Detail
Článek
Článek online
FT
Medvik - BMČ
  • Je něco špatně v tomto záznamu ?

Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents

V. Wijaya, O. Janďourek, J. Křoustková, K. Hradiská-Breiterová, J. Korábečný, K. Sobolová, E. Kohelová, A. Hošťálková, K. Konečná, M. Šafratová, R. Vrabec, J. Kuneš, L. Opletal, J. Chlebek, L. Cahlíková

. 2022 ; 12 (6) : . [pub] 20220617

Jazyk angličtina Země Švýcarsko

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/bmc22017982

Tuberculosis (TB) is a widespread infectious disease caused by Mycobacterium tuberculosis. The increasing incidence of multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains has created a need for new antiTB agents with new chemical scaffolds to combat the disease. Thus, the key question is: how to search for new antiTB and where to look for them? One of the possibilities is to search among natural products (NPs). In order to search for new antiTB drugs, the detailed phytochemical study of the whole Dicranostigma franchetianum plant was performed isolating wide spectrum of isoquinoline alkaloids (IAs). The chemical structures of the isolated alkaloids were determined by a combination of MS, HRMS, 1D, and 2D NMR techniques, and by comparison with literature data. Alkaloids were screened against Mycobacterium tuberculosis H37Ra and four other mycobacterial strains (M. aurum, M. avium, M. kansasii, and M. smegmatis). Alkaloids 3 and 5 showed moderate antimycobacterial activity against all tested strains (MICs 15.625-31.25 μg/mL). Furthermore, ten semisynthetic berberine (16a-16k) derivatives were developed and tested for antimycobacterial activity. In general, the derivatization of berberine was connected with a significant increase in antimycobacterial activity against all tested strains (MICs 0.39-7.81 μg/mL). Two derivatives (16e, 16k) were identified as compounds with micromolar MICs against M. tuberculosis H37Ra (MIC 2.96 and 2.78 μM). All compounds were also evaluated for their in vitro hepatotoxicity on a hepatocellular carcinoma cell line (HepG2), exerting lower cytotoxicity profile than their MIC values, thereby potentially reaching an effective concentration without revealing toxic side effects.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc22017982
003      
CZ-PrNML
005      
20220804134508.0
007      
ta
008      
220720s2022 sz f 000 0|eng||
009      
AR
024    7_
$a 10.3390/biom12060844 $2 doi
035    __
$a (PubMed)35740968
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a sz
100    1_
$a Wijaya, Viriyanata $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000189416771
245    10
$a Alkaloids of Dicranostigma franchetianum (Papaveraceae) and Berberine Derivatives as a New Class of Antimycobacterial Agents / $c V. Wijaya, O. Janďourek, J. Křoustková, K. Hradiská-Breiterová, J. Korábečný, K. Sobolová, E. Kohelová, A. Hošťálková, K. Konečná, M. Šafratová, R. Vrabec, J. Kuneš, L. Opletal, J. Chlebek, L. Cahlíková
520    9_
$a Tuberculosis (TB) is a widespread infectious disease caused by Mycobacterium tuberculosis. The increasing incidence of multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains has created a need for new antiTB agents with new chemical scaffolds to combat the disease. Thus, the key question is: how to search for new antiTB and where to look for them? One of the possibilities is to search among natural products (NPs). In order to search for new antiTB drugs, the detailed phytochemical study of the whole Dicranostigma franchetianum plant was performed isolating wide spectrum of isoquinoline alkaloids (IAs). The chemical structures of the isolated alkaloids were determined by a combination of MS, HRMS, 1D, and 2D NMR techniques, and by comparison with literature data. Alkaloids were screened against Mycobacterium tuberculosis H37Ra and four other mycobacterial strains (M. aurum, M. avium, M. kansasii, and M. smegmatis). Alkaloids 3 and 5 showed moderate antimycobacterial activity against all tested strains (MICs 15.625-31.25 μg/mL). Furthermore, ten semisynthetic berberine (16a-16k) derivatives were developed and tested for antimycobacterial activity. In general, the derivatization of berberine was connected with a significant increase in antimycobacterial activity against all tested strains (MICs 0.39-7.81 μg/mL). Two derivatives (16e, 16k) were identified as compounds with micromolar MICs against M. tuberculosis H37Ra (MIC 2.96 and 2.78 μM). All compounds were also evaluated for their in vitro hepatotoxicity on a hepatocellular carcinoma cell line (HepG2), exerting lower cytotoxicity profile than their MIC values, thereby potentially reaching an effective concentration without revealing toxic side effects.
650    _2
$a antibakteriální látky $x farmakologie $7 D000900
650    12
$a berberin $x farmakologie $7 D001599
650    _2
$a lidé $7 D006801
650    _2
$a mikrobiální testy citlivosti $7 D008826
650    12
$a Mycobacterium tuberculosis $7 D009169
650    12
$a Papaveraceae $7 D028101
650    12
$a tuberkulóza $7 D014376
655    _2
$a časopisecké články $7 D016428
655    _2
$a práce podpořená grantem $7 D013485
700    1_
$a Janďourek, Ondřej $u Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000346332062 $7 xx0230412
700    1_
$a Křoustková, Jana $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
700    1_
$a Hradiská-Breiterová, Kateřina $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000347845601
700    1_
$a Korábečný, Jan $u Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000169777596 $7 xx0119837
700    1_
$a Sobolová, Kateřina $u Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic
700    1_
$a Kohelová, Eliška $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
700    1_
$a Hošťálková, Anna $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000332053767
700    1_
$a Konečná, Klára $u Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000156707767
700    1_
$a Šafratová, Marcela $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
700    1_
$a Vrabec, Rudolf $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000193909202
700    1_
$a Kuneš, Jiří $u Department of Bioorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
700    1_
$a Opletal, Lubomír $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000238743729 $7 jn20000620258
700    1_
$a Chlebek, Jakub $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000206975242
700    1_
$a Cahlíková, Lucie $u ADINACO Research Group, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic $1 https://orcid.org/0000000215558870 $7 xx0062498
773    0_
$w MED00188737 $t Biomolecules $x 2218-273X $g Roč. 12, č. 6 (2022)
856    41
$u https://pubmed.ncbi.nlm.nih.gov/35740968 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y p $z 0
990    __
$a 20220720 $b ABA008
991    __
$a 20220804134502 $b ABA008
999    __
$a ok $b bmc $g 1821864 $s 1169225
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2022 $b 12 $c 6 $e 20220617 $i 2218-273X $m Biomolecules $n Biomolecules $x MED00188737
LZP    __
$a Pubmed-20220720

Najít záznam

Citační ukazatele

Pouze přihlášení uživatelé

Možnosti archivace