Citation: LING Huiping, CHEN Xiaoqing, XIE Shengnan, CHEN Yuejian, SHE Zhigang, LIN Yongcheng, TAO Yiwen. Dihydroisocoumarin Compounds from Endophytic Fungi of Rhizophora apiculata and Its Antibacterial Activity[J]. Chinese Journal of Applied Chemistry, ;2018, 35(6): 708-713. doi: 10.11944/j.issn.1000-0518.2018.06.170281 shu

Dihydroisocoumarin Compounds from Endophytic Fungi of Rhizophora apiculata and Its Antibacterial Activity

a.
School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou 511436, China
b.
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China

Corresponding author: TAO Yiwen, yywentao@aliyun.com
Received Date: 10 August 2017
Revised Date: 8 November 2017
Accepted Date: 29 November 2017

Fund Project: the Natural Science Program of Guangdong Province 2016A030313588Supported by the Natural Science Program of Guangdong Province(No.2016A030313588), the Education Bureau Project of Guangzhou City(No.1201610155), the Projects of Guangdong Oceanic and Fishery Administration in 2017(No.A201701C07), the Open-Laboratory Project of Guangzhou Medical University in 2018the Projects of Guangdong Oceanic and Fishery Administration in 2017 A201701C07the Education Bureau Project of Guangzhou City 1201610155

Figures(2)

In order to study the secondary metabolites of dihydroisocoumarin compounds from mangrove endophytic fungi Fusarium sp. F67 and B42, the metabolites of strains F67 and B42 were isolated and purified by chromatographic techniques, and their structures were determined as follows:3, 6, 8-trihydroxy-3, 4, 5, 7-tetramethyl-3, 4-dihydroisocoumarin(sclerotinin A)(1), dihydrocitrinone(2), 5-methylmellein(3), 5-carboxymellein(4), 4-hydroxymellein(5) and mellein(6). Antibacterial activities of compounds 1~4 in 1.0 g/L show that the inhibitory zone against the tested strains ranges from 5.1 to 11.0 mm. Among them, compound 4 has the strongest antibacterial activities and the broadest bacteriostatic spectra. These results provide supplement to the research and development of new antibacterial drug.
- Rhizophora apiculata,
- endophytic fungi,
- dihydroisocoumarins,
- antibacterial activity
1. [1]
  Park H, Perez C, Perry E. Activating and Attenuating the Amicoumacin Antibiotics[J]. Molecules, 2016,21(7)824. doi: 10.3390/molecules21070824
2. [2]
  BI Yunmei, ZHAO Qianrong, A Fang. 3, 4-Dihydroisocoumarins from Secondary Metabolites of Microorganisms[J]. Yunnan Chem Technol, 2005(4):47-50.
3. [3]
  LOU Jie, LI Limei, WANG Yuede. A New Cytotoxic Isocoumarin from Endophytic Fungus Aspergillus versicolor[J]. China J Chinese Mater Med, 2016(1):92-95.
4. [4]
  WEI Meiyan, HU Guping, ZHENG Caijuan. Dihydroisocoumarin Derivatives of Mangrove Endophytic Fungus Microsphaeropsis sp. Isolated from the South China Sea[J]. Acta Sci Nat Univ Sunyatseni, 2010,49(2):92-95.
5. [5]
  WANG Huijun, SHI Wensi, ZHU Huajie. A New Isocoumarin Compound from Marine-derived Fungus Hansfordia sinuosae[J]. Nat Prod Res Dev, 2016(2):179-181.
6. [6]
  Santiago C, Lin S, Munro M H G. Polyketide and Benzopyran Compounds of an Endophytic Fungus Isolated from Cinnamomum Mollissimum:Biological Activity and Structure[J]. Asian Pac J Trop Biomed, 2014,4(8):627-632. doi: 10.12980/APJTB.4.2014APJTB-2014-0030
7. [7]
  LI Ying, LI Jinjun, WANG Lu. Isolation and Structural Elucidation of the Antibacterial Metabolites Produced by Marine-Derived Aspergillus Strain F5[J]. Chinese J Antibiot, 2013,38(3):191-199.
8. [8]
  BI Yunmei, BAO Lei, BAO Wei. Studies on Antibacterial Activities of Secondary Metabolites from Fungus Cephalosporium sp.AL031[J]. J Chinese Med Mater, 2004,27(4):270-272.
9. [9]
  Macías-Rubalcava M L, Sánchez-Fernández R E. Secondary Metabolites of Endophytic Xylaria Species with Potential Applications in Medicine and Agriculture[J]. World J Microbiol Biotechnol, 2017,33(1)15. doi: 10.1007/s11274-016-2174-5
10. [10]
  Tanaka A K, Sato C, Shibata Y. Growth Promoting Activities of Sclerotinin A and Its Analogs[J]. Agric Biol Chem, 1974,38(7):1311-1315. doi: 10.1080/00021369.1974.10861325
11. [11]
  Tao Y W, Wang Y. 3, 6, 8-Trihydroxy-3, 4, 5, 7-tetramethyl-3, 4-dihydroisocoumarin[J]. Acta Cryst, 2011,E67O1675.
12. [12]
  Xin Z H, Li T, Zhu T J. Isocoumarin Derivatives from the Sea Squirt-derived Fungus Penicillium stoloniferum QY2-10 and the Halotolerant Fungus Penicillium notatum B-52[J]. Arch Pharm, 2007,30(7):816-819. doi: 10.1007/BF02978830
13. [13]
  Ardus J A, Gillman I G, Manderville R A. On the Role of Copper and Iron in DNA Cleavage by Ochratoxin A, Structure-Activity Relationships in Metal Binding and Copper-Mediated DNA Cleavage[J]. Can J Chem, 1998,76(6):907-918. doi: 10.1139/v98-088
14. [14]
  Moore J. Production, Extraction, Characterization, Quantitation, and Biological Activity of Mellein, 4-Hydroxymellein, and Ochratoxin A from Aspergillus ochraceus[J]. J Nat Prod, 1971146.
15. [15]
  Chinworrungsee M, Kittakoop P, Isaka M. Antimalarial Halorosellinic Acid from the Marine Fungus Halorosellinia oceanica[J]. Bioorg Med Chem Lett, 2001,11:1965-1969. doi: 10.1016/S0960-894X(01)00327-4
16. [16]
  HU Liqing, SUN Dinghe, WANG Sheng. Feasibility study of Allicin Agar Disc Diffusion Combining Antimicrobial Susceptibility Testing[J]. Chinese J Health Lab Technol, 2017(6):767-770.
17. [17]
  DONG Haijiao. The Synthesis of Six Isocounmarin Derivatives[D]. Agricultural University of Hebei, 2015(in Chinese).
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沈阳化工大学材料科学与工程学院沈阳 110142