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Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka

Ozcinar, Ozge; Tag, Ozgur; Yusufoglu, Hasan; Kivcak, Bijen; Bedir, Erdal


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      {
        "affiliation": "Ege Univ, Fac Pharm, Dept Pharmacognosy, TR-35100 Bornova, Turkey", 
        "name": "Ozcinar, Ozge"
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      {
        "affiliation": "Bionorm Nat Prod Prod & Mkt Corp, ITOB, TR-35477 Menderes Izmir, Turkey", 
        "name": "Tag, Ozgur"
      }, 
      {
        "affiliation": "Prince Sattam Bin Abdulaziz Univ, Coll Pharm, Dept Pharmacognosy, Al Kharj 11942, Saudi Arabia", 
        "name": "Yusufoglu, Hasan"
      }, 
      {
        "affiliation": "Ege Univ, Fac Pharm, Dept Pharmacognosy, TR-35100 Bornova, Turkey", 
        "name": "Kivcak, Bijen"
      }, 
      {
        "affiliation": "Izmir Inst Technol, Fac Engn, Dept Bioengn, TR-35430 Urla Izmir, Turkey", 
        "name": "Bedir, Erdal"
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    "description": "Biotransformation of neoruscogenin (NR, 1, spirosta-5,25(27)-diene-1 beta,3 beta-diol), the major bioactive sapogenin of Ruscus preparations, was carried out with the endophytic fungus Alternaria eureka. Fourteen new biotransformation products (2-15) were isolated, and their structures were elucidated by NMR and HRESIMS data analyses. A. eureka affected mainly oxygenation, oxidation, and epoxidation reactions on the B and C rings of the sapogenin to afford compounds 8-15. In addition to these, cleavage of the spiroketal system as in compounds 2-7 and subsequent transformations provided unusual metabolites. This is the first study reporting conversion of the spirostanol skeleton to cholestane-type metabolites 2-5. Additionally, the cleavage of the C-22/C-26 oxygen bridge yielding a furostanol-type steroidal framework and subsequent formation of the epoxy bridge between C-18 and C-22 in 7 was encountered for the first time in steroid chemistry.", 
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      "issue": "6", 
      "pages": "1357-1367", 
      "title": "JOURNAL OF NATURAL PRODUCTS", 
      "volume": "81"
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    "title": "Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka"
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