TY - JOUR
T1 - Novel ent-beyeran-19-oic acids from biotransformations of isosteviol metabolites by Mortierella isabellina
AU - Lin, Che Ling
AU - Lin, Shwu Jiuan
AU - Huang, Wei Jan
AU - Ku, Yuan Ling
AU - Tsai, Tung Hu
AU - Hsu, Feng-Lin
PY - 2007/12
Y1 - 2007/12
N2 - Biotransformations of ent-16β-hydroxybeyeran-19-oic acid (1) by Mortierella isabellina produced hydroxylated metabolites. The isolated metabolites included three new compounds, ent-14β,16β- dihydroxybeyeran-19-oic acid (3), ent-12β-hydroxy-16-oxobeyeran-19-oic acid (4), and enr-7α,12β-dihydroxy-16-oxobeyeran-19-oic acid (5), and one known compound, ent-7α,16β-dihydroxybeyeran-19-oic acid (2). The structural elucidation was achieved by detailed analysis of LC-MS chromatograms, and MS and NMR spectroscopic data. In this study, M. isabellina hydroxylated the basic skeleton beyeran-19-oic acid at the 7β-, 12α-, and 14α-positions, and oxidized the skeleton at the 16-position. All compounds were evaluated with the cell viability assay. The results of the bioassay indicated that MTT formazan exocytosis occurs upon treatment of the cells with 1.
AB - Biotransformations of ent-16β-hydroxybeyeran-19-oic acid (1) by Mortierella isabellina produced hydroxylated metabolites. The isolated metabolites included three new compounds, ent-14β,16β- dihydroxybeyeran-19-oic acid (3), ent-12β-hydroxy-16-oxobeyeran-19-oic acid (4), and enr-7α,12β-dihydroxy-16-oxobeyeran-19-oic acid (5), and one known compound, ent-7α,16β-dihydroxybeyeran-19-oic acid (2). The structural elucidation was achieved by detailed analysis of LC-MS chromatograms, and MS and NMR spectroscopic data. In this study, M. isabellina hydroxylated the basic skeleton beyeran-19-oic acid at the 7β-, 12α-, and 14α-positions, and oxidized the skeleton at the 16-position. All compounds were evaluated with the cell viability assay. The results of the bioassay indicated that MTT formazan exocytosis occurs upon treatment of the cells with 1.
KW - ent-16β-Hydroxybeyeran-19-oic acid
KW - Hydroxylation
KW - Isoteviol
KW - Microbial biotransformations
KW - Mortierella isabellina
KW - MTT formazan exocytosis
KW - Stevioside
KW - ent-16β-Hydroxybeyeran-19-oic acid
KW - Hydroxylation
KW - Isoteviol
KW - Microbial biotransformations
KW - Mortierella isabellina
KW - MTT formazan exocytosis
KW - Stevioside
UR - http://www.scopus.com/inward/record.url?scp=38149053013&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=38149053013&partnerID=8YFLogxK
U2 - 10.1055/s-2007-993756
DO - 10.1055/s-2007-993756
M3 - Article
C2 - 18080234
AN - SCOPUS:38149053013
SN - 0032-0943
VL - 73
SP - 1581
EP - 1587
JO - Planta Medica
JF - Planta Medica
IS - 15
ER -