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Serpulanines A to C, N-Oxidized Tyrosine Derivatives Isolated from the Sri Lankan Fungus Serpula sp.: Structure Elucidation, Synthesis, and Histone Deacetylase Inhibition.
Williams, David E; Gunasekara, Niranjan W; Ratnaweera, Pamoda B; Zheng, Zehua; Ellis, Samantha; Dada, Sarah; Patrick, Brian O; Wijesundera, Ravi L C; Nanayakkara, Chandrika M; Jefferies, Wilfred A; de Silva, E Dilip; Andersen, Raymond J.
Affiliation
  • Williams DE; Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
  • Gunasekara NW; Departments of Chemistry and Plant Science, University of Colombo , Colombo 03, Sri Lanka.
  • Ratnaweera PB; Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
  • Zheng Z; Departments of Chemistry and Plant Science, University of Colombo , Colombo 03, Sri Lanka.
  • Ellis S; Department of Science and Technology, Uva Wellassa University , Badulla, Sri Lanka.
  • Dada S; Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
  • Patrick BO; The Michael Smith Laboratories; Vancouver Prostate Centre; Departments of Medical Genetics, Microbiology & Immunology, and Zoology; and The Centre for Blood Research and Djavad Mowafaghian Centre for Brain Health, University of British Columbia , Vancouver, BC, Canada.
  • Wijesundera RLC; The Michael Smith Laboratories; Vancouver Prostate Centre; Departments of Medical Genetics, Microbiology & Immunology, and Zoology; and The Centre for Blood Research and Djavad Mowafaghian Centre for Brain Health, University of British Columbia , Vancouver, BC, Canada.
  • Nanayakkara CM; Department of Chemistry, University of British Columbia , 2036 Main Mall, Vancouver, BC, Canada V6T 1Z1.
  • Jefferies WA; Departments of Chemistry and Plant Science, University of Colombo , Colombo 03, Sri Lanka.
  • de Silva ED; Departments of Chemistry and Plant Science, University of Colombo , Colombo 03, Sri Lanka.
  • Andersen RJ; The Michael Smith Laboratories; Vancouver Prostate Centre; Departments of Medical Genetics, Microbiology & Immunology, and Zoology; and The Centre for Blood Research and Djavad Mowafaghian Centre for Brain Health, University of British Columbia , Vancouver, BC, Canada.
J Nat Prod ; 81(1): 78-84, 2018 01 26.
Article in En | MEDLINE | ID: mdl-29303267
ABSTRACT
Serpulanines A (1), B (2), and C (3) have been isolated from extracts of the rare Sri Lankan macrofungus Serpula sp. The structures of 1, 2, and 3 were elucidated by a combination of spectroscopic and single-crystal X-ray diffraction analyses. Serpulanines A (1) and B (2) both contain the rare (E)-2-hydroxyimino hydroxamic acid functional group array. A proposed biogenesis for serpulanine B (2) suggests that its (E)-2-hydroxyimino hydroxamic acid moiety arises from a diketopiperazine precursor. Synthetic serpulanine A (1) inhibited class I/II histone deacetylases in murine metastatic lung carcinoma cells with an IC50 of 7 µM.
Subject(s)

Full text: 1 Database: MEDLINE Main subject: Tyrosine / Basidiomycota / Histone Deacetylase Inhibitors Limits: Animals / Humans Language: En Year: 2018 Type: Article

Full text: 1 Database: MEDLINE Main subject: Tyrosine / Basidiomycota / Histone Deacetylase Inhibitors Limits: Animals / Humans Language: En Year: 2018 Type: Article