Production of biologically active oxidized derivatives of finasteride through metabolism by Aspergillus niger culture

Figures & data

Scheme 1. Microbial transformation of Finasteride I with Aspergillus niger: I. R1= R2= H; II. R1= OH, R2= H; III. R1= H, R2= OH

Table 1. ¹³C- and ¹H NMR chemical shift assignments of compounds II and III.

II			III
Carbon	δC	δH (J = Hz)	δC	δH (J = Hz)
1	157.9	8.06 d (10.2)	153.6	6.94 d (9.5)
2	121.3	5.62 d (10.2)	123.2	5.62 d (10.2)
3	168.8	–	168.8	–
4	–	–	–	–
5	60.6	2.41 t (8.4)	61.1	3.33 dd (12.0, 4.0)
6	26.7	1.54, 1.73 m	26.4	1.62, 1.67 m
7	25.3	1.23, 1.67 m	29.7	1.31, 2.10 m
8	35.6	1.45 m	33.0	1.83 m
9	54.5	1.19 t (10.2)	49.3	1.10 m
10	41.5	–	40.6	–
11	70.0	4.0 d t (10.8,	22.2	1.45, 1.78 m
12	50.0	4.2)	40.4	1.32, 1.81 m
13	45.5	1.41, 2.05 m	45.0	–
14	56.2	–	61.0	0.99 overlap
15	24.2	1.23 m	71.0	4.24 br t (6.0)
16	30.6	1.21, 1.67 m	37.6	1.09, 2.13 m
17	57.4	1.09, 1.75 m	58.1	2.14 overlap
18	15.2	2.24 t (8.4)	16.5	0.93 s
19	12.2	0.70 s	12.2	0.98 s
20	174.2	1.06 s	173.9	–
1’	51.9	–	52.0	–
2’–4’	29.2	–	29.2	1.33 s
		1.33 s

Figure 1. Important HMBC correlations of metabolite II.

Figure 2. Important NOESY Correlation for metabolite II.

Figure 3. Important COSY interactions for metabolite II.

Figure 4. Selected HMBC correlation for metabolite III.

Figure 5. Important COSY interactions for metabolite III.

Figure 6. Selected NOESY interactions for metabolite III.

Table 2. In vitro quantitative inhibition of lipoxygenase by compounds I, II and III.

Sample	IC50 (μM)
I	N/A
II	186.05 ± 1.34
III	112.56 ± 2.23
Baicalein	22.0 ± 0.05 (μM)

IC₅₀ values are the mean ± standard error mean (S.E.M) of three assays.