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  • SMB00609 - 6,6′-Dihydroxythiobinupharidine

SMB00609 Sigma-Aldrich


≥95% (HPLC)

Synonym: 6,6′-Dihydroxythionuphlutine A, Nuphleine

  • CAS Number 30343-70-5

  • Empirical Formula (Hill Notation) C30H42N2O4S

  • Molecular Weight 526.73



Related Categories Alkaloid, Cell Biology, Nutrition Research, Phytochemicals by Chemical Classification
assay   ≥95% (HPLC)
form   powder
Mode of action   enzyme | inhibits
antibiotic activity spectrum   Gram-positive bacteria
storage temp.   −20°C


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.

Safety & Documentation

Safety Information

NONH for all modes of transport
Protocols & Articles
Peer-Reviewed Papers


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