzo-furan-6-yl)-2-methylbutanoic acid (5), norpestaphthalides A (6) and B (7), 5, 7-dihydroxy-4-methylisobenzofuran-1(3H)-one (8), 6, 8-dihydroxy-3-(hydroxymethyl)-1H-isochromen-1-one (9), brevianamides A (10) and E (11), respectively. Compound 3 displayed good cytotoxicities against murine leukemia P388 cell, human oral epithelial carcinoma KB cell, human colorectal cancer HT29 cell, human breast cancer MCF-7 cell, and human lung cancer A549 cell as well as good antifungal activity against Candida albicans with the IC₅₀ values of 0.4~5.29 μmol·L^-1, and a half maximal inhibitory concentration (MIC) value of 4.7 μmol·L^-1, respectively. In addition, four new compounds, (-)-7-O-methylbrevicolide A (12a), (+)-7-O-methyl-brevicolide A (12b), (-)-7-O-methyl-brevicolide B (13a) and (+)-7-O-methylbrevicolide B (13b) were also synthesized.
- marine fungi,
- Penicillium brevicompactum,
- mycophenolic acid analogues,
- cytotoxicity,
- antifungal activity
1. [1]
  Zhao, C.-Y.; Zhu, T.-H.; Zhu, W.-M. Chin. J. Org. Chem. 2013, 33, 1195(in Chinese).
2. [2]
  Ma, H.-G.; Liu, Q.; Zhu, G.-L.; Liu, H.-S.; Zhu, W.-M. J. Asian Nat. Prod. Res. 2016, 18, 92. doi: 10.1080/10286020.2015.1127230
3. [3]
  Regina, S.; Christina, B.; Alban, R.; Jens, H. ISME J. 2010, 4, 159. doi: 10.1038/ismej.2009.106
4. [4]
  Jekkel, A.; Barta, I.; Boros, S.; Sütő, J.; Horváth, G.; Szabó, Z.; Ambrus, G. J. Mol. Catal. B:Enzym. 2002, 19~20, 209.
5. [5]
  Habib, E.; León, F.; Bauer, J. D.; Hill, R. A.; Carvalho, P.; Cutler, H. G.; Cutler, S. J. J. Nat. Prod. 2008, 71, 1915. doi: 10.1021/np8003497
6. [6]
  Hemphill, C. F. P.; Daletos, G.; Liu, Z.; Lin, W.-H.; Proksch, P. Tetrahedron Lett. 2016, 57, 2078. doi: 10.1016/j.tetlet.2016.03.101
7. [7]
  Kumagai, H.; Amemiya, M.; Naganawa, H.; Sawa, T.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1994, 47, 440. doi: 10.7164/antibiotics.47.440
8. [8]
  Williams, R. M.; Kwast, E.; Coffman, H.; Glinka, T. J. Am. Chem. Soc. 1989, 111, 3064. doi: 10.1021/ja00190a050
9. [9]
  Jia, Y.-L.; Guan, F.-F.; Ma, J.; Wang, C.-Y.; Shao, C.-L. Chin. J. Mar. Drugs 2016, 35, 35(in Chinese).
10. [10]
  Kato, H.; Nakamura, Y.; Finefield, J. M.; Umaoka, H.; Nakahara, T.; Williams, R. M.; Tsukamoto, S. Tetrahedron Lett. 2011, 52, 6923. doi: 10.1016/j.tetlet.2011.10.065
11. [11]
  Kato, H.; Nakamura, Y.; Finefield, J. M.; Umaoka, H.; Nakahara, T.; Williams, R. M.; Tsukamoto, S. Tetrahedron Lett. 2014, 55, 559. doi: 10.1016/j.tetlet.2013.11.076
12. [12]
  Lu, X.-H.; Zheng, Z.-H.; Zhang, H.; Huo, C.-H.; Dong, Y.-S.; Ma, Y.; Ren, X.; Ke, A.-B.; He, J.-G.; Gu, Y.-C.; Shi, Q.-W. J. Antibiot. 2009, 62, 527. doi: 10.1038/ja.2009.54
13. [13]
  Campbell, I. M.; Calzadilla, C. H.; McCorkindale, N. J. Tetrahedron Lett. 1966, 42, 5107.
14. [14]
  Allison, A. C.; Eugui, E. M. Clin. Transplant. 1993, 7, 96.
15. [15]
  Bentley, R. Chem. Rev. 2000, 100, 3801. doi: 10.1021/cr990097b
16. [16]
  Chen, Z.; Zheng, Z.; Huang, H.; Song, Y.; Zhang, X.; Ma, J.; Wang, B.; Zhang, C.; Ju, J. Bioorg. Med. Chem. Lett. 2012, 22, 3332. doi: 10.1016/j.bmcl.2012.02.106
17. [17]
  Jones, D. F.; Moore, R. H.; Crawley, G. C. J. Chem. Soc. C 1970, 12, 1725.
18. [18]
  Uchida, K.; Watanabe, H.; Usui, T.; Osada, H.; Kitahara, T. Heterocycles 1998, 48, 2049. doi: 10.3987/COM-98-8246
19. [19]
  Fujimoto, H.; Fujimaki, T.; Okuyama, E.; Yamazaki, M. Chem. Pharm. Bull. 1999, 47, 1426. doi: 10.1248/cpb.47.1426
20. [20]
  Ayer, W. A.; Browne, L. M.; Feng, M. C.; Orszanska, H.; Saeedighomi, H. Can. J. Chem. 1986, 64, 904. doi: 10.1139/v86-149
21. [21]
  Birch, A. J.; Wright, J. J. Tetrahedron 1970, 26, 2329. doi: 10.1016/S0040-4020(01)92812-1
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1.
沈阳化工大学材料科学与工程学院沈阳 110142