An insight into the curdione biotransformation pathway by Aspergillus niger.
Curdione (1), a sesquiterpene with a germacrane skeleton from rhizomes of Curcuma wenyujin, has attracted attention due to its important pharmacological properties. Herein, we investigated the chemo-biotransformation of curdione (1) systematically using Aspergillus niger AS 3.739. Regio- and stereoselective hydroxylation of curdione with filamentous fungus A. niger AS 3.739 led to seven metabolites including four new compounds 3α-hydroxycurcumalactone, 2β-hydroxycurcumalactone, (10S)-9,10-dihydroxy-curcumalactone and (10R)-9,10-dihydroxy-curcumalactone. Their structures were determined by spectroscopic techniques including two-dimensional NMR and TOF-MS (Time of Flight Mass Spectrometry). Based upon the analysis of biological and chemical conversions of curdione, a tentative metabolic pathway via chemo-bio cascade reactions is proposed in A. niger system, which provides an insight into the corresponding metabolism of curdione in animal systems. In addition, experiments with selected monooxygenase inhibitors suggest that cytochrome P450 monooxygenase played a crucial role in the hydroxylation of curdione.
a School of Life Science and Biopharmaceutics , Shenyang Pharmaceutical University , Shenyang 110016 , P.R. China.
Yinan
Y
Chen
Lang
L
Zhang
Bin
B
Qin
Xin
X
Zhang
Xian
X
Jia
Xiaoying
X
Wang
Danni
D
Jin
Song
S
You
D000818:Animals; D001234:Aspergillus niger / Q000378:metabolism*; D030024:Curcuma / Q000737:chemistry*; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000737:chemistry; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D013237:Stereoisomerism
D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; C577164:curcumalactone; C504126:curdione; D003577:Cytochrome P-450 Enzyme System