Hinokinin Explained

Hinokinin is a dibenzylbutyrolactone lignan, derived from various species of plants. It is a potential antichagonistic agent.[1] In vitro, it has been shown to have potential neuroprotective effects[2] as well as anti-inflammatory, anti-tumor, antiviral and antifungal properties.[3]

Hinokinin was isolated for the first time by Yoshiki and Ishiguro in 1933 from hinoki wood.[4]

Chemical properties

Hinokinin is a colourless crystalline compound.

It can be isolated from various species of Chamaecyparis, Zanthoxylum, Phyllanthus, Aristolochia, Piper, Virola, Linum and Bursera. It is also synthesised from pinoresinol.

Biological effects

Cytotoxic actions

Hinokinin has shown to induce apoptosis and promote antitumor actions on various cancer cell lines in vitro.[5]

Anti-inflammatory actions

Hinokinin has been shown to inhibit the generation of superoxide molecules by neutrophils and also decreases elastase secretion from neutrophils.[6] 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.[7]

Anti-parasitic actions

Hinokinin has been shown to be an antitrypanosomal agent. Its use as a treatment for trypanosomiasis is still being researched.[8]

Anti-viral actions

It has shown significant antiviral activity against human hepatitis B virus, HIV and SARS-CoV.[9]

See also

Notes and References

  1. Marcotullio. Maria. Pelosi. Azzurra. Curini. Massimo. 2014-09-17. Hinokinin, an Emerging Bioactive Lignan. Molecules. 19. 9. 14862–14878. 10.3390/molecules190914862. 25232707. 6271885. 1420-3049. free.
  2. Timple. Julie Marie V.. Magalhães. Lizandra Guidi. Souza Rezende. Karen Cristina. Pereira. Ana Carolina. Cunha. Wilson Roberto. Andrade e Silva. Márcio Luis. Mortensen. Ole Valente. Fontana. Andréia C. K.. 2013-10-10. The Lignan (−)-Hinokinin Displays Modulatory Effects on Human Monoamine and GABA Transporter Activities. Journal of Natural Products. 76. 10. 1889–1895. 10.1021/np400452n. 24112084. 0163-3864.
  3. Zhou. Qi-Long. Wang. Hui-Jing. Tang. Pei. Song. Hao. Qin. Yong. October 2015. Total Synthesis of Lignan Lactone (–)-Hinokinin. Natural Products and Bioprospecting. 5. 5. 255–261. 10.1007/s13659-015-0073-3. 26458924. 4607678. 2192-2195. free.
  4. Yoshiki. Y.. Ishiguro. T.. 1933. Ueber die kristallisierten Bestandteile des Hinokiöls. Yakugaku Zasshi. 53. 2. 73–151. 10.1248/yakushi1881.53.2_73. 0031-6903. free.
  5. Cao. Xue-li. Xu. Jing. Bai. Ge. Zhang. Hong. Liu. Yan. Xiang. Jun-feng. Tang. Ya-lin. June 2013. Isolation of anti-tumor compounds from the stem bark of Zanthoxylum ailanthoides Sieb. & Zucc. by silica gel column and counter-current chromatography. Journal of Chromatography B. 929. 6–10. 10.1016/j.jchromb.2013.04.006. 23660246. 1570-0232.
  6. Chen. JJ. Chung. CY. Hwang. TL. Chen. JF. July 2009. Amides and Benzenoids from Zanthoxylum ailanthoides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils. Planta Medica. 75. 9. 10.1055/s-0029-1234991. 0032-0943.
  7. Desai. Dattatraya C.. Jacob. Jeenu. Almeida. Asha. Kshirsagar. Rajendra. Manju. S.L.. 2014-05-23. Isolation, structural elucidation and anti-inflammatory activity of astragalin, (−)hinokinin, aristolactam I and aristolochic acids (I & II) fromAristolochia indica. Natural Product Research. 28. 17. 1413–1417. 10.1080/14786419.2014.905563. 24854204. 20632496. 1478-6419.
  8. Saraiva. Juliana. Lira. Ana Amélia Moreira. Esperandim. Viviane Rodrigues. da Silva Ferreira. Daniele. Ferraudo. Antônio Sérgio. Bastos. Jairo Kenupp. e Silva. Márcio Luís Andrade. de Gaitani. Cristiane Masetto. de Albuquerque. Sérgio. Marchetti. Juliana Maldonado. 2010-01-28. (−)−Hinokinin-loaded poly(D,L-lactide-co-glycolide) microparticles for Chagas disease. Parasitology Research. 106. 3. 703–708. 10.1007/s00436-010-1725-1. 20107838. 31990739. 0932-0113.
  9. Wen. Chih-Chun. Kuo. Yueh-Hsiung. Jan. Jia-Tsrong. Liang. Po-Huang. Wang. Sheng-Yang. Liu. Hong-Gi. Lee. Ching-Kuo. Chang. Shang-Tzen. Kuo. Chih-Jung. Lee. Shoei-Sheng. Hou. Chia-Chung. August 2007. Specific Plant Terpenoids and Lignoids Possess Potent Antiviral Activities against Severe Acute Respiratory Syndrome Coronavirus. Journal of Medicinal Chemistry. 50. 17. 4087–4095. 10.1021/jm070295s. 17663539. 0022-2623.

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