Ginkgetin (BioDeep_00000007768)

 

Secondary id: BioDeep_00000861493

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-

化学式: C32H22O10 (566.1212912)
中文名称: 银杏双黄酮, 白果双黄酮, 银杏黄素, 银杏素
谱图信息: 最多检出来源 Mentha canadensis(plant) 58.49%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1cc(c(cc1)OC)c1c(cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)O)O)OC
InChI: InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3

描述信息

Ginkgetin is a biflavonoid that is the 7,4-dimethyl ether derivative of amentoflavone. Isolated from Ginkgo biloba and Dioon, it exhibits anti-HSV-1, antineoplastic and inhibitory activities towards arachidonate 5-lipoxygenase and cyclooxygenase 2. It has a role as an anti-HSV-1 agent, a cyclooxygenase 2 inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antineoplastic agent and a metabolite. It is a biflavonoid, a hydroxyflavone, a methoxyflavone and a ring assembly. It is functionally related to an amentoflavone.
Ginkgetin is a natural product found in Selaginella sinensis, Selaginella willdenowii, and other organisms with data available.
A biflavonoid that is the 7,4-dimethyl ether derivative of amentoflavone. Isolated from Ginkgo biloba and Dioon, it exhibits anti-HSV-1, antineoplastic and inhibitory activities towards arachidonate 5-lipoxygenase and cyclooxygenase 2.
From Ginkgo biloba (ginkgo). Ginkgetin is found in ginkgo nuts and fats and oils.
Ginkgetin is found in fats and oils. Ginkgetin is from Ginkgo biloba (ginkgo
Ginkgetin, a biflavone, is isolated from Ginkgo biloba leaves. Ginkgetin exhibit anti-tumor, anti-inflammatory, neuroprotective, anti-fungal activities. Ginkgetin is also a potent inhibitor of Wnt signaling, with an IC50 of 5.92 μΜ[1][2][3][4][5].
Ginkgetin, a biflavone, is isolated from Ginkgo biloba leaves. Ginkgetin exhibit anti-tumor, anti-inflammatory, neuroprotective, anti-fungal activities. Ginkgetin is also a potent inhibitor of Wnt signaling, with an IC50 of 5.92 μΜ[1][2][3][4][5].

同义名列表

25 个代谢物同义名

4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-chromen-2-yl)-2-methoxy-phenyl]-2-(4-hydroxyphenyl)chromen-4-one; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one; 4,5,5,7-tetrahydroxy-4,7-dimethoxy-(3->8)-biflavone; 3,8-Biflavone, 4,5,5,7-tetrahydroxy-4,7-dimethoxy-; Ginkgetin 7-O-beta-D-glucopyranoside; Amentoflavone 7,4-dimethyl ether; 7,4-Dimethylamentoflavone; jm5b01461, Compound 89; Spectrum4_001610; Spectrum5_000339; Spectrum2_000054; Spectrum3_001727; UNII-HY5EZW8269; KBio2_007605; KBio2_002469; KBio3_002594; KBio2_005037; HY5EZW8269; Ginkgetin; Ginkgetin



数据库引用编号

21 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)

106 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

  • Zhu Tao, Shaoliang Bai, Guodong Wu, Shengbing Zhai, Pei Zhang, Chunhua Fu, Longjiang Yu. Therapeutic effect of ginkgetin on smoke-induced airway inflammation by down-regulating the c/EBPβ signaling pathway and CCL2 expression. Journal of ethnopharmacology. 2024 Sep; 331(?):118284. doi: 10.1016/j.jep.2024.118284. [PMID: 38735420]
  • Shweta Sharma, Manisha Mahanty, Suneha G Rahaman, Pritha Mukherjee, Bidisha Dutta, Mohammad Imran Khan, Karunakaran Reddy Sankaran, Xiaoming He, Lakshmyya Kesavalu, Wei Li, Shaik O Rahaman. Avocado-derived extracellular vesicles loaded with ginkgetin and berberine prevent inflammation and macrophage foam cell formation. Journal of cellular and molecular medicine. 2024 Apr; 28(7):e18177. doi: 10.1111/jcmm.18177. [PMID: 38494843]
  • Ali Akbar, Muhammad Umar Ijaz. Pharmacotherapeutic potential of ginkgetin against polystyrene microplastics-instigated testicular toxicity in rats: A biochemical, spermatological, and histopathological assessment. Environmental science and pollution research international. 2024 Feb; 31(6):9031-9044. doi: 10.1007/s11356-023-31662-7. [PMID: 38182957]
  • Liangrong Wu, Chenchen Qian, Weiqi Zhang, Mengyun Shi, Xiuxiu Chen, Yi Wang, Feng Lin. Ginkgetin suppresses ovarian cancer growth through inhibition of JAK2/STAT3 and MAPKs signaling pathways. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Apr; 116(?):154846. doi: 10.1016/j.phymed.2023.154846. [PMID: 37172479]
  • Siyu Zhang, Yujie Sun, Fengli Yao, Hongju Li, Yacong Yang, Xionghao Li, Zhongyue Bai, Yu Hu, Peng Wang, Ximing Xu. Ginkgo Biflavones Cause p53 Wild-Type Dependent Cell Death in a Transcription-Independent Manner of p53. Journal of natural products. 2023 Feb; 86(2):346-356. doi: 10.1021/acs.jnatprod.2c00959. [PMID: 36700552]
  • Guoqing Ren, Gonghao Xu, Renshi Li, Haifeng Xie, Zhengguo Cui, Lei Wang, Chaofeng Zhang. Modulation of Bleomycin-induced oxidative stress and pulmonary fibrosis by ginkgetin in mice via AMPK. Current molecular pharmacology. 2022 Mar; ?(?):. doi: 10.2174/1874467215666220304094058. [PMID: 35249515]
  • Lin Wei, Pan Jian, Huang Erjiong, Zhu Qihan. Ginkgetin alleviates high glucose-evoked mesangial cell oxidative stress injury, inflammation, and extracellular matrix (ECM) deposition in an AMPK/mTOR-mediated autophagy axis. Chemical biology & drug design. 2021 10; 98(4):620-630. doi: 10.1111/cbdd.13915. [PMID: 34148304]
  • Mazen O Alharbi, Bidisha Dutta, Rishov Goswami, Shweta Sharma, Kai Y Lei, Shaik O Rahaman. Identification and functional analysis of a biflavone as a novel inhibitor of transient receptor potential vanilloid 4-dependent atherogenic processes. Scientific reports. 2021 04; 11(1):8173. doi: 10.1038/s41598-021-87696-9. [PMID: 33854174]
  • Jian-Shu Lou, Li-Ping Zhao, Zhi-Hui Huang, Xia-Yin Chen, Jing-Ting Xu, William Chi-Shing Tai, Karl W K Tsim, Yi-Tao Chen, Tian Xie. Ginkgetin derived from Ginkgo biloba leaves enhances the therapeutic effect of cisplatin via ferroptosis-mediated disruption of the Nrf2/HO-1 axis in EGFR wild-type non-small-cell lung cancer. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Jan; 80(?):153370. doi: 10.1016/j.phymed.2020.153370. [PMID: 33113504]
  • Zhaohua Tian, Congyao Tang, Zhigang Wang. Neuroprotective effect of ginkgetin in experimental cerebral ischemia/reperfusion via apoptosis inhibition and PI3K/Akt/mTOR signaling pathway activation. Journal of cellular biochemistry. 2019 10; 120(10):18487-18495. doi: 10.1002/jcb.29169. [PMID: 31265179]
  • Jianxia Cheng, Yun Li, Jianping Kong. Ginkgetin inhibits proliferation of HeLa cells via activation of p38/NF-κB pathway. Cellular and molecular biology (Noisy-le-Grand, France). 2019 Apr; 65(4):79-82. doi: . [PMID: 31078156]
  • Qin Li, Tao Ye, Ting Long, Xuemei Peng. Ginkgetin exerts anti-inflammatory effects on cerebral ischemia/reperfusion-induced injury in a rat model via the TLR4/NF-κB signaling pathway. Bioscience, biotechnology, and biochemistry. 2019 Apr; 83(4):675-683. doi: 10.1080/09168451.2018.1553608. [PMID: 30570395]
  • Young-Lai Cho, Jong-Gil Park, Hyo Jin Kang, Wooil Kim, Min Ji Cho, Ju-Hong Jang, Min-Gi Kwon, Sungsik Kim, Sang-Hyun Lee, Jangwook Lee, Yeon-Gu Kim, Young-Jun Park, Won Kon Kim, Kwang-Hee Bae, Byoung-Mog Kwon, Sang J Chung, Jeong-Ki Min. Ginkgetin, a biflavone from Ginkgo biloba leaves, prevents adipogenesis through STAT5-mediated PPARγ and C/EBPα regulation. Pharmacological research. 2019 01; 139(?):325-336. doi: 10.1016/j.phrs.2018.11.027. [PMID: 30472463]
  • Naqi Lian, Jing Tong, Wenwen Li, Jingzhen Wu, Yu Li. Ginkgetin ameliorates experimental atherosclerosis in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jun; 102(?):510-516. doi: 10.1016/j.biopha.2018.03.107. [PMID: 29579712]
  • Xiao Ruan, Liu-Ye Yan, Xian-Xian Li, Ben Liu, Huan Zhang, Qiang Wang. Optimization of process parameters of extraction of amentoflavone, quercetin and ginkgetin from Taxus chinensis using supercritical CO2 plus co-solvent. Molecules (Basel, Switzerland). 2014 Oct; 19(11):17682-96. doi: 10.3390/molecules191117682. [PMID: 25365294]
  • Ok Heui You, Sun-Hee Kim, Bonglee Kim, Eun Jung Sohn, Hyo-Jeong Lee, Bum-Sang Shim, Miyong Yun, Byung-Mog Kwon, Sung-Hoon Kim. Ginkgetin induces apoptosis via activation of caspase and inhibition of survival genes in PC-3 prostate cancer cells. Bioorganic & medicinal chemistry letters. 2013 May; 23(9):2692-5. doi: 10.1016/j.bmcl.2013.02.080. [PMID: 23523142]
  • Young Bae Ryu, Hyung Jae Jeong, Jang Hoon Kim, Young Min Kim, Ji-Young Park, Doman Kim, Thi Thanh Hanh Nguyen, Su-Jin Park, Jong Sun Chang, Ki Hun Park, Mun-Chual Rho, Woo Song Lee. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition. Bioorganic & medicinal chemistry. 2010 Nov; 18(22):7940-7. doi: 10.1016/j.bmc.2010.09.035. [PMID: 20934345]
  • Xiang-Qian Liu, Xiao-Dan Zhang, Yu-Lin Zhu, Bum-Young Shin, Shi-Xu Wu. [Structrue identification of biflavones and determination of Taxol from Taxus Madia]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Oct; 31(10):1498-501. doi: . [PMID: 19230397]
  • Mi Kyeong Lee, Song Won Lim, Hyekyung Yang, Sang Hyun Sung, Heum-Sook Lee, Mi Jung Park, Young Choong Kim. Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana. Bioorganic & medicinal chemistry letters. 2006 Jun; 16(11):2850-4. doi: 10.1016/j.bmcl.2006.03.018. [PMID: 16574412]
  • Jong Keun Son, Min Jung Son, Eunkyung Lee, Tae Chul Moon, Kun Ho Son, Cheorl-Ho Kim, Hyun Pyo Kim, Sam Sik Kang, Hyeun Wook Chang. Ginkgetin, a Biflavone from Ginko biloba leaves, inhibits cyclooxygenases-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Biological & pharmaceutical bulletin. 2005 Dec; 28(12):2181-4. doi: 10.1248/bpb.28.2181. [PMID: 16327145]
  • Wie-Jong Kwak, Chang Kyun Han, Kun Ho Son, Hyeun Wook Chang, Sam Sik Kang, Byoung Kyu Park, Hyun Pyo Kim. Effects of Ginkgetin from Ginkgo biloba Leaves on cyclooxygenases and in vivo skin inflammation. Planta medica. 2002 Apr; 68(4):316-21. doi: 10.1055/s-2002-26742. [PMID: 11988854]
  • Mario Dell'Agli, Enrica Bosisio. Biflavones of Ginkgo biloba stimulate lipolysis in 3T3-L1 adipocytes. Planta medica. 2002 Jan; 68(1):76-9. doi: 10.1055/s-2002-19876. [PMID: 11842336]
  • H K Kim, K H Son, H W Chang, S S Kang, H P Kim. Inhibition of rat adjuvant-induced arthritis by ginkgetin, a biflavone from ginkgo biloba leaves. Planta medica. 1999 Jun; 65(5):465-7. doi: 10.1055/s-2006-960815. [PMID: 10418340]
  • J D Chi, X F He, A R Liu, L X Xu. [HPLC determination of six flavonoid constituents in Ginkgo biloba leaves]. Yao xue xue bao = Acta pharmaceutica Sinica. 1997 Aug; 32(8):625-8. doi: . [PMID: 11596315]
  • C M Sun, W J Syu, Y T Huang, C C Chen, J C Ou. Selective cytotoxicity of ginkgetin from Selaginella moellendorffii. Journal of natural products. 1997 Apr; 60(4):382-4. doi: 10.1021/np960608e. [PMID: 9134745]
  • K Hayashi, T Hayashi, N Morita. Mechanism of action of the antiherpesvirus biflavone ginkgetin. Antimicrobial agents and chemotherapy. 1992 Sep; 36(9):1890-3. doi: 10.1128/aac.36.9.1890. [PMID: 1329635]
  • S Bourgoin, F Héry, J P Ternaux, M Hanson. Effects of benzodiazepines on the binding of tryptophan in serum. Consequences on 5-hydroxyindoles concentrations in the rat brain. Psychopharmacology communications. 1975; 1(2):209-16. doi: NULL. [PMID: 4860]