Spinosin (BioDeep_00000000164)

 

Secondary id: BioDeep_00000183919

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


6-((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

化学式: C28H32O15 (608.1741122)
中文名称: 斯皮诺素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 5%

分子结构信息

SMILES: C(O)C(O2)[C@H](O)[C@H](O)[C@@H]([C@@H]2c(c5OC)c(c(c(c5)4)C(=O)C=C(O4)c(c3)ccc(c3)O)O)O[C@@H]([C@@H](O)1)OC([C@H](O)[C@@H]1O)CO
InChI: InChI=1S/C28H32O15/c1-39-14-7-15-18(12(32)6-13(40-15)10-2-4-11(31)5-3-10)22(35)19(14)26-27(24(37)21(34)16(8-29)41-26)43-28-25(38)23(36)20(33)17(9-30)42-28/h2-7,16-17,20-21,23-31,33-38H,8-9H2,1H3/t16-,17-,20-,21-,23+,24+,25-,26+,27-,28+/m1/s1

描述信息

Spinosin is a flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5 and 4, a methoxy group at position 7 and a 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 6 via a C-glycosidic linkage. It has a role as a plant metabolite and an anxiolytic drug. It is a flavone C-glycoside, a dihydroxyflavone and a monomethoxyflavone. It is functionally related to a flavone.
Spinosin is a natural product found in Clutia abyssinica, Galipea trifoliata, and other organisms with data available.
A flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5 and 4, a methoxy group at position 7 and a 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 6 via a C-glycosidic linkage.
Spinosyn a C-glycoside flavonoid isolated from the seeds of Zizyphus jujube, with neuroprotective effects. Spinosin inhibits Aβ1-42 production and aggregation via activating Nrf2/HO-1 pathway[1][2][3].
Spinosyn a C-glycoside flavonoid isolated from the seeds of Zizyphus jujube, with neuroprotective effects. Spinosin inhibits Aβ1-42 production and aggregation via activating Nrf2/HO-1 pathway[1][2][3].

同义名列表

16 个代谢物同义名

6-((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one; 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one; (1S)-1,5-anhydro-2-O-beta-D-glucopyranosyl-1-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-6-yl]-D-glucitol; 4H-1-Benzopyran-4-one, 6-(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-; 6-(2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 2-O-glycosylswertisin; flavoayamenin; Spinosin; 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromen-4-one; 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-2-tetrahydropyranyl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-chromenone; 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-methylol-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromone; 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chromen-4-one; 2-O-beta-D-Glucopyranosylswertisin; 72063-39-9; 6- (2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl) -5-hydroxy-2- (4-hydroxyphenyl) -7-methoxy-4H-1-benzopyran-4-one; SCHEMBL2980654



数据库引用编号

17 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)

13 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

  • Gang Lin, Weibin Li, Wenbin Hong, Desheng Zhu, Hongyu Hu, Jiqiang Fu, Yanfang Gao, Shuaijie Chen, Dajun Chai, Jin-Zhang Zeng. Spinosin inhibits activated hepatic stellate cell to attenuate liver fibrosis by targeting Nur77/ASK1/p38 MAPK signaling pathway. European journal of pharmacology. 2023 Dec; 966(?):176270. doi: 10.1016/j.ejphar.2023.176270. [PMID: 38096970]
  • Zhang Xiaoying, Wang Ruixuan, Wang Yiqing, X U Fanxing, Yan Tingxu, W U Bo, Zhang Ming, Jia Ying. Spinosin protects Neuro-2a/APP695 cells from oxidative stress damage by inactivating p38. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2023 10; 43(5):868-875. doi: 10.19852/j.cnki.jtcm.20220907.001. [PMID: 37679974]
  • Dongdong Wang, Chi-Tang Ho, Naisheng Bai. Ziziphi Spinosae Semen: An updated review on pharmacological activity, quality control, and application. Journal of food biochemistry. 2022 07; 46(7):e14153. doi: 10.1111/jfbc.14153. [PMID: 35403720]
  • Hao Xu, Yuyu Niu, Yan Sun, Menglin Xia, Daozheng Lin, Wei Qiao. Separation and purification of magnoflorine, spinosin, and 6‴-feruloyspinosin from Ziziphi Spinosae Semen by high-speed counter-current chromatography. Journal of separation science. 2021 Jun; 44(12):2391-2398. doi: 10.1002/jssc.202100122. [PMID: 33848379]
  • Xiaofang Xue, Ailing Zhao, Yongkang Wang, Haiyan Ren, Junjie Du, Dengke Li, Yi Li. Composition and content of phenolic acids and flavonoids among the different varieties, development stages, and tissues of Chinese Jujube (Ziziphus jujuba Mill.). PloS one. 2021; 16(10):e0254058. doi: 10.1371/journal.pone.0254058. [PMID: 34648512]
  • Ying Liu, Xiaotong Zhao, Tingting Lin, Qing Wang, Yanqing Zhang, Junbo Xie. Molecular mechanisms of polysaccharides from Ziziphus jujuba Mill var. spinosa seeds regulating the bioavailability of spinosin and preventing colitis. International journal of biological macromolecules. 2020 Nov; 163(?):1393-1402. doi: 10.1016/j.ijbiomac.2020.07.229. [PMID: 32755709]
  • Fanxing Xu, Xiaoying Zhang, Jinyu Wang, Xu Li, Bosai He, Feng Xiao, Tingxu Yan, Bo Wu, Ying Jia, Zhenzhong Wang. Spinosin protects N2a cells from H2 O2 -induced neurotoxicity through inactivation of p38MAPK. The Journal of pharmacy and pharmacology. 2020 Nov; 72(11):1607-1614. doi: 10.1111/jphp.13334. [PMID: 32667705]
  • Abbes Benmerache, Abdulmagid Alabdul Magid, Ahmed Kabouche, Dominique Harakat, Laurence Voutquenne-Nazabadioko, Zahia Kabouche. 6''-O-acetylisospinosin, a new C-glycosylflavone and known compounds from the aerial parts of Cladanthus mixtus. Natural product research. 2020 Oct; 34(20):2887-2893. doi: 10.1080/14786419.2019.1596100. [PMID: 30961391]
  • Shuhua Shan, Yue Xie, Chengying Zhang, Bin Jia, Hanqing Li, Zhuoyu Li. Identification of polyphenol from Ziziphi spinosae semen against human colon cancer cells and colitis-associated colorectal cancer in mice. Food & function. 2020 Sep; 11(9):8259-8272. doi: 10.1039/d0fo01375g. [PMID: 32966479]
  • Yan Chen, Enci Jiang, Jizhong Yan, Yi Tao. Validation of an analytical method using UPLC-MS/MS to quantify four bioactive components in rat plasma and its application to pharmacokinetic study of traditional and dispensing granules decoction of Ziziphi Spinosae Semen. Biomedical chromatography : BMC. 2020 Apr; 34(4):e4797. doi: 10.1002/bmc.4797. [PMID: 31989669]
  • Chae Bin Lee, Jee Sun Min, Soon Uk Chae, Hye Min Kim, Jun Hee Jang, In Ho Jung, Yu Fen Zheng, Jong Hoon Ryu, Soo Kyung Bae. Simultaneous determination of donepezil, 6-O-desmethyl donepezil and spinosin in beagle dog plasma using liquid chromatography‒tandem mass spectrometry and its application to a drug-drug interaction study. Journal of pharmaceutical and biomedical analysis. 2020 Jan; 178(?):112919. doi: 10.1016/j.jpba.2019.112919. [PMID: 31654856]
  • Minhua Gu, Peikun He, Chenfei Lyu, Xiaoyu Liu, Yuling Xu, Saibo Cheng, Yong Gu, Yuhua Jia. Spinosin and 6'''‑Feruloylspinosin protect the heart against acute myocardial ischemia and reperfusion in rats. Molecular medicine reports. 2019 Nov; 20(5):4253-4261. doi: 10.3892/mmr.2019.10686. [PMID: 31545438]
  • Hongjuan Li, Jiling Shi, Yuanyuan Li, Chunhua Wang, Guige Hou, Wei Cong, Feng Zhao. Purification of spinosin from Ziziphi Spinosae Semen using macroporous resins followed by preparative high-performance liquid chromatography. Journal of separation science. 2019 Oct; 42(19):3134-3140. doi: 10.1002/jssc.201900433. [PMID: 31364279]
  • Baoai Wu, Chenhuan Qu, Yaxin Wang, Jinfeng Zhao, Huizhi Du. Comparison of the Quenching Effects of Two Main Components of Ziziphi Spinosae Semen on Serum Albumin Fluorescence. Journal of fluorescence. 2019 Sep; 29(5):1113-1123. doi: 10.1007/s10895-019-02422-z. [PMID: 31396829]
  • Biao Zhang, Yan-Chuan Li, Hong Feng, Hong-Liang Xu, Lan-Lan Zhang, Ping Li. [Synthesis and identification of artificial antigen of spinosin]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Jul; 43(13):2747-2750. doi: 10.19540/j.cnki.cjcmm.20180404.001. [PMID: 30111026]
  • Ajing Zhao, Li Zhang, Rong Li, Jiao Shang, Huihui Yi, Yuan Wang, Dian Zhang, Shixiang Wang, Minfeng Fang. Development and validation of an LC-MS/MS method for the simultaneous quantification of seven constituents in rat plasma and application in a pharmacokinetic study of the Zaoren Anshen prescription. Biomedical chromatography : BMC. 2018 Feb; 32(2):. doi: 10.1002/bmc.4055. [PMID: 28744886]
  • Lijuan Jiao, Yaxin Li, Yanqing Zhang, Junjun Liu, Junbo Xie, Kunsheng Zhang, Aimin Zhou. Degradation Kinetics of 6‴-p-Coumaroylspinosin and Identification of Its Metabolites by Rat Intestinal Flora. Journal of agricultural and food chemistry. 2017 Jun; 65(22):4449-4455. doi: 10.1021/acs.jafc.7b01486. [PMID: 28513155]
  • Yan Yan, Qiang Li, Chen-hui Du, Jin-ping Jia, Hong-xia Feng, Xue-mei Qin. [Investigation of the potentially effective components of Semen Ziziphi Spinosae based on “in vitro to in vivo” translation approach]. Yao xue xue bao = Acta pharmaceutica Sinica. 2017 Feb; 52(2):283-90. doi: NULL. [PMID: 29979520]
  • Longdong Qiao, Yan Liu, Xiaoyan Chen, Junbo Xie, Yanqing Zhang, Ke Yang, Hongjian Zhou, Yayun Duan, Wei Zheng, Wenlin Xie. A HPLC-MS/MS method for determination of 6'''-feruloylspinosin in rat plasma and tissues: Pharmacokinetics and tissue distribution study. Journal of pharmaceutical and biomedical analysis. 2016 Mar; 121(?):77-83. doi: 10.1016/j.jpba.2016.01.005. [PMID: 26780157]
  • Rong Gao, Shan Li, Xian-jin Chen, Xiao-feng Wang, Shi-xiang Wang, Min-feng Fang. [Pharmacokinetic effect of combined administration on spinosin and ferulic acid in monarch drug Ziziphi Spinosae Semen kernel]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2015 Aug; 40(16):3293-7. doi: . [PMID: 26790310]
  • Sheng Guo, Jin-Ao Duan, Jin-Long Zhao, Da-Wei Qian, Wen-Jie Zhang. [Chemical constituents from seeds of Ziziphus mauritiana]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Mar; 37(3):432-5. doi: . [PMID: 25174108]
  • Won Il Kim, Bing Tian Zhao, Hai Yan Zhang, Je Hyun Lee, Jong Keun Son, Mi Hee Woo. Quantitative and pattern recognition analyses of magnoflorine, spinosin, 6'''-feruloyl spinosin and jujuboside A by HPLC in Zizyphi Semen. Archives of pharmacal research. 2014; 37(9):1139-47. doi: 10.1007/s12272-013-0295-z. [PMID: 24310099]
  • Bosai He, Qing Li, Ying Jia, Longshan Zhao, Feng Xiao, Chunxiao Lv, Huarong Xu, Xiaohui Chen, Kaishun Bi. A UFLC-MS/MS method for simultaneous quantitation of spinosin, mangiferin and ferulic acid in rat plasma: application to a comparative pharmacokinetic study in normal and insomnic rats. Journal of mass spectrometry : JMS. 2012 Oct; 47(10):1333-40. doi: 10.1002/jms.3072. [PMID: 23019165]
  • Rong-Hua Ma, Jie Yang, Lian-Wen Qi, Gui-Zhong Xin, Chong-Zhi Wang, Chun-Su Yuan, Xiao-Dong Wen, Ping Li. In vivo microdialysis with LC-MS for analysis of spinosin and its interaction with cyclosporin A in rat brain, blood and bile. Journal of pharmaceutical and biomedical analysis. 2012 Mar; 61(?):22-9. doi: 10.1016/j.jpba.2011.11.014. [PMID: 22169469]
  • Lin Zhang, Zhi-Lin Xu, Chun-Fu Wu, Jing-Yu Yang, Yoshihiro Kano, Dan Yuan. Two new flavonoid glycosides from Semen Ziziphi Spinosae. Journal of Asian natural products research. 2012; 14(2):121-8. doi: 10.1080/10286020.2011.637491. [PMID: 22296152]
  • Yuan-Yuan Xie, Zhi-Lin Xu, Hui Wang, Yoshihiro Kano, Dan Yuan. A novel spinosin derivative from Semen Ziziphi Spinosae. Journal of Asian natural products research. 2011 Dec; 13(12):1151-7. doi: 10.1080/10286020.2011.623128. [PMID: 22115038]
  • Suk-Hyun Choi, Jun-Bae Ahn, Nobuyuki Kozukue, Carol E Levin, Mendel Friedman. Distribution of free amino acids, flavonoids, total phenolics, and antioxidative activities of Jujube (Ziziphus jujuba) fruits and seeds harvested from plants grown in Korea. Journal of agricultural and food chemistry. 2011 Jun; 59(12):6594-604. doi: 10.1021/jf200371r. [PMID: 21574660]
  • Ligia Moreiras Sena, Silvana Maria Zucolotto, Flávio Henrique Reginatto, Eloir Paulo Schenkel, Thereza Christina Monteiro De Lima. Neuropharmacological activity of the pericarp of Passiflora edulis flavicarpa degener: putative involvement of C-glycosylflavonoids. Experimental biology and medicine (Maywood, N.J.). 2009 Aug; 234(8):967-75. doi: 10.3181/0902-rm-84. [PMID: 19491371]
  • Kang-De Bao, Ping Li, Lian-Wen Qi, Hui-Jun Li, Ling Yi, Wei Wang, Ya-Qiong Wang. Characterization of flavonoid metabolites in rat plasma, urine, and feces after oral administration of Semen Ziziphi Spinosae extract by HPLC-diode-array detection (DAD) and ion-trap mass spectrometry (MS(n)). Chemical & pharmaceutical bulletin. 2009 Feb; 57(2):144-8. doi: 10.1248/cpb.57.144. [PMID: 19182403]
  • Lei Zhang, Cheng Xiang, Bin Wang, Yuying Zhao, Qingying Zhang. [Metabolism and excretion of total flavonoids of Semen Ziziphi Spinosae in rat urine and feces]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Feb; 34(3):340-3. doi: NULL. [PMID: 19445163]
  • Silvia Aquila, Rosa M Giner, María C Recio, Etile D Spegazzini, José Luis Ríos. Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots. Journal of ethnopharmacology. 2009 Jan; 121(2):333-7. doi: 10.1016/j.jep.2008.11.002. [PMID: 19041703]
  • Yujuan Li, Meicun Yao, Shan Cheng. Quantitative determination of spinosin in rat plasma by liquid chromatography-tandem mass spectrometry method. Journal of pharmaceutical and biomedical analysis. 2008 Dec; 48(4):1169-73. doi: 10.1016/j.jpba.2008.08.025. [PMID: 18834689]
  • Wiyada Kaewkrud, Hideaki Otsuka, Somsak Ruchirawat, Tripetch Kanchanapoom. Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl. Journal of natural medicines. 2008 Jan; 62(1):124-5. doi: 10.1007/s11418-007-0192-1. [PMID: 18404358]
  • Yu-Juan Li, Yue-Han Dai, Ye-Ling Yu, Yan Li, Yu-Lin Deng. Pharmacokinetics and tissue distribution of spinosin after intravenous administration in rats. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2007 Aug; 127(8):1231-5. doi: 10.1248/yakushi.127.1231. [PMID: 17666874]
  • Jingjing Liu, Bo Chen, Shouzhuo Yao. Simultaneous analysis and identification of main bioactive constituents in extract of Zizyphus jujuba var. sapinosa (Zizyphi spinosi semen) by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. Talanta. 2007 Feb; 71(2):668-75. doi: 10.1016/j.talanta.2006.05.014. [PMID: 19071358]
  • Yu-Juan Li, Kai-Shun Bi. Study on the therapeutic material basis of traditional chinese medicinal preparation Suanzaoren decoction. Chemical & pharmaceutical bulletin. 2006 Jun; 54(6):847-51. doi: 10.1248/cpb.54.847. [PMID: 16755056]
  • Yu-juan Li, Xin-miao Liang, Hong-bin Xiao, Kai-shun Bi. Pharmacokinetic study on spinosin in rat plasma after oral administration of suanzaoren extract at a single dose. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jun; 38(6):448-50. doi: . [PMID: 14513806]
  • Yujuan Li, Xinmiao Liang, Hongbin Xiao, Kaishun Bi. Determination of spinosin in rat plasma by reversed-phase high-performance chromatography after oral administration of Suanzaoren decoction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Apr; 787(2):421-5. doi: 10.1016/s1570-0232(02)01001-2. [PMID: 12650764]