(-)-lariciresinol (BioDeep_00000015395)

 

Secondary id: BioDeep_00000180394

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(-)-lariciresinol

化学式: C20H24O6 (360.1573)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 13.06%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O
InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m1/s1

描述信息

A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2R,3S,4S-diastereomer).

同义名列表

1 个代谢物同义名

(-)-lariciresinol



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

172 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(170)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

73 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。

亚细胞结构定位 关联基因列表


文献列表

  • Jingxian Feng, Yuan Yao, Yuqi Qiao, Xueqi Ma, Zongtai Wu, Yonghao Duan, Peng Di, Wansheng Chen, Ying Xiao. Effect of pinoresinol-lariciresinol reductases on biosynthesis of lignans with substrate selectivity in Schisandra chinensis. Phytochemistry. 2024 May; 221(?):114053. doi: 10.1016/j.phytochem.2024.114053. [PMID: 38479587]
  • Mona Soltani, Reza Fotovat, Mohsen Sharifi, Najmeh Ahmadian Chashmi, Mehrdad Behmanesh. In Vitro Comparative Study on Antineoplastic Effects of Pinoresinol and Lariciresinol on Healthy Cells and Breast Cancer-Derived Human Cells. Iranian journal of medical sciences. 2024 Jan; 49(1):30-39. doi: 10.30476/ijms.2023.94805.2611. [PMID: 38322161]
  • Sikiru Olaitan Balogun, Amilcar Sabino Damazo, Eduarda Pavan, Fabiana de Freitas Figueiredo, Karuppusamy Arunachalam, Leonardo M de Souza Mesquita, Wagner Vilegas, Domingos Tabajara de Oliveira Martins. Evidence for the Involvement of Cytokines Modulation and Prokinetic Properties in Gastric Ulcer Healing Effects of Helicteres sacarolha A. St.-Hil. A. Juss. Chemistry & biodiversity. 2022 Dec; 19(12):e202200322. doi: 10.1002/cbdv.202200322. [PMID: 36269048]
  • Joanda P R E Silva, Laiane C O Pereira, Lucas S Abreu, Francisca S V Lins, Thalisson A de Souza, Renan F do Espírito-Santo, Renata P C Barros, Cristiane F Villarreal, José I M de Melo, Marcus T Scotti, Vicente C de O Costa, Lucas H Martorano, Fernando M Dos Santos, Raimundo Braz Filho, Marcelo S da Silva, Josean F Tavares. Targeted Isolation of Anti-inflammatory Lignans from Justicia aequilabris by Molecular Networking Approach. Journal of natural products. 2022 09; 85(9):2184-2191. doi: 10.1021/acs.jnatprod.2c00478. [PMID: 35998343]
  • Lu Yang, Huiqiang Wang, Haiyan Yan, Kun Wang, Shuo Wu, Yuhuan Li. (-)-Lariciresinol Isolated from the Roots of Isatis indigotica Fortune ex Lindl. Inhibits Hepatitis B Virus by Regulating Viral Transcription. Molecules (Basel, Switzerland). 2022 May; 27(10):. doi: 10.3390/molecules27103223. [PMID: 35630700]
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  • Bushra Asad, Taimoor Khan, Faiza Zareen Gul, Muhammad Asad Ullah, Samantha Drouet, Sara Mikac, Laurine Garros, Manon Ferrier, Shankhamala Bose, Thibaut Munsch, Duangjai Tungmunnithum, Arnaud Lanoue, Nathalie Giglioli-Guivarc'h, Christophe Hano, Bilal Haider Abbasi. Scarlet Flax Linum grandiflorum (L.) In Vitro Cultures as a New Source of Antioxidant and Anti-Inflammatory Lignans. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154511. [PMID: 34361665]
  • Ying Xiao, Kai Shao, Jingwen Zhou, Lian Wang, Xueqi Ma, Di Wu, Yingbo Yang, Junfeng Chen, Jingxian Feng, Shi Qiu, Zongyou Lv, Lei Zhang, Peng Zhang, Wansheng Chen. Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases. Nature communications. 2021 05; 12(1):2828. doi: 10.1038/s41467-021-23095-y. [PMID: 33990581]
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  • Yingling Wu, Dawei Xing, Guoliang Ma, Xinlong Dai, Liping Gao, Tao Xia. A variable loop involved in the substrate selectivity of pinoresinol/lariciresinol reductase from Camellia sinensis. Phytochemistry. 2019 Jun; 162(?):1-9. doi: 10.1016/j.phytochem.2019.02.003. [PMID: 30844490]
  • Lucija Markulin, Cyrielle Corbin, Sullivan Renouard, Samantha Drouet, Laurent Gutierrez, Ivan Mateljak, Daniel Auguin, Christophe Hano, Elisabeth Fuss, Eric Lainé. Pinoresinol-lariciresinol reductases, key to the lignan synthesis in plants. Planta. 2019 Jun; 249(6):1695-1714. doi: 10.1007/s00425-019-03137-y. [PMID: 30895445]
  • Yun-Seo Kil, Seong Min Kim, Unwoo Kang, Hae Young Chung, Eun Kyoung Seo. Peroxynitrite-Scavenging Glycosides from the Stem Bark of Catalpa ovata. Journal of natural products. 2017 08; 80(8):2240-2251. doi: 10.1021/acs.jnatprod.7b00139. [PMID: 28787158]
  • Beixian Zhou, Jing Li, Xiaoli Liang, Zifeng Yang, Zhihong Jiang. Transcriptome profiling of influenza A virus-infected lung epithelial (A549) cells with lariciresinol-4-β-D-glucopyranoside treatment. PloS one. 2017; 12(3):e0173058. doi: 10.1371/journal.pone.0173058. [PMID: 28273165]
  • Zhan-Jun Ma, Xue-Xi Wang, Gang Su, Jing-Jing Yang, Ya-Juan Zhu, You-Wei Wu, Jing Li, Li Lu, Long Zeng, Hai-Xia Pei. Proteomic analysis of apoptosis induction by lariciresinol in human HepG2 cells. Chemico-biological interactions. 2016 Aug; 256(?):209-19. doi: 10.1016/j.cbi.2016.07.011. [PMID: 27417256]
  • Yue-ping Jiang, Yu-feng Liu, Qing-lan Guo, Cheng-bo Xu, Sheng Lin, Cheng-gen Zhu, Yong-chun Yang, Jian-gong Shi. [Lignanoids from an aqueous extract of the roots of Codonopsis pilosula]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 04; 51(4):616-25. doi: . [PMID: 29860746]
  • Nuoendagula, Naofumi Kamimura, Tetsuya Mori, Ryo Nakabayashi, Yukiko Tsuji, Shojiro Hishiyama, Kazuki Saito, Eiji Masai, Shinya Kajita. Expression and functional analyses of a putative phenylcoumaran benzylic ether reductase in Arabidopsis thaliana. Plant cell reports. 2016 Mar; 35(3):513-26. doi: 10.1007/s00299-015-1899-1. [PMID: 26601823]
  • Ying Xiao, Qian Ji, Shouhong Gao, Hexin Tan, Ruibing Chen, Qing Li, Junfeng Chen, Yingbo Yang, Lei Zhang, Zhengtao Wang, Wansheng Chen, Zhibi Hu. Combined transcriptome and metabolite profiling reveals that IiPLR1 plays an important role in lariciresinol accumulation in Isatis indigotica. Journal of experimental botany. 2015 Oct; 66(20):6259-71. doi: 10.1093/jxb/erv333. [PMID: 26163698]
  • Ya-mei Zhang, Pu-zhao Zhang. [Lignans from Stem Bark of Styrax perkinsiae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1202-5. doi: ". [PMID: 26762060]
  • Sullivan Renouard, Marie-Aude Tribalatc, Frederic Lamblin, Gaëlle Mongelard, Ophélie Fliniaux, Cyrielle Corbin, Djurdjica Marosevic, Serge Pilard, Hervé Demailly, Laurent Gutierrez, Christophe Hano, François Mesnard, Eric Lainé. RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: consequences on lignans and neolignans accumulation. Journal of plant physiology. 2014 Sep; 171(15):1372-7. doi: 10.1016/j.jplph.2014.06.005. [PMID: 25046758]
  • Eliana Spilioti, Bjarne Holmbom, Athanasios G Papavassiliou, Paraskevi Moutsatsou. Lignans 7-hydroxymatairesinol and 7-hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells. Molecular nutrition & food research. 2014 Apr; 58(4):749-59. doi: 10.1002/mnfr.201300318. [PMID: 24311533]
  • Oue-artorn Rajachan, Somdej Kanokmedhakul, Phitak Nasomjai, Kwanjai Kanokmedhakul. Chemical constituents and biological activities from roots of Enkleia siamensis. Natural product research. 2014; 28(4):268-70. doi: 10.1080/14786419.2013.838241. [PMID: 24047498]
  • Satoshi Yamauchi, Mitsuko Kumamoto, Yuki Ochi, Hisashi Nishiwaki, Yoshihiro Shuto. Structure-plant growth inhibitory activity relationship of lariciresinol. Journal of agricultural and food chemistry. 2013 Dec; 61(50):12297-306. doi: 10.1021/jf404292w. [PMID: 24274795]
  • Laila Meija, Paivi Söderholm, Adile Samaletdin, Gita Ignace, Inese Siksna, Rafaels Joffe, Aivars Lejnieks, Vilnis Lietuvietis, Indrikis Krams, Herman Adlercreutz. Dietary intake and major sources of plant lignans in Latvian men and women. International journal of food sciences and nutrition. 2013 Aug; 64(5):535-43. doi: 10.3109/09637486.2013.765835. [PMID: 23373826]
  • Y Fukuhara, N Kamimura, M Nakajima, S Hishiyama, H Hara, D Kasai, Y Tsuji, S Narita-Yamada, S Nakamura, Y Katano, N Fujita, Y Katayama, M Fukuda, S Kajita, E Masai. Discovery of pinoresinol reductase genes in sphingomonads. Enzyme and microbial technology. 2013 Jan; 52(1):38-43. doi: 10.1016/j.enzmictec.2012.10.004. [PMID: 23199737]
  • Alexandrine During, Céline Debouche, Thomas Raas, Yvan Larondelle. Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells. The Journal of nutrition. 2012 Oct; 142(10):1798-805. doi: 10.3945/jn.112.162453. [PMID: 22955517]
  • Liang Chen, Lei Wang, Qingwen Zhang, Shengyuan Zhang, Wencai Ye. [Non-alkaloid chemical constituents from Coptis chinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(9):1241-4. doi: 10.4268/cjcmm20120915. [PMID: 22803368]
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  • Sullivan Renouard, Cyrielle Corbin, Tatiana Lopez, Josiane Montguillon, Laurent Gutierrez, Frédéric Lamblin, Eric Lainé, Christophe Hano. Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds. Planta. 2012 Jan; 235(1):85-98. doi: 10.1007/s00425-011-1492-y. [PMID: 21837520]
  • Hisashi Nishiwaki, Mitsuko Kumamoto, Yoshihiro Shuto, Satoshi Yamauchi. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities. Journal of agricultural and food chemistry. 2011 Dec; 59(24):13089-95. doi: 10.1021/jf203222w. [PMID: 22066904]
  • Bomi Hwang, Jaeyong Cho, In-sok Hwang, Hong-Guang Jin, Eun-Rhan Woo, Dong Gun Lee. Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans. Biochemical and biophysical research communications. 2011 Jul; 410(3):489-93. doi: 10.1016/j.bbrc.2011.06.004. [PMID: 21679690]
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  • Ji-feng Liu, Xue-mei Zhang, Duo-qing Xue, Zhi-yong Jiang, Qiong Gu, Ji-jun Chen. [Studies on chemical constituents from leaves of Isatis indigotica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Dec; 31(23):1961-5. doi: . [PMID: 17348190]
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  • Heidi Schwartz, Gerhard Sontag. Determination of secoisolariciresinol, lariciresinol and isolariciresinol in plant foods by high performance liquid chromatography coupled with coulometric electrode array detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jul; 838(2):78-85. doi: 10.1016/j.jchromb.2006.03.058. [PMID: 16750660]
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