Structure determination of two new monocillin I derivatives.
Biotransformation of monocillin I (1) by Beauveria bassiana ATCC 7159 was investigated. Two new derivatives 2 and 3 were isolated and identified on the basis of the spectroscopic data. Compounds 2 and 3 are synthesized by hydration at 10,11-double bond and hydrolysis of 14,15-epoxide, respectively. The R configuration of 11-OH in 2 was established by the modified 2-methoxy-2-trifluoromethylphenylacetic acid (MTPA) method. The conversion of 1 to 2 and 3 was reconstituted in an acid solution, indicating that the formation of 2 and 3 is an acid-catalyzed instead of an enzymatic process.
Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT84322-4105, USA. jixun.zhan@usu.edu
Jixun
J
Zhan
E M Kithsiri
EM
Wijeratne
A A Leslie
AA
Gunatilaka
D001203:Ascomycota / Q000737:chemistry*; D052982:Beauveria / Q000378:metabolism*; D001688:Biological Products / Q000032:analysis*; D001711:Biotransformation; D006868:Hydrolysis; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000032:analysis*
D001688:Biological Products; D007783:Lactones; D011083:Polycyclic Compounds; C444505:monocillin I