Biotransformation of dehydroepiandrosterone with Macrophomina phaseolina and β-glucuronidase inhibitory activity of transformed products

Figures & data

Figure 1.  Biotransformation of dehydroepiandrosterone (1)by Macrophomina phaseolina.

Table 1.  ¹H-NMR data of compound 2–9 at 300, 400, 500 MHz; in CDCl₃ and CH₃OH; δ in ppm, J and W_1/2 in Hz

Position	Compounds
	1	2	3	4	5	6	7	8	9
1	1.05, 1.83	1.34, 1.98	2.01, 2.46	1.54, 2.03	2.41, 2.56	1.05, 1.80	1.79, 2.41	1.49, 1.62	1.14, 1.84
2	1.22, 1.44	2.28, 2.34	2.35, 2.42	2.30, 2.41	1.70, 1.98	1.44, 1.48	1.14, 2.27	1.83, 1.98	1.48, 1.77
3	3.51 m W1/2 = 24.6	—	—	—	—	3.44 m W1/2 = 25.7	4.34 br sW1/2 = 23.8	3.43 ddd J = 15.5, 4.0, 2.0	3.47 m
4	2.21, 2.30	2.08, 2.26	5.73 s	5.71 s	5.65 s	2.18, 2.25	6.18 s	5.24 s	2.25, 2.35
5	—	1.53	—	—	—	—	—	—	—
6	5.36 d J = 4.8	1.36, 1.41	2.29, 2.40	2.26, 2.39	6.08 s	5.29 d J = 5.4	—	2.22, 2.28	5.55 d J = 4.4
7	1.66, 2.01	0.97, 1.79	1.25, 1.85	0.98, 1.85	6.08 s	1.77, 1.95	1.75, 2.04	3.71 d J = 8.0	3.75 t J = 3.6
8	2.14	1.58	1.72	1.72	2.23 t J = 10.8	1.45	2.37	1.47	1.49
9	0.99	0.77	0.97	0.91	1.19	0.87	0.96	1.03	1.30
10	—	—	—	—	—	—	—	—	—
11	1.42, 1.65	1.37, 1.67	1.45, 1.67	1.38, 1.57	1.36, 1.60	1.42, 1.55	1.41, 1.67	1.61, 1.91	1.52, 1.62
12	1.65, 1.84	1.24, 1.83	1.11, 1.97	1.06, 1.83	1.14, 1.87	1.03, 1.78	1.27, 1.86	1.11, 1.94	1.05, 1.81
13	—	—	—	—	—	—	—	—	—
14	1.23	1.27	1.28	0.97	1.17	0.90	1.33	1.06	1.43
15	1.46, 1.93	1.48, 1.92	1.55, 1.95	1.25, 1.62	1.48, 1.79	1.21, 1.53	1.57, 1.98	0.96, 1.78	1.25, 1.75
16	2.04, 2.42	2.06, 2.41	1.68, 2.42	1.44, 2.07	1.46, 2.13	1.40, 1.98	2.11, 2.47	1.45, 1.95	1.50, 2.00
17	—	—	—	3.63 s	3.68 ddJ = 6.4, 7.6	3.56 t J = 8.4	—	3.55 tJ = 8.5	3.60 tJ = 8.4
18	0.87	0.87 s	0.89 s	0.77 s	0.82 s	0.69	0.90 s	0.75 s	0.74 s
19	1.01	1.02 s	1.19 s	1.17 s	1.10 s	0.96	1.19 s	1.07 s	1.00 s

Table 2.  ¹³C-NMR data of compounds 1–9, σ in ppm.

C	Compounds
	1	2	3	4	5	6	7	8	9
1	37.2	38.4	35.7^a	35.7^a	33.9^a	37.2	33.7^a	21.9	38.1
2	31.5^a	38.1	33.9	33.9	33.9^a	31.5	40.1	30.8	32.1
3	71.6	211.8	199.3	199.5	199.5	71.4	68.4	72.1	71.9
4	42.1	44.6	124.2	123.9	123.7	42.0	120.1	127.4	42.9
5	140.8	46.6	170.3	171.2	163.6	140.9	170.4	144.2	146.6
6	121.0	28.6	32.6	32.8	128.0	121.3	199.1	42.6	124.8
7	31.3^a	30.5	31.3	31.5	140.3	31.3	36.3	74.0	65.4
8	30.7	34.9	35.1	35.7^a	37.7	31.9	33.8^a	41.2	39.1
9	50.0	53.8	53.8	53.9	50.8	50.2	53.8	50.1	43.6^a
10	36.1	35.8^a	38.6	38.7	36.1	37.2	39.1	37.7^a	38.5
11	20.0	20.7	20.3	20.6	20.3	20.6	20.3	32.3	21.5
12	31.2^a	31.5	30.8	36.4	36.3	36.5	31.2	37.8^a	37.5
13	47.0	47.8	50.8	42.8	43.8	42.3	47.5	44.3	43.5^a
14	51.6	51.2	49.7	50.5	48.3	51.3	50.6	52.3	45.3
15	21.5	21.8	21.7	23.3	22.9	23.4	21.8	38.3	24.2
16	35.5	35.8^a	35.8^a	30.5	30.4	30.1	35.7	26.6	30.6
17	220.8	221.2	220.4	81.6	81.3	81.6	219.9	82.3	82.5
18	13.3	13.8	13.7	11.0	10.9	10.9	13.7	11.5	11.4
19	19.5	11.5	17.4	17.4	16.3	19.4	18.3	19.5	18.7

Note: ^aInterchangeable δ values.

CDCl₃ at 75 MHz (2, 8).

CDCl₃ at 100 MHz (4, 7).

CDCl₃ at 150 MHz (5, 6).

CD₃OD at 125 MHz (3).

CD₃OD at 150 MHz (9).

Table 3.  β-Glucuronidase inhibitory activity of compounds 1–9.

Compound	IC50 (µM) ± SEM^c
1	77.9 ± 1.95
2	373.5 ± 9.57
3	430 ± 7.13
4	NA^a
5	NA^a
6	NA^a
7	221.6 ± 12.5
8	191.4 ± 1.17
9	NA^a
D-Saccharic acid-1,4-lactone^b	48.4

^aNot active.

^bStandard used.

^cStandard error mean.

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