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
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
3. [3]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
4. [4]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
5. [5]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
6. [6]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
7. [7]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
8. [8]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
9. [9]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
10. [10]
  Xiao Liu , Guangzhong Cao , Mingli Gao , Hong Wu , Hongyan Feng , Chenxiao Jiang , Tongwen Xu . Seawater Salinity Gradient Energy’s Job Application in the Field of Membranes. University Chemistry, 2024, 39(9): 279-282. doi: 10.3866/PKU.DXHX202306043
11. [11]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
12. [12]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
13. [13]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
14. [14]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
15. [15]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
16. [16]
  Congying Lu , Fei Zhong , Zhenyu Yuan , Shuaibing Li , Jiayao Li , Jiewen Liu , Xianyang Hu , Liqun Sun , Rui Li , Meijuan Hu . Experimental Improvement of Surfactant Interface Chemistry: An Integrated Design for the Fusion of Experiment and Simulation. University Chemistry, 2024, 39(3): 283-293. doi: 10.3866/PKU.DXHX202308097
17. [17]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
18. [18]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221
19. [19]
  Xueqi Yang , Juntao Zhao , Jiawei Ye , Desen Zhou , Tingmin Di , Jun Zhang . 调节NNU-55(Fe)的d带中心以增强CO₂吸附和光催化活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100074-. doi: 10.1016/j.actphy.2025.100074
20. [20]
  Peiling Li , Qing Feng , Hongling Yuan , Qin Wang . Live Interview Recording about the Penicillin Family. University Chemistry, 2024, 39(9): 122-127. doi: 10.3866/PKU.DXHX202311022

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(2057)
HTML views(275)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142