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Key Documents
SMB00609
6,6′-Dihydroxythiobinupharidine
≥95% (HPLC)
Synonim(y):
6,6′-Dihydroxythionuphlutine A, Nuphleine
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About This Item
Wzór empiryczny (zapis Hilla):
C30H42N2O4S
Numer CAS:
Masa cząsteczkowa:
526.73
Kod UNSPSC:
51102829
NACRES:
NA.76
Polecane produkty
Poziom jakości
Próba
≥95% (HPLC)
Postać
powder
spektrum działania antybiotyku
Gram-positive bacteria
Tryb działania
enzyme | inhibits
temp. przechowywania
−20°C
ciąg SMILES
O[C@H]1N2[C@@]([C@H](C)CC[C@H]2C3=COC=C3)([H])CC[C@@]14SC[C@]5(C4)CC[C@]([C@H](C)CC[C@H]6C7=COC=C7)([H])N6[C@@H]5O
Opis ogólny
6,6′-Dihydroxythiobinupharidine is an active compound found in Nuphar lutea extract. It is a dimeric sesquiterpene thioalkaloid which presents multiple activities.
Działania biochem./fizjol.
6,6′-Dihydroxythiobinupharidine inhibits NFκB activation, leading to an induction of apoptosis via cleavage of procaspase-9 and poly (ADP-ribose) polymerase (PARP).
It was also found to act synergistically with cytotoxic drugs such as cisplatin and etoposide, enabling their cytotoxic effect at lower concentrations.
6,6′-Dihydroxythiobinupharidine was found to have cytotoxic activity at a concentration of ~10 μM on human leukemia cells (U937), mouse melanoma cells (B16F10), and human fibroblasts (HT1080).
In addition, Nuphar lutea extract was effective against both Leishmania promastigote and amastigote forms (IC50 = 2 ± 0.12 μg/mL; ID50 = 0.65 ± 0.023 μg/mL; LD50 = 2.1 ± 0.096 μg/mL, STI = 3.23). A synergistic antileishmanial activity was demonstrated with the antileishmanial drug, paromomycin.
Recently 6,6′-dihydroxythiobinupharidine was found to be active against MRSA and VRE strains with an MIC of 1-4 μg/mL. Inhibition of DNA topoisomerase IV but not DNA gyrase in S. aureus was suggested as the mechanism of action. 6,6′-Dihydroxythiobinupharidine was also shown to promote neutrophil effector bactericidal functions.
It was also found to act synergistically with cytotoxic drugs such as cisplatin and etoposide, enabling their cytotoxic effect at lower concentrations.
6,6′-Dihydroxythiobinupharidine was found to have cytotoxic activity at a concentration of ~10 μM on human leukemia cells (U937), mouse melanoma cells (B16F10), and human fibroblasts (HT1080).
In addition, Nuphar lutea extract was effective against both Leishmania promastigote and amastigote forms (IC50 = 2 ± 0.12 μg/mL; ID50 = 0.65 ± 0.023 μg/mL; LD50 = 2.1 ± 0.096 μg/mL, STI = 3.23). A synergistic antileishmanial activity was demonstrated with the antileishmanial drug, paromomycin.
Recently 6,6′-dihydroxythiobinupharidine was found to be active against MRSA and VRE strains with an MIC of 1-4 μg/mL. Inhibition of DNA topoisomerase IV but not DNA gyrase in S. aureus was suggested as the mechanism of action. 6,6′-Dihydroxythiobinupharidine was also shown to promote neutrophil effector bactericidal functions.
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Kod klasy składowania
11 - Combustible Solids
Klasa zagrożenia wodnego (WGK)
WGK 3
Temperatura zapłonu (°F)
Not applicable
Temperatura zapłonu (°C)
Not applicable
Certyfikaty analizy (CoA)
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We screened thirty-four methanolic plant extracts for inhibition of the constitutive nuclear factor kappaB (NFkappaB) activity by a NFkappaB-luciferase reporter gene assay. Strong inhibition of NFkappaB activity was found in extracts of leaf and rhizome from Nuphar lutea L. SM.
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Multidrug-resistant bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococci (VRE), cause serious infections at clinical sites, for which the development of new drugs is necessary. We screened candidates for new antibiotics and investigated its action mechanism. An
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