Bruceine (BioDeep_00000000405)
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C20H26O9 (410.1577)
中文名称: 鸦胆子苦素D, 鸦胆子素 D, 鸦胆子素D
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 64.15%
分子结构信息
SMILES: CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O
InChI: InChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3
描述信息
Bruceine D is a quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 14 and 15 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity. It has a role as a metabolite, an antineoplastic agent and a plant metabolite. It is a delta-lactone, a pentol, a quassinoid, an organic heteropentacyclic compound and a secondary alpha-hydroxy ketone. It derives from a hydride of a picrasane.
Brucein D is a natural product found in Brucea javanica, Brucea mollis, and Samadera indica with data available.
A quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 11, 12, 14 and 15 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity.
Bruceine D is a Notch inhibitor with anti-cancer activity and induces apoptosis in several human cancer cells. Bruceine D is an effective botanical insect antifeedant with outstanding systemic properties, causing potent pest growth inhibitory activity[1][2]. Bruceine D has strong anthelmintic activity against D. intermedius with an EC50 value of 0.57 mg/L[3].
Bruceine D is a Notch inhibitor with anti-cancer activity and induces apoptosis in several human cancer cells. Bruceine D is an effective botanical insect antifeedant with outstanding systemic properties, causing potent pest growth inhibitory activity[1][2]. Bruceine D has strong anthelmintic activity against D. intermedius with an EC50 value of 0.57 mg/L[3].
同义名列表
10 个代谢物同义名
(1R,2S,3R,3aR,3a1R,4R,6aR,7aS,11S,11aS,11bR)-1,2,3a,4,11-pentahydroxy-3,8,11a-trimethyl-1,2,3,3a,4,7,7a,11,11a,11b-decahydro-5H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6aH)-dione; (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-Pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione; (1beta,11beta,12alpha,15beta)-1,11,12,14,15-pentahydroxy-13,20-epoxypicras-3-ene-2,16-dione; bruceine D; BruceineD; Brucein D; AC1L9BNP; Bruceine; 2,3,12,15,16-Pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione; Bruceine D
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:68931
- KEGG: C08752
- PubChem: 71463728
- PubChem: 441788
- PubChem: 432922
- Metlin: METLIN67171
- ChEMBL: CHEMBL4759543
- MeSH: bruceine D
- chemspider: 390380
- CAS: 21499-66-1
- medchemexpress: HY-N3014
- PMhub: MS000020160
- MetaboLights: MTBLC68931
- PubChem: 10945
- KNApSAcK: C00003702
- 3DMET: B02377
- NIKKAJI: J34.225D
- KNApSAcK: 68931
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)
6 个相关的物种来源信息
- 210348 - Brucea javanica:
- 210348 - Brucea javanica (L.)Merr.: -
- 43723 - Brucea mollis:
- 33090 - Plants: -
- 459147 - Samadera indica: 10.1016/S0031-9422(00)94782-4
- 33090 - 鸦胆子: -
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
- Xinhao Chen, Hua Li. Bruceine D and Narclasine inhibit the proliferation of breast cancer cells and the prediction of potential drug targets.
PloS one.
2024; 19(1):e0297203. doi:
10.1371/journal.pone.0297203. [PMID: 38215156] - Yao Tong, Shan-Chi Yi, Shu-Yu Liu, Lin Xu, Zhuo-Xun Qiu, Dong-Qiang Zeng, Wen-Wei Tang. Bruceine D may affect the phenylpropanoid biosynthesis by acting on ADTs thus inhibiting Bidens pilosa L. seed germination.
Ecotoxicology and environmental safety.
2022 Sep; 242(?):113943. doi:
10.1016/j.ecoenv.2022.113943. [PMID: 35999761] - Juan Zhang, Hong-Xi Xu, William Chi Shing Cho, Wah Cheuk, Yang Li, Qiong-Hui Huang, Wen Yang, Yan-Fang Xian, Zhi-Xiu Lin. Brucein D augments the chemosensitivity of gemcitabine in pancreatic cancer via inhibiting the Nrf2 pathway.
Journal of experimental & clinical cancer research : CR.
2022 Mar; 41(1):90. doi:
10.1186/s13046-022-02270-z. [PMID: 35272669] - 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] - Jian-Hui Xie, Zheng-Quan Lai, Xing-Han Zheng, Yan-Fang Xian, Qian Li, Siu-Po Ip, You-Liang Xie, Jian-Nan Chen, Zi-Ren Su, Zhi-Xiu Lin, Xiao-Bo Yang. Apoptosis induced by bruceine D in human non‑small‑cell lung cancer cells involves mitochondrial ROS‑mediated death signaling.
International journal of molecular medicine.
2019 Dec; 44(6):2015-2026. doi:
10.3892/ijmm.2019.4363. [PMID: 31638181] - Jiyeon Baek, Hyejeong Jeong, Youngwook Ham, Yang Hee Jo, Miri Choi, Mingu Kang, Bora Son, Sangho Choi, Hyung Won Ryu, Janghwan Kim, Haihong Shen, Kongmany Sydara, Sang Woo Lee, Soo-Yong Kim, Sang-Bae Han, Sei-Ryang Oh, Sungchan Cho. Improvement of spinal muscular atrophy via correction of the SMN2 splicing defect by Brucea javanica (L.) Merr. extract and Bruceine D.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Dec; 65(?):153089. doi:
10.1016/j.phymed.2019.153089. [PMID: 31563042] - Biqin Tan, Yuyu Huang, Lihua Lan, Bo Zhang, Lijun Ye, Wei Yan, Fei Wang, Nengming Lin. Bruceine D induces apoptosis in human non-small cell lung cancer cells through regulating JNK pathway.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2019 Sep; 117(?):109089. doi:
10.1016/j.biopha.2019.109089. [PMID: 31226632] - Yao-Xing Dou, Jiang-Tao Zhou, Tong-Tong Wang, Yan-Feng Huang, Vicky Ping Chen, You-Liang Xie, Zhi-Xiu Lin, Jian-Sheng Gao, Zi-Ren Su, Hui-Fang Zeng. Self-nanoemulsifying drug delivery system of bruceine D: a new approach for anti-ulcerative colitis.
International journal of nanomedicine.
2018; 13(?):5887-5907. doi:
10.2147/ijn.s174146. [PMID: 30319255] - Farahdina Man, Chee-Yan Choo. HPLC-MS/MS method for bioavailability study of bruceines D & E in rat plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Sep; 1063(?):183-188. doi:
10.1016/j.jchromb.2017.08.037. [PMID: 28869873] - Ziying Cheng, Xing Yuan, Yi Qu, Xia Li, Guozhen Wu, Chenwei Li, Xianpeng Zu, Niao Yang, Xisong Ke, Juan Zhou, Ning Xie, Xike Xu, Shanrong Liu, Yunheng Shen, Huiliang Li, Weidong Zhang. Bruceine D inhibits hepatocellular carcinoma growth by targeting β-catenin/jagged1 pathways.
Cancer letters.
2017 09; 403(?):195-205. doi:
10.1016/j.canlet.2017.06.014. [PMID: 28645563] - Yining Zhang, Yong Zhen, Ying Zhang, Shouyue Liu. Development and validation of a sensitive LC-MS/MS assay for quantification of bruceine D in rat plasma.
Biomedical chromatography : BMC.
2016 Nov; 30(11):1873-1876. doi:
10.1002/bmc.3724. [PMID: 27012305] - Lin Li, Po Sing Leung. Use of herbal medicines and natural products: an alternative approach to overcoming the apoptotic resistance of pancreatic cancer.
The international journal of biochemistry & cell biology.
2014 Aug; 53(?):224-36. doi:
10.1016/j.biocel.2014.05.021. [PMID: 24875648] - Zhangang Xiao, Sheung Ching Chow, Chi Han Li, Shing Chun Tang, Stephen K W Tsui, Zhixiu Lin, Yangchao Chen. Role of microRNA-95 in the anticancer activity of Brucein D in hepatocellular carcinoma.
European journal of pharmacology.
2014 Apr; 728(?):141-50. doi:
10.1016/j.ejphar.2014.02.002. [PMID: 24530415] - Hui Chen, Jian Bai, Zhen-Feng Fang, Shi-Shan Yu, Shuang-Gang Ma, Song Xu, Yong Li, Jing Qu, Jin-Hong Ren, Li Li, Yi-Kang Si, Xiao-Guang Chen. Indole alkaloids and quassinoids from the stems of Brucea mollis.
Journal of natural products.
2011 Nov; 74(11):2438-45. doi:
10.1021/np200712y. [PMID: 22070654] - Ajmi NoorShahida, Tin Wui Wong, Chee Yan Choo. Hypoglycemic effect of quassinoids from Brucea javanica (L.) Merr (Simaroubaceae) seeds.
Journal of ethnopharmacology.
2009 Jul; 124(3):586-91. doi:
10.1016/j.jep.2009.04.058. [PMID: 19439174] - Jian-Guo Shen, Zheng-Kun Zhang, Zu-Jian Wu, Ming-An Ouyang, Lian-Hui Xie, Qi-Ying Lin. Antiphytoviral activity of bruceine-D from Brucea javanica seeds.
Pest management science.
2008 Feb; 64(2):191-6. doi:
10.1002/ps.1465. [PMID: 17912689]
