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
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
UR - http://www.scopus.com/inward/record.url?scp=84896280271&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84896280271&partnerID=8YFLogxK
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 -