6882-68-4 Usage
Description
Sophoridine is a quinolizidine alkaloid isolated from traditional Chinese herbs, which exists in the stems and leafs of Leguminous plant Sophora alopecuroides L., Euchresta japonica Benth., and the roots of Sophora alopecuroides Ait. Sophoridine-induced synchronous oscillations in the hippocampus could elicit the generation and development of seizure. Accumulating evidence demonstrates remarkable pharmacological effects of Sophoridine, including anti-inflammatory, anti-virus and anti-cancer effects.
Definition
Sophoridine is a quinolizidine alkaloid isolated from leafs of Leguminous plant Sophora alopecuroides.L. Sophoridine induces apoptosis. Sophoridine has the potential to be a novel, potent and selective antitumor drug candidate for pancreatic cancer with well-tolerated toxicity.
General Description
Sophoridine, a natural anticancer drug, has been used in China for decades. A series of novel N-substituted Sophoridinic acid derivatives were synthesized and evaluated for their cytotoxicity with 1 as the lead. The structure-activity relationship indicated that introduction of an aliphatic acyl on the nitrogen atom might significantly enhance the anticancer activity. Among the compounds, 6b bearing bromoacetyl side-chain afforded a potential effect against four human tumor cell lines (liver, colon, breast, and lung). The mechanism of action of 6b is to inhibit the activity of DNA topoisomerase I, followed by the S-phase arrest and then cause apoptotic cell death, similar to that of its parent 1.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 6882-68-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,8,8 and 2 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6882-68:
(6*6)+(5*8)+(4*8)+(3*2)+(2*6)+(1*8)=134
134 % 10 = 4
So 6882-68-4 is a valid CAS Registry Number.
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
6882-68-4Relevant articles and documents
Regio-selective Reduction of Oxysophoridine by Microorganism Isolated from Soil
Fu, Shaobin,Li, Yi,Meng, Qingfeng,Yue, Changwu,Sun, Yongzhen,Wei, Gang
, p. 331 - 335 (2016)
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.
The alkaloid constituents of Euchresta japonica and the stereochemical assignment of two isomeric sophoridine N-oxides
Ohmiya,Otomasu,Haginiwa,Murakoshi
, p. 546 - 551 (2007/10/02)
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