A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by <i>Mucor plumbeus</i>

SANTOS, GABRIEL F. DOS; TAKAHASHI, JACQUELINE A.

doi:10.1590/0001-3765201720170240

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Chemical Sciences • An. Acad. Bras. Ciênc. 89 (3 Suppl) • 2017 • https://doi.org/10.1590/0001-3765201720170240 copy

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.

Key words:
acetylcholinesterase inhibitors; biotransformation; green glycosylation; Mucor plumbeus; trachyloban-19-oic acid

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[1] Correspondence to: Jacqueline Aparecida Takahashi E-mail: jat@qui.ufmg.br

Position	1		5			6
Position	δ _C	δ_H (J in Hz)	δ _C	δ_H (J in Hz)	HMBC	δ _C	δ_H (J in Hz)	HMBC
1	39.4	0.76, dd (4.0, 13.3)	40.0	1.00, dd (3.8, 13.4)	C-3	38.2	0.74, dd (3.6, 13.4)	C-2, C-20
		1.56, dt (4.1, 13.3)		1.61, m			1.26, m
2	18.7	1.37, m	19.6	1.47, m		18.1	1.26, m
				2.28, m			1.30, m
3	37.8	0.98, m	38.9	1.15, m		37.4	0.97, m	C-1, C-4, C-6, C-18, C-20
		2.12, m		2.50, m			2.06, m
4	43.7	-	43.6	-		43.0	-
5	57.0	1.01, m	47.9	2.20, dd (5.6, 9.4)	C-4, C-6, C-7, C-10, C-18, C-19, C-20	56.3	0.98, dd (2.1, 9.5)	C-10, C-19, C-20
6	21.7	1.74, m	31.0	2.45, m	C-3, C-5, C-7, C-8	21.0	1.65, m
7	39.2	1.31, m	75.0	3.87, t (3.1)	C-15	38.2	1.42, m
		1.45, dt (3.2, 13.3)
8	40.7	-	46.1	-		40.8	-
9	52.8	1.08, dd (7.9, 11.1)	47.1	1.92, dd (5.6, 11.3)	C-8, C-10, C-11, C-14, C-20	51.9	1.15, m
10	38.9	-	39.3	-		39.3	-
11	19.7	1.66, m	19.7	1.80, m		19.2	1.61, m	C-7, C-9, C-12, C-16
		1.88, m		2.02, m			1.81, m
12	20.5	0.57, dt (2.6, 7.8)	21.1	0.65, dt (2.9, 7.7)	C-15, C-17	19.8	0.57, dt (2.6, 7.7)	C-9, C-17
13	24.3	0.82, dd (3.1, 7.8)	24.6	0.92, dd (2.9, 7.7)		23.5	0.82, dd (2.9, 7.7)
14	33.1	1.19, m	33.0	1.31, m		32.5	1.14, m
		2.04, d (11.7)		2.11, d (11.6)	C-8, C-13, C-16		2.01, m	C-8, C-9, C-13, C-15, C-16
15	50.3	1.39, d (11.3)	46.5	1.74, d (11.7)	C-7, C-8, C-16, C-17	49.7	1.22, d (11.3)
		1.23, d (11.3)		1.99, d (11.7)	C-8, C-13, C-14, C-16		1.33, d (11.3)	C-8, C-9, C-12, C-16
16	22.4	-	23.2	-		21.8	-
17	20.5	1.13, s	20.8	1.21, s	C-12, C-13, C-15, C-16	20.3	1.11, s	C-12, C-13, C-15, C-16
18	28.9	1.21, s	29.2	1.42, s	C-3, C-4, C-5, C-19	28.0	1.12, s	C-3, C-4, C-5, C-19
19	184.5	-	180.5	-		175.4	-
20	12.4	0.88, s	12.9	1.21, s	C-5, C-10	12.2	0.80, s	C-1, C-5, C-9, C-10
1’						94.0	5.30, d (8.2)	C-19, C-3’
2’						72.5	3.14, m
3’						77.6	3.15, m
4’						69.5	3.14, m
5’						76.8	3.24, m
6’						60.5	3.45, dd (5.5, 11.5)	C-5’
							3.63, dd (4.5, 11.5)	C-4’

Compounds	AChE Inhibitory (%)	Standard Deviation
Galantamine	94.21	0.20
1	52.23	4.10
2	88.36	4.19
3	60.39	4.76
4	30.99	4.38
5	51.95	1.93
6	92.89	0.18