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Published December 31, 2019 | Version v1
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The genuine localization of indole alkaloids in Vinca minor and Catharanthus roseus

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  • 1. ∗ & Institute for Plant Biology, Technische Universität Braunschweig, Mendelssohnsstr. 4, 38106, Braunschweig, Germany & Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt

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Abouzeid, Sara, Hijazin, Tahani, Lewerenz, Laura, Hänsch, Robert, Selmar, Dirk (2019): The genuine localization of indole alkaloids in Vinca minor and Catharanthus roseus. Phytochemistry 168: 1-9, DOI: 10.1016/j.phytochem.2019.112110, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112110

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urn:lsid:plazi.org:pub:623DFFC0A132CA60FFB8FFD2B653BF0B

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Figure: 10.5281/zenodo.10483756 (DOI)
Figure: 10.5281/zenodo.10483758 (DOI)
Figure: 10.5281/zenodo.10483760 (DOI)
Figure: 10.5281/zenodo.10483762 (DOI)
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Figure: 10.5281/zenodo.10483766 (DOI)
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References

  • Abouzeid, S., 2018. Modulation of Indole Alkaloids Composition in Vinca Minor. Ph.D. (Faculty of Life Sciences, TU Braunschweig.
  • Abouzeid, S., Beutling, U., Surup, F., Abdel Bar, F.M., Amer, M.M., Badria, F.A., Yahyazadeh, M., Bronstrup, M., Selmar, D., 2017. Treatment of Vinca minor leaves with methyl jasmonate extensively alters the pattern and composition of indole alkaloids. J. Nat. Prod. 8 0, 2905-2909.
  • Abouzeid, S., Beutling, U., Selmer, D., 2019. Stress-induced modification of indole alkaloids: phytomodificines as a new category of specialized metabolites. Phytochemistry 159, 102-107.
  • Bahadori, F., Topcu, G., Boga, M., Turkekul, A., Kolak, U., Kartal, M., 2012. Indole alkaloids from Vinca major and V. minor growing in Turkey. Nat Prod Commun 7, 731-734.
  • Bewick, T.A., Shilling, D.G., Querns, R., 1993. Evaluation of epicuticular wax removal from whole leaves with chloroform. Weed Technol. 7, 706-716.
  • Bilger, W., Schreiber, U., Lange, O.L., 1987. Chlorophyll fluorescence as an indicator of heat induced limitation of photosynthesis in Arbutus unedo L. In: In: Tenhunen, J.D., Catarino, F.M., Lange, O.L., Oechel, W.C. (Eds.), Plant Response to Stress. NATO ASI Series (Series G: Ecological Sciences), vol. 15. Springer, Berlin, Heidelberg, pp. 391-399.
  • Bytof, G., Knopp, S.-E., Schieberle, P., Teutsch, I., Selmar, D., 2005. Influence of processing on the generation of γ- aminobutyric acid in green coffee beans. Ann. Bot. 220, 245-250.
  • Carqueijeiro, I., Noronha, H., Duarte, P., Geros, H., Sottomayor, M., 2013. Vacuolar transport of the medicinal alkaloids from Catharanthus roseus is mediated by a protondriven antiport. Plant Physiol. 162, 1486-1496.
  • Croce, R., Muller, M.G., Bassi, R., Holzwarth, A.R., 2001. Carotenoid-to-Chlorophyll energy transfer in recombinant major light-harvesting complex (LHCII) of higher plants. I. Femtosecond transient absorption measurements. Biophys. J. 80, 901-915.
  • Cronin, M.T.D., Livingstone, D.J., 2004. Calculation of physicochemical properties. In: Cronin, M.T.D., Livingstone, D.J. (Eds.), Predicting Chemical Toxicity and Fate. CRC Press, Boca Raton, pp. 31-40.
  • D'Amelio Sr., F.S., Mirhom, Y.W., Williamson, Y.V., Schulbaum, P.L., Krueger, E.B., 2012. Comparative study of the alkaloids extracted from Vinca minor and those present in the homeopathic tincture 1X. Planta Med. 78 (11).
  • Demessie, Z., Woolfson, K.N., Yu, F., Qu, Y., De Luca, V., 2017. The ATP binding cassette transporter, VmTPT2/VmABCG1, is involved in export of the monoterpenoid indole alkaloid, vincamine in Vinca minor leaves. Phytochemistry 140, 118-124.
  • Duge de Bernonville, T., Clastre, M., Besseau, S., Oudin, A., Burlat, V., Glevarec, G., Lanoue, A., Papon, N., Giglioli-Guivarc'h, N., St-Pierre, B., Courdavault, V., 2015. Phytochemical genomics of the Madagascar periwinkle: unravelling the last twists of the alkaloid engine. Phytochemistry 113, 9-23.
  • Edge, A., Qu, Y., Easson, M.L.A.E., Thamm, A.M.K., Kim, K.H., De Luca, V., 2018. A tabersonine 3-reductase Catharanthus roseus mutant accumulates vindoline pathway intermediates. Planta 247, 155-169.
  • El-Sayed, M., Verpoorte, R., 2007. Catharanthus terpenoid indole alkaloids: biosynthesis and regulation. Phytochem. Rev. 6, 277-305.
  • Fjell, I., 1983. Anatomy of the xeromorphic leaves of Allamanda neriifolia, Thevetia peruviana and Vinca minor (Apocynaceae). Nord. J. Bot. 3, 383-392.
  • Giddings, L.-A., Liscombe, D.K., Hamilton, J.P., Childs, K.L., DellaPenna, D., Buell, C.R., O'Connor, S.E., 2011. A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus. J. Biol. Chem. 286, 16751-16757.
  • Gigant, B., Wang, C., Ravelli, R.B.G., Roussi, F., Steinmetz, M.O., Curmi, P.A., Sobel, A., Knossow, M., 2005. Structural basis for the regulation of tubulin by vinblastine. Nature 435 (7041), 519-522.
  • Gillbro, T., Cogdell, R.J., 1989. Carotenoid fluorescence. Chem. Phys. Lett. 158, 312-316.
  • Guirimand, G., Guihur, A., Ginis, O., Poutrain, P., Hericourt, F., Oudin, A., Lanoue, A., St-Pierre, B., Burlat, V., Courdavault, V., 2011. The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites. FEBS J. 278, 749-763.
  • Hasa, D., Perissutti, B., Dall'Acqua, S., Chierotti, M.R., Gobetto, R., Grabnar, I., Cepek, C., Voinovich, D., 2013. Rationale of using Vinca minor Linne dry extract phytocomplex as a vincamine's oral bioavailability enhancer. Eur. J. Pharm. Biopharm. 84, 138-144.
  • Holt, N.E., Kennis, J., Dall'Osto, L., Bassi, R., Fleming, G.R., 2003. Carotenoid to chlorophyll energy transfer in light harvesting complex II from Arabidopsis thaliana probed by femtosecond fluorescence upconversion. Chem. Phys. Lett. 379, 305-313.
  • Kavallaris, M., 2010. Microtubules and resistance to tubulin-binding agents. Nat. Rev. Cancer 10, 194-204.
  • Kellner, F., Geu-Flores, F., Sherden, N.H., Brown, S., Foureau, E., Courdavault, V., O'Connor, S.E., 2015. Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids. Chem. Commun. 51, 7626-7628.
  • Knight, A., 2007. A Guide to Poisonous House and Garden Plants. Teton NewMedia), pp. 279.
  • Kubo, I., Matsumoto, A., 1984. Secreted oleanolic acid on the cuticle Olea europaea (Oleaceae); a chemical barrier to fungal attack. Experientia 40, 937-938.
  • LoPresti, E.F., 2016. Chemicals on plant surfaces as a heretofore unrecognized, but ecologically informative, class for investigations into plant defence. Biol. Rev. Camb. Philos. Soc. 91, 1102-1117.
  • Lu, H.-T., Jiang, Y., Chen, F., 2004. Application of preparative high-speed counter-current chromatography for separation of chlorogenic acid from Flos Lonicerae. J. Chromatogr. A 1026, 185-190.
  • Mahroug, S., Burlat, V., St-Pierre, B., 2007. Cellular and sub-cellular organisation of the monoterpenoid indole alkaloid pathway in Catharanthus roseus. Phytochem. Rev. 6, 363-381.
  • Matile, P., 1976. Localization of alkaloids and mechanism of their accumulation in vacuoles of Chelidonium majus laticifers. Nova Acta Leopold. 7 (Suppl. l), 139-156.
  • Matsuura, H.N., Rau, M.R., Fett-Neto, A.G., 2014. Oxidative stress and production of bioactive monoterpene indole alkaloids: biotechnological implications. Biotechnol. Lett. 36, 191-200.
  • Murata, J., Roepke, J., Gordon, H., De Luca, V., 2008. The leaf epidermome of Catharanthus roseus reveals its biochemical specialization. Plant Cell 20, 524-542.
  • Nowak, M., Selmar, D., 2016. Cellular distribution of alkaloids and their translocation via phloem and xylem: the importance of compartment pH. Plant Biol. 18 (6), 879-882.
  • O'Connor, S.E., Maresh, J.J., 2006. Chemistry and biology of monoterpene indole alkaloid biosynthesis. Nat. Prod. Rep. 23, 532-547.
  • Pakdeechanuan, P., Shoji, T., Hashimoto, T., 2012. Root-to-shoot translocation of alkaloids is dominantly suppressed in Nicotiana alata. Plant Cell Physiol. 53, 1247-1254.
  • Pan, Q., Mustafa, N.R., Tang, K., Choi, Y.H., Verpoorte, R., 2016. Monoterpenoid indole alkaloids biosynthesis and its regulation in Catharanthus roseus: a literature review from genes to metabolites. Phytochem. Rev. 15, 221-250.
  • Proksa, B., Grossmann, E., 1991. High performance liquid chromatographic determination of alkaloids from Vinca minor L. Phytochem. Anal. 2, 74-76.
  • Qu, Y., Easson, M.L.A.E., Froese, J., Simionescu, R., Hudlicky, T., De Luca, V., 2015. Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proc. Natl. Acad. Sci. 112, 6224-6229.
  • Qu, Y., Thamm, A.M.K., Czerwinski, M., Masada, S., Kim, K.H., Jones, G., Liang, P., De Luca, V., 2018. Geissoschizine synthase controls flux in the formation of monoterpenoid indole alkaloids in a Catharanthus roseus mutant. Planta 247, 625-634.
  • Roepke, J., Salim, V., Wu, M., Thamm, A.M.K., Murata, J., Ploss, K., Boland, W., De Luca, V., 2010. Vinca drug components accumulate exclusively in leaf exudates of Madagascar periwinkle. Proc. Natl. Acad. Sci. 107, 15287-15292.
  • Ruan, Y.L., Patrick, J.W., Brady, C.J., 1996. The composition of apoplast fluid recovered from intact developing tomato fruit. Aust. J. Plant Physiol. 23 (1), 9-13.
  • Solomon, P.S., Oliver, R.P., 2001. The nitrogen content of the tomato leaf apoplast increases during infection by Cladosporium.fulvum. Planta 213, 241-249.
  • St-Pierre, B., 1999. Multicellular compartmentation of Catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate. Plant Cell 11, 887-900.
  • Thamm, A.M.K., Qu, Y., De Luca, V., 2016. Discovery and metabolic engineering of iridoid/secoiridoid and monoterpenoid indole alkaloid biosynthesis. Phytochem. Rev. 15 (3), 339-361.
  • Trapp, S., Legind, C.N., 2011. Uptake of organic contaminants from soil into vegetables and fruits. In: Swartjes, F. (Ed.), Dealing with Contaminated Sites. Springer, Dordrecht, pp. 369-408.
  • Valant-Vetschera, K.M., Bhutia, T.D., Wollenweber, E., 2010. Chemodiversity of exudate flavonoids in Dionysia (Primulaceae): a comparative study. Phytochemistry 71, 937-947.
  • Van der Heijden, R., Jacobs, D.I., Snoeijer, W., Hallard, D., Verpoorte, R., 2004. The Catharanthus alkaloids: pharmacognosy and biotechnology. Curr. Med. Chem. 11, 607-628.
  • Vas, A., Gulyas, B., 2005. Eburnamine derivatives and the brain. Med. Res. Rev. 25, 737-757.
  • Vrieling, K., Derridj, S., 2003. Pyrrolizidine alkaloids in and on the leaf surface of Senecio jacobaea L. Phytochemistry 64, 1223-1228.
  • Yamamoto, K., Takahashi, K., Mizuno, H., Anegawa, A., Ishizaki, K., Fukaki, H., Ohnishi, M., Yamazaki, M., Masujima, T., Mimura, T., 2016. Cell-specific localization of alkaloids in Catharanthus roseus stem tissue measured with Imaging MS and Single-cell MS. Proc. Natl. Acad. Sci. 113, 3891-3896.
  • Yazaki, K., Sugiyama, A., Morita, M., Shitan, N., 2008. Secondary transport as an efficient membrane transport mechanism for plant secondary metabolites. Phytochem. Rev. 7, 513-524.
  • Yu, F., De Luca, V., 2013. ATP-binding cassette transporter controls leaf surface secretion of anticancer drug components in Catharanthus roseus. Proc. Natl. Acad. Sci. 110, 15830-15835.
  • Zhu, J., Wang, M., Wen, W., Yu, R., 2015. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus. Pharmacogn. Rev. 9, 24-28.