Vindoline (BioDeep_00000002650)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Methyl (1S,9S,10R,11S,12S,19S)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

化学式: C25H32N2O6 (456.226)
中文名称: 文朵灵, 文多灵
谱图信息: 最多检出来源 Homo sapiens(blood) 24.18%

分子结构信息

SMILES: CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
InChI: InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3

描述信息

Vindoline is a vinca alkaloid, an alkaloid ester, an organic heteropentacyclic compound, a methyl ester, an acetate ester, a tertiary amino compound and a tertiary alcohol. It is a conjugate base of a vindolinium(1+).
Vindoline is a natural product found in Catharanthus ovalis, Catharanthus trichophyllus, and other organisms with data available.
Vindoline is an indole alkaloid that exhibits antimitotic activity by inhibiting microtubule assembly. (NCI)
D000970 - Antineoplastic Agents > D014748 - Vinca Alkaloids
C1744 - Multidrug Resistance Modulator
Vindoline, a vinca alkaloid extracted from the leaves of Catharanthus roseus, weakly inhibits tubulin self-assembly[1].
Vindoline, a vinca alkaloid extracted from the leaves of Catharanthus roseus, weakly inhibits tubulin self-assembly[1].

同义名列表

22 个代谢物同义名

Methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-5-hydroxy-8- methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1- cd]carbazole-5-carboxylate; ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYL-, METHYL ESTER, (2.BETA.,3.BETA.,4.BETA.,5.ALPHA.,12R,19.ALPHA.)-; (2.BETA.,3.BETA.,4.BETA.,5.ALPHA.,12.BETA.,19.ALPHA.)-4-(ACETYLOXY)-6,7-DIDEHYDRO-3-HYDROXY-16-METHOXY-1-METHYLASPIDOSPERMIDINE-3-CARBOXYLIC ACID METHYL ESTER; Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-; Aspidospermidine-3-carboxylic acid,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2.beta.,3.beta.,4.beta.,5.alpha.,12.beta.,19.alpha.)-; methyl 4beta-acetyloxy-3beta-hydroxy-16-methoxy-1-methyl-6,7-didehydro-2beta,5alpha,12beta,19alpha-aspidospermidine-3alpha-carboxylate; (2beta,3beta,4beta,5alpha,12beta,19alpha)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic acid; Methyl 4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; vindoline, monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer; vindoline, citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer; Vindoline, >=98.0\\% (HPLC); VINDOLINE [MI]; (-)-Vindoline; MEGxp0_001802; ACon1_000494; NCI60_042033; SMP2_000150; Vindoline; Vindolin; Methyl (1S,9S,10R,11S,12S,19S)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate; Methyl 11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate; Vindoline



数据库引用编号

28 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)

86 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 9 ABCB1, AIMP2, CASP9, CAT, CYP2B6, CYP3A4, PMP2, TNFSF11, TUBB4B
Peripheral membrane protein 3 CYP1B1, CYP2B6, GBA1
Endoplasmic reticulum membrane 4 CYP1A2, CYP1B1, CYP2B6, CYP3A4
Nucleus 4 AIMP2, CASP9, PMP2, TUBB4B
cytosol 7 AIMP2, CASP9, CAT, EHHADH, GSR, PMP2, TUBB4B
trans-Golgi network 1 GBA1
Cell membrane 3 ABCB1, TNF, TNFSF11
Multi-pass membrane protein 1 ABCB1
cell surface 2 ABCB1, TNF
Golgi apparatus 1 GBA1
Golgi membrane 1 INS
lysosomal membrane 2 GAA, GBA1
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 2 GAA, GBA1
plasma membrane 4 ABCB1, GAA, TNF, TNFSF11
Membrane 7 ABCB1, AIMP2, CAT, CYP1B1, CYP3A4, GAA, TNFSF11
apical plasma membrane 1 ABCB1
extracellular exosome 7 ABCB1, CAT, GAA, GBA1, GSR, PMP2, TUBB4B
Lysosome membrane 2 GAA, GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 1 GBA1
extracellular space 4 IL10, INS, TNF, TNFSF11
lysosomal lumen 2 GAA, GBA1
mitochondrion 5 CASP9, CAT, CYP1B1, GATC, GSR
protein-containing complex 2 CASP9, CAT
intracellular membrane-bounded organelle 6 CAT, CYP1A2, CYP1B1, CYP2B6, CYP3A4, GAA
Microsome membrane 4 CYP1A2, CYP1B1, CYP2B6, CYP3A4
Secreted 5 GAA, IL10, INS, PRB1, TNFSF11
extracellular region 8 CAT, GAA, IL10, INS, PRB1, TNF, TNFSF11, TUBB4B
mitochondrial matrix 2 CAT, GSR
external side of plasma membrane 2 GSR, TNF
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 1 TUBB4B
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Apical cell membrane 1 ABCB1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 1 CAT
microtubule 1 TUBB4B
Peroxisome 2 CAT, EHHADH
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, EHHADH
peroxisomal membrane 1 CAT
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
endosome lumen 1 INS
axonemal microtubule 1 TUBB4B
tertiary granule membrane 1 GAA
myelin sheath 1 PMP2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
transport vesicle 1 INS
azurophil granule membrane 1 GAA
azurophil granule lumen 1 TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
apoptosome 1 CASP9
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCB1
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
glutamyl-tRNA(Gln) amidotransferase complex 1 GATC
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
autolysosome lumen 1 GAA
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

  • Pooja Singh, Seema Yadav, Saumya Shah, Karuna Shanker, Velusamy Sundaresan, Ashutosh K Shukla. Characterization of a CrPME indicates its possible role in determining vindoline accumulation in Catharanthus roseus leaves. Physiologia plantarum. 2024 Mar; 176(2):e14276. doi: 10.1111/ppl.14276. [PMID: 38566244]
  • Maneesha Mall, Karuna Shanker, Dinesh A Nagegowda, Abdul Samad, Alok Kalra, Alok Pandey, Velusamy Sundaresan, Ashutosh K Shukla. Temperature-induced lipocalin-mediated membrane integrity: Possible implications for vindoline accumulation in Catharanthus roseus leaves. Physiologia plantarum. 2023 Sep; 175(5):e13994. doi: 10.1111/ppl.13994. [PMID: 37882277]
  • Maneesha Mall, Karuna Shanker, Abdul Samad, Alok Kalra, Velusamy Sundaresan, Ashutosh K Shukla. Stress responsiveness of vindoline accumulation in Catharanthus roseus leaves is mediated through co-expression of allene oxide cyclase with pathway genes. Protoplasma. 2022 May; 259(3):755-773. doi: 10.1007/s00709-021-01701-6. [PMID: 34459997]
  • Wenzhu Tang, Xiaoqi Liu, Yuning He, Fan Yang. Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation. Marine drugs. 2022 Mar; 20(3):. doi: 10.3390/md20030188. [PMID: 35323487]
  • Szabolcs Mayer, Nóra Nagy, Péter Keglevich, Áron Szigetvári, Miklós Dékány, Csaba Szántay Junior, László Hazai. Synthesis of Novel Vindoline-Chrysin Hybrids. Chemistry & biodiversity. 2022 Jan; 19(1):e202100725. doi: 10.1002/cbdv.202100725. [PMID: 34874114]
  • Natalja Kulagina, Grégory Guirimand, Céline Melin, Pamela Lemos-Cruz, Ines Carqueijeiro, Johan-Owen De Craene, Audrey Oudin, Vladimir Heredia, Konstantinos Koudounas, Marianne Unlubayir, Arnaud Lanoue, Nadine Imbault, Benoit St-Pierre, Nicolas Papon, Marc Clastre, Nathalie Giglioli-Guivarc'h, Jillian Marc, Sébastien Besseau, Vincent Courdavault. Enhanced bioproduction of anticancer precursor vindoline by yeast cell factories. Microbial biotechnology. 2021 11; 14(6):2693-2699. doi: 10.1111/1751-7915.13898. [PMID: 34302444]
  • Tengfei Liu, Ying Huang, Lihong Jiang, Chang Dong, Yuanwei Gou, Jiazhang Lian. Efficient production of vindoline from tabersonine by metabolically engineered Saccharomyces cerevisiae. Communications biology. 2021 09; 4(1):1089. doi: 10.1038/s42003-021-02617-w. [PMID: 34531512]
  • Pamela Lemos Cruz, Natalja Kulagina, Grégory Guirimand, Johan-Owen De Craene, Sébastien Besseau, Arnaud Lanoue, Audrey Oudin, Nathalie Giglioli-Guivarc'h, Nicolas Papon, Marc Clastre, Vincent Courdavault. Optimization of Tabersonine Methoxylation to Increase Vindoline Precursor Synthesis in Yeast Cell Factories. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123596. [PMID: 34208368]
  • Mediline Goboza, Mervin Meyer, Yapo G Aboua, Oluwafemi O Oguntibeju. In Vitro Antidiabetic and Antioxidant Effects of Different Extracts of Catharanthus roseus and Its Indole Alkaloid, Vindoline. Molecules (Basel, Switzerland). 2020 Nov; 25(23):. doi: 10.3390/molecules25235546. [PMID: 33256043]
  • Yongliang Liu, Barunava Patra, Sitakanta Pattanaik, Ying Wang, Ling Yuan. GATA and Phytochrome Interacting Factor Transcription Factors Regulate Light-Induced Vindoline Biosynthesis in Catharanthus roseus. Plant physiology. 2019 07; 180(3):1336-1350. doi: 10.1104/pp.19.00489. [PMID: 31123092]
  • Mediline Goboza, Yapo G Aboua, Novel Chegou, Oluwafemi O Oguntibeju. Vindoline effectively ameliorated diabetes-induced hepatotoxicity by docking oxidative stress, inflammation and hypertriglyceridemia in type 2 diabetes-induced male Wistar rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Apr; 112(?):108638. doi: 10.1016/j.biopha.2019.108638. [PMID: 30784928]
  • Yang Qu, Olga Safonova, Vincenzo De Luca. Completion of the canonical pathway for assembly of anticancer drugs vincristine/vinblastine in Catharanthus roseus. The Plant journal : for cell and molecular biology. 2019 01; 97(2):257-266. doi: 10.1111/tpj.14111. [PMID: 30256480]
  • Yang Qu, Antje M K Thamm, Matthew Czerwinski, Sayaka Masada, Kyung Hee Kim, Graham Jones, Ping Liang, Vincenzo De Luca. Geissoschizine synthase controls flux in the formation of monoterpenoid indole alkaloids in a Catharanthus roseus mutant. Planta. 2018 Mar; 247(3):625-634. doi: 10.1007/s00425-017-2812-7. [PMID: 29147812]
  • Bilal Ahmad, Anindyajit Banerjee, Harshita Tiwari, Shrabasti Jana, Sudeshna Bose, Saikat Chakrabarti. Structural and functional characterization of the Vindoline biosynthesis pathway enzymes of Catharanthus roseus. Journal of molecular modeling. 2018 Feb; 24(3):53. doi: 10.1007/s00894-018-3590-2. [PMID: 29442186]
  • Alison Edge, Yang Qu, Michael L A E Easson, Antje M K Thamm, Kyung Hee Kim, Vincenzo De Luca. A tabersonine 3-reductase Catharanthus roseus mutant accumulates vindoline pathway intermediates. Planta. 2018 Jan; 247(1):155-169. doi: 10.1007/s00425-017-2775-8. [PMID: 28894945]
  • Yuqian Zhang, Yupeng Sun, Xiyan Mu, Lin Yuan, Qiao Wang, Lantong Zhang. Identification of metabolites of vindoline in rats using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Aug; 1060(?):126-137. doi: 10.1016/j.jchromb.2017.05.038. [PMID: 28609700]
  • Alexis Kotland, Sébastien Chollet, Catherine Diard, Jean-Marie Autret, Jeremy Meucci, Jean-Hugues Renault, Luc Marchal. Industrial case study on alkaloids purification by pH-zone refining centrifugal partition chromatography. Journal of chromatography. A. 2016 Nov; 1474(?):59-70. doi: 10.1016/j.chroma.2016.10.039. [PMID: 27816224]
  • Shiv S Pandey, Sucheta Singh, C S Vivek Babu, Karuna Shanker, N K Srivastava, Ashutosh K Shukla, Alok Kalra. Fungal endophytes of Catharanthus roseus enhance vindoline content by modulating structural and regulatory genes related to terpenoid indole alkaloid biosynthesis. Scientific reports. 2016 05; 6(?):26583. doi: 10.1038/srep26583. [PMID: 27220774]
  • Wenjin Zhang, Jiazeng Yang, Jiachen Zi, Jianhua Zhu, Liyan Song, Rongmin Yu. Effects of Adding Vindoline and MeJA on Production of Vincristine and Vinblastine, and Transcription of their Biosynthetic Genes in the Cultured CMCs of Catharanthus roseus. Natural product communications. 2015 Dec; 10(12):2095-6. doi: . [PMID: 26882673]
  • Pengfei Zhou, Jiazeng Yang, Jianhua Zhu, Shuijie He, Wenjin Zhang, Rongmin Yu, Jiachen Zi, Liyan Song, Xuesong Huang. Effects of β-cyclodextrin and methyl jasmonate on the production of vindoline, catharanthine, and ajmalicine in Catharanthus roseus cambial meristematic cell cultures. Applied microbiology and biotechnology. 2015 Sep; 99(17):7035-45. doi: 10.1007/s00253-015-6651-9. [PMID: 25981997]
  • Franziska Kellner, Fernando Geu-Flores, Nathaniel H Sherden, Stephanie Brown, Emilien Foureau, Vincent Courdavault, Sarah E O'Connor. Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids. Chemical communications (Cambridge, England). 2015 May; 51(36):7626-8. doi: 10.1039/c5cc01309g. [PMID: 25850027]
  • Chongliang Lin, Jinzhang Cai, Xuezhi Yang, Lufeng Hu, Guanyang Lin. Liquid chromatography mass spectrometry simultaneous determination of vindoline and catharanthine in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2015 Jan; 29(1):97-102. doi: 10.1002/bmc.3244. [PMID: 24828449]
  • Priyanka Verma, Abhishek Sharma, Shamshad Ahmad Khan, Ajay Kumar Mathur, Karuna Shanker. Morphogenetic and chemical stability of long-term maintained Agrobacterium-mediated transgenic Catharanthus roseus plants. Natural product research. 2015; 29(4):315-20. doi: 10.1080/14786419.2014.940348. [PMID: 25102992]
  • Sébastien Besseau, Franziska Kellner, Arnaud Lanoue, Antje M K Thamm, Vonny Salim, Bernd Schneider, Fernando Geu-Flores, René Höfer, Grégory Guirimand, Anthony Guihur, Audrey Oudin, Gaëlle Glevarec, Emilien Foureau, Nicolas Papon, Marc Clastre, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Danièle Werck-Reichhart, Vincent Burlat, Vincenzo De Luca, Sarah E O'Connor, Vincent Courdavault. A pair of tabersonine 16-hydroxylases initiates the synthesis of vindoline in an organ-dependent manner in Catharanthus roseus. Plant physiology. 2013 Dec; 163(4):1792-803. doi: 10.1104/pp.113.222828. [PMID: 24108213]
  • Xin-gang Yao, Fanglei Chen, Ping Li, Lingling Quan, Jing Chen, Liang Yu, Hong Ding, Chenjing Li, Lili Chen, Zhaobing Gao, Ping Wan, Lihong Hu, Hualiang Jiang, Xu Shen. Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models. Journal of ethnopharmacology. 2013 Oct; 150(1):285-97. doi: 10.1016/j.jep.2013.08.043. [PMID: 24012527]
  • Inês Carqueijeiro, Henrique Noronha, Patrícia Duarte, Hernâni Gerós, Mariana Sottomayor. Vacuolar transport of the medicinal alkaloids from Catharanthus roseus is mediated by a proton-driven antiport. Plant physiology. 2013 Jul; 162(3):1486-96. doi: 10.1104/pp.113.220558. [PMID: 23686419]
  • Priyanka Verma, Ajay K Mathur, Karuna Shanker. Increased availability of tryptophan in 5-methyltryptophan-tolerant shoots of Catharanthus roseus and their postharvest in vivo elicitation induces enhanced vindoline production. Applied biochemistry and biotechnology. 2012 Oct; 168(3):568-79. doi: 10.1007/s12010-012-9797-2. [PMID: 22798187]
  • Fansong Mu, Liuqing Yang, Wei Wang, Meng Luo, Yujie Fu, Xiaorui Guo, Yuangang Zu. Negative-pressure cavitation extraction of four main vinca alkaloids from Catharanthus roseus leaves. Molecules (Basel, Switzerland). 2012 Jul; 17(8):8742-52. doi: 10.3390/molecules17088742. [PMID: 22832876]
  • Weibin Song, Lingjun Hu, Yuhui Meng, Lei Ma, Dean Guo, Xuan Liu, Lihong Hu. The effect of vindoline C-16 substituents on the biomimetic coupling reaction: synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues. Bioorganic & medicinal chemistry letters. 2012 May; 22(10):3485-7. doi: 10.1016/j.bmcl.2012.03.082. [PMID: 22525316]
  • David K Liscombe, Sarah E O'Connor. A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus. Phytochemistry. 2011 Nov; 72(16):1969-77. doi: 10.1016/j.phytochem.2011.07.001. [PMID: 21802100]
  • Qinhua Chen, Na Li, Wenpeng Zhang, Jing Chen, Zilin Chen. Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry. Journal of separation science. 2011 Oct; 34(20):2885-92. doi: 10.1002/jssc.201100359. [PMID: 21735550]
  • Ill-Min Chung, Eun-Hye Kim, Mai Li, Christie A M Peebles, Woo-Suk Jung, Hog-Keun Song, Joung-Kuk Ahn, Ka-Yiu San. Screening 64 cultivars Catharanthus roseus for the production of vindoline, catharanthine, and serpentine. Biotechnology progress. 2011 Jul; 27(4):937-43. doi: 10.1002/btpr.557. [PMID: 21674816]
  • Lesley-Ann Giddings, David K Liscombe, John P Hamilton, Kevin L Childs, Dean DellaPenna, C Robin Buell, Sarah E O'Connor. A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus. The Journal of biological chemistry. 2011 May; 286(19):16751-7. doi: 10.1074/jbc.m111.225383. [PMID: 21454651]
  • Grégory Guirimand, Anthony Guihur, Pierre Poutrain, François Héricourt, Samira Mahroug, Benoit St-Pierre, Vincent Burlat, Vincent Courdavault. Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus. Journal of plant physiology. 2011 Apr; 168(6):549-57. doi: 10.1016/j.jplph.2010.08.018. [PMID: 21047699]
  • Serkan Sertel, Yujie Fu, Yuangang Zu, Blanka Rebacz, Badireenath Konkimalla, Peter K Plinkert, Alwin Krämer, Jürg Gertsch, Thomas Efferth. Molecular docking and pharmacogenomics of vinca alkaloids and their monomeric precursors, vindoline and catharanthine. Biochemical pharmacology. 2011 Mar; 81(6):723-35. doi: 10.1016/j.bcp.2010.12.026. [PMID: 21219884]
  • C Lopez, B Claude, Ph Morin, J-P Max, R Pena, J-P Ribet. Synthesis and study of a molecularly imprinted polymer for the specific extraction of indole alkaloids from Catharanthus roseus extracts. Analytica chimica acta. 2011 Jan; 683(2):198-205. doi: 10.1016/j.aca.2010.09.051. [PMID: 21167971]
  • Lihong He, Li Yang, Ronghui Tan, Shujuan Zhao, Zhibi Hu. Enhancement of vindoline production in suspension culture of the Catharanthus roseus cell line C20hi by light and methyl jasmonate elicitation. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2011; 27(12):1243-8. doi: 10.2116/analsci.27.1243. [PMID: 22156254]
  • Jinghua Yu, Shusheng Yuan, Haihe Pang, Xueke Zhang, Xueying Jia, Zhonghua Tang, Yuangang Zu. [Distribution and accumulation of vindoline, catharanthine and vinblastine in Catharanthus roseus cultivated in China]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Dec; 35(23):3093-6. doi: 10.4268/cjcmm20102301. [PMID: 21355225]
  • Jonathan Roepke, Vonny Salim, Maggie Wu, Antje M K Thamm, Jun Murata, Kerstin Ploss, Wilhelm Boland, Vincenzo De Luca. Vinca drug components accumulate exclusively in leaf exudates of Madagascar periwinkle. Proceedings of the National Academy of Sciences of the United States of America. 2010 Aug; 107(34):15287-92. doi: 10.1073/pnas.0911451107. [PMID: 20696903]
  • Wen-Ying He, Zhen-Fan Sun, Xiao-Jun Yao, Guang-Ying Chen. [The characterization on the site of vindoline binding to human serum albumin]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 May; 45(5):608-14. doi: NULL. [PMID: 20931763]
  • Xiang-Zhang Zhong, Guo-Cai Wang, Ying Wang, Xiao-Qi Zhang, Wen-Cai Ye. [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Apr; 45(4):471-4. doi: . [PMID: 21355212]
  • Freddy Campos-Tamayo, Elizabeta Hernández-Domínguez, Felipe Vázquez-Flota. Vindoline formation in shoot cultures of Catharanthus roseus is synchronously activated with morphogenesis through the last biosynthetic step. Annals of botany. 2008 Sep; 102(3):409-15. doi: 10.1093/aob/mcn108. [PMID: 18587132]
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