Regio- and stereo-selective hydroxylations of ingenane diterpenoids by Mortierella ramanniana and Gibberella fujikuroi / 中国天然药物
Chinese Journal of Natural Medicines (English Ed.)
;
(6): 939-945, 2016.
Article
in English
| WPRIM
| ID: wpr-812537
ABSTRACT
The regio- and stereo-selective hydroxylations of two ingenane diterpenoids, 20-deoxyingenol (1) and 13-oxyingenol dodecanoat (2), by the filamentous fungi Mortierella ramanniana and Gibberella fujikuroi were investigated in the present study. Four undescribed metabolites (3-6) of substrate 1 and two undescribed metabolites (7 and 8) of substrate 2 were isolated. All the metabolites were identified as hydroxylated ingenane derivatives by extensive NMR and HR-ESI-MS data analyses. All the biotransformed compounds and the substrates were evaluated for their cytotoxicities against three human cancer cell lines, including human colon cancer Caco-2, breast cancer MCF-7, and adriamycin (ADM)-resistant MCF-7/ADM cell lines. All ingenane alcohols (1, and 3-6) displayed no significant cytotoxic activities. The substrate 13-oxyingenol dodecanoat (2) showed moderate cytotoxicity with IC values being 35.59 ± 5.37 μmol·L (Caco-2), 24.04 ± 4.70 μmol·L (MCF-7), and 22.24 ± 5.19 μmol·L (MCF-7/ADM). However, metabolites 7 and 8 displayed no significant cytotoxicity. These results indicated that the hydroxylation at the C-13 aliphatic acid ester of substrate 2 can significantly reduce the cytotoxic activity.
Full text:
Available
Index:
WPRIM (Western Pacific)
Main subject:
Stereoisomerism
/
Biotransformation
/
Molecular Structure
/
Chemistry
/
Mortierella
/
Cell Line, Tumor
/
Diterpenes
/
Gibberella
/
Hydroxylation
/
Metabolism
Limits:
Humans
Language:
English
Journal:
Chinese Journal of Natural Medicines (English Ed.)
Year:
2016
Type:
Article
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