Open Access
Scientific Reports, volume 9, issue 1, publication number 12066
Examination of molecular space and feasible structures of bioactive components of humic substances by FTICR MS data mining in ChEMBL database
Orlov Alexey A.
1, 2, 3
,
Zherebker Alexander
1, 2
,
Eletskaya Anastasia A
3, 4
,
Chernikov Viktor S
3
,
Kozlovskaya Liubov I
3, 5
,
Zhernov Yury
6
,
Kostyukevich Yury
1
,
Palyulin Vladimir A.
2
,
Nikolaev Eugene N
1
,
Osolodkin Dmitry I.
2, 3, 5
,
Perminova Irina V
2
Publication type: Journal Article
Publication date: 2019-08-19
PubMed ID:
31427609
Multidisciplinary
Abstract
Humic substances (HS) are complex natural mixtures comprising a large variety of compounds produced during decomposition of decaying biomass. The molecular composition of HS is extremely diverse as it was demonstrated with the use of high resolution mass spectrometry. The building blocks of HS are mostly represented by plant-derived biomolecules (lignins, lipids, tannins, carbohydrates, etc.). As a result, HS show a wide spectrum of biological activity. Despite that, HS remain a ‘biological activity black-box’ due to unknown structures of constituents responsible for the interaction with molecular targets. In this study, we investigated the antiviral activity of eight HS fractions isolated from peat and coal, as well as of two synthetic humic-like materials. We determined molecular compositions of the corresponding samples using ultra-high resolution Fourier-transform ion cyclotron resonance mass-spectrometry (FTICR MS). Inhibitory activity of HS was studied with respect to reproduction of tick-borne encephalitis virus (TBEV), which is a representative of Flavivirus genus, and to a panel of enteroviruses (EVs). The samples of natural HS inhibited TBEV reproduction already at a concentration of 1 µg/mL, but they did not inhibit reproduction of EVs. We found that the total relative intensity of FTICR MS formulae within elemental composition range commonly attributed to flavonoid-like structures is correlating with the activity of the samples. In order to surmise on possible active structural components of HS, we mined formulae within FTICR MS assignments in the ChEMBL database. Out of 6502 formulae within FTICR MS assignments, 3852 were found in ChEMBL. There were more than 71 thousand compounds related to these formulae in ChEMBL. To support chemical relevance of these compounds to natural HS we applied the previously developed approach of selective isotopic exchange coupled to FTICR MS to obtain structural information on the individual components of HS. This enabled to propose compounds from ChEMBL, which corroborated the labeling data. The obtained results provide the first insight onto the possible structures, which comprise antiviral components of HS and, respectively, can be used for further disclosure of antiviral activity mechanism of HS.
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Orlov A. A. et al. Examination of molecular space and feasible structures of bioactive components of humic substances by FTICR MS data mining in ChEMBL database // Scientific Reports. 2019. Vol. 9. No. 1. 12066
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Orlov A. A., Zherebker A., Eletskaya A. A., Chernikov V. S., Kozlovskaya L., Zhernov Y., Kostyukevich Y., Palyulin V. A., Nikolaev E. N., Osolodkin D. I., Perminova I. V. Examination of molecular space and feasible structures of bioactive components of humic substances by FTICR MS data mining in ChEMBL database // Scientific Reports. 2019. Vol. 9. No. 1. 12066
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TY - JOUR
DO - 10.1038/s41598-019-48000-y
UR - https://doi.org/10.1038%2Fs41598-019-48000-y
TI - Examination of molecular space and feasible structures of bioactive components of humic substances by FTICR MS data mining in ChEMBL database
T2 - Scientific Reports
AU - Orlov, Alexey A.
AU - Zherebker, Alexander
AU - Eletskaya, Anastasia A
AU - Chernikov, Viktor S
AU - Kozlovskaya, Liubov I
AU - Zhernov, Yury
AU - Kostyukevich, Yury
AU - Palyulin, Vladimir A.
AU - Nikolaev, Eugene N
AU - Osolodkin, Dmitry I.
AU - Perminova, Irina V
PY - 2019
DA - 2019/08/19 00:00:00
PB - Springer Nature
IS - 1
VL - 9
PMID - 31427609
SN - 2045-2322
ER -
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@article{2019_Orlov,
author = {Alexey A. Orlov and Alexander Zherebker and Anastasia A Eletskaya and Viktor S Chernikov and Liubov I Kozlovskaya and Yury Zhernov and Yury Kostyukevich and Vladimir A. Palyulin and Eugene N Nikolaev and Dmitry I. Osolodkin and Irina V Perminova},
title = {Examination of molecular space and feasible structures of bioactive components of humic substances by FTICR MS data mining in ChEMBL database},
journal = {Scientific Reports},
year = {2019},
volume = {9},
publisher = {Springer Nature},
month = {aug},
url = {https://doi.org/10.1038%2Fs41598-019-48000-y},
number = {1},
doi = {10.1038/s41598-019-48000-y}
}
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