Matrine

{{Short description|Tetracyclic plant alkaloid}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 426582743

| IUPAC_name = (1R,2R,9S,17S)-7,13-Diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadecan-6-one

| image = Matrine structure.svg

| tradename =

| pregnancy_category =

| legal_status = Unscheduled, sold OTC in US

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 519-02-8

| ATC_prefix = none

| PubChem = 91466

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 82591

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 204860

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = N390W430AC

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 6700

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C10774

| C=15 | H=24 | N=2 | O=1

| smiles = C1C[C@@H]2[C@H]3CCCN4[C@H]3[C@@H](CCC4)CN2C(=O)C1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZSBXGIUJOOQZMP-JLNYLFASSA-N

}}

Matrine is an alkaloid found in plants from the family Fabaceae. It has a variety of pharmacological effects, including in-vitro anti-cancer effects,{{cite journal | vauthors = Zhang Y, Zhang H, Yu P, Liu Q, Liu K, Duan H, Luan G, Yagasaki K, Zhang G | display-authors = 6 | title = Effects of matrine against the growth of human lung cancer and hepatoma cells as well as lung cancer cell migration | journal = Cytotechnology | volume = 59 | issue = 3 | pages = 191–200 | date = April 2009 | pmid = 19649719 | pmc = 2774570 | doi = 10.1007/s10616-009-9211-2 }} as well as κ-opioid and μ-opioid receptor agonism.{{cite journal | vauthors = Xiao P, Kubo H, Ohsawa M, Higashiyama K, Nagase H, Yan YN, Li JS, Kamei J, Ohmiya S | display-authors = 6 | title = kappa-Opioid receptor-mediated antinociceptive effects of stereoisomers and derivatives of (+)-matrine in mice | journal = Planta Medica | volume = 65 | issue = 3 | pages = 230–233 | date = April 1999 | pmid = 10232067 | doi = 10.1055/s-1999-14080 | bibcode = 1999PlMed..65..230X | s2cid = 260280876 }}{{cite journal | vauthors = Higashiyama K, Takeuchi Y, Yamauchi T, Imai S, Kamei J, Yajima Y, Narita M, Suzuki T | display-authors = 6 | title = Implication of the descending dynorphinergic neuron projecting to the spinal cord in the (+)-matrine- and (+)-allomatrine-induced antinociceptive effects | journal = Biological & Pharmaceutical Bulletin | volume = 28 | issue = 5 | pages = 845–848 | date = May 2005 | pmid = 15863891 | doi = 10.1248/bpb.28.845 | doi-access = free }}

Matrine possesses strong antitumor activities in vitro and in vivo. Inhibition of cell proliferation and induction of apoptosis are the likely mechanisms responsible for matrine's antitumor activities.{{cite journal | vauthors = Ma L, Wen S, Zhan Y, He Y, Liu X, Jiang J | title = Anticancer effects of the Chinese medicine matrine on murine hepatocellular carcinoma cells | journal = Planta Medica | volume = 74 | issue = 3 | pages = 245–251 | date = February 2008 | pmid = 18283616 | doi = 10.1055/s-2008-1034304 | bibcode = 2008PlMed..74..245M | s2cid = 260282269 }} Matrine can be commercially extracted from the traditional Chinese medical herb Sophora flavescens Ait.

Mu opioid agonism is associated with euphoria, while kappa opioid agonism is associated with dysphoria and psychotomimetic hallucinations (as seen in the kappa-agonist Salvinorin A). Both receptors are known to produce analgesia when activated.

Matrine and the related compound oxymatrine have a toxic effect against the formosan subterranean termite.{{cite journal | vauthors = Mao L, Henderson G | title = Antifeedant activity and acute and residual toxicity of alkaloids from Sophora flavescens (leguminosae) against formosan subterranean termites (Isoptera: Rhinotermitidae) | journal = Journal of Economic Entomology | volume = 100 | issue = 3 | pages = 866–870 | date = June 2007 | pmid = 17598549 | doi = 10.1093/jee/100.3.866 }} Additionally, it acts as a nematicide against the pine wood nematode which causes pine wilt,{{cite journal | doi = 10.1021/jf00001a038 | vauthors = Matsuda K, Yamada K, Kimura M, Hamada M | title = Nematicidal activity of matrine and its derivatives against pine wood nematodes | journal = Journal of Agricultural and Food Chemistry | year = 1991 | volume = 39 | issue = 1 | pages = 189–191 | bibcode = 1991JAFC...39..189M }} as well as pathogenic nematodes which target humans.{{cite journal | vauthors = Terada M, Sano M, Ishii AI, Kino H, Fukushima S, Noro T | title = [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)] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 79 | issue = 2 | pages = 105–111 | date = February 1982 | pmid = 7200047 | doi = 10.1254/fpj.79.105 | doi-access = free }}

Matrine alleviates neuro-inflammation and oxidative stress in the brain caused by acute liver injury, thus producing antianxiety and antidepression effects.{{cite journal | vauthors = Khan A, Shal B, Naveed M, Shah FA, Atiq A, Khan NU, Kim YS, Khan S | display-authors = 6 | title = Matrine ameliorates anxiety and depression-like behaviour by targeting hyperammonemia-induced neuroinflammation and oxidative stress in CCl4 model of liver injury | journal = Neurotoxicology | volume = 72 | pages = 38–50 | date = May 2019 | pmid = 30738807 | doi = 10.1016/j.neuro.2019.02.002 | bibcode = 2019NeuTx..72...38K | s2cid = 73445828 }}