TY - JOUR
T1 - Biotransformation of α-mangostin by Colletotrichum sp. MT02 and Phomopsis euphorbiae K12
AU - Arunrattiyakorn, Panarat
AU - Suwannasai, Nuttika
AU - Aree, Thammarat
AU - Kanokmedhakul, Somdej
AU - Ito, Hideyuki
AU - Kanzaki, Hiroshi
N1 - Funding Information:
This work was supported by the Thailand Research Fund for the research Grant ( MRG5480126 ). The collaboration of a scientific cooperation program under the Asian Core Program (JSPS-NRCT) on Capacity Building and Development of Microbial Potential and Fermentation Technology toward a New Era is also gratefully acknowledged. The authors are grateful to the SC-NMR Laboratory of Okayama University and the MS Laboratory of Faculty of Agriculture, Okayama University for providing the facilities to conduct our experiments. T. Aree thanks for the partially financial support from the Chulalongkorn University Centenary Academic Development Project and the Thailand National Research University Project.
PY - 2014/4
Y1 - 2014/4
N2 - The microbial transformation of the major mangosteen pericarp xanthone, α-mangostin (1) by the endophytic fungi Colletotrichum sp. MT02 and Phomopsis euphorbiae K12 resulted in the production of the five metabolites 2-6. Biotransformation with Colletotrichum sp. MT02 converted 1 into 17,18-dihydroxymangostanin (2) and cyclomangostanin (3), while incubation with P. euphorbiae K12 gave 12,13,20-trihydroxymangostin (4), 12,13,19- trihydroxymangostin (5), and 20-hydroxymangostanin (6) as transformation products. The structures of these metabolites were elucidated via spectroscopic analyses, and for compound 3, the structure was confirmed by X-ray crystallographic analysis. All metabolites are new, and metabolite 3 possessed an unusual structure of bis-ring fused xanthene in nature. In addition, substrate and all products were evaluated for the antimycobacterial activity against Mycobacterium tuberculosis as well as the cytotoxicity against breast cancer (MCF-7) cell lines.
AB - The microbial transformation of the major mangosteen pericarp xanthone, α-mangostin (1) by the endophytic fungi Colletotrichum sp. MT02 and Phomopsis euphorbiae K12 resulted in the production of the five metabolites 2-6. Biotransformation with Colletotrichum sp. MT02 converted 1 into 17,18-dihydroxymangostanin (2) and cyclomangostanin (3), while incubation with P. euphorbiae K12 gave 12,13,20-trihydroxymangostin (4), 12,13,19- trihydroxymangostin (5), and 20-hydroxymangostanin (6) as transformation products. The structures of these metabolites were elucidated via spectroscopic analyses, and for compound 3, the structure was confirmed by X-ray crystallographic analysis. All metabolites are new, and metabolite 3 possessed an unusual structure of bis-ring fused xanthene in nature. In addition, substrate and all products were evaluated for the antimycobacterial activity against Mycobacterium tuberculosis as well as the cytotoxicity against breast cancer (MCF-7) cell lines.
KW - Biotransformation
KW - Colletotrichum sp.
KW - Phomopsis euphorbiae
KW - Prenylated xanthone
KW - α-Mangostin
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U2 - 10.1016/j.molcatb.2014.02.010
DO - 10.1016/j.molcatb.2014.02.010
M3 - Article
AN - SCOPUS:84896280271
VL - 102
SP - 174
EP - 179
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
SN - 1381-1177
ER -
