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1. (Article ID: 9215)
Wu JS, Yao GS, Shi XH, Rehman SU, Xu Y, Fu XM, Zhang XL, Liu Y, Wang CY
Epigenetic agents trigger the production of bioactive nucleoside derivatives and bisabolane sesquiterpenes from the marine-derived fungus Aspergillus versicolor
Frontiers in Microbiology 11 (2020)
ID 85
Epigenetic agents, histone deacetylase inhibitor (SAHA) and DNA methyltransferase inhibitor (5-Aza), were added to Czapek-Dox medium to trigger the chemical diversity of marine-derived fungus Aspergillus versicolor XS-20090066. By HPLC and 1H NMR analysis, the diversity of fungal secondary metabolites was significantly increased compared with the control. With the aid of MS/MS-based molecular networking, two new nucleoside derivatives, kipukasins K (1) and L (2) were obtained. Meanwhile, the yields of four known nucleoside derivatives were significantly enhanced. In addition, one new bisabolane sesquiterpene, aspergillusene E (7), along with ten known derivatives were also isolated. The structures were elucidated by comprehensive spectroscopic methods of NMR and HRESIMS analysis. Compounds 1 and 7 displayed antibacterial activities against Staphylococcus epidermidis and Staphylococcus aureus with the MIC values of 8-16 μg/mL. Our study revealed that the fungus A. versicolor XS-20090066 has been effectively induced by chemical epigenetic manipulation with a combination of SAHA and 5-Aza to produce new metabolites.
Aspergillus versicolor, DNA methyltransferase inhibitor, histone deacetylase inhibitor, antibacterial activities, antifouling activities, bisabolane sesquiterpenes, nucleoside derivatives
NCBI PubMed ID: 32082294Publication DOI: 10.3389/fmicb.2020.00085Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Liu Y
agrar.uni-giessen.de>; Wang CY ouc.edu.cn>
Institutions: Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, China, Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, China, Institute of Oceanography, Minjiang University, Fuzhou, China, Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, Shenzhen Engineering Laboratory for Marine Algal Biotechnology, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen, China, Institute for Insect Biotechnology, Justus Liebig University Giessen, Giessen, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, IR, DNA sequencing, biological assays, HPLC, UV, extraction, optical rotation measurement, CC, cell growth, LC-ESI-QTOF MS/MS, HR-ESI-MS, antibacterial assay, cytotoxicity assay, antifungal activity test, ECD, antifouling assay
The publication contains the following compound(s):
- Compound ID: 22498
|
Subst1-(7-5)-+
|
Ors2Me-(7-3)-U
Subst1 = 3,4-dihydroxybenzoic acid, protocatehuic acid = SMILES O={7}C(O)C1=CC(O)=C(O)C=C1 |
Show graphically |
Structure type: monomer
; 543.1265 [M-H]-
C25H24N2O12
Trivial name: kipukasin K
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
- Compound ID: 22499
|
Subst1-(7-5)-+
|
Ors2Me-(7-2)-U
Subst1 = 3,4-dihydroxybenzoic acid, protocatehuic acid = SMILES O={7}C(O)C1=CC(O)=C(O)C=C1 |
Show graphically |
Structure type: monomer
; 543.1265 [M-H]-
C25H24N2O12
Trivial name: kipukasin L
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
- Compound ID: 22500
Structure type: monomer
Trivial name: kipukasin I
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
- Compound ID: 22501
Structure type: monomer
Trivial name: kipukasin H
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
- Compound ID: 22502
Structure type: monomer
Trivial name: kipukasin D
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
- Compound ID: 22503
Structure type: monomer
Trivial name: kipukasin E
Compound class: glycoside
Reference(s) to other database(s): GenDB:HM535361
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