Forsythin (BioDeep_00001103624)

Main id: BioDeep_00000000149

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2S,3R,4S,5S,6R)-2-[4-[(3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

化学式: C27H34O11 (534.2101)
中文名称: 连翘苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC(C=C1[C@@H]2[C@](CO[C@H]3C4=CC(OC)=C(OC)C=C4)([H])[C@]3([H])CO2)=C(C=C1)O[C@@H]([C@@H]([C@@H](O)[C@@H]5O)O)O[C@@H]5CO
InChI: InChI=1S/C27H34O11/c1-32-17-6-4-13(8-19(17)33-2)25-15-11-36-26(16(15)12-35-25)14-5-7-18(20(9-14)34-3)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,15-16,21-31H,10-12H2,1-3H3/t15-,16-,21+,22+,23-,24+,25?,26+,27+/m0/s1

描述信息

Phillyrin is isolated from Forsythia suspensa Vahl (Oleaceae), has antibacterial and anti-inflammatory activities. Phillyrin has potential inductive effects on rat CYP1A2 and CYP2D1 activities, without affecting CYP2C11 and CYP3A1/2 activities[1]. Phillyrin has anti-influenza A virus activities[2].
Phillyrin is isolated from Forsythia suspensa Vahl (Oleaceae), has antibacterial and anti-inflammatory activities. Phillyrin has potential inductive effects on rat CYP1A2 and CYP2D1 activities, without affecting CYP2C11 and CYP3A1/2 activities[1]. Phillyrin has anti-influenza A virus activities[2].

同义名列表

4 个代谢物同义名

(2S,3R,4S,5S,6R)-2-[4-[(3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; Forsythin; Phillyrin; Forsythin



数据库引用编号

7 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

56 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

  • Hong-Yan Guo, Xiaoting Li, Xiao-Tong Sang, Zhe-Shan Quan, Qing-Kun Shen. Design and synthesis of forsythin derivatives as anti-inflammatory agents for acute lung injury. European journal of medicinal chemistry. 2024 Mar; 267(?):116223. doi: 10.1016/j.ejmech.2024.116223. [PMID: 38342013]
  • Shanyu Zhang, Fengzhi Sun, Jinlu Zhu, Jianhong Qi, Wenjing Wang, Ziming Liu, Wenqian Li, Chuanguo Liu, Xuehuan Liu, Nonghan Wang, Xinyu Song, Dan Zhang, Dongmei Qi, Xiaolong Wang. Phillyrin ameliorates influenza a virus-induced pulmonary inflammation by antagonizing CXCR2 and inhibiting NLRP3 inflammasome activation. Virology journal. 2023 Nov; 20(1):262. doi: 10.1186/s12985-023-02219-4. [PMID: 37957672]
  • Jing Li, Qiao Qin, Sheng-Hua Zha, Qing-Sheng Zhao, Hang Li, Lu-Peng Liu, Shou-Bu Hou, Bing Zhao. Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method. Molecules (Basel, Switzerland). 2022 Oct; 27(20):. doi: 10.3390/molecules27207055. [PMID: 36296648]
  • Wang Jun Yuan, Su Ping Zhang, Zhi Yin He, Yan Xia He, She Qi He, Li Jun Liu, Xin Sun, Qin Li. Comparative transcriptome analyses identify genes involved into the biosynthesis of forsythin and forsythoside A in Forsythia suspensa. Functional & integrative genomics. 2022 10; 22(5):731-741. doi: 10.1007/s10142-022-00887-z. [PMID: 35870023]
  • Chenyu Zhou, Mengya Lu, Jialei Cheng, Emelda Rosseleena Rohani, Hamizah Shahirah Hamezah, Rongchun Han, Xiaohui Tong. Review on the Pharmacological Properties of Phillyrin. Molecules (Basel, Switzerland). 2022 Jun; 27(12):. doi: 10.3390/molecules27123670. [PMID: 35744798]
  • Xin Guo, Pingping Cao, Xiongfeng Lian, Meng Hu, Jingyi Zhao, Wenjing Shen, Haili Wang, Hailong Yu, Yingzhu Chen. The neuroprotective effect of phillyrin in intracerebral hemorrhagic mice is produced by activation of the Nrf2 signaling pathway. European journal of pharmacology. 2021 Oct; 909(?):174439. doi: 10.1016/j.ejphar.2021.174439. [PMID: 34425100]
  • Lu-Lu Pan, Tao Chen, Min Hui, Shuo Wang, Li Fu, Cui-Yun Li, Hong Zhang, Yan-Hua Ding, Yong Yang, Da-Fang Zhong. Simultaneous determination of forsythin and its major metabolites in human plasma via liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2021 May; 198(?):113992. doi: 10.1016/j.jpba.2021.113992. [PMID: 33676168]
  • Sansei Nishibe, Kumiko Mitsui-Saitoh, Junichi Sakai, Takahiko Fujikawa. The Biological Effects of Forsythia Leaves Containing the Cyclic AMP Phosphodiesterase 4 Inhibitor Phillyrin. Molecules (Basel, Switzerland). 2021 Apr; 26(8):. doi: 10.3390/molecules26082362. [PMID: 33921630]
  • Zibin Lu, Huihui Cao, Dongyi Liu, Yuanru Zheng, Chunyang Tian, Shanhong Liu, Jingyu Quan, Lingzhu Shi, Junshan Liu, Linzhong Yu. Optimal combination of anti-inflammatory components from Chinese medicinal formula Liang-Ge-San. Journal of ethnopharmacology. 2021 Apr; 269(?):113747. doi: 10.1016/j.jep.2020.113747. [PMID: 33359185]
  • Qinhai Ma, Runfeng Li, Weiqi Pan, Wenbo Huang, Bin Liu, Yuqi Xie, Zhoulang Wang, Chufang Li, Haiming Jiang, Jicheng Huang, Yongxia Shi, Jun Dai, Kui Zheng, Xiaobo Li, Min Hui, Li Fu, Zifeng Yang. Phillyrin (KD-1) exerts anti-viral and anti-inflammatory activities against novel coronavirus (SARS-CoV-2) and human coronavirus 229E (HCoV-229E) by suppressing the nuclear factor kappa B (NF-κB) signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Nov; 78(?):153296. doi: 10.1016/j.phymed.2020.153296. [PMID: 32890913]
  • Qian Jiang, Jun Chen, Xiaobing Long, Xiaolong Yao, Xin Zou, Yiping Yang, Guangying Huang, Huaqiu Zhang. Phillyrin protects mice from traumatic brain injury by inhibiting the inflammation of microglia via PPARγ signaling pathway. International immunopharmacology. 2020 Feb; 79(?):106083. doi: 10.1016/j.intimp.2019.106083. [PMID: 31923823]
  • Xiaoqing Xu, Fatma S A Saadeldeen, Lanting Xu, Yingying Zhao, Jinfeng Wei, Hui-Min David Wang, Zhenhua Liu, Wenyi Kang. The Mechanism of Phillyrin from the Leaves of Forsythia suspensa for Improving Insulin Resistance. BioMed research international. 2019; 2019(?):3176483. doi: 10.1155/2019/3176483. [PMID: 31355254]
  • Xinsheng Fang, Shubo Gu, Zongyuan Jin, Mingqian Hao, Zhenzhen Yin, Jianhua Wang. Optimization of Ultrasonic-Assisted Simultaneous Extraction of Three Active Compounds from the Fruits of Forsythia suspensa and Comparison with Conventional Extraction Methods. Molecules (Basel, Switzerland). 2018 Aug; 23(9):. doi: 10.3390/molecules23092115. [PMID: 30142873]
  • Hong-Bo Xiao, Guo-Guang Sui, Xiang-Yang Lu. Phillyrin lowers body weight in obese mice via the modulation of PPAR/-ANGPTL 4 pathway. Obesity research & clinical practice. 2018 Jan; 12(Suppl 2):71-79. doi: 10.1016/j.orcp.2017.02.002. [PMID: 28320596]
  • Liling Yang, Xiangjun Zhou, Weijuan Huang, Qin Fang, Jianlan Hu, Linzhong Yu, Ning Ma, Wenqing Zhang. Protective Effect of Phillyrin on Lethal LPS-Induced Neutrophil Inflammation in Zebrafish. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2017; 43(5):2074-2087. doi: 10.1159/000484192. [PMID: 29059681]
  • Xin-Yan Qu, Qing-Jun Li, Hui-Min Zhang, Xiao-Juan Zhang, Peng-Hui Shi, Xiu-Juan Zhang, Jing Yang, Zhe Zhou, Sheng-Qi Wang. Protective effects of phillyrin against influenza A virus in vivo. Archives of pharmacal research. 2016 Jul; 39(7):998-1005. doi: 10.1007/s12272-016-0775-z. [PMID: 27323762]
  • Lei Zhang, Haiyu Zhao, Yang Liu, Honghuan Dong, Beiran Lv, Min Fang, Huihui Zhao. Metabolic routes along digestive system of licorice: multicomponent sequential metabolism method in rat. Biomedical chromatography : BMC. 2016 Jun; 30(6):902-12. doi: 10.1002/bmc.3626. [PMID: 26418123]
  • Hairong Wang, Xiaoxu Zhang, Peipei Jia, Yanfen Zhang, Siwen Tang, Hongtao Wang, Song Li, Xinluan Yu, Yingfei Li, Lantong Zhang. Metabolic profile of phillyrin in rats obtained by UPLC-Q-TOF-MS. Biomedical chromatography : BMC. 2016 Jun; 30(6):913-22. doi: 10.1002/bmc.3629. [PMID: 26425840]
  • Wei-ze Li, Ning Zhao, Ze Liang, Han-fang Kang, Jin-jie Li. [Effects of Forsythia suspensa Volatile Oil Loaded Nanomicellar on Transdermal and Transmucosal Drug Delivery of Phillyrin in Vitro]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jan; 39(1):134-7. doi: ". [PMID: 30080015]
  • Yun Luo, Guo-Wei Zhao, Xin-Li Liang, Jing Zhang, Xiao-Fei Zhang, Qin Zheng, Ming Yang, Zheng-Gen Liao. [Changes of specific chromatograms and contents of five components in Yinqiao powder decoctions during decocting process]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Jan; 41(1):60-64. doi: 10.4268/cjcmm20160112. [PMID: 28845641]
  • Jinping Jia, Fusheng Zhang, Zhenyu Li, Xuemei Qin, Liwei Zhang. Comparison of Fruits of Forsythia suspensa at Two Different Maturation Stages by NMR-Based Metabolomics. Molecules (Basel, Switzerland). 2015 May; 20(6):10065-81. doi: 10.3390/molecules200610065. [PMID: 26035103]
  • Chang Li, Zhi-Hong Yao, Zi-Fei Qin, Jin-Bo Zhang, Rui-Yuan Cao, Yi Dai, Xin-Sheng Yao. Isolation and identification of phase I metabolites of phillyrin in rats. Fitoterapia. 2014 Sep; 97(?):92-7. doi: 10.1016/j.fitote.2014.05.011. [PMID: 24879901]
  • Poren Kong, Linlin Zhang, Yuyu Guo, Yingli Lu, Dongping Lin. Phillyrin, a natural lignan, attenuates tumor necrosis factor α-mediated insulin resistance and lipolytic acceleration in 3T3-L1 adipocytes. Planta medica. 2014 Jul; 80(11):880-6. doi: 10.1055/s-0034-1368614. [PMID: 24995500]
  • Wei-ting Zhong, Yi-chun Wu, Xian-xing Xie, Xuan Zhou, Miao-miao Wei, Lanan-Wassy Soromou, Xin-xin Ci, Da-cheng Wang. Phillyrin attenuates LPS-induced pulmonary inflammation via suppression of MAPK and NF-κB activation in acute lung injury mice. Fitoterapia. 2013 Oct; 90(?):132-9. doi: 10.1016/j.fitote.2013.06.003. [PMID: 23751215]
  • Xinsheng Fang, Yingzi Wang, Jianhua Wang, Jin Zhang, Xin Wang. Microwave-assisted extraction followed by RP-HPLC for the simultaneous extraction and determination of forsythiaside A, rutin, and phillyrin in the fruits of Forsythia suspensa. Journal of separation science. 2013 Aug; 36(16):2672-9. doi: 10.1002/jssc.201300317. [PMID: 23913652]
  • Minh Truong Do, Hyung Gyun Kim, Jae Ho Choi, Tilak Khanal, Bong Hwan Park, Thu Phuong Tran, Yong Pil Hwang, Minkyun Na, Hye Gwang Jeong. Phillyrin attenuates high glucose-induced lipid accumulation in human HepG2 hepatocytes through the activation of LKB1/AMP-activated protein kinase-dependent signalling. Food chemistry. 2013 Jan; 136(2):415-25. doi: 10.1016/j.foodchem.2012.09.012. [PMID: 23122079]
  • Bing He, Shi-Yan Yang, Yan Zhang. [A new method of calibration and positioning in quantitative analysis of multicomponents by single marker]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 Dec; 47(12):1653-9. doi: . [PMID: 23460972]
  • Qingmiao Zhang, Xiying Wei, Jiawen Wang. Phillyrin produced by Colletotrichum gloeosporioides, an endophytic fungus isolated from Forsythia suspensa. Fitoterapia. 2012 Dec; 83(8):1500-5. doi: 10.1016/j.fitote.2012.08.017. [PMID: 22960349]
  • Chiara Beatrice Vicentini, Lorenzo Altieri, Stefano Manfredini. In search of Cinchona substitutes in nineteenth-century Italy. Pharmacy in history. 2012; 54(1):33-6. doi: ". [PMID: 24620481]
  • Jiqing Bai, Xiaoping Wang, Linlin Cao, Ning Zhang, Zhao Zhang. [Effect of habitat processing method on phillyrin and forsythiaside A of Forsythiae Fructus]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Dec; 36(23):3258-61. doi: . [PMID: 22393731]
  • Yun-xia Li, Cheng Peng, Liang-hong Ye, Ruo-Qi Zhang, Xue-hua Jiang. Investigation on the absorption of phillyrin and forsythiaside in rat digestive tract. European journal of drug metabolism and pharmacokinetics. 2011 Jun; 36(2):79-85. doi: 10.1007/s13318-011-0031-3. [PMID: 21547451]
  • Yun-Xia Li, Liang-Hong Ye, Xue-Hua Jiang, Cheng Peng. Assessment and modulation of phillyrin absorption by P-gp using Caco-2 cells and MDR1-MDCKII cells. European journal of drug metabolism and pharmacokinetics. 2011 Mar; 36(1):41-7. doi: 10.1007/s13318-011-0026-0. [PMID: 21336515]
  • En-Qin Xia, Xu-Xia Ai, Sheng-Ye Zang, Ting-Ting Guan, Xiang-Rong Xu, Hua-Bin Li. Ultrasound-assisted extraction of phillyrin from Forsythia suspensa. Ultrasonics sonochemistry. 2011 Mar; 18(2):549-52. doi: 10.1016/j.ultsonch.2010.09.015. [PMID: 20980187]
  • Fan-Lin Zeng, Zhi-Bin Shen, Xin Zhang. [Study on pharmacokinetics of phillyrin in Shuanghuanglian for injection]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Oct; 33(10):1602-5. doi: NULL. [PMID: 21355201]
  • Yang Cui, Qiao Wang, Xiaowei Shi, Xiaowei Zhang, Xiaona Sheng, Lantong Zhang. Simultaneous quantification of 14 bioactive constituents in Forsythia suspensa by liquid chromatography-electrospray ionisation-mass spectrometry. Phytochemical analysis : PCA. 2010 May; 21(3):253-60. doi: 10.1002/pca.1194. [PMID: 20151400]
  • Yonggang Xia, Bingyou Yang, Qiuhong Wang, Jun Liang, Youhe Wei, Hedan Yu, Qingbo Zhang, Haixue Kuang. Quantitative analysis and chromatographic fingerprinting for the quality evaluation of Forsythia suspensa extract by HPLC coupled with photodiode array detector. Journal of separation science. 2009 Dec; 32(23-24):4113-25. doi: 10.1002/jssc.200900488. [PMID: 19950349]
  • Yun-Xia Li, Cheng Peng, Ruo-Qi Zhang, Xue Li, Xue-Hua Jiang. Pharmacokinetics of phillyrin and forsythiaside following iv administration to Beagle dog. European journal of drug metabolism and pharmacokinetics. 2009 Apr; 34(2):79-83. doi: 10.1007/bf03191155. [PMID: 19645216]
  • Xiang-Lan Piao, Moon Hee Jang, Jian Cui, Xiangshu Piao. Lignans from the fruits of Forsythia suspensa. Bioorganic & medicinal chemistry letters. 2008 Mar; 18(6):1980-4. doi: 10.1016/j.bmcl.2008.01.115. [PMID: 18295482]
  • Wei-Jian Li, Xian-En Li, Jian-Jun Qi. [Studies on diversity of quality of Forsythia suspensa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Mar; 32(5):381-4. doi: ". [PMID: 17511138]
  • Hua-Bin Li, Feng Chen. Preparative isolation and purification of phillyrin from the medicinal plant Forsythia suspensa by high-speed counter-current chromatography. Journal of chromatography. A. 2005 Aug; 1083(1-2):102-5. doi: 10.1016/j.chroma.2005.06.025. [PMID: 16078694]
  • Yongmei Zhao, Farong Li, Jianxiong Yang, Xiaoning An, Minjuan Zhou. [Effect of phillyrin on the anti-obesity in nutritive obesity mice]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2005 Feb; 28(2):123-4. doi: NULL. [PMID: 15981888]
  • Magdalena Tokar, Barbara Klimek. The content of lignan glycosides in Forsythia flowers and leaves. Acta poloniae pharmaceutica. 2004 Jul; 61(4):273-8. doi: . [PMID: 15575593]
  • You-qi Liu, Xing-chun Tang, De-tian Cai. [Studies on callus growth and phillyrin accumulation of Forsythia suspensa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Apr; 28(4):321-3. doi: ". [PMID: 15139138]
  • A M Díaz Lanza, M J Abad Martínez, L Fernández Matellano, C Recuero Carretero, L Villaescusa Castillo, A M Silván Sen, P Bermejo Benito. Lignan and phenylpropanoid glycosides from Phillyrea latifolia and their in vitro anti-inflammatory activity. Planta medica. 2001 Apr; 67(3):219-23. doi: 10.1055/s-2001-12004. [PMID: 11345691]
  • Z Wu, W Su, X He. [Study on quality evaluation of Forsythia suspensa with grey pattern recognition]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2000 Sep; 23(9):536-8. doi: ". [PMID: 12575279]