Dihydrosanguinarine - CAS 3606-45-9
Catalog number: 3606-45-9
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H15NO4
Molecular Weight:
333.34
COA:
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Targets:
Others
Description:
Dihydrosanguinarine (DHSG) is a metabolite of Sanguinarine with antifungal activity.
Purity:
>98%
Synonyms:
13,14-Dihydrosanguinarine
MSDS:
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InChIKey:
CIUHLXZTZWTVFL-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
CN1CC2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(C=C5C=C4)OCO6
1.[Chemical constituents of the roots of Macleaya microcarpa and activation efficacy of benzophenanthridine alkaloids for the transcription of xbp1 gene].
Liu Y, Deng AJ, Ma L, Zhang HJ, Zhang ZH, Wu LQ, Shen ZF, Wang WJ, Qin HL. Yao Xue Xue Bao. 2015 Feb;50(2):207-10.
Ongoing study on the chemical constituents of the roots of Macleaya microcarpa led to the isolation of eight compounds of derivatives of triterpenes and organic acids in addition to some previously identified benzophenanthridines. The eight compounds were identified by spectroscopic methods as well as comparison with literature values as 1-oxo-2, 22 (30)-hopandien-29-oic acid (1), 3-oxo-12-oleanen-30-oic acid (2), 3α-hydroxy-12-oleanen-30-oic acid (3), 3β-hydroxy-12-oleanen-30-oic acid (4), ferulic acid (5), ferulic acid 4-O-β-D-glucoside (6), 3-O-feruloylquinic acid (7), and methyl 3-O-feruloylquinate (8). Of which, 1 is a new triterpenoid of hopanes and 2-8 are isolated from M microcarpa for the first time. In order to discover natural active compounds as potential agents of anti-ulcerative colitis (UC), an in vitro drug high-throughput screening model targeted x-box-binding protein 1 (xbp1) was employed to evaluate the activity of the major chemical constituents of M microcarpa.
2.Analysis of benzo[c]phenanthridine alkaloids in Eschscholtzia californica cell culture using HPLC-DAD and HPLC-ESI-MS/MS.
Son SY1, Rhee HS, Lee MW, Park JM. Biosci Biotechnol Biochem. 2014;78(7):1103-11. doi: 10.1080/09168451.2014.917264.
Effective HPLC-DAD and HPLC-ESI-MS/MS methods have been developed for the analysis of eight benzo[c]phenanthridine alkaloids (sanguinarine, chelirubine, macarpine, chelerythrine, dihydrosanguinarine, dihydrochelirubine, dihydromacarpine and dihydrochelerythrine), which are important metabolites in Eschscholtzia californica cell culture. By adopting a ternary gradient pump system, the dihydro-form alkaloids hardly separable from each other could be successfully separated, and all the target alkaloids could be simultaneously quantified with the LOD values of 0.01-0.79 μg/mL and the LOQ values of 0.03-3.59 μg/mL. This HPLC-DAD method was further confirmed by HPLC-ESI-MS/MS system in multiple reaction monitoring mode. Each separated HPLC peak was identified as the target alkaloid, showing its relevant ionized molecule and selected fragment ion. By applying the established method, alkaloid production during the E. californica cell culture could be successfully monitored and some valuable information on its metabolism could be deduced.
3.Reconstitution of a 10-gene pathway for synthesis of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae.
Fossati E1, Ekins A1, Narcross L1, Zhu Y2, Falgueyret JP3, Beaudoin GA4, Facchini PJ4, Martin VJ2. Nat Commun. 2014;5:3283. doi: 10.1038/ncomms4283.
Benzylisoquinoline alkaloids (BIAs) represent a large class of plant secondary metabolites, including pharmaceuticals such as morphine, codeine and their derivatives. Large-scale production of BIA-based pharmaceuticals is limited to extraction and derivatization of alkaloids that accumulate in planta. Synthesis of BIAs in microbial hosts could bypass such limitations and transform both industrial production of BIAs with recognized value and research into uncharacterized BIAs. Here we reconstitute a 10-gene plant pathway in Saccharomyces cerevisiae that allows for the production of dihydrosanguinarine and its oxidized derivative sanguinarine from (R,S)-norlaudanosoline. Synthesis of dihydrosanguinarine also yields the side-products N-methylscoulerine and N-methylcheilanthifoline, the latter of which has not been detected in plants. This work represents the longest reconstituted alkaloid pathway ever assembled in yeast and demonstrates the feasibility of the production of high-value alkaloids in microbial systems.
4.New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C.
Tatton MR1, Simpson I, Donohoe TJ. Chem Commun (Camb). 2014 Oct 7;50(77):11314-6. doi: 10.1039/c4cc05209a.
A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl amine products formed in the key cyclisation.
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CAS 3606-45-9 Dihydrosanguinarine

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