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Matrine

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From Wikipedia, the free encyclopedia

Tetracyclic plant alkaloid

Pharmaceutical compound

Matrine
Clinical data

ATC code	none
Legal status
Legal status	Unscheduled, sold OTC in US
Identifiers
IUPAC name (1R,2R,9S,17S)-7,13-Diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one
CAS Number	519-02-8^Y
PubChemCID	91466
ChemSpider	82591^N
UNII	N390W430AC
KEGG	C10774^N
ChEBI	CHEBI:6700^N
ChEMBL	ChEMBL204860^N
CompTox Dashboard(EPA)	DTXSID00274188
ECHA InfoCard	100.117.486
Chemical and physical data
Formula	C₁₅H₂₄N₂O
Molar mass	248.370 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1C[C@@H]2[C@H]3CCCN4[C@H]3[C@@H](CCC4)CN2C(=O)C1
InChI InChI=1S/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-/m0/s1^N Key:ZSBXGIUJOOQZMP-JLNYLFASSA-N^N
^NY (what is this?) (verify)

Matrine is analkaloid found in plants from the familyFabaceae. It has a variety of pharmacological effects, includingin-vitro anti-cancer effects,^[1] as well asκ-opioid andμ-opioid receptor agonism.^[2]^[3]

Matrine possesses strong antitumor activitiesin vitro andin vivo. Inhibition of cell proliferation and induction of apoptosis are the likely mechanisms responsible for matrine's antitumor activities.^[4] Matrine can be commercially extracted from the traditional Chinese medical herbSophora flavescens Ait.

Mu opioid agonism is associated witheuphoria, while kappa opioid agonism is associated withdysphoria andpsychotomimetic hallucinations (as seen in the kappa-agonistSalvinorin A). Both receptors are known to produceanalgesia when activated.

Matrine and the related compoundoxymatrine have a toxic effect against theformosan subterranean termite.^[5] Additionally, it acts as anematicide against thepine wood nematode which causespine wilt,^[6] as well as pathogenic nematodes which target humans.^[7]

Matrine alleviates neuro-inflammation andoxidative stress in the brain caused by acute liver injury, thus producing antianxiety and antidepression effects.^[8]

References

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^Zhang Y, Zhang H, Yu P, Liu Q, Liu K, Duan H, et al. (April 2009)."Effects of matrine against the growth of human lung cancer and hepatoma cells as well as lung cancer cell migration".Cytotechnology.59 (3):191–200.doi:10.1007/s10616-009-9211-2.PMC 2774570.PMID 19649719.
^Xiao P, Kubo H, Ohsawa M, Higashiyama K, Nagase H, Yan YN, et al. (April 1999). "kappa-Opioid receptor-mediated antinociceptive effects of stereoisomers and derivatives of (+)-matrine in mice".Planta Medica.65 (3):230–233.Bibcode:1999PlMed..65..230X.doi:10.1055/s-1999-14080.PMID 10232067.S2CID 260280876.
^Higashiyama K, Takeuchi Y, Yamauchi T, Imai S, Kamei J, Yajima Y, et al. (May 2005)."Implication of the descending dynorphinergic neuron projecting to the spinal cord in the (+)-matrine- and (+)-allomatrine-induced antinociceptive effects".Biological & Pharmaceutical Bulletin.28 (5):845–848.doi:10.1248/bpb.28.845.PMID 15863891.
^Ma L, Wen S, Zhan Y, He Y, Liu X, Jiang J (February 2008). "Anticancer effects of the Chinese medicine matrine on murine hepatocellular carcinoma cells".Planta Medica.74 (3):245–251.Bibcode:2008PlMed..74..245M.doi:10.1055/s-2008-1034304.PMID 18283616.S2CID 260282269.
^Mao L, Henderson G (June 2007). "Antifeedant activity and acute and residual toxicity of alkaloids from Sophora flavescens (leguminosae) against formosan subterranean termites (Isoptera: Rhinotermitidae)".Journal of Economic Entomology.100 (3):866–870.doi:10.1093/jee/100.3.866.PMID 17598549.
^Matsuda K, Yamada K, Kimura M, Hamada M (1991). "Nematicidal activity of matrine and its derivatives against pine wood nematodes".Journal of Agricultural and Food Chemistry.39 (1):189–191.Bibcode:1991JAFC...39..189M.doi:10.1021/jf00001a038.
^Terada M, Sano M, Ishii AI, Kino H, Fukushima S, Noro T (February 1982)."[Studies on chemotherapy of parasitic helminths (IV). Effects of alkaloids from Sophora flavescens on the motility of parasitic helminths and isolated host tissues (author's transl)]".Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica.79 (2):105–111.doi:10.1254/fpj.79.105.PMID 7200047.
^Khan A, Shal B, Naveed M, Shah FA, Atiq A, Khan NU, et al. (May 2019). "Matrine ameliorates anxiety and depression-like behaviour by targeting hyperammonemia-induced neuroinflammation and oxidative stress in CCl4 model of liver injury".Neurotoxicology.72:38–50.Bibcode:2019NeuTx..72...38K.doi:10.1016/j.neuro.2019.02.002.PMID 30738807.S2CID 73445828.