Bavachin (BioDeep_00000229957)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

化学式: C20H20O4 (324.1362)
中文名称: 补骨脂甲素, 补骨脂二氢黄酮, 补骨脂素, 补骨脂甲素:补骨脂黄酮
谱图信息: 最多检出来源 Viridiplantae(plant) 25%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

Bavachin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/bavachin (retrieved 2025-02-04) (BioDeep RN: BioDeep_00000229957). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1(O)=CC2OC(C3C=CC(O)=CC=3)CC(=O)C=2C=C1C/C=C(/C)\C
InChI: InChI=1S/C20H20O4/c1-12(2)3-4-14-9-16-18(23)11-19(24-20(16)10-17(14)22)13-5-7-15(21)8-6-13/h3,5-10,19,21-22H,4,11H2,1-2H3

描述信息

Bavachin is a natural product found in Broussonetia papyrifera, Cullen corylifolium, and other organisms with data available.
Bavachin, a flavonoid first isolated from seeds of P. corylifolia, acts as a phytoestrogen that activates the estrogen receptors ERα and ERβ with EC50s of 320 and 680 nM, respectively.
Bavachin, a flavonoid first isolated from seeds of P. corylifolia, acts as a phytoestrogen that activates the estrogen receptors ERα and ERβ with EC50s of 320 and 680 nM, respectively.

同义名列表

9 个代谢物同义名

Bavachin; 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-, (2S)-; (2S)-7-hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one; (S)-7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one; 7-Hydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one; corylifolin (flavonoid); Corylifolin; CORYFOLIN; (S) -2,3-Dihydro-7-hydroxy-2- (4-hydroxyphenyl) -6- (3-methyl-2-butenyl) -4H-1-benzopyran-4-one



数据库引用编号

12 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)

29 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

  • Mengmeng Lin, Yingying Li, Bo Cao, Jing Xu, Yujun Zhang, Guohui Li, Xiaohe Xiao, Chunyu Li. Bavachin combined with epimedin B induce idiosyncratic liver injury under immunological stress conditions. Chemico-biological interactions. 2023 Oct; 386(?):110774. doi: 10.1016/j.cbi.2023.110774. [PMID: 37866487]
  • Cong-Shu Huang, Hui-Fang Deng, Lei Zhou, Pan Shen, Yu-Hao Ni, Ning-Ning Wang, Gao-Fu Li, Lan-Xin Yue, Yong-Qiang Zhou, Wei Zhou, Yue Gao. Undesirable ER stress induced by bavachin contributed to follicular atresia in zebrafish ovary. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Oct; 166(?):115322. doi: 10.1016/j.biopha.2023.115322. [PMID: 37586115]
  • Ying Yang, Wei Zhou, Yihao Wang, Yunxuan Ge, Zheng Fan, Qingquan Liu, Yue Gao. Bavachin induces liver injury and cell apoptosis by targeting Wnt/β-catenin/DRP1 signaling pathway mediated mitochondrial dysfunction. Toxicology letters. 2023 Sep; 387(?):1-13. doi: 10.1016/j.toxlet.2023.09.006. [PMID: 37748667]
  • Xiang Wei, Li Lin, Qian-Qian Yuan, Xiu-Yun Wang, Qing Zhang, Xiao-Min Zhang, Ke-Chao Tang, Man-Yu Guo, Ting-Yu Dong, Wei Han, Da-Ke Huang, Yin-Liang Qi, Mei Zhang, Hua-Bing Zhang. Bavachin protects against diet-induced hepatic steatosis and obesity in mice. Acta pharmacologica Sinica. 2023 Jul; 44(7):1416-1428. doi: 10.1038/s41401-023-01056-z. [PMID: 36721007]
  • Mengru Wang, Baopeng Tian, Jie Shen, Shilin Xu, Cong Liu, Ling Guan, Min Guo, Jie Dou. Bavachin induces apoptosis in colorectal cancer cells through Gadd45a via the MAPK signaling pathway. Chinese journal of natural medicines. 2023 Jan; 21(1):36-46. doi: 10.1016/s1875-5364(23)60383-8. [PMID: 36641231]
  • Zheng Liang, Zecheng Luo, Jian Chen, Baojie Li, Lin Li, Chongyang Shen. Bavachin inhibits IL-4 expression by downregulating STAT6 phosphorylation and GATA-3 expression and ameliorates asthma inflammation in an animal model. Immunobiology. 2022 03; 227(2):152182. doi: 10.1016/j.imbio.2022.152182. [PMID: 35134627]
  • Ge-Zi Shi, Di Song, Peng-Yan Li, Shuai-Shuai Chen, Le Zhang, Shan-Shan Li, Xiao-He Xiao, Xu-Hua Qin, Jia-Bo Wang. Screening of hepatotoxic compounds in Psoralea corylifolia L., a traditional Chinese herbal and dietary supplement, using high-resolution mass spectrometry and high-content imaging. Biomedical chromatography : BMC. 2021 Sep; 35(9):e5140. doi: 10.1002/bmc.5140. [PMID: 33830528]
  • Nan Qin, Guang Xu, Yan Wang, Xiaoyan Zhan, Yuan Gao, Zhilei Wang, Shubin Fu, Wei Shi, Xiaorong Hou, Chunyu Wang, Ruisheng Li, Yan Liu, Jiabo Wang, Haiping Zhao, Xiaohe Xiao, Zhaofang Bai. Bavachin enhances NLRP3 inflammasome activation induced by ATP or nigericin and causes idiosyncratic hepatotoxicity. Frontiers of medicine. 2021 Aug; 15(4):594-607. doi: 10.1007/s11684-020-0809-2. [PMID: 33909257]
  • Ying Yang, Guiming Guo, Wei Zhou, Yunxuan Ge, Zheng Fan, Qingquan Liu, Yue Gao. Sestrin2 protects against bavachin induced ER stress through AMPK/mTORC1 signaling pathway in HepG2 cells. Journal of pharmacological sciences. 2021 Feb; 145(2):175-186. doi: 10.1016/j.jphs.2020.11.012. [PMID: 33451752]
  • Zhi-Xing Zhou, Li Yang, Li-Yuan Cheng, Ying-Li Yu, Lei Song, Kun Zhou, Ying-Liang Wu, Yue Zhang. Simultaneous characterization of multiple Psoraleae Fructus bioactive compounds in rat plasma by ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry for application in sex-related differences in pharmacokinetics. Journal of separation science. 2020 Jul; 43(14):2804-2816. doi: 10.1002/jssc.202000286. [PMID: 32384213]
  • Chen Cheng, Shen Yu-Feng, Hu Yang, Liu Lei, Chen Wei-Chao, Wang Gao-Xue, Zhu Bin. Highly efficient inhibition of spring viraemia of carp virus replication in vitro mediated by bavachin, a major constituent of psoralea corlifonia Lynn. Virus research. 2018 08; 255(?):24-35. doi: 10.1016/j.virusres.2018.06.002. [PMID: 29913251]
  • Nidhi Gupta, Arem Qayum, Arun Raina, Ravi Shankar, Sumeet Gairola, Shashank Singh, Payare L Sangwan. Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents. European journal of medicinal chemistry. 2018 Feb; 145(?):511-523. doi: 10.1016/j.ejmech.2018.01.006. [PMID: 29335212]
  • Ying Yang, Xianglin Tang, Feiran Hao, Zengchun Ma, Yuguang Wang, Lili Wang, Yue Gao. Bavachin Induces Apoptosis through Mitochondrial Regulated ER Stress Pathway in HepG2 Cells. Biological & pharmaceutical bulletin. 2018 Feb; 41(2):198-207. doi: 10.1248/bpb.b17-00672. [PMID: 29187671]
  • Hyejin Lee, Hua Li, Minsoo Noh, Jae-Ha Ryu. Bavachin from Psoralea corylifolia Improves Insulin-Dependent Glucose Uptake through Insulin Signaling and AMPK Activation in 3T3-L1 Adipocytes. International journal of molecular sciences. 2016 Apr; 17(4):527. doi: 10.3390/ijms17040527. [PMID: 27070585]
  • Ze-Bin Weng, Qian-Qian Gao, Fang Wang, Gen-Hua Zhao, Fang-Zhou Yin, Bao-Chang Cai, Zhi-Peng Chen, Wei-Dong Li. Positive skeletal effect of two ingredients of Psoralea corylifolia L. on estrogen deficiency-induced osteoporosis and the possible mechanisms of action. Molecular and cellular endocrinology. 2015 Dec; 417(?):103-13. doi: 10.1016/j.mce.2015.09.025. [PMID: 26419930]
  • Xin-Xin Wang, Xia Lv, Shi-Yang Li, Jie Hou, Jing Ning, Jia-Yue Wang, Yun-Feng Cao, Guang-Bo Ge, Bin Guo, Ling Yang. Identification and characterization of naturally occurring inhibitors against UDP-glucuronosyltransferase 1A1 in Fructus Psoraleae (Bu-gu-zhi). Toxicology and applied pharmacology. 2015 Nov; 289(1):70-8. doi: 10.1016/j.taap.2015.09.003. [PMID: 26348140]
  • Gyeong-Je Lee, In-A Cho, Kyeong-Rok Kang, Do Kyung Kim, Hong-Moon Sohn, Jae-Won You, Ji-Su Oh, Yo-Seob Seo, Sang-Joun Yu, Jae-Seek You, Chun Sung Kim, Su-Gwan Kim, Hee-Jeong Im, Jae-Sung Kim. Biological Effects of the Herbal Plant-Derived Phytoestrogen Bavachin in Primary Rat Chondrocytes. Biological & pharmaceutical bulletin. 2015; 38(8):1199-207. doi: 10.1248/bpb.b15-00198. [PMID: 26235583]
  • Haiyan Zhao, Zilin Chen. Screening of neuraminidase inhibitors from traditional Chinese medicines by integrating capillary electrophoresis with immobilized enzyme microreactor. Journal of chromatography. A. 2014 May; 1340(?):139-45. doi: 10.1016/j.chroma.2014.03.028. [PMID: 24679826]
  • Yulin Zhang, Zilin Chen. Separation of isomeric bavachin and isobavachalcone in the fructus Psoraleae by capillary electrophoresis-mass spectrometry. Journal of separation science. 2012 Jul; 35(13):1644-50. doi: 10.1002/jssc.201200173. [PMID: 22761143]
  • Seung Woong Lee, Bo Ra Yun, Mi Hwa Kim, Chan Sun Park, Woo Song Lee, Hyun-Mee Oh, Mun-Chual Rho. Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation. Planta medica. 2012 Jun; 78(9):903-6. doi: 10.1055/s-0031-1298482. [PMID: 22573369]
  • Yuan Li, Fang Wang, Zilin Chen. Determination of bavachin and isobavachalcone in Fructus Psoraleae by high-performance liquid chromatography with electrochemical detection. Journal of separation science. 2011 Mar; 34(5):514-9. doi: 10.1002/jssc.201000801. [PMID: 21265020]
  • Osamu Ohno, Taeko Watabe, Kazuhiko Nakamura, Masaru Kawagoshi, Nobuo Uotsu, Tomohiro Chiba, Masayoshi Yamada, Kohji Yamaguchi, Kaoru Yamada, Kenji Miyamoto, Daisuke Uemura. Inhibitory effects of bakuchiol, bavachin, and isobavachalcone isolated from Piper longum on melanin production in B16 mouse melanoma cells. Bioscience, biotechnology, and biochemistry. 2010; 74(7):1504-6. doi: 10.1271/bbb.100221. [PMID: 20622433]
  • Maya Mori-Hongo, Hiroyuki Takimoto, Takayuki Katagiri, Makoto Kimura, Yu Ikeda, Toshio Miyase. Melanin synthesis inhibitors from Lespedeza floribunda. Journal of natural products. 2009 Feb; 72(2):194-203. doi: 10.1021/np800395j. [PMID: 19132934]
  • Maya Mori-Hongo, Hiromi Yamaguchi, Tsutomu Warashina, Toshio Miyase. Melanin synthesis inhibitors from Lespedeza cyrtobotrya. Journal of natural products. 2009 Jan; 72(1):63-71. doi: 10.1021/np800535g. [PMID: 19102656]
  • Chun-Feng Qiao, Quan-Bin Han, Jing-Zheng Song, Shi-Fu Mo, Ling-Dong Kong, Hsiang-Fu Kung, Hong-Xi Xu. Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography. Journal of separation science. 2007 Apr; 30(6):813-8. doi: 10.1002/jssc.200600339. [PMID: 17536725]
  • Hiroyuki Haraguchi, Junji Inoue, Yukiyoshi Tamura, Kenji Mizutani. Antioxidative components of Psoralea corylifolia (Leguminosae). Phytotherapy research : PTR. 2002 Sep; 16(6):539-44. doi: 10.1002/ptr.972. [PMID: 12237811]
  • D Wang, F Li, Z Jiang. Osteoblastic proliferation stimulating activity of Psoralea corylifolia extracts and two of its flavonoids. Planta medica. 2001 Nov; 67(8):748-9. doi: 10.1055/s-2001-18343. [PMID: 11731919]
  • M E Wall, M C Wani, G Manikumar, P Abraham, H Taylor, T J Hughes, J Warner, R McGivney. Plant antimutagenic agents, 2. Flavonoids. Journal of natural products. 1988 Nov; 51(6):1084-91. doi: 10.1021/np50060a006. [PMID: 3069957]