Protopine (BioDeep_00000000076)

 

Secondary id: BioDeep_00000397983

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one

化学式: C20H19NO5 (353.12631640000006)
中文名称: 双花母草素, 原阿片碱, 原鸦片碱, 全能花素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

分子结构信息

SMILES: CN(C5)Cc(c1CC(=O)c(c3)c(C5)cc(O4)c(OC4)3)c(O2)c(OC2)cc1
InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

描述信息

Protopine is a dibenzazecine alkaloid isolated from Fumaria vaillantii. It has a role as a plant metabolite.
Protopine is a natural product found in Corydalis heterocarpa var. japonica, Fumaria capreolata, and other organisms with data available.
Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic.
See also: Sanguinaria canadensis root (part of); Chelidonium majus flowering top (part of).
Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic [HMDB]
Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic.

Protopine is an alkaloid occurring in opium poppy,[2] Corydalis tubers[3] and other plants of the family papaveraceae, like Fumaria officinalis.[4] Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.[5]

It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[6][7]

Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].
Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].

同义名列表

42 个代谢物同义名

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one; 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0⁴,¹².0⁶,¹⁰.0¹⁸,²²]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one; 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one; 7-methyl-4H,6H,8H,9H,12H,16H-1,3-dioxoleno[4,5-3,4]benzo[1,2-8, 9]azecino[5,4-2,1]benzo[4,5-d]1,3-dioxolan-15-one; 7-methyl-6,8,9,16-tetrahydro-[1,3]dioxolo[4,5:5,6]benzo[1,2-c][1,3]dioxolo[5,4:4,5]benzo[1,2-g]azecin-15(7H)-one; 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5:5,6]benzo[1,2-c][1,3]dioxolo[5,4:4,5]benzo[1,2-g]azecin-15(16H)-one; 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5:5,6]benzo[1,2-c][1,3]dioxolo[5,4:4,5]benzo[1,2-g]azecin-; Bis[1,3]benzodioxolo[4,5-c:5,6-g]azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-; Bis(1,3)benzodioxolo(4,5-C:5,6-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-; 4,6,7,14-tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5,6-g)azecin-13(5H)-one; 7-Methyl-6,8,9,16-tetrahydrodi[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one #; 4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c-5,6-g]azecin-13(5H)-one; 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c:5,6-g)azecin-13(5h)-one; 7-methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one; 7-methyl-6,8,9,16-tetrahydrobis(1,3)benzodioxolo(4,5-c:5,6-g)azecin-15(7H)-one; 4,6,7,14-Tetrahydro-5-methylbis[1,3]benzodioxolo[4,5-c:5,6-g]azecin-13(5H)-one; 7-Methyl-6,8,9,16-tetrahydrodi[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one; 7-methyl-2,3:9,10-bis(methylenebis(oxy))-7,13a-secoberbin-13a-one; 7-methyl-2,3:9,10-bis[methylenebis(oxy)]-7,13a-secoberbin-13a-one; 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-; 7-Methyl-2,3:9,10-bis(methylenedioxy)-7,13a-secoberbin-13a-one; 2D13E16B-20F9-4670-AD3E-02EE26A53C9C; Protopine, analytical standard; GPTFURBXHJWNHR-UHFFFAOYSA-N; protopine hydrochloride; Protopine (Corydinine); protopine mesylate; PROTOPINE [MI]; Oprea1_718853; Oprea1_722246; HSCI1_000268; ACon1_001550; Corydalis C; Hypercorine; Corydinine; Protopine; AI3-62909; Biflorine; Macleyine; fumarine; Protopin; Alk-3



数据库引用编号

55 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

27 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(25)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

273 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

  • Hongjie Chen, Yiming Zhong, Weilin Sang, Cong Wang, Haiming Lu, Peng Lai, Libo Zhu, Jinzhong Ma. Protopine protects chondrocytes from undergoing ferroptosis by activating Nrf2 pathway. Biochemical and biophysical research communications. 2024 May; 710(?):149599. doi: 10.1016/j.bbrc.2024.149599. [PMID: 38608493]
  • Meishan Yue, Jialu Huang, Xiaolan Ma, Peng Huang, Yisong Liu, Jianguo Zeng. Protopine Alleviates Dextran Sodium Sulfate-Induced Ulcerative Colitis by Improving Intestinal Barrier Function and Regulating Intestinal Microbiota. Molecules (Basel, Switzerland). 2023 Jul; 28(13):. doi: 10.3390/molecules28135277. [PMID: 37446938]
  • Sravan Gopalkrishnashetty Sreenivasmurthy, Ashok Iyaswamy, Senthilkumar Krishnamoorthi, Sanjib Senapati, Sandeep Malampati, Zhou Zhu, Cheng-Fu Su, Jia Liu, Xin-Jie Guan, Benjamin Chun-Kit Tong, King-Ho Cheung, Jie-Qiong Tan, Jia-Hong Lu, Siva Sundara Kumar Durairajan, Ju-Xian Song, Min Li. Protopine promotes the proteasomal degradation of pathological tau in Alzheimer's disease models via HDAC6 inhibition. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Feb; 96(?):153887. doi: 10.1016/j.phymed.2021.153887. [PMID: 34936968]
  • Xiaohui Zhang, Yule Wang, Kai Zhang, Hongda Sheng, Yuhan Wu, Huimin Wu, Yingchao Wang, Jianli Guan, Qingfen Meng, Huahuan Li, Zhenhao Li, Guanwei Fan, Yi Wang. Discovery of tetrahydropalmatine and protopine regulate the expression of dopamine receptor D2 to alleviate migraine from Yuanhu Zhitong formula. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Oct; 91(?):153702. doi: 10.1016/j.phymed.2021.153702. [PMID: 34419734]
  • Tian-Hua Wu, Jun-Hui Zhou, Yu-Yang Zhao, Yu-Jie Wei, Fang Chen, Yong-Fu Gong, Yuan Yuan, Lu-Qi Huang. [Genetic diversity of protopine-6-hydroxylase in three medicinal Papaver plants]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2021 Aug; 46(16):4111-4116. doi: 10.19540/j.cnki.cjcmm.20210522.102. [PMID: 34467721]
  • K B Pandeya, Aditya Ganeshpurkar, Mahendra Kumar Mishra. Natural RNA dependent RNA polymerase inhibitors: Molecular docking studies of some biologically active alkaloids of Argemone mexicana. Medical hypotheses. 2020 Nov; 144(?):109905. doi: 10.1016/j.mehy.2020.109905. [PMID: 32535456]
  • Beibei Zhang, Mengnan Zeng, Meng Li, Yuxuan Kan, Benke Li, Ruiqi Xu, Yuanyuan Wu, Shengchao Wang, Xiaoke Zheng, Weisheng Feng. Protopine Protects Mice against LPS-Induced Acute Kidney Injury by Inhibiting Apoptosis and Inflammation via the TLR4 Signaling Pathway. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010015. [PMID: 31861525]
  • Jerald J Nair, Johannes van Staden. Antiprotozoal alkaloid principles of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2019 10; 29(20):126642. doi: 10.1016/j.bmcl.2019.126642. [PMID: 31515186]
  • Minghui Sun, Lingling Zhao, Kai Wang, Lida Han, Jihao Shan, Liming Wu, Xiaofeng Xue. Rapid identification of 'mad honey' from Tripterygium wilfordii Hook. f. and Macleaya cordata (Willd) R. Br using UHPLC/Q-TOF-MS. Food chemistry. 2019 Oct; 294(?):67-72. doi: 10.1016/j.foodchem.2019.05.028. [PMID: 31126506]
  • Cuiting Wu, Xin Wang, Ming Xu, Youping Liu, Xin Di. Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132410. [PMID: 31261913]
  • Younglim Son, Younju An, Jaeyeon Jung, Sora Shin, InWha Park, Jungsug Gwak, Bong Gun Ju, Young-Hwa Chung, MinKyun Na, Sangtaek Oh. Protopine isolated from Nandina domestica induces apoptosis and autophagy in colon cancer cells by stabilizing p53. Phytotherapy research : PTR. 2019 Jun; 33(6):1689-1696. doi: 10.1002/ptr.6357. [PMID: 30932278]
  • Ke Li, Junfang Li, Jin Su, Xuefeng Xiao, Xiujuan Peng, Feng Liu, Defeng Li, Yi Zhang, Tao Chong, Haiyu Xu, Changxiao Liu, Hongjun Yang. Identification of quality markers of Yuanhu Zhitong tablets based on integrative pharmacology and data mining. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):212-219. doi: 10.1016/j.phymed.2018.03.002. [PMID: 29551644]
  • Hongbing Zhang, Xin Wu, Jun Xu, Suxiao Gong, Yanqi Han, Tiejun Zhang, Changxiao Liu. The comparative pharmacokinetic study of Yuanhu Zhitong prescription based on five quality-markers. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):148-154. doi: 10.1016/j.phymed.2018.02.005. [PMID: 29523382]
  • Ya-Jun Huang, Pi Cheng, Zhuo-Yi Zhang, Shi-Jie Tian, Zhi-Liang Sun, Jian-Guo Zeng, Zhao-Ying Liu. Biotransformation and tissue distribution of protopine and allocryptopine and effects of Plume Poppy Total Alkaloid on liver drug-metabolizing enzymes. Scientific reports. 2018 01; 8(1):537. doi: 10.1038/s41598-017-18816-7. [PMID: 29323165]
  • Elsayed Mickdam, Ratchaneewan Khiaosa-Ard, Barbara U Metzler-Zebeli, Fenja Klevenhusen, Remigius Chizzola, Qendrim Zebeli. Rumen microbial abundance and fermentation profile during severe subacute ruminal acidosis and its modulation by plant derived alkaloids in vitro. Anaerobe. 2016 Jun; 39(?):4-13. doi: 10.1016/j.anaerobe.2016.02.002. [PMID: 26868619]
  • Vamshi K Manda, Mohamed A Ibrahim, Olivia R Dale, Mallika Kumarihamy, Stephen J Cutler, Ikhlas A Khan, Larry A Walker, Ilias Muhammad, Shabana I Khan. Modulation of CYPs, P-gp, and PXR by Eschscholzia californica (California Poppy) and Its Alkaloids. Planta medica. 2016 Apr; 82(6):551-8. doi: 10.1055/s-0042-103689. [PMID: 27054913]
  • Rica Capistrano I, An Wouters, Filip Lardon, Claudia Gravekamp, Sandra Apers, Luc Pieters. In vitro and in vivo investigations on the antitumour activity of Chelidonium majus. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Dec; 22(14):1279-87. doi: 10.1016/j.phymed.2015.10.013. [PMID: 26626193]
  • Lidiya Georgieva, Ivan Ivanov, Andrey Marchev, Ina Aneva, Panteley Denev, Vasil Georgiev, Atanas Pavlov. Protopine production by fumaria cell suspension cultures: effect of light. Applied biochemistry and biotechnology. 2015 May; 176(1):287-300. doi: 10.1007/s12010-015-1574-6. [PMID: 25820387]
  • Tsvetelina Doncheva, Amgalan Solongo, Nadezhda Kostova, Yadamsuren Gerelt-Od, Dangaa Selenge, Stefan Philipov. Leptopyrine, new alkaloid from Leptopyrum fumarioides L. (Ranunculaceae). Natural product research. 2015; 29(9):853-6. doi: 10.1080/14786419.2014.991322. [PMID: 25529023]
  • Jia-jia Yu, Deng-li Cong, Ying Jiang, Yuan Zhou, Yan Wang, Chun-fang Zhao. [Study on alkaloids of Corydalis ochotensis and their antitumor bioactivity]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Oct; 37(10):1795-8. doi: . [PMID: 25895386]
  • C Moser, S P Vickers, R Brammer, S C Cheetham, J Drewe. Antidiabetic effects of the Cimicifuga racemosa extract Ze 450 in vitro and in vivo in ob/ob mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Sep; 21(11):1382-9. doi: 10.1016/j.phymed.2014.06.002. [PMID: 25022210]
  • Xiaochen Huang, Shulan Su, Wenxia Cui, Pei Liu, Jin-Ao Duan, Jianming Guo, Zhenhao Li, Erxin Shang, Dawei Qian, Zhijun Huang. Simultaneous determination of paeoniflorin, albiflorin, ferulic acid, tetrahydropalmatine, protopine, typhaneoside, senkyunolide I in Beagle dogs plasma by UPLC-MS/MS and its application to a pharmacokinetic study after Oral Administration of Shaofu Zhuyu Decoction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 962(?):75-81. doi: 10.1016/j.jchromb.2014.05.032. [PMID: 24907546]
  • Kai He, Jian-Li Gao. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2014; 11(2):415-24. doi: 10.4314/ajtcam.v11i2.28. [PMID: 25435628]
  • Phurpa Wangchuk, Wangchuk Phurpa, Paul A Keller, Stephen G Pyne, Wilford Lie, Anthony C Willis, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan. A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. Journal of ethnopharmacology. 2013 Dec; 150(3):953-9. doi: 10.1016/j.jep.2013.09.052. [PMID: 24120516]
  • Lamine Bournine, Sihem Bensalem, Jean-Noël Wauters, Mokrane Iguer-Ouada, Fadila Maiza-Benabdesselam, Fatiha Bedjou, Vincent Castronovo, Akeila Bellahcène, Monique Tits, Michel Frédérich. Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum. International journal of molecular sciences. 2013 Dec; 14(12):23533-44. doi: 10.3390/ijms141223533. [PMID: 24317429]
  • Sanggil Choe, Eunjung Lee, Gang-nam Jin, Yang Han Lee, Soo Young Kim, Hwakyung Choi, Heesun Chung, Bang Yeon Hwang, Suncheun Kim. Genetic and chemical components analysis of Papaver setigerum naturalized in Korea. Forensic science international. 2012 Oct; 222(1-3):387-93. doi: 10.1016/j.forsciint.2012.08.002. [PMID: 22921420]
  • Hongda Ma, Qingchun Zhao, Yongjun Wang, Tao Guo, Ye An, Guobing Shi. Design and evaluation of self-emulsifying drug delivery systems of Rhizoma corydalis decumbentis extracts. Drug development and industrial pharmacy. 2012 Oct; 38(10):1200-6. doi: 10.3109/03639045.2011.643897. [PMID: 22512784]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Anthony C Willis, Sumalee Kamchonwongpaisan. Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. Journal of ethnopharmacology. 2012 Aug; 143(1):310-3. doi: 10.1016/j.jep.2012.06.037. [PMID: 22796506]
  • Xiaomeng Chen, Yingchun Zhang, Shuo Lin, Hongjun Yang, Hongwei Wu, Shaojing Li, Defeng Li, Haiyu Xu. [Study on absorption ingredients of yuanhuzhitong pill by everted intestinal sac method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jul; 37(13):2005-11. doi: . [PMID: 23019888]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Thanapat Sastraruji, Malai Taweechotipatr, Roonglawan Rattanajak, Aunchalee Tonsomboon, Sumalee Kamchonwongpaisan. Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa. Natural product communications. 2012 May; 7(5):575-80. doi: . [PMID: 22799079]
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  • Zhiying Dou, Kefeng Li, Ping Wang, Liu Cao. Effect of wine and vinegar processing of Rhizoma Corydalis on the tissue distribution of tetrahydropalmatine, protopine and dehydrocorydaline in rats. Molecules (Basel, Switzerland). 2012 Jan; 17(1):951-70. doi: 10.3390/molecules17010951. [PMID: 22258341]
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