Show legend Show as text

Structure type: monomer ; 559.3239 [M+Na]+
C₃₀H₄₈O₈
Trivial name: resorcinoside A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8872
  Choi B-K, Phan THT, Hwang S, Oh D-C, Kang JS, Lee H-S, Ngo TDN, Tran TTV, Shin HJ "Resorcinosides A and B, glycosylated alkylresorcinols from a marine-derived strain of the fungus Penicillium janthinellum" - Journal of Natural Products 82(11) (2019) 3186–3190
  

  Two new glycosylated alkylresorcinols, resorcinosides A (1) and B (2), were isolated from a strain of the fungus Penicillium janthinellum derived from a marine sediment sample collected from Cu Lao Cham Island, Vietnam. The structures of 1 and 2 were established by interpretation of 1D and 2D NMR and high-resolution ESIMS data, and their absolute configurations were confirmed by the coupling constant of the anomeric proton, acid hydrolysis, subsequent HPLC analysis, Mosher's method, and quantum-mechanics-based computational analysis of NMR chemical shifts. The structure elucidation indicated that 1 and 2 are new alkylresorcinols with D-glucose, and 2 has an α-pyrone moiety attached to the aromatic ring. Compound 1 exhibited cytotoxic activity against the NUGC-3 cancer cell line with a GI50 value of 9.3 μM.

  cytotoxicity, resorcinosides, Penicillium janthinellum

  NCBI PubMed ID: 31668073
  Publication DOI: 10.1021/acs.jnatprod.9b00776
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Shin HJ
  Institutions: Department of Marine Biotechnology, University of Science and Technology (UST), Daejeon, South Korea, Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology (KIOST), Busan, South Korea, Nha Trang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, Nha Trang, Vietnam, Graduate University of Science and Technology, Vietnam Academy of Science and Technology, Ha Noi, Vietnam, Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, South Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, DNA sequencing, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, CC, RP-HPLC, cell growth, HR-ESI-MS, cytotoxicity assay, derivatization, BLAST
  
   
  
  Penicillium janthinellum 168CLC-17.1
  CSDB ID 49606 (all data & tools)

Show legend Show as text

Structure type: monomer ; 559.3248 [M+Na]+
C₃₀H₄₈O₈
Trivial name: peniresorcinoside A
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9484
  Yong K, Kaleem S, Wu B, Zhang Z "New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750" - Marine Drugs 19(9) (2021) 483
  

  Seven novel compounds, namely peniresorcinosides A-E (1-5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8-17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher's method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

  structure elucidation, Marine fungus, antiglioma activity, Penicillium sp.ZZ1750, penidifarnesylin A, penipyridinone A, peniresorcinosides A-E

  NCBI PubMed ID: 34564145
  Publication DOI: 10.3390/md19090483
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: wubin@zju.edu.cn; yongkuo@zju.edu.cn
  Institutions: Ocean College, Zhejiang University, Zhoushan Campus, Zhoushan 316021, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, enzymatic hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, HR-ESI-MS, ECD
  
   
  
  Penicillium sp. ZZ1750
  CSDB ID 40959 (all data & tools)