SMB00609
6,6′-Dihydroxythiobinupharidine
≥95% (HPLC)
Synonym(s):
6,6′-Dihydroxythionuphlutine A, Nuphleine
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About This Item
Empirical Formula (Hill Notation):
C30H42N2O4S
CAS Number:
Molecular Weight:
526.73
UNSPSC Code:
51102829
NACRES:
NA.76
Quality Level
Assay
≥95% (HPLC)
form
powder
antibiotic activity spectrum
Gram-positive bacteria
Mode of action
enzyme | inhibits
storage temp.
−20°C
SMILES string
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
General description
6,6′-Dihydroxythiobinupharidine is an active compound found in Nuphar lutea extract. It is a dimeric sesquiterpene thioalkaloid which presents multiple activities.
Biochem/physiol Actions
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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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