6882-68-4

Basic information

• Product Name: SOPHORIDINE
• Synonyms: (5-beta)-matridin-15-on;l-sophoridine;5-EPIDIHYDROSOPHOCARPINE;DIHYDRO-5-EPISOPHOCARPINE;I-SOPHORIDINE;Matridin-15-one,(5β)-;(5β)-Matridin-15-one;Sophoridine
• CAS NO: 6882-68-4
• Molecular Formula: C₁₅H₂₄N₂O
• Molecular Weight: 248.36
• EINECS: 1592732-453-0
• Product Categories: Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6882-68-4.mol

Chemical Properties

• Melting Point: 109-110 °C
• Boiling Point: 396.738 °C at 760 mmHg
• Flash Point: 172.748 °C
• Appearance: /
• Density: 1.164 g/cm³
• Storage Temp.: 2-8°C
• PKA: 9.47±0.20(Predicted)
• CAS DataBase Reference: SOPHORIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: SOPHORIDINE(6882-68-4)
• EPA Substance Registry System: SOPHORIDINE(6882-68-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 6882-68-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sophoridine is used as a pharmaceutical agent for its anti-inflammatory, anti-viral, and anti-cancer effects. Its diverse pharmacological properties make it a promising candidate for the development of new drugs to treat various diseases and conditions.
Used in Neurological Research:
Sophoridine is used as a research tool in the study of the generation and development of seizures, as it can induce synchronous oscillations in the hippocampus. This property allows researchers to investigate the underlying mechanisms of seizure activity and develop potential treatments for neurological disorders.
Used in Traditional Chinese Medicine:
Sophoridine is used in traditional Chinese medicine as a natural remedy for various ailments, leveraging its anti-inflammatory, anti-viral, and anti-cancer properties. Its long history of use in herbal medicine suggests potential benefits in treating a range of health issues.

Biological Activity

Sophoridine is promising to be a novel, potent and selective antitumor drug candidate for pancreatic cancer. It was shown that sophoridine is able to suppress hepatocellular carcinoma in vitro and vivo. Sophoridine dose- and time-dependently blocks the RANKL-induced osteoclasts formation and the activation of ERK and c-Fos as well as the induction and nucleus translocation of NFATc1.

Mechanism of action

Sophoridine is an active quinolizidine alkaloid isolated from leaves of Leguminous plant Sophora alopecuroides. L. Accumulating evidence demonstrated that Sophoridine displays remarkable pharmacological effects in inflammatory diseases , infectious diseases and cancers . In particular, Sophoridine and its derivatives have drawn more and more attention owing to their potent anti-tumor effects in different tumor cell lines and animal models. The underlying anti-tumor mechanisms of Sophoridine including increase of intracellular ROS levels, activation of the phosphorylation of ERK and JNK, induction of S phase arrest in pancreatic cancer cells; inhibition of growth and invasion in human colorectal cancer cells via directly binding to MAPKAPK2 and inactivates its phosphorylation; inhibition of ubiquitin-proteasome pathway in human glioma cells.

in vitro

Sophoridine (0-500 μM; 48 hours) exhibits remarkable inhibition effects to the growth of human pancreatic, gastric, liver, colon, gallbladder, and prostate carcinoma cells with IC50 values of about 20 μM to 200 μM.Sophoridine (0-20 μM; 48 hours) increases S phase cell population from 26.23% (control) to 38.67% in Miapaca-2 cells and from 29.56% (control) to 39.16% in PANC-1 cells, about a 1.5-fold and a 1.3-fold increase, respectively.Sophoridine (0-20 μM; 48 hours) significantly increases bad and bax levels, and decreases bcl-2 and bcl-xl levels in contrast, with a significant increase in Bax/Bcl-2 ratio.

Source

Sophoridine is a bioactive alkaloid found in many Chinese herbs, such as Sophora alopecuroides l, Euchresta japonica Benth and Sophora moocrorftinan. Sophoridine hydrochloride injection has been approved as an anticancer drug in China.

InChI:InChI=1/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12-,13-,15+/m1/s1

Upstream product

• 16837-52-8 (3aS,6aR,11aR,11bR,11cS)-3a-Oxy-dodecahydro-3a,7a-diaza-benzo[de]anthracen-8-one 
• 54809-74-4 sophoridine N-oxide 

Relevant articles and documents

Regio-selective Reduction of Oxysophoridine by Microorganism Isolated from Soil

Oxysophoridine (OSR), an alkaloid extracted from a traditional Chinese medicine, attracted more and more attention because of remarkable biological activities. Biocatalysis of OSR by 86 stains including soil microbes and endophytic fungi were investigated. Incubation of OSR with soil bacteria T003 identified as Escherichia coli could lead to only one reductive product with highly regio-selectivity. The structural elucidations of transformation product were achieved mainly by the NMR spectroscopic methods and references. Effect of pH, substrate concentration, conversion time and strain concentration was studied, the optimization of reaction was analyzed by LC-MS. The production of sophoridine (SR) from OSR was highest at pH 7.0, 36 h of incubation and in presence of 625 μg/mL substrate concentration, 50 μL/mL strain concentration respectively. Biocatalysis was considered the alternatives to preparation of sophoridine with green and sustainable synthetic processes except for less time-consuming and more environmentally friendly.

Synthesis and biological evaluation of nitric oxide-releasing matrine derivatives as anticancer agents

A series of furoxan-based nitric oxide-releasing matrine derivatives (10a-f) were synthesized. The biological evaluation showed that compounds 10a, 10b, 10e and 10f had stronger cytotoxic activities than 5-fluorouracil against human hepatoma cells (HepG2) in vitro.