Hinokinin (BioDeep_00000395956)

Main id: BioDeep_00000004298

 

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


(3R,4R)-3,4-bis(benzo(d)(1,3)dioxol-5-ylmethyl)dihydrofuran-2(3H)-one

化学式: C20H18O6 (354.1103328)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(C(=O)O1)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
InChI: 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

描述信息

Hinokinin is a lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer). It has a role as a trypanocidal drug. It is a lignan, a gamma-lactone and a member of benzodioxoles.
Hinokinin is a natural product found in Piper nigrum, Chamaecyparis obtusa, and other organisms with data available.
A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).
Hinokinin (Compound 1) is a compound isolated from the stems of Hypoestes aristate. Hinokinin exhibits moderate activity of HIV-1 protease enzyme[1].
Hinokinin (Compound 1) is a compound isolated from the stems of Hypoestes aristate. Hinokinin exhibits moderate activity of HIV-1 protease enzyme[1].

同义名列表

16 个代谢物同义名

(3R,4R)-3,4-bis(benzo(d)(1,3)dioxol-5-ylmethyl)dihydrofuran-2(3H)-one; (3R,4R)-3,4-Bis(benzo[d][1,3]dioxol-5-ylmethyl)dihydrofuran-2(3H)-one; 2(3H)-Furanone, 3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydro-, (3R,4R)-; (3R-trans)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-one; (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)dihydrofuran-2(3H)-one; (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-one; (2r,3r)-2,3-di-(3,4-methylenedioxybenzyl)-butyrolactone; 3,4-Bis[(2H-1,3-benzodioxol-5-yl)methyl]oxolan-2-one; (-)-hinoquinin; (-)-hinokinin; hinoquinin; Hinokinin; (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)-2-tetrahydrofuranone; (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-one; 26543-89-5; C10627



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • hinokinin biosynthesis: (-)-matairesinol + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ (-)-pluviatolide + H2O + an oxidized [NADPH-hemoprotein reductase]

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • hinokinin biosynthesis: (-)-matairesinol + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ (-)-pluviatolide + H2O + an oxidized [NADPH-hemoprotein reductase]

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Qitong Lu, Rui Zheng, Pengcheng Zhu, Jinhui Bian, Zhiyong Liu, Junjie Du. Hinokinin alleviates high fat diet/streptozotocin-induced cardiac injury in mice through modulation in oxidative stress, inflammation and apoptosis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111361. doi: 10.1016/j.biopha.2021.111361. [PMID: 33761596]
  • Tshifhiwa Ramabulana, Luki-Marié Scheepers, Thirshen Moodley, Vinesh J Maharaj, André Stander, Ntombenhle Gama, Daneel Ferreira, Molahlehi S Sonopo, Mamoalosi A Selepe. Bioactive Lignans from Hypoestes aristata. Journal of natural products. 2020 08; 83(8):2483-2489. doi: 10.1021/acs.jnatprod.0c00443. [PMID: 32786879]
  • Rosa Mariana Montiel-Ruiz, Marcos Córdova-de la Cruz, Manasés González-Cortázar, Alejandro Zamilpa, Abraham Gómez-Rivera, Ricardo López-Rodríguez, Carlos Ernesto Lobato-García, Ever A Blé-González. Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061454. [PMID: 32213823]
  • Matheus Souza de Paula Carlis, Aline Féboli, Antonio Carlos de Laurentiz, Rosemeire da Silva Filardi, Anna Helena Prizantelli de Oliveira, Márcio Luis Andrade E Silva, Luciano Alves Dos Anjos, Lizandra Guidi Magalhães, Rosangela da Silva de Laurentiz. In vitro anthelmintic activity of the crude hydroalcoholic extract of Piper cubeba fruits and isolated natural products against gastrointestinal nematodes in sheep. Veterinary parasitology. 2019 Nov; 275(?):108932. doi: 10.1016/j.vetpar.2019.108932. [PMID: 31600614]
  • Morina Adfa, Rizki Rahmad, Masayuki Ninomiya, Salprima Yudha S, Kaori Tanaka, Mamoru Koketsu. Antileukemic activity of lignans and phenylpropanoids of Cinnamomum parthenoxylon. Bioorganic & medicinal chemistry letters. 2016 Feb; 26(3):761-764. doi: 10.1016/j.bmcl.2015.12.096. [PMID: 26774581]
  • Viola Müller, Christa Lankes, Andreas Albert, J Barbro Winkler, Benno F Zimmermann, Georg Noga, Mauricio Hunsche. Concentration of hinokinin, phenolic acids and flavonols in leaves and stems of Hydrocotyle leucocephala is differently influenced by PAR and ecologically relevant UV-B level. Journal of plant physiology. 2015 Jan; 173(?):105-15. doi: 10.1016/j.jplph.2014.09.003. [PMID: 25462084]
  • Maria Carla Marcotullio, Azzurra Pelosi, Massimo Curini. Hinokinin, an emerging bioactive lignan. Molecules (Basel, Switzerland). 2014 Sep; 19(9):14862-78. doi: 10.3390/molecules190914862. [PMID: 25232707]
  • Julie Marie V Timple, Lizandra Guidi Magalhães, Karen Cristina Souza Rezende, Ana Carolina Pereira, Wilson Roberto Cunha, Márcio Luis Andrade e Silva, Ole Valente Mortensen, Andréia C K Fontana. The lignan (-)-hinokinin displays modulatory effects on human monoamine and GABA transporter activities. Journal of natural products. 2013 Oct; 76(10):1889-95. doi: 10.1021/np400452n. [PMID: 24112084]
  • Xue-Li Cao, Jing Xu, Ge Bai, Hong Zhang, Yan Liu, Jun-Feng Xiang, Ya-Lin Tang. 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, Analytical technologies in the biomedical and life sciences. 2013 Jun; 929(?):6-10. doi: 10.1016/j.jchromb.2013.04.006. [PMID: 23660246]
  • Flávia Aparecida Resende, Lilian Cristina Barbosa, Denise Crispim Tavares, Mariana Santoro de Camargo, Karen Cristina de Souza Rezende, Márcio Luis de Andrade E Silva, Eliana Aparecida Varanda. Mutagenicity and antimutagenicity of (-)-hinokinin a trypanosomicidal compound measured by Salmonella microsome and comet assays. BMC complementary and alternative medicine. 2012 Oct; 12(?):203. doi: 10.1186/1472-6882-12-203. [PMID: 23114276]
  • Tayyab A Mansoor, Rita M Ramalho, Cecília M P Rodrigues, Maria-José U Ferreira. Dibenzylbutane- and butyrolactone-type lignans as apoptosis inducers in human hepatoma HuH-7 cells. Phytotherapy research : PTR. 2012 May; 26(5):692-6. doi: 10.1002/ptr.3629. [PMID: 22002659]
  • Zahra A Amin, Mehmet Bilgen, Mohammed A Alshawsh, Hapipah M Ali, A Hamid A Hadi, Mahmood A Abdulla. Protective Role of Phyllanthus niruri Extract against Thioacetamide-Induced Liver Cirrhosis in Rat Model. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):241583. doi: 10.1155/2012/241583. [PMID: 22649471]
  • Patrícia Sartorelli, Camila Salomone Carvalho, Juliana Quero Reimão, Harri Lorenzi, André Gustavo Tempone. Antitrypanosomal activity of a diterpene and lignans isolated from Aristolochia cymbifera. Planta medica. 2010 Sep; 76(13):1454-6. doi: 10.1055/s-0029-1240952. [PMID: 20301059]
  • Rozália Pusztai, Marta Abrantes, Julianna Serly, Julia Sherly, Noélia Duarte, Joseph Molnar, Maria-José U Ferreira. Antitumor-promoting activity of lignans: inhibition of human cytomegalovirus IE gene expression. Anticancer research. 2010 Feb; 30(2):451-4. doi: ". [PMID: 20332453]
  • Tzong-Huei Lee, Yuan-Hsiang Chiang, Chin-Hui Chen, Pi-Yu Chen, Ching-Kuo Lee. A new flavonol galloylrhamnoside and a new lignan glucoside from the leaves of Koelreuteria henryi Dummer. Journal of natural medicines. 2009 Apr; 63(2):209-14. doi: 10.1007/s11418-009-0314-z. [PMID: 19184275]
  • Wen Zhang, Sheng-An Tang, Hong-Quan Duan. [Studies on chemical constituents of rhizome of Buddleia davidii]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Apr; 32(4):515-7. doi: ". [PMID: 19645234]
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  • Jih-Jung Chen, Ching-Yi Chung, Tsong-Long Hwang, Jinn-Fen Chen. Amides and benzenoids from Zanthoxylum ailanthoides with inhibitory activity on superoxide generation and elastase release by neutrophils. Journal of natural products. 2009 Jan; 72(1):107-11. doi: 10.1021/np800689b. [PMID: 19128011]
  • Marta Abrantes, Tânia Mil-Homens, Noélia Duarte, Dinora Lopes, Pedro Cravo, Maria do Madureira, Maria-José U Ferreira. Antiplasmodial activity of lignans and extracts from Pycnanthus angolensis. Planta medica. 2008 Sep; 74(11):1408-12. doi: 10.1055/s-2008-1081317. [PMID: 18671202]
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