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In vitro evaluation of anthraquinones from Aloe vera (Aloe barbadensis Miller) roots and several derivatives against strains of influenza virus.

ABSTRACT: Aloe vera is a crop of wide economic value of worldwide distribution, and a rich source of quinone components. Recently, antiviral aloe anthraquinones had been reported against human influenza virus. In the present work two anthraquinones, aloesaponarin-I (1) and aloesaponarin-II (2) were isolated from A. vera roots, and six derivatives were obtained by methylation (3), acetylation (4) and O-glycosyl (5-6) reactions starting from (1). Additionally, a new Tetra-O-acetyl-?-d-glucopyranosyl derivative from 2 was also prepared. All compounds were evaluated against two strains of influenza virus AH1N1 by cytopathic effect reduction assay (CPE). The antiviral activity was determined by the ability of compounds to inhibit virus replication on Madin Darby Canine Kidney cells (MDCK). New derivatives 3-(2´,3´,4´,6´-Tetra-O-acetyl-?-d-glucopyranosyl-aloesaponarin-I (5) and 3-(2´,3´,4´,6´-Tetra-O-acetyl-?-d-glucopyranosyl- aloesaponarin-II (7) showed a cytopathic reduction effect against influenza strain A/Yucatán/2370/09 with IC50 of 30.77 and 13.70??M, and against the virus A/Mexico/InDRE797/10 with IC50 of 62.28 and 19.47??M, respectively. To assess the effect of derivatives 5 and 7 during one cycle of replication (0-10?h), a time-of-addition experiment was performed. As a result it was found that both compounds were most effective when added 6-10?h post-infection and significantly inhibited viral titre (> 70%) at the concentrations of 50 and 100??M. Based on the structural analysis of the compounds, it was suggested that the Tetra-O-acetyl-?-d-glucopyranosyl substituent at the C3 position of the anthraquinone might have an effect against the influenza AH1N1 virus.

SUBMITTER: Borges-Argaez R

PROVIDER: S-EPMC7138392 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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In vitro evaluation of anthraquinones from Aloe vera (Aloe barbadensis Miller) roots and several derivatives against strains of influenza virus.

Borges-Argáez Rocío R Chan-Balan Reyna R Cetina-Montejo Lisseth L Ayora-Talavera Guadalupe G Sansores-Peraza Pablo P Gómez-Carballo Jesús J Cáceres-Farfán Mirbella M

Industrial crops and products 20190307

Aloe vera is a crop of wide economic value of worldwide distribution, and a rich source of quinone components. Recently, antiviral aloe anthraquinones had been reported against human influenza virus. In the present work two anthraquinones, aloesaponarin-I (1) and aloesaponarin-II (2) were isolated from A. vera roots, and six derivatives were obtained by methylation (3), acetylation (4) and O-glycosyl (5-6) reactions starting from (1) ...[more]

PMID: 32288269

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Project description:IntroductionIsolated bioactive components of plants or their raw extract are utilized as complementary or alternate remedy in copious illnesses. The current research was aimed at assessing the activity of aloin A isolated from Aloe barbadensis Miller and its formulated ointment against six (6) selected clinical isolates.MethodsThe column chromatography was utilized in isolating aloin A from chloroform/methanol solvent polarity. The characterization of the isolated compound was performed by spectroscopy techniques corresponding to UV, IR, 1H- and 13C-NMR spectroscopy. It was formulated as ointment using polyethylene glycol (PEG) and both the ointment and the isolated compound were probed for in vitro antimicrobial activity.ResultsAloin A has been isolated from chloroform/methanol solvent mixture. The structure has been explicated as (10S)-10-β-d-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone(1S)-1,5-anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydro-9-anthracenyl]-d-glucitol. The minimum inhibitory concentration (MIC) of the isolated aloin A on the pathogens ranged from 2.5 to 5.0 mg/ml and 0.32 to 5.0 mg/ml for both aloin A and the formulated ointment respectively. It was further revealed that the activity of aloin A showed dose dependence against all the test microorganisms. There was no significant difference in the activity of the drug against K. pneumoniae, S. aureus, E. coli, C. albicans and T. flavus (P > 0.05) when the concentration was raised from 2.5 to 5 mg/ml, however, there was significant difference (P ˂ 0.05) in activity against P. aeruginosa. The formulated ointment exhibited dose dependent activity against all test microorganisms. At low concentrations, the ointment showed no significant difference in diameter zone of inhibition against all test microorganisms (P > 0.05) except P. aeruginosa which exhibited a highly significant difference (P < 0.05).ConclusionBoth the isolated aloin A and its formulated ointment demonstrated substantial inhibition of growth of the pathogenic strains. These findings sturdily suggest that aloin A is a nascent drug that could be explored as skin and wound transmittable agent.

Dataset Information

In vitro evaluation of anthraquinones from Aloe vera (Aloe barbadensis Miller) roots and several derivatives against strains of influenza virus.

Publications

<i>In vitro</i> evaluation of anthraquinones from <i>Aloe vera</i> (<i>Aloe barbadensis</i> Miller) roots and several derivatives against strains of influenza virus.

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