Biotransformation of alpha- and 6beta-santonin by fungus and plant cell cultures.
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.
Yang
L
L
Niigata University, Department of Chemistry and Chemical Engineering, Ikarashi 2-8050, Niigata, 950-2181, Japan.
Dai
J
J
Sakai
J-I
JI
Ando
M
M
D027761:Asparagus Plant / Q000166:cytology / Q000378:metabolism*; D001711:Biotransformation; D002478:Cells, Cultured; D005658:Fungi / Q000166:cytology / Q000378:metabolism*; D015394:Molecular Structure; D012500:Santonin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*
D012500:Santonin