Obacunone (BioDeep_00000000395)

 

Secondary id: BioDeep_00000307680

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)-

化学式: C26H30O7 (454.1991)
中文名称: 黄柏酮
谱图信息: 最多检出来源 Homo sapiens(otcml) 33.33%

分子结构信息

SMILES: CC1(C)OC(=O)C=CC2(C)C1CC(=O)C1(C)C2CCC2(C)C(c3ccoc3)OC(=O)C3OC321
InChI: InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3

描述信息

Constituent of Citrus subspecies, Fortunella margarita (oval kumquat) and Casimiroa edulis (Mexican apple). Obacunone is found in many foods, some of which are pomes, sweet orange, lemon, and fruits.
Obacunone is found in fruits. Obacunone is a constituent of Citrus species, Fortunella margarita (oval kumquat) and Casimiroa edulis (Mexican apple)
Obacunone is a limonoid.
Obacunone is a natural product found in Limonia acidissima, Citrus latipes, and other organisms with data available.
Obacunone, isolated from Citrus fruits, exhibits anti-tumor activity by the induction of apoptosis[1].
Obacunone, isolated from Citrus fruits, exhibits anti-tumor activity by the induction of apoptosis[1].

同义名列表

13 个代谢物同义名

Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)-; (1S,3aS,4aR,4bR,6aR,11aR,11bR,13aS)-1-(furan-3-yl)-4b,7,7,11a,13a-pentamethyl-1,6a,7,11a,11b,12,13,13a-octahydrooxepino[4,3:3,4]benzo[1,2-f]oxireno[2,3-d]isochromene-3,5,9(3aH,4bH,6H)-trione; 8-(Furan-3-yl)-1,1,5a,7a,11b-pentamethyl-5b,6,7,7a,8,11b,13,13a-octahydrooxireno[4,5]pyrano[4,3:5,6]naphtho[2,1-c]oxepine-3,10,12(1H,5aH,10aH)-trione; (1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione; 7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione; Obacunone, analytical standard; Obacunoic acid, eta-lactone; Casimirolide; Tricoccin S3; Obacunone; AI3-37934; OBACUNON; Obacunone



数据库引用编号

24 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)

113 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
Cytoplasm 14 AKT1, ARG1, BCL2, CASP3, CASP9, CYP3A4, EGFR, GPBAR1, HPGDS, MAPK14, MIF, NFE2L2, PTGS2, TNFSF11
Peripheral membrane protein 1 PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 5 BCL2, CYP19A1, CYP3A4, EGFR, PTGS2
Nucleus 10 AKT1, ARG1, BCL2, CASP3, CASP9, EGFR, GPX4, MAPK14, NFE2L2, PCNA
cytosol 10 AKT1, ARG1, BCL2, CASP3, CASP9, GPX4, HPGDS, MAPK14, MIF, NFE2L2
nuclear body 1 PCNA
centrosome 2 NFE2L2, PCNA
nucleoplasm 7 AKT1, CASP3, HPGDS, MAPK14, MIF, NFE2L2, PCNA
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 6 AKT1, EGFR, GPBAR1, GPRC5A, TNF, TNFSF11
lamellipodium 1 AKT1
ruffle membrane 1 EGFR
Cytoplasmic granule 1 ARG1
Early endosome membrane 1 EGFR
Multi-pass membrane protein 3 CYP19A1, GPBAR1, GPRC5A
cell cortex 1 AKT1
cell junction 1 EGFR
cell surface 3 EGFR, MIF, TNF
glutamatergic synapse 4 AKT1, CASP3, EGFR, MAPK14
Golgi apparatus 1 NFE2L2
Golgi membrane 1 EGFR
neuronal cell body 2 CASP3, TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 1 NFE2L2
endosome 1 EGFR
plasma membrane 8 AKT1, EGFR, GPBAR1, GPRC5A, MIF, NFE2L2, TNF, TNFSF11
Membrane 6 AKT1, BCL2, CYP19A1, CYP3A4, EGFR, TNFSF11
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 4 GPRC5A, GPX4, MIF, PCNA
endoplasmic reticulum 3 BCL2, CYP19A1, PTGS2
extracellular space 6 ARG1, EGFR, IL6, MIF, TNF, TNFSF11
perinuclear region of cytoplasm 1 EGFR
mitochondrion 4 BCL2, CASP9, GPX4, MAPK14
protein-containing complex 6 AKT1, BCL2, CASP9, EGFR, GPX4, PTGS2
intracellular membrane-bounded organelle 3 CYP3A4, GPRC5A, HPGDS
Microsome membrane 3 CYP19A1, CYP3A4, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EGFR
Secreted 3 IL6, MIF, TNFSF11
extracellular region 6 ARG1, IL6, MAPK14, MIF, TNF, TNFSF11
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
external side of plasma membrane 1 TNF
microtubule cytoskeleton 1 AKT1
nucleolus 1 GPRC5A
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
vesicle 3 AKT1, GPRC5A, MIF
Membrane raft 2 EGFR, TNF
pore complex 1 BCL2
focal adhesion 1 EGFR
spindle 1 AKT1
intracellular vesicle 1 EGFR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 3 EGFR, GPBAR1, GPRC5A
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 2 NFE2L2, PCNA
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
spindle pole 1 MAPK14
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
nuclear envelope 1 GPX4
Cytoplasmic vesicle membrane 1 GPRC5A
replication fork 1 PCNA
myelin sheath 1 BCL2
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 2 MAPK14, MIF
secretory granule lumen 2 MAPK14, MIF
endoplasmic reticulum lumen 2 IL6, PTGS2
male germ cell nucleus 1 PCNA
specific granule lumen 1 ARG1
azurophil granule lumen 1 ARG1
apoptosome 1 CASP9
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
nuclear lamina 1 PCNA
clathrin-coated endocytic vesicle membrane 1 EGFR
protein-DNA complex 1 NFE2L2
death-inducing signaling complex 1 CASP3
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
BAD-BCL-2 complex 1 BCL2
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Wenhao Zheng, Shi Yang, Xin Chen. The pharmacological and pharmacokinetic properties of obacunone from citrus fruits: A comprehensive narrative review. Fitoterapia. 2023 Sep; 169(?):105569. doi: 10.1016/j.fitote.2023.105569. [PMID: 37315716]
  • Yongli Han, Lingling Luo, Hongli Li, Lijun Zhang, Yingxuan Yan, Minglv Fang, Jing Yu, Xiaoyan Gao, Ying Liu, Cheng Huang, Shengjie Fan. Nomilin and its analogue obacunone alleviate NASH and hepatic fibrosis in mice via enhancing antioxidant and anti-inflammation capacity. BioFactors (Oxford, England). 2023 Jul; ?(?):. doi: 10.1002/biof.1987. [PMID: 37401768]
  • Jie Pan, Chutian Wu, Rong Tan, Yufen Liao, Guode Zhao, Wei Li, Ying Peng, Weiwei Li, Jiang Zheng. Difference in hepatotoxicity of furan-containing components in cortex dictamni correlates the efficiency of their metabolic activation. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 114(?):154778. doi: 10.1016/j.phymed.2023.154778. [PMID: 36996529]
  • Huimin Hu, Xiaodong Wang, Yansheng Huang, Baorong He, Jinwen Zhu, Kai Sun, Chaoyang Deng, Yunshan Guo, Dingjun Hao, Bin Jian. Obacunone inhibits RANKL/M-CSF-mediated osteoclastogenesis by suppressing integrin- FAK-Src signaling. Cytokine. 2023 Feb; 164(?):156134. doi: 10.1016/j.cyto.2023.156134. [PMID: 36804257]
  • Jianbo He, Lin Zheng, Xiaojuan Li, Furong Huang, Sitao Hu, Lei Chen, Manya Jiang, Xianfeng Lin, Haibo Jiang, Yifan Zeng, Tianshen Ye, Dingkun Lin, Qian Liu, Jiake Xu, Kai Chen. Obacunone targets macrophage migration inhibitory factor (MIF) to impede osteoclastogenesis and alleviate ovariectomy-induced bone loss. Journal of advanced research. 2023 Jan; ?(?):. doi: 10.1016/j.jare.2023.01.003. [PMID: 36657717]
  • Raduis Melong, Pierre Carolle Tamokoue Kengne, Jean Paul Dzoyem, Angelbert Awantu Fusi, Eric Allemann, Florence Delie, Christian G Bochet, Uwe Beifuss, Gilbert Deccaux Wabo Fotso Kapche. New cytotoxic obacunone-type limonoid and others constituents from the stem bark of Carapa procera DC (Meliaceae). Natural product research. 2022 Jun; 36(11):2783-2790. doi: 10.1080/14786419.2021.1927024. [PMID: 33993799]
  • Qian Li, Yong Gao, Maoyu Wang. Selective and reliable determination of obacunone in rat plasma using solid-phase extraction by liquid chromatography tandem mass spectrometry: Application to a pharmacokinetic study. Biomedical chromatography : BMC. 2021 Apr; 35(4):e5031. doi: 10.1002/bmc.5031. [PMID: 33217008]
  • Armelle T Mbaveng, Cédric G T Noulala, Anne R M Samba, Simplice B Tankeo, Ghislain W Fotso, Emmanuel N Happi, Bonaventure T Ngadjui, Veronique P Beng, Victor Kuete, Thomas Efferth. Cytotoxicity of botanicals and isolated phytochemicals from Araliopsis soyauxii Engl. (Rutaceae) towards a panel of human cancer cells. Journal of ethnopharmacology. 2021 Mar; 267(?):113535. doi: 10.1016/j.jep.2020.113535. [PMID: 33166626]
  • Da-Rui Huang, Chang-Ming Dai, Shu-Yan Li, Xiao-Feng Li. Obacunone protects retinal pigment epithelium cells from ultra-violet radiation-induced oxidative injury. Aging. 2021 02; 13(8):11010-11025. doi: 10.18632/aging.202437. [PMID: 33535179]
  • Yongquan Bai, Wenwen Wang, Li Wang, Lirong Ma, Dongsheng Zhai, Furong Wang, Rui Shi, Chaoyang Liu, Qing Xu, Guo Chen, Zifan Lu. Obacunone Attenuates Liver Fibrosis with Enhancing Anti-Oxidant Effects of GPx-4 and Inhibition of EMT. Molecules (Basel, Switzerland). 2021 Jan; 26(2):. doi: 10.3390/molecules26020318. [PMID: 33435504]
  • Yulin Ren, A Douglas Kinghorn. Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones. Journal of medicinal chemistry. 2020 12; 63(24):15410-15448. doi: 10.1021/acs.jmedchem.0c01449. [PMID: 33289552]
  • Xiaoping Luo, Zhilun Yu, Bei Yue, Junyu Ren, Jing Zhang, Sridhar Mani, Zhengtao Wang, Wei Dou. Obacunone reduces inflammatory signalling and tumour occurrence in mice with chronic inflammation-induced colorectal cancer. Pharmaceutical biology. 2020 Dec; 58(1):886-897. doi: 10.1080/13880209.2020.1812673. [PMID: 32878512]
  • Xiuzhuang Lang, Xiangmei Zhang, Daoquan Wang, Weiqing Zhou. In Vitro and In Vivo Metabolic Activation of Obacunone, A Bioactive and Potentially Hepatotoxic Constituent of Dictamni Cortex. Planta medica. 2020 Jul; 86(10):686-695. doi: 10.1055/a-1152-8169. [PMID: 32365393]
  • Jing Xie, Ai-Hua Zhang, Shi Qiu, Tian-Lei Zhang, Xian-Na Li, Guang-Li Yan, Hui Sun, Liang Liu, Xi-Jun Wang. Identification of the perturbed metabolic pathways associating with prostate cancer cells and anticancer affects of obacunone. Journal of proteomics. 2019 08; 206(?):103447. doi: 10.1016/j.jprot.2019.103447. [PMID: 31326558]
  • Jie Zhou, Tianyang Wang, Haoze Wang, Yinjie Jiang, Shaojun Peng. Obacunone attenuates high glucose-induced oxidative damage in NRK-52E cells by inhibiting the activity of GSK-3β. Biochemical and biophysical research communications. 2019 05; 513(1):226-233. doi: 10.1016/j.bbrc.2019.03.201. [PMID: 30954216]
  • Qiongyin Fan, Baosheng Zhao, Chunguo Wang, Jingxuan Zhang, Jinying Wu, Ting Wang, Anlong Xu. Subchronic Toxicity Studies of Cortex Dictamni Extracts in Mice and Its Potential Hepatotoxicity Mechanisms in Vitro. Molecules (Basel, Switzerland). 2018 Sep; 23(10):. doi: 10.3390/molecules23102486. [PMID: 30274140]
  • Yuan Gao, Rui Hou, Fen Liu, Haibo Liu, Qiaoling Fei, Yixin Han, Runlan Cai, Cheng Peng, Yun Qi. Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro-inflammatory mediators through intracellular MIF. Journal of cellular biochemistry. 2018 01; 119(1):837-849. doi: 10.1002/jcb.26248. [PMID: 28657665]
  • Taijun Yin, Guanyi Yang, Yong Ma, Beibei Xu, Ming Hu, Ming You, Song Gao. Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). Journal of ethnopharmacology. 2015 Aug; 172(?):195-201. doi: 10.1016/j.jep.2015.06.019. [PMID: 26099633]
  • Kotamballi N Chidambara Murthy, Guddadarangavvanahally K Jayaprakasha, Bhimanagouda S Patil. Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death. Toxicology. 2015 Mar; 329(?):88-97. doi: 10.1016/j.tox.2015.01.008. [PMID: 25592883]
  • Wei Ren, Yan Li, Ran Zuo, Hong-Jie Wang, Nan Si, Hai-Yu Zhao, Ling-Yu Han, Jian Yang, Bao-Lin Bian. Species-related difference between limonin and obacunone among five liver microsomes and zebrafish using ultra-high-performance liquid chromatography coupled with a LTQ-Orbitrap mass spectrometer. Rapid communications in mass spectrometry : RCM. 2014 Nov; 28(21):2292-300. doi: 10.1002/rcm.7026. [PMID: 25279742]
  • Jeongyeon Yoon, Minjin Park, Jeong hyung Lee, Byung Sun Min, Sungwoo Ryoo. Endothelial nitric oxide synthase activation through obacunone-dependent arginase inhibition restored impaired endothelial function in ApoE-null mice. Vascular pharmacology. 2014 Mar; 60(3):102-9. doi: 10.1016/j.vph.2014.01.006. [PMID: 24509132]
  • Pei Wang, Jianbo Sun, Enze Gao, Yunli Zhao, Wei Qu, Zhiguo Yu. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jun; 928(?):44-51. doi: 10.1016/j.jchromb.2013.03.018. [PMID: 23611843]
  • Chao Zhang. [Determination of obacunone and obaculactone in different processing products of Phellodendri amurensis cortex]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Feb; 36(2):205-8. doi: . [PMID: 23901643]
  • Yian Wang, Ruisheng Yao, Song Gao, Weidong Wen, Yinqiu Du, Eva Szabo, Ming Hu, Ronald A Lubet, Ming You. Chemopreventive effect of a mixture of Chinese Herbs (antitumor B) on chemically induced oral carcinogenesis. Molecular carcinogenesis. 2013 Jan; 52(1):49-56. doi: 10.1002/mc.20877. [PMID: 22086836]
  • Eri Ono, Jun Inoue, Tsutomu Hashidume, Makoto Shimizu, Ryuichiro Sato. Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. Biochemical and biophysical research communications. 2011 Jul; 410(3):677-81. doi: 10.1016/j.bbrc.2011.06.055. [PMID: 21693102]
  • Kotamballi N Chidambara Murthy, Guddadarangavvanahally K Jayaprakasha, Bhimanagouda S Patil. Apoptosis mediated cytotoxicity of citrus obacunone in human pancreatic cancer cells. Toxicology in vitro : an international journal published in association with BIBRA. 2011 Jun; 25(4):859-67. doi: 10.1016/j.tiv.2011.02.006. [PMID: 21333732]
  • Qian Zhang, Lifen Cai, Guoyue Zhong, Weizao Luo. [Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Aug; 35(16):2061-4. doi: . [PMID: 21046728]
  • Jeong Seon Yoon, Sang Hyun Sung, Young Choong Kim. Neuroprotective limonoids of root bark of Dictamnus dasycarpus. Journal of natural products. 2008 Feb; 71(2):208-11. doi: 10.1021/np070588o. [PMID: 18198838]
  • Giuseppe Ruberto, Agatino Renda, Corrado Tringali, Edoardo M Napoli, Monique S J Simmonds. Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study. Journal of agricultural and food chemistry. 2002 Nov; 50(23):6766-74. doi: 10.1021/jf020607u. [PMID: 12405773]
  • J K Rugutt, K J Rugutt, D K Berner. Limonoids from Nigerian Harrisonia abyssinica and their stimulatory activity against Striga hermonthica seeds. Journal of natural products. 2001 Nov; 64(11):1434-8. doi: 10.1021/np0100183. [PMID: 11720527]
  • K Fukuda, T Ohta, Y Yamazoe. Grapefruit component interacting with rat and human P450 CYP3A: possible involvement of non-flavonoid components in drug interaction. Biological & pharmaceutical bulletin. 1997 May; 20(5):560-4. doi: 10.1248/bpb.20.560. [PMID: 9178939]