{{Chembox | Watchedfields = changed | verifiedrevid = 403346640 | Name = | ImageFile = Hinokinin.png | ImageSize = | ImageAlt = | ImageFile1 = | ImageAlt1 = | PIN = (3''R'',4''R'')-3,4-Bis[(2''H''-1,3-benzodioxol-5-yl)methyl]oxolan-2-one | OtherNames = (3''R'',4''R'')-3,4-Bis(1,3-benzodioxol-5-ylmethyl)dihydro-2(3''H'')-furanone | Section1 = {{Chembox Identifiers | InChIKey = DDWGQGZPYDSYEL-LSDHHAIUSA-N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DDWGQGZPYDSYEL-LSDHHAIUSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 26543-89-5 | PubChem = 442879 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 242011 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 391188 | SMILES = C1C(C(C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5 | InChI = 1S/C20H18O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15H,5-6,9-11H2/t14-,15+/m0/s1 }} | Section2 = {{Chembox Properties | C=20| H=18 | O=6 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} | Section4 = | Section5 = | Section6 = }} '''Hinokinin''' is a dibenzylbutyrolactone lignan, derived from various species of plants.<ref>{{cite web | title=Hinokinin | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/Hinokinin | access-date=2025-04-25}}</ref> It is a potential antichagonistic agent.<ref name=":0">{{Cite journal|last1=Marcotullio|first1=Maria|last2=Pelosi|first2=Azzurra|last3=Curini|first3=Massimo|date=2014-09-17|title=Hinokinin, an Emerging Bioactive Lignan|journal=Molecules|volume=19|issue=9|pages=14862–14878|doi=10.3390/molecules190914862|pmid=25232707|pmc=6271885|issn=1420-3049|doi-access=free}}</ref> ''In vitro'', it has been shown to have potential neuroprotective effects<ref>{{Cite journal|last1=Timple|first1=Julie Marie V.|last2=Magalhães|first2=Lizandra Guidi|last3=Souza Rezende|first3=Karen Cristina|last4=Pereira|first4=Ana Carolina|last5=Cunha|first5=Wilson Roberto|last6=Andrade e Silva|first6=Márcio Luis|last7=Mortensen|first7=Ole Valente|last8=Fontana|first8=Andréia C. K.|date=2013-10-10|title=The Lignan (−)-Hinokinin Displays Modulatory Effects on Human Monoamine and GABA Transporter Activities|journal=Journal of Natural Products|volume=76|issue=10|pages=1889–1895|doi=10.1021/np400452n|pmid=24112084|issn=0163-3864}}</ref> as well as anti-inflammatory, anti-tumor, antiviral and antifungal properties.<ref>{{Cite journal|last1=Zhou|first1=Qi-Long|last2=Wang|first2=Hui-Jing|last3=Tang|first3=Pei|last4=Song|first4=Hao|last5=Qin|first5=Yong|date=October 2015|title=Total Synthesis of Lignan Lactone (–)-Hinokinin|journal=Natural Products and Bioprospecting|volume=5|issue=5|pages=255–261|doi=10.1007/s13659-015-0073-3|pmid=26458924|pmc=4607678|issn=2192-2195|doi-access=free}}</ref> Historically, it was isolated, for the first time, by Yoshiki and Ishiguro in 1933 from hinoki wood.<ref>{{Cite journal|last1=Yoshiki|first1=Y.|last2=Ishiguro|first2=T.|date=1933|title=Ueber die kristallisierten Bestandteile des Hinokiöls|journal=Yakugaku Zasshi|volume=53|issue=2|pages=73–151|doi=10.1248/yakushi1881.53.2_73|issn=0031-6903|doi-access=free}}</ref>
==Characteristics== Hinokinin is a colourless crystalline compound.<ref>{{cite journal | last=Marcotullio | first=Maria | last2=Pelosi | first2=Azzurra | last3=Curini | first3=Massimo | title=Hinokinin, an Emerging Bioactive Lignan | journal=Molecules | publisher=MDPI AG | volume=19 | issue=9 | date=2014-09-17 | issn=1420-3049 | doi=10.3390/molecules190914862 | doi-access=free | pages=14862–14878| pmc=6271885 }}</ref> It can be isolated from various species of ''Chamaecyparis'', ''Zanthoxylum'', ''Phyllanthus'', ''Aristolochia'', ''Piper'', ''Virola'', ''Linum'' and ''Bursera''. It is also synthesised from pinoresinol.<ref name=":0" />
==Actions as a bioactive compound== Hinokinin has shown to induce apoptosis and promote antitumor actions on various cancer cell lines ''in vitro''.<ref>{{Cite journal|last1=Cao|first1=Xue-li|last2=Xu|first2=Jing|last3=Bai|first3=Ge|last4=Zhang|first4=Hong|last5=Liu|first5=Yan|last6=Xiang|first6=Jun-feng|last7=Tang|first7=Ya-lin|date=June 2013|title=Isolation of anti-tumor compounds from the stem bark of Zanthoxylum ailanthoides Sieb. & Zucc. by silica gel column and counter-current chromatography|journal=Journal of Chromatography B|volume=929|pages=6–10|doi=10.1016/j.jchromb.2013.04.006|pmid=23660246|issn=1570-0232}}</ref>
Hinokinin has been shown to inhibit the generation of superoxide molecules by neutrophils and also decreases elastase secretion from neutrophils.<ref>{{Cite journal|last1=Chen|first1=JJ|last2=Chung|first2=CY|last3=Hwang|first3=TL|last4=Chen|first4=JF|date=July 2009|title=Amides and Benzenoids from Zanthoxylum ailanthoides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils|journal=Planta Medica|volume=75|issue=9|doi=10.1055/s-0029-1234991|issn=0032-0943}}</ref> It has also shown to reduce LPS induced nitric oxide production from macrophages.The anti-inflammatory property of hinokinin is mediated by the NF-''kB'' signalling mechanism.<ref>{{Cite journal|last1=Desai|first1=Dattatraya C.|last2=Jacob|first2=Jeenu|last3=Almeida|first3=Asha|last4=Kshirsagar|first4=Rajendra|last5=Manju|first5=S.L.|date=2014-05-23|title=Isolation, structural elucidation and anti-inflammatory activity of astragalin, ( − )hinokinin, aristolactam I and aristolochic acids (I & II) fromAristolochia indica|journal=Natural Product Research|volume=28|issue=17|pages=1413–1417|doi=10.1080/14786419.2014.905563|pmid=24854204|s2cid=20632496|issn=1478-6419}}</ref>
Hinokinin has been shown to be an antitrypanosomal agent. Its use as a treatment for trypanosomiasis is still being researched.<ref>{{Cite journal|last1=Saraiva|first1=Juliana|last2=Lira|first2=Ana Amélia Moreira|last3=Esperandim|first3=Viviane Rodrigues|last4=da Silva Ferreira|first4=Daniele|last5=Ferraudo|first5=Antônio Sérgio|last6=Bastos|first6=Jairo Kenupp|last7=e Silva|first7=Márcio Luís Andrade|last8=de Gaitani|first8=Cristiane Masetto|last9=de Albuquerque|first9=Sérgio|last10=Marchetti|first10=Juliana Maldonado|date=2010-01-28|title=(−)−Hinokinin-loaded poly(<small>D</small>,<small>L</small>-lactide-co-glycolide) microparticles for Chagas disease|journal=Parasitology Research|volume=106|issue=3|pages=703–708|doi=10.1007/s00436-010-1725-1|pmid=20107838|s2cid=31990739|issn=0932-0113}}</ref>
It has shown significant antiviral activity against human hepatitis B virus, HIV and SARS-CoV.<ref>{{Cite journal|last1=Wen|first1=Chih-Chun|last2=Kuo|first2=Yueh-Hsiung|last3=Jan|first3=Jia-Tsrong|last4=Liang|first4=Po-Huang|last5=Wang|first5=Sheng-Yang|last6=Liu|first6=Hong-Gi|last7=Lee|first7=Ching-Kuo|last8=Chang|first8=Shang-Tzen|last9=Kuo|first9=Chih-Jung|last10=Lee|first10=Shoei-Sheng|last11=Hou|first11=Chia-Chung|date=August 2007|title=Specific Plant Terpenoids and Lignoids Possess Potent Antiviral Activities against Severe Acute Respiratory Syndrome Coronavirus|journal=Journal of Medicinal Chemistry|volume=50|issue=17|pages=4087–4095|doi=10.1021/jm070295s|pmid=17663539|issn=0022-2623|url=http://ntur.lib.ntu.edu.tw/bitstream/246246/162827/1/05.pdf }}</ref>
==See also== * Cubebin
==References== {{Reflist}}
Category:Lignans Category:Antiviral drugs Category:Severe acute respiratory syndrome Category:Anti-inflammatory agents Category:Antifungals Category:Benzodioxoles Category:Furanones Category:Tree-derived bioactive compounds