Cashmirins A and B, new antifungal and urease inhibitory prenylated coumarins from <i>Sorbus cashmiriana</i>

Khan, Sadia; Kazmi, Mehdi Hassan; Fatima, Itrat; Malik, Abdul; Inamullah, Farah; Farheen, Sadia; Abbas, Tanveer

doi:10.1590/s2175-97902022e21493

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e21493 copy

Cashmirins A and B, new antifungal and urease inhibitory prenylated coumarins from Sorbus cashmiriana

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Cashmirins A (1) and B (2), new prenylated coumarins, have been isolated from the EtOAc- soluble fraction of the whole plant of Sorbus cashmiriana Hedlung, Monog. along with seselin (3), scopoletin (4), 3-hydroxyxanthyletin (5) and luteolin (6), reported for the first time from this species. Their structures were elucidated by spectroscopic techniques including MS, 1D and 2D NMR spectroscopy. Both new compounds 1 and 2 were investigated for biological activities and showed significant antifungal and urease inhibitory activities. Compounds 1 and 2 exhibited significant activity against Aspergillus flavus, Macrophomina phaseolina, Trichophyton simii, Trichophyton schoenleinii, and Pseudallescheria boydri. Both compounds also exhibited significant inhibitory activity against Jack bean urease with IC₅₀ values of 28.2±0.12 µM and 30.3±0.18 µM, respectively compared to thiourea used as positive control.

Keywords:
Sorbus cashmiriana; Prenylated coumarins; Cashmirins; Antifungal activity; Urease inhibition

Position	1		2
	δ_H	δ_C	δ_H	δ_C
2	-	161.4	-	160.8
3	-	128.2	-	128.5
4	7.29 s	139.2	7.64 s	140.0
5	7.09 s	120.7	-	151.8
6	-	116.7	-	110.2
7	-	166.7	-	169.1
8	-	111.5	-	100.8
9	-	109.3	-	101.2
10	-	155.0	-	156.5
1'	3.23 d (7.0)	30.2	3.21 d (7.0)	30.4
2'	5.25 m	121.7	5.26 m	121.5
3'	-	133.2	-	132.9
4'	1.62 s	18.9	1.61 s	18.9
5'	1.75 s	25.0	1.76 s	25.5
4''	6.41 d (9.5)	123.0	6.53 d (9.5)	118.2
5''	5.49 d (9.5)	129.4	5.67 d (9.5)	129.7
6''	-	75.2	-	75.2
6''-2Me	1.38 s	28.0	1.39 s	28.0
1'''	-	164.0	-	164.0
1'''-OMe	3.78 s	56.4	3.79 s	56.2
5-OMe	-	-	3.89 s	62.2

Organisms	Inhibition (%) of crude extract	Inhibition (%)		Standard drugs	Inhibition (%) of standard drugs
Organisms	Inhibition (%) of crude extract	1	2	Standard drugs	Inhibition (%) of standard drugs
A. flavus	68	78	80	Amphotericin-B	100
A. niger	50	54	62	Miconazole	90
M. phaseolina	58	69	72	Miconazole	100
T. simii	67	80	82	Ketoconazole	100
M. canis	35	16	25	Benlate	90
T. schoenleinii	62	75	78	Ketoconazole	100
F. solani	48	57	60	Benlate	100
P. boydri	60	74	78	Nystain	90
C. glabrata	58	60	65	Miconazole	100
R. solani	24	11	17	Ketoconazole	100

Compound	IC₅₀ ± S.E.M (µM)
1	28.2 ± 0.12
2	30.3 ± 0.18
Thiourea	22.4 ± 0.15

Universidade de São Paulo, Faculdade de Ciências Farmacêuticas Av. Prof. Lineu Prestes, n. 580, 05508-000 S. Paulo/SP Brasil, Tel.: (55 11) 3091-3824 - São Paulo - SP - Brazil
E-mail: bjps@usp.br

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[1] *Correspondence: A Malik. International Centre for Chemical and Biological Sciences. HEJ Research Institute of Chemistry. University of Karachi. Karachi-75270, Pakistan. E-mail: abdulmalik.hej@gmail.com. ORCID: https://orcid.org/0000-0002-9862-9813