Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H15NO4 |
| Molecular Weight | 333.3374 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CC2=C3OCOC3=CC=C2C4=C1C5=C(C=C4)C=C6OCOC6=C5
InChI
InChIKey=CIUHLXZTZWTVFL-UHFFFAOYSA-N
InChI=1S/C20H15NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-7H,8-10H2,1H3
| Molecular Formula | C20H15NO4 |
| Molecular Weight | 333.3374 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
The quaternary benzo[c]phenanthridine alkaloid sanguinarine (SG) is the main component of Sangrovit, a natural livestock feed additive. Dihydrosanguinarine (DHSG) has been identified as an SG metabolite in rats. Therefore, the conversion of SG to DHSG is a likely elimination pathway of SG in mammals. Dihydrosanguinarine can also be isolated from Macleaya macrocarpa. DHSG has also been shown to have antiparasytic and anti fungal properties. It has been identified as a potential antiparasitic treatment for Ichthyopthirius multifiliis infection in Squaliobarbus curriculus.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells. | 2014-02-10 |
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| A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. | 2013-12-12 |
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| Phytochemical and antimicrobial characterization of Macleaya cordata herb. | 2010-12 |
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| Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. | 2010-11-18 |
|
| Fluorescence of sanguinarine: spectral changes on interaction with amino acids. | 2010-10-07 |
|
| In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. | 2010-08 |
|
| Interaction of sanguinarine and its dihydroderivative with the Na+/K+-ATPase. Complex view on the old problem. | 2010-06-16 |
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| Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus. | 2010-04 |
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| Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates. | 2009-09-25 |
|
| Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms. | 2009-09 |
|
| [Alkaloids from Macleaya cordata]. | 2009-07 |
|
| Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. | 2009-06 |
|
| Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. | 2009-03-13 |
|
| The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study. | 2008-07 |
|
| Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures. | 2008-05-20 |
|
| Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract. | 2008-02 |
|
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | 2008-01-22 |
|
| [Alkaloid constituents of Corydalis adunca]. | 2007-11 |
|
| Disposition of sanguinarine in the rat. | 2007-05 |
|
| Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. | 2007-04 |
|
| Metabolism of sanguinarine: the facts and the myths. | 2007-02 |
|
| Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification. | 2006-02 |
|
| A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. | 2006-01-02 |
|
| Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. | 2005-10-15 |
|
| [Studies on the alkaloids from the herb of Corydalis adunca]. | 2005-02 |
|
| Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts of Hylomecon species by high performance liquid chromatography. | 2003-02 |
|
| Argemone oil induced cellular damage in the reproductive tissues of transgenic Drosophila melanogaster: protective role of 70 kDa heat shock protein. | 2003 |
|
| Direct determination of alkaloid contents in Fumaria species by GC-MS. | 2002-12-24 |
|
| Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry. | 2002-07-09 |
|
| Two antimicrobial alkaloids from Bocconia arborea. | 1999-08 |
Sample Use Guides
male Wistar rats: at concentrations of 100 and 500 ppm Dihydrosanguinarine (DHSG) in feed for 90 days (average doses of 14 and 58 mg DHSG/kg body weight/day)
Route of Administration:
Oral
The antifungal activities of dihydrosanguinarine, isolated from the leaves of Macleaya microcarpa, was evaluated on 12 plant pathogenic fungi. Among the 11 tested plant pathogenic fungi in vitro, compound showed the highest antifungal activity against B. cinerea Pers, with 95.16% mycelial growth inhibition at 50 µg mL⁻¹.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 19:54:29 GMT 2025
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Mon Mar 31 19:54:29 GMT 2025
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| Record UNII |
3H1ZKG80F7
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| Record Status |
Validated (UNII)
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| Record Version |
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DIHYDROSANGUINARINE
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