Document Detail

Biotransformation of alpha- and 6beta-santonin by fungus and plant cell cultures.
MedLine Citation:
PMID:  16864442     Owner:  NLM     Status:  MEDLINE    
One fungus, Abisidia coerulea IFO 4011, and suspended cell cultures of one plant, Asparagus officinalis, were employed to bioconvert alpha- and 6beta-santonin. Incubation of alpha-santonin with the cell cultures of the fungus afforded two products, 11beta-hydroxy-alpha-santonin (1, in 76.5% yield) and 8alpha-hydroxy-alpha-santonin (2, in 2.0% yield). And from 6beta-santonin, four major products (3, 4, 5 and 6) and four minor products (7, 8, 9 and 10) were obtained, including 8alpha-hydroxylated products in trace yields. Very interestingly, a skeletal rearrangement occurred and a guaiane product (13) formed in a very low yield when alpha-santonin incubating with A.officinalis cell cultures, while not in the case of 6beta-santonin as substrate. Among the obtained 15 products, 2, 7, 8, 9, 10 and 12 are new compounds. The fact of 8alpha hydroxylation of santonin enables the formation of 8,12-eudesmanolide instead of 6,12-eudesmanolide and some useful modification at C-8 position. In addition, these reactions would provide evidence for the biogenesis between different types of eudesmane and/or guaiane compounds in the plants in nature.
L Yang; J Dai; J-I Sakai; M Ando
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of Asian natural products research     Volume:  8     ISSN:  1028-6020     ISO Abbreviation:  J Asian Nat Prod Res     Publication Date:  2006 Jun 
Date Detail:
Created Date:  2006-07-25     Completed Date:  2007-02-27     Revised Date:  2009-07-21    
Medline Journal Info:
Nlm Unique ID:  100888334     Medline TA:  J Asian Nat Prod Res     Country:  England    
Other Details:
Languages:  eng     Pagination:  317-26     Citation Subset:  IM    
Niigata University, Department of Chemistry and Chemical Engineering, Ikarashi 2-8050, Niigata, 950-2181, Japan.
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MeSH Terms
Asparagus Plant / cytology,  metabolism*
Cells, Cultured
Fungi / cytology,  metabolism*
Molecular Structure
Santonin / analogs & derivatives*,  chemistry,  metabolism*
Reg. No./Substance:

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