30343-70-5 Usage
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.
Check Digit Verification of cas no
The CAS Registry Mumber 30343-70-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,3,4 and 3 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 30343-70:
(7*3)+(6*0)+(5*3)+(4*4)+(3*3)+(2*7)+(1*0)=75
75 % 10 = 5
So 30343-70-5 is a valid CAS Registry Number.
30343-70-5Relevant articles and documents
Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids
Korotkov, Alexander,Li, Hui,Chapman, Charles W.,Xue, Haoran,Macmillan, John B.,Eastman, Alan,Wu, Jimmy
supporting information, p. 10604 - 10607 (2015/09/02)
Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.
