Vincamine (BioDeep_00000000029)

 

Secondary id: BioDeep_00000411037

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

化学式: C21H26N2O3 (354.19433260000005)
中文名称: 阿朴长春胺酸乙酯, 太司尼克酸, 长春蔓胺, 长春花素, 长春花胺, 长春胺
谱图信息: 最多检出来源 Viridiplantae(otcml) 1.08%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Vincamine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/vincamine (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000000029). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)(C(=O)OC)O
InChI: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3

描述信息

Vincamine is a vinca alkaloid, an alkaloid ester, an organic heteropentacyclic compound, a methyl ester and a hemiaminal. It has a role as an antihypertensive agent, a vasodilator agent and a metabolite. It is functionally related to an eburnamenine.
Vincamine is a monoterpenoid indole alkaloid obtained from the leaves of *Vinca minor* with a vasodilatory property. Studies indicate that vincamine increases the regional cerebral blood flow.
Vincamine is a natural product found in Vinca difformis, Vinca major, and other organisms with data available.
A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.

Vincamine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1617-90-9 (retrieved 2024-07-01) (CAS RN: 1617-90-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2].
Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2].

同义名列表

82 个代谢物同义名

Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate; Methyl(41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate; methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate; methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0?,?.0?,??.0??,??]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate; methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate; methyl(15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate; (3.ALPHA.,14.BETA.,16.ALPHA.)-14,15-DIHYDRO-14-HYDROXYEBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER; Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-; Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-,methyl ester, (3alpha,14beta,16alpha)-; Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.); (3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acidmethyl ester; Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methylester, (3a,14b,16a)-; methyl 14beta-hydroxy-14,15-dihydro-3alpha,16alpha-eburnamenine-14alpha-carboxylate; methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate; 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester; Vincamine, analytical reference material; Alkaloid obtained from Vinca minor; VINCAMINE [EP MONOGRAPH]; Vincamine [INN:BAN:DCF]; Vincaminum [INN-Latin]; Methyl vincaminate; VINCAMINE [WHO-DD]; VINCAMINE [MART.]; Prestwick0_000271; Anasclerol (base); Prestwick1_000271; Cetal retard (TN); Prestwick2_000271; Prestwick3_000271; VINCAMINE [HSDB]; BCBcMAP01_000080; Vincamina [DCIT]; Vincamine, 98\\%; Vincamine (INN); VINCAMINE [INN]; Vinodrel retard; Tox21_111342_1; VINCAMINE [MI]; (+)-Vincamine; BPBio1_000158; Arteriovinca; Cetal retard; Pervincamine; Vincasaunier; Tox21_111342; Tox21_301968; Vinca-Minor; Cerebroxine; Vinkametrin; Vincafolina; Vinca-Ecobi; SMP1_000314; Anasclerol; Vincaminum; Vincapront; Vincamidol; Vincachron; Vincamina; Tripervan; Vincamine; Devincan; Angiopac; Minorine; Vincafor; Vincamin; Vincimax; Ocu-vinc; Vincapan; Vincadar; Decincan; Devinkan; Oxygeron; Vincagil; Monorin; Minorin; Pervone; Oxybral; Novicet; Equipur; Perval; Vraap; Isovincamine



数据库引用编号

60 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)

7 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

  • Ana-Maria Neculai, Gabriela Stanciu, Magdalena Mititelu. Determination of Active Ingredients, Mineral Composition and Antioxidant Properties of Hydroalcoholic Macerates of Vinca minor L. Plant from the Dobrogea Area. Molecules (Basel, Switzerland). 2023 Jul; 28(15):. doi: 10.3390/molecules28155667. [PMID: 37570636]
  • Hossam S El-Beltagi, Salwa M El-Sayed, Ahmed N Abdelhamid, Karim M Hassan, Walaa A Elshalakany, Mona Ibrahim Nossier, Nadiyah M Alabdallah, Nadi Awad Al-Harbi, Salem Mesfir Al-Qahtani, Doaa Bahaa Eldin Darwish, Zahid Khorshid Abbas, Hemmat A Ibrahim. Potentiating Biosynthesis of Alkaloids and Polyphenolic Substances in Catharanthus roseus Plant Using ĸ-Carrageenan. Molecules (Basel, Switzerland). 2023 Apr; 28(8):. doi: 10.3390/molecules28083642. [PMID: 37110876]
  • Dawn Su-Yin Sim, Sin-Yee Tang, Yun-Yee Low, Siew-Huah Lim, Toh-Seok Kam. Vobasine, vincamine, voaphylline, tacaman, and iboga alkaloids from Tabernaemontana corymbosa. Phytochemistry. 2022 Nov; 203(?):113384. doi: 10.1016/j.phytochem.2022.113384. [PMID: 36007666]
  • Akshata Patangrao Renushe, Anil Kumar Banothu, Kala Kumar Bharani, Lakshman Mekala, Jerald Mahesh Kumar, Dinesh Neeradi, Donga Durga Veera Hanuman, Ambica Gadige, Amit Khurana. Vincamine, an active constituent of Vinca rosea ameliorates experimentally induced acute lung injury in Swiss albino mice through modulation of Nrf-2/NF-κB signaling cascade. International immunopharmacology. 2022 Jul; 108(?):108773. doi: 10.1016/j.intimp.2022.108773. [PMID: 35453074]
  • Michael A Fawzy, Sherif A Maher, Mahmoud A El-Rehany, Nermeen N Welson, Nisreen K A Albezrah, Gaber El-Saber Batiha, Moustafa Fathy. Vincamine Modulates the Effect of Pantoprazole in Renal Ischemia/Reperfusion Injury by Attenuating MAPK and Apoptosis Signaling Pathways. Molecules (Basel, Switzerland). 2022 Feb; 27(4):. doi: 10.3390/molecules27041383. [PMID: 35209172]
  • Lu Li, Yu Su, Juejun Liu, Changzheng Chen. Efficacy of Vincamine treatment in a rat model of anterior ischemic optic neuropathy. European journal of ophthalmology. 2021 Nov; 31(6):3442-3449. doi: 10.1177/1120672120974283. [PMID: 33222520]
  • Rehab M El-Sayed, Rehab E Abo El Gheit, Ghada A Badawi. Vincamine protects against cisplatin induced nephrotoxicity via activation of Nrf2/HO-1 and hindering TLR4/ IFN-γ/CD44 cells inflammatory cascade. Life sciences. 2021 May; 272(?):119224. doi: 10.1016/j.lfs.2021.119224. [PMID: 33610575]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Sarah Al-Rashed, Abu Baker, Syed Sayeed Ahmad, Asad Syed, Ali H Bahkali, Abdallah M Elgorban, Mohd Sajid Khan. Vincamine, a safe natural alkaloid, represents a novel anticancer agent. Bioorganic chemistry. 2021 02; 107(?):104626. doi: 10.1016/j.bioorg.2021.104626. [PMID: 33450545]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Youssef M Shalaby, Esther T Menze, Samar S Azab, Azza S Awad. Involvement of Nrf2/HO-1 antioxidant signaling and NF-κB inflammatory response in the potential protective effects of vincamine against methotrexate-induced nephrotoxicity in rats: cross talk between nephrotoxicity and neurotoxicity. Archives of toxicology. 2019 05; 93(5):1417-1431. doi: 10.1007/s00204-019-02429-2. [PMID: 31020375]
  • Sara Abouzeid, Ulrike Beutling, Dirk Selmar. Stress-induced modification of indole alkaloids:Phytomodificines as a new category of specialized metabolites. Phytochemistry. 2019 Mar; 159(?):102-107. doi: 10.1016/j.phytochem.2018.12.015. [PMID: 30605851]
  • H S Nandini, Prakash Ramachandra Naik. Antidiabetic, antihyperlipidemic and antioxidant effect of Vincamine, in streptozotocin-induced diabetic rats. European journal of pharmacology. 2019 Jan; 843(?):233-239. doi: 10.1016/j.ejphar.2018.11.034. [PMID: 30496743]
  • David Braun, Douglas L Feinstein. The locus coeruleus neuroprotective drug vindeburnol normalizes behavior in the 5xFAD transgenic mouse model of Alzheimer's disease. Brain research. 2019 01; 1702(?):29-37. doi: 10.1016/j.brainres.2017.12.028. [PMID: 29274883]
  • Priyanka Verma, Shamshad Ahmad Khan, Nusrat Masood, N Manika, Abhishek Sharma, Neha Verma, Suaib Luqman, Ajay K Mathur. Differential rubisco content and photosynthetic efficiency of rol gene integrated Vinca minor transgenic plant: Correlating factors associated with morpho-anatomical changes, gene expression and alkaloid productivity. Journal of plant physiology. 2017 Dec; 219(?):12-21. doi: 10.1016/j.jplph.2017.09.004. [PMID: 28957691]
  • Sara Abouzeid, Ulrike Beutling, Frank Surup, Fatma M Abdel Bar, Mohamed M Amer, Farid A Badria, Mahdi Yahyazadeh, Mark Brönstrup, Dirk Selmar. Treatment of Vinca minor Leaves with Methyl Jasmonate Extensively Alters the Pattern and Composition of Indole Alkaloids. Journal of natural products. 2017 11; 80(11):2905-2909. doi: 10.1021/acs.jnatprod.7b00424. [PMID: 29131648]
  • Zerihun Demessie, Kathlyn N Woolfson, Fang Yu, Yang Qu, Vincenzo De Luca. The ATP binding cassette transporter, VmTPT2/VmABCG1, is involved in export of the monoterpenoid indole alkaloid, vincamine in Vinca minor leaves. Phytochemistry. 2017 Aug; 140(?):118-124. doi: 10.1016/j.phytochem.2017.04.019. [PMID: 28478314]
  • Ren Na, Liu Jiajia, Yang Dongliang, Peng Yingzi, Hong Juan, Liu Xiong, Zhao Nana, Zhou Jing, Luo Yitian. Indentification of vincamine indole alkaloids producing endophytic fungi isolated from Nerium indicum, Apocynaceae. Microbiological research. 2016 Nov; 192(?):114-121. doi: 10.1016/j.micres.2016.06.008. [PMID: 27664729]
  • Choy-Eng Nge, Kam-Weng Chong, Noel F Thomas, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam. Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution. Journal of natural products. 2016 05; 79(5):1388-99. doi: 10.1021/acs.jnatprod.6b00129. [PMID: 27077800]
  • Amir Akhgari, Into Laakso, Tuulikki Seppänen-Laakso, Teijo Yrjönen, Heikki Vuorela, Kirsi-Marja Oksman-Caldentey, Heiko Rischer. Determination of terpenoid indole alkaloids in hairy roots of Rhazya stricta (Apocynaceae) by GC-MS. Phytochemical analysis : PCA. 2015 Sep; 26(5):331-8. doi: 10.1002/pca.2567. [PMID: 26095837]
  • Kun Xu, Thomas Gilles, Bernhard Breit. Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines. Nature communications. 2015 Jul; 6(?):7616. doi: 10.1038/ncomms8616. [PMID: 26137886]
  • Hanlin Pu, Hua Jiang, Rongrong Chen, Hongcui Wang. Studies on the interaction between vincamine and human serum albumin: a spectroscopic approach. Luminescence : the journal of biological and chemical luminescence. 2014 Aug; 29(5):471-9. doi: 10.1002/bio.2572. [PMID: 24039032]
  • Priyanka Verma, Shamshad Ahmad Khan, Ajay Kumar Mathur, Karuna Shanker, Raj Kishori Lal. Regulation of vincamine biosynthesis and associated growth promoting effects through abiotic elicitation, cyclooxygenase inhibition, and precursor feeding of bioreactor grown Vinca minor hairy roots. Applied biochemistry and biotechnology. 2014 Jun; 173(3):663-72. doi: 10.1007/s12010-014-0883-5. [PMID: 24723203]
  • Dritan Hasa, Beatrice Perissutti, Stefano Dall'Acqua, Michele R Chierotti, Roberto Gobetto, Iztok Grabnar, Cinzia Cepek, Dario Voinovich. Rationale of using Vinca minor Linne dry extract phytocomplex as a vincamine's oral bioavailability enhancer. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2013 May; 84(1):138-44. doi: 10.1016/j.ejpb.2012.11.025. [PMID: 23238273]
  • Wen-Chuan Lee, Chih-Hsien Chang, Chih-Min Huang, Yu-Tse Wu, Liang-Cheng Chen, Chung-Li Ho, Tsui-Jung Chang, Te-Wei Lee, Tung-Hu Tsai. Correlation between radioactivity and chemotherapeutics of the (111)In-VNB-liposome in pharmacokinetics and biodistribution in rats. International journal of nanomedicine. 2012; 7(?):683-92. doi: 10.2147/ijn.s28279. [PMID: 22359447]
  • Hong Yin, Yu-Hong Sun. Vincamine-producing endophytic fungus isolated from Vinca minor. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Jun; 18(8-9):802-5. doi: 10.1016/j.phymed.2011.01.005. [PMID: 21315568]
  • Berrin Ozçelik, Murat Kartal, Ilkay Orhan. Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharmaceutical biology. 2011 Apr; 49(4):396-402. doi: 10.3109/13880209.2010.519390. [PMID: 21391841]
  • Entai Hou, Yingjuan Wang, Duowei Li, Na Li, Hongdong Chen, Huaiyu Bu. [Tissue culture of Vinca minor and determination of vincamine]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Apr; 36(7):823-7. doi: 10.4268/cjcmm20110702. [PMID: 21761716]
  • Abdel-Hasseb A Fayed. Brain trace element concentration of rats treated with the plant alkaloid, vincamine. Biological trace element research. 2010 Sep; 136(3):314-9. doi: 10.1007/s12011-009-8550-3. [PMID: 19902161]
  • Kuan-Hon Lim, Noel F Thomas, Zanariah Abdullah, Toh-Seok Kam. Seco-tabersonine alkaloids from Tabernaemontana corymbosa. Phytochemistry. 2009 Feb; 70(3):424-9. doi: 10.1016/j.phytochem.2009.01.001. [PMID: 19217125]
  • Amr Mohamed Beltagi. Development and validation of an adsorptive stripping voltammetric method for the quantification of vincamine in its formulations and human serum using a Nujol-based carbon paste electrode. Chemical & pharmaceutical bulletin. 2008 Dec; 56(12):1651-7. doi: 10.1248/cpb.56.1651. [PMID: 19043234]
  • B S Nayak, Lexley M Pinto Pereira. Catharanthus roseus flower extract has wound-healing activity in Sprague Dawley rats. BMC complementary and alternative medicine. 2006 Dec; 6(?):41. doi: 10.1186/1472-6882-6-41. [PMID: 17184528]
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  • Ying-Ping Juan, Tung-Hu Tsai. Measurement and pharmacokinetics of vincamine in rat blood and brain using microdialysis. Journal of chromatography. A. 2005 Sep; 1088(1-2):146-51. doi: 10.1016/j.chroma.2005.01.043. [PMID: 16130744]
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