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Skimmianine

$336

  • Brand : BIOFRON

  • Catalogue Number : BD-P0556

  • Specification : 98.0%(HPLC)

  • CAS number : 83-95-4

  • Formula : C14H13NO4

  • Molecular Weight : 259.3

  • PUBCHEM ID : 6760

  • Volume : 10mg

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Catalogue Number

BD-P0556

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

259.3

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Skimmia japonica

Structure Type

Category

SMILES

COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC

Synonyms

skimmiamine/7,8-Dimethoxydictamnine/Skimmianine/b-fagarine/β-Fagarine/Chloroxylonine/4,7,8-Trimethoxyfuro[2,3-b]quinoline/Skimmianin/Furo[2,3-b]quinoline, 4,7,8-trimethoxy-

IUPAC Name

Applications

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

196.7±27.3 °C

Boiling Point

401.6±40.0 °C at 760 mmHg

Melting Point

178°

InChl

InChl Key

SLSIBLKBHNKZTB-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:83-95-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28333075

Abstract

Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family. It has been reported to have analgesic, antispastic, sedative, anti-inflammatory, and other pharmacologic activities. Despite its critical pharmacological function, its metabolite profiling is still unclear. In this study, the in vivo metabolite profiling of skimmianine in rats was investigated using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS). The metabolites were predicted using MetabolitePilotTM software. These predicted metabolites were further analyzed by MS² spectra, and compared with the detailed fragmentation pathway of the skimmianine standard and literature data. A total of 16 metabolites were identified for the first time in rat plasma, urine, and feces samples after oral administration of skimmianine. Skimmianine underwent extensive Phase I and Phase II metabolism in rats. The Phase I biotransformations of skimmianine consist of epoxidation of olefin on its furan ring (M1) followed by the hydrolysis of the epoxide ring (M4), hydroxylation (M2, M3), O-demethylation (M5-M7), didemethylation (M14-M16). The Phase II biotransformations include glucuronide conjugation (M8-M10) and sulfate conjugation (M11-M13). The epoxidation of 2,3-olefinic bond followed by the hydrolysis of the epoxide ring and O-demethylation were the major metabolic pathways of skimmianine. The results provide key information for understanding the biotransformation processes of skimmianine and the related furoquinoline alkaloids.

KEYWORDS

UPLC/Q-TOF-MS; furoquinoline; metabolites; skimmianine

Title

Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry.

Author

Huang A1,2, Xu H3, Zhan R4, Chen W5, Liu J6, Chi Y7, Chen D8, Ji X9, Luo C10.

Publish date

2017 Mar 23

PMID

29187005

Abstract

The present research was to investigate the effects of skimmianine (SK) in four non-small cell lung cancer (NSCLC) cells. We found that SK can significantly inhibit the growth of NSCLC cells and markedly induce apoptosis in NSCLC cells. The effects of growth inhibition and apoptosis induction were in a concentration-response relationship and caspase-dependent manner.

KEYWORDS

Skimmianine; induce apoptosis; lung cancer; proteins expression

Title

Study on the activity and mechanism of skimmianine against human non-small cell lung cancer.

Author

Zuo Y1, Pu J2, Chen G3, Shen W4, Wang B5.

Publish date

2019 Mar

PMID

7829541

Abstract

1. Skimmianine, kokusaginine and confusameline, three furoquinolines extracted from the leaves of Evodia merrillii (Rutaceae), were investigated to characterize their selective effects on subtypes of 5-hydroxytryptamine (5-HT) receptors. 2. In the isolated membranes of rat cerebrocortex, using [3H]-5-HT and [3H]-ketanserin as radioligands, skimmianine and the two other furoquinolines displaced radioligand bindings in a concentration-dependent manner. Lower concentrations were required to affect [3H]-ketanserin binding than [3H]-5-HT binding in the order skimmianine > kokusaginine > confusameline. 3. Furoquinolines inhibited 5-HT-induced contraction mediated by 5-HT2 receptors in the presence of methiothepin in rat isolated aorta. Also, the combination of furoquinolines with ketanserin showed an additive antagonism. 4. These furoquinolines were inactive on the 5-carboxamidotryptamine-induced relaxation of guinea-pig ileum, a 5-HT1-mediated event. However, 5-HT-induced contraction via 5-HT2 receptors was reduced by these furoquinolines in a way similar to that in blood vessels. 5. The failure of these compounds to affect the 5-HT-induced Bezold-Jarisch-like reflex in anaesthetized rats, the major 5-HT3-mediated action, ruled out an action on 5-HT3 receptors. 6. The results obtained suggest that three furoquinoline alkaloids may act on 5-HT receptors in animals, more selectively to the 5-HT2 subtype, in the order of skimmianine > kokusaginine > confusameline.

Title

Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals.

Author

Cheng JT1, Chang TK, Chen IS.

Publish date

1994 Oct;