Skimmianine - a natural alkaloid from family Rutaceae – University of Copenhagen

NaToxAq > Toxin of the week > Skimmianine

09 September 2019

Skimmianine - a natural alkaloid from family Rutaceae

Natural toxin

Skimmianine is found to be mutagenic and can affect subtypes of 5-hydroxytryptamine (5-HT2) receptors in liver.

Skimmianine (4,7,8-trimethoxyfuro[2,3-b]quinoline) is an natural alkaloid classified within furoquinoline alkaloids. They are produced by plant, mainly in the plant family Rutaceae, including Dictamnus dasycarpus, Rutagravelens L., Zanthoxylum nitidum and Zanthoxylum simulans. Skimmianine is the most abundant alkaloids in the family. The plant family comprises more than 2,000 species across 160 genera, are important food crops, and some are grown as garden ornamentals. They are distributed worldwide across tropical and sub-tropical areas.

Structure of skimmianine. Click image for interactive 3D structure 

Furoquinoline alkaloids and Skimmianine are anthranilic acid derivatives.  They are containing the quinoline ring system with furo group attached to the ring system.

It is found to be mutagenic, especially towards strain TA100 (77 revertant colonies per μg) and TA98 (27 revertant colonies per μg) in rat liver. In addition, as other furoquinoline alkaloids, skimmianine can affect subtypes of 5-hydroxytryptamine (5-HT2) receptors in liver.

The environmental fate of skimmianine and related furoquinoline alkaloids are unknown in the environment. However, basic skimmianine can be considered as mobile toxins based on predictions (log Koc=2.370, EPISuite) and persistent (persistence time 82 days, EPISuite) in the aquatic environment. Skimmianine may reach surface water where close to agricultural fields or wetland, because of its abundance and chemical properties.


CAS: 83-95-4
SMILES: COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC

References:

  • Kanamori H, Sakamoto I, Mizuta M, 1986. Further study on mutagenic furoquinoline alkaloids of dictamniradiciscortex: isolation of skimmianine and high-performance iquidchromatographic analysis. Biol. Pharm. Bull. 34, 1826–1829.
  • Yang Z, Zhang D, Ren J et al. 2012. Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitorMed Chem Res. 21: 722.
  • Huang A, Xu H, Zhan R, Chen W, Liu J, Chi Y, Chen D, Ji X, Luo C.  Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry. Molecules. 2017 Mar 23;22(4). pii: E489.
  • Cheng JT, Chang TK, Chen IS. 1994. Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals. J Auton Pharmacol. 14(5):365-74.

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