SMB00609
6,6′-Dihydroxythiobinupharidine
≥95% (HPLC)
Synonyme(s) :
6,6′-Dihydroxythionuphlutine A, Nuphleine
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About This Item
Formule empirique (notation de Hill):
C30H42N2O4S
Numéro CAS:
Poids moléculaire :
526.73
Code UNSPSC :
12352200
Produits recommandés
Niveau de qualité
Pureté
≥95% (HPLC)
Forme
powder
Spectre d'activité de l'antibiotique
Gram-positive bacteria
Mode d’action
enzyme | inhibits
Température de stockage
−20°C
Chaîne 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
Description générale
6,6′-Dihydroxythiobinupharidine is an active compound found in Nuphar lutea extract. It is a dimeric sesquiterpene thioalkaloid which presents multiple activities.
Actions biochimiques/physiologiques
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.
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
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Sulfur containing alkaloids from Nuphar luteum
LaLonde, R.T. and Wong, C.F.
Phytochemistry, 11, 3305-3306 (1972)
Esha D Dalvie et al.
Bioorganic & medicinal chemistry letters, 29(15), 1881-1885 (2019-06-12)
A number of natural products with medicinal properties increase DNA cleavage mediated by type II topoisomerases. In an effort to identify additional natural compounds that affect the activity of human type II topoisomerases, a blind screen of a library of
J El-On et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 16(8), 788-792 (2009-03-24)
Several anti-leishmanial drugs of choice are of plant origin. Many of the available drugs against the disease are toxic and in certain cases parasite drug resistance is developed. The development of new compounds is urgently required. To determine the leishmanicidal
Janet Ozer et al.
Cancer biology & therapy, 8(19), 1860-1868 (2009-08-29)
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.
Shinya Okamura et al.
Biochimica et biophysica acta, 1850(6), 1245-1252 (2015-03-04)
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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