Published August 31, 2021
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Anti-phytopathogen terpenoid glycosides from the root bark of Chytranthus macrobotrys and Radlkofera calodendron
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- 1. * & PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Sant´e, Universit´e de Bourgogne Franche-Comte´, BP 87900, 21079, Dijon, Cedex, France
- 2. Centre de Recherche Phytochimique, Universite´de Li`ege, Institut de Chimie-B6, Sart Tilman, 4000, Li`ege I, Belgium
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Petit, Bastien, Mitaine-Offer, Anne-Claire, Fischer, Jochen, Schüffler, Anja, Cl, Delaude, ement, Miyamoto, Tomofumi, Tanaka, Chiaki, Thines, Eckhard, Lacaille-Dubois, Marie-Aleth (2021): Anti-phytopathogen terpenoid glycosides from the root bark of Chytranthus macrobotrys and Radlkofera calodendron. Phytochemistry (112797) 188: 1-12, DOI: 10.1016/j.phytochem.2021.112797, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112797
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- urn:lsid:plazi.org:pub:EE086F51233BFF88FFB2D6151B50FF9B
References
- Abbruscato, P., Tosi, S., Crispino, L., Biazzi, E., Menin, B., Picco, A.M., Pecetti, L., Avato, P., Tava, A., 2014. Triterpenoid glycosides from Medicago sativa as antifungal agents against Pyricularia oryzae. J. Agric. Food Chem. 62, 11030-11036. https:// doi.org/10.1021/jf5049063.
- Adesanya, S.A., Martin, M.-T., Hill, B., Dumontet, V., Tri, M.V., S´evenet, T., Pais, M., 1999. Rubiginoside, a farnesyl glycoside from Lepisanthes rubiginosa. Phytochemistry 51, 1039-1041. https://doi.org/10.1016/s0031-9422(98)00701-8.
- Adeyemi, T.O., Ogundipe, O.T., Olowokudejo, J.D., 2012. Distribution and DNA conservation of Sapindaceae juss. In western africa. Int. J. Bot. 8, 31-37. https://doi. org/10.3923/ijb.2012.31.37.
- Avato, P., Bucci, R., Tava, A., Vitali, C., Rosato, A., Bialy, Z., Jurzysta, M., 2006. Antimicrobial activity of saponins from Medicago sp.: structure-activity relationship. Phytother Res. 20, 454-457. https://doi.org/10.1002/ptr.1876.
- Barile, E., Bonanomi, G., Antignani, V., Zolfaghari, B., Sajjadi, S.E., Scala, F., Lanzotti, V., 2007. Saponins from Allium minutiflorum with antifungal activity. Phytochemistry 68, 596-603. https://doi.org/10.1016/j.phytochem.2006.10.009.
- Biang, A.E.M., Kamto, E.L.D., Simo, L.M., Antheaume, C., Lavedan, P., Vedrenne, M., Not´e, O.P., Pegnyemb, D.E., Mbing, J.N., Haddad, M., 2020. Triterpenoid saponins from the stem barks of Chytranthus klaineanus Radlk. ex Engl. Phytochem. Lett. 37, 37-41. https://doi.org/10.1016/j.phytol.2020.04.006.
- Bouarab, K., Melton, R., Peart, J., Baulcombe, D., Osbourn, A.E., 2002. A saponindetoxifying enzyme mediates suppression of plant defences. Nature 418, 889-892. https://doi.org/10.1038/nature00950.
- Braca, A., Autore, G., Simone, F.D., Marzocco, S., Morelli, I., Venturella, F., Tommasi, N. D., 2004. Cytotoxic saponins from Schefflera rotundifolia. Planta Med. 70, 960-966. https://doi.org/10.1055/s-2004-832623.
- Buerki, S., Forest, F., Acevedo-Rodriguez, P., Callmander, M.W., Nylander, J.A.A., Harrington, M., Sanmartin, I., Kupfer, P., Alvarez, N., 2009. Plastid and nuclear DNA markers reveal intricate relationships at subfamilial and tribal levels in the soapberry family (Sapindaceae). Mol. Phylogenet. Evol. 51, 238-258. https://doi.org/ 10.1016/j.ympev.2009.01.012.
- Cobos, R., Mateos, R.M., Alvarez-P ´´erez, J.M., Olego, M.A., Sevillano, S., Gonz´alez- Garcia, S., Garzon-Jimeno ´, E., Coque, J.J.R., 2015. Effectiveness of natural antifungal compounds in controlling infection by grapevine trunk disease pathogens through pruning wounds. Appl. Environ. Microbiol. 81, 6474-6483. https://doi.org/ 10.1128/AEM.01818-15.
- Delaude, C., 1974. Chemical study of the saponins of Sapindaceae. Identification of the saponin of Radlkofera calodendra. Bull. Soc. R. Sci. Liege 43, 693-696.
- Delaude, C., Breyne, H., Welter, A., 1976. Contribution to the study of saponins contained in Sapindaceae. Study of the saponoside from Chytranthus macrobotrys (Gilg.) Exell & Mendonca and Lecaniodiscus cupanoides. Planch.. Bull. Soc. R. Sci. Li`ege 45, 458-461.
- Dong, S., Yang, X., Zhao, L., Zhang, F., Hou, Z., Xue, P., 2020. Antibacterial activity and mechanism of action saponins from Chenopodium quinoa Willd. husks against foodborne pathogenic bacteria. Ind. Crop. Prod. 149, 112350 https://doi.org/ 10.1016/j.indcrop.2020.112350.
- Ekabo, O.A., Farnsworth, N.R., Henderson, T.O., Mao, G., Mukherjee, R., 1996. Antifungal and molluscicidal saponins from Serjania salzmanniana. J. Nat. Prod. 59, 431-435. https://doi.org/10.1021/np960208r.
- Encarnacion ´, R., Kenne, L., Samuelsson, G., Sandberg, F., 1981. Structural studies on some saponins from Lecaniodiscus cupanioides. Phytochemistry 20, 1939-1942. https://doi.org/10.1016/0031-9422(81)84039-3.
- Faleye, F.J., Ajayi, C.B., 2018. Antioxidant potentials of the methanol seed and leaves extracts of Chytranthus macrobotrys (Gilg.) Exell & Mendonca. J. Chem. Biol. Phys. Sci. 8, 475-481. https://doi.org/10.24214/jcbps.B.8.2.47581.
- Faleye, F.J., Ajayi, C.B., Akinwumi, O.A., Popoola, O.K., 2019. Evaluation of methanolic extract of Chytranthus macrobotrys seed (cms) for antimicrobial, α- glucosidase and α- amylase inhibitory activities. Int. J. Pharma Sci. Res. 10, 678-685. https://doi. org/10.13040/IJPSR.0975-8232.10(2).678-85.
- Hara, S., Okabe, H., Mihashi, K., 1987. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2- (polyhydroxyalkyl) -thiazolidine-4 (R) -carboxylates. Chem. Pharm. Bull. 35, 501-506. https://doi.org/10.1248/ cpb.35.501.
- Harrington, M., Edwards, K., Johnson, S., Chase, M., Gadek, P., 2005. Phylogenetic inference in Sapindaceae sensu lato using plastid matk and rbcl DNA sequences. Syst. Bot. 30, 366-382. https://doi.org/10.1600/0363644054223549.
- Hern´andez-Montelongo, J., Nascimento, V.F., Murillo, D., Taketa, T.B., Sahoo, P., de Souza, A.A., Beppu, M.M., Cotta, M.A., 2016. Nanofilms of hyaluronan/chitosan assembled layer-by-layer: an antibacterial surface for Xylella fastidiosa. Carbohydr. Polym. 136, 1-11. https://doi.org/10.1016/j.carbpol.2015.08.076.
- Hu, Q., Chen, Y.-Y., Jiao, Q.-Y., Khan, A., Li, F., Han, D.-F., Cao, G.-D., Lou, H.-X., 2018. Triterpenoid saponins from the pulp of Sapindus mukorossi and their antifungal activities. Phytochemistry 147, 1-8. https://doi.org/10.1016/j. phytochem.2017.12.004.
- Ishii, H., Kitagawa, I., Matsushita, K., Shirakawa, K., Tori, K., Tozyo, T., Yoshikawa, M., Yoshimura, Y., 1981. The configuration and conformation of the arabinose moiety in platycodins, saponins isolated from Platycodon grandiflorum, and mi-saponins from Madhuca longifolia based on carbon-13 and hydrogen-1 nmr spectroscopic evidence: the total structures of the saponins. Tetrahedron Lett. 22, 1529-1532. https://doi. org/10.1016/S0040-4039(01)90369-7.
- Kasai, R., Fujino, H., Kuzuki, T., Wong, W.-H., Goto, C., Yata, N., Tanaka, O., Yasuhara, F., Yamaguchi, S., 1986. Acyclic sesquiterpene oligoglycosides from pericarps of Sapindus mukurossi. Phytochemistry 25, 871-876. https://doi.org/ 10.1016/0031-9422(86)80019-X.
- Kim, B., Han, J.W., Thi Ngo, M., Le Dang, Q., Kim, J.-C., Kim, H., Choi, G.J., 2018. Identification of novel compounds, oleanane- and ursane-type triterpene glycosides, from Trevesia palmata: their biocontrol activity against phytopathogenic fungi. Sci. Rep. 8, 14522. https://doi.org/10.1038/s41598-018-32956-4.
- Lacaille-Dubois, M.-A., Delaude, C., Mitaine-Offer, A.-C., 2013. Triterpenoid saponins: a focus on Polygalaceae. Natural Products. Springer, Berlin, Heidelberg,
- Lavaud, C., Crublet, M.-L., Pouny, I., Litaudon, M., S´evenet, T., 2001. Triterpenoid saponins from the stem bark of Elattostachys apetala. Phytochemistry 57, 469-478. https://doi.org/10.1016/s0031-9422(01)00063-2.
- Lunga, P.K., Qin, X.-J., Yang, X.W., Kuiate, J.-R., Du, Z.Z., Gatsing, D., 2014. Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata. BMC Compl. Alternative Med. 14, 369. https://doi.org/10.1186/ 1472-6882-14-369.
- Maddox, C.E., Laur, L.M., Tian, L., 2009. Antibacterial activity of phenolic compounds against the phytopathogen Xylella fastidiosa. Curr. Microbiol. 60, 53-58. https://doi. org/10.1007/s00284-009-9501-0.
- Magid, A.A., Voutquenne-Nazabadioko, L., Litaudon, M., Lavaud, C., 2005. Acylated farnesyl diglycosides from Guioa crenulata. Phytochemistry 66, 2714-2718. https:// doi.org/10.1016/j.phytochem.2005.09.009.
- Mandal, P., Sinha Babu, S.P., Mandal, N.C., 2005. Antimicrobial activity of saponins from Acacia auriculiformis. Fitoterapia 76, 462-465. https://doi.org/10.1016/j. fitote.2005.03.004.
- Mazzola, E.P., Parkinson, A., Kennelly, E.J., Coxon, B., Einbond, L.S., Freedberg, D.I., 2011. Utility of coupled-hsqc experiments in the intact structural elucidation of three complex saponins from Blighia sapida. Carbohydr. Res. 346, 759-768. https://doi. org/10.1016/j.carres.2011.02.019.
- Mimaki, Y., Yokosuka, A., Hamanaka, M., Sakuma, C., Yamori, T., Sashida, Y., 2004. Triterpene saponins from the roots of Clematis chinensis. J. Nat. Prod. 67, 1511-1516. https://doi.org/10.1021/np040088k.
- Njateng, G.S.S., Du, Z., Gatsing, D., Nanfack Donfack, A.R., Feussi Talla, M., Kamdem Wabo, H., Tane, P., Mouokeu, R.S., Luo, X., Kuiate, J.-R., 2015. Antifungal properties of a new terpernoid saponin and other compounds from the stem bark of Polyscias fulva Hiern (Araliaceae). BMC Compl. Alternative Med. 15, 25. https://doi.org/ 10.1186/s12906-015-0541-7.
- Osbourn, A.E., 2003. Saponins in cereals. Phytochemistry 62, 1-4. https://doi.org/ 10.1016/s0031-9422(02)00393-x.
- Osbourn, A.E., Clarke, B.R., Lunness, P., Scott, P.R., Daniels, M.J., 1994. An oat species lacking avenacin is susceptible to infection by Gaeumannomyces graminis var. tritici. Physiol. Mol. Plant Pathol. 45, 457-467. https://doi.org/10.1016/s0885-5765(05) 80042-6.
- Pensec, F., 2013. Les triterp´enoides chez la vigne: quantifications, voies de biosynth`ese et int´erˆet pour la lutte contre des bioagresseurs. Sciences agricoles. Universite ´de Haute Alsace - Mulhouse.
- Pertuit, D., Mitaine-Offer, A.-C., Miyamoto, T., Tanaka, C., Delaude, C., Lacaille-Dubois, M.-A., 2018. Terpenoid glycosides from the root' s barks of Eriocoelum microspermum Radlk. ex Engl. Phytochemistry 152, 182-190. https://doi.org/ 10.1016/j.phytochem.2018.04.009.
- Petit, B., Mitaine-Offer, A.-C., Delaude, C., Miyamoto, T., Tanaka, C., Lacaille-Dubois, M.- A., 2019. Hederagenin glycosides from the fruits of Blighia unijugata. Phytochemistry 162, 260-269. https://doi.org/10.1016/j.phytochem.2019.03.020.
- Petit, B., Mitaine-Offer, A.-C., Real Fernandez, F., Papini, A.M., Delaude, C., Miyamoto, T., Tanaka, C., Rovero, P., Lacaille-Dubois, M.-A., 2020. Triterpene glycosides from Blighia welwitschii and evaluation of their antibody recognition capacity in multiple sclerosis. Phytochemistry 176, 112392. https://doi.org/ 10.1016/j.phytochem.2020.112392.
- Porsche, F.M., Molitor, D., Beyer, M., Charton, S., Andr´e, C., Kollar, A., 2018. Antifungal activity of saponins from the fruit pericarp of Sapindus mukorossi against Venturia inaequalis and Botrytis cinerea. Plant Dis. 102, 991-1000. https://doi.org/10.1094/ pdis-06-17-0906-re.
- Rezgui, A., Mitaine-Offer, A.-C., Miyamoto, T., Tanaka, C., Delemasure, S., Dutartre, P., Lacaille-Dubois, M.-A., 2016. Oleanolic acid and hederagenin glycosides from Weigela stelzneri. Phytochemistry 123, 40-47. https://doi.org/10.1016/j. phytochem.2015.12.016.
- Roblin, G., Luini, E., Fleurat-Lessard, P., Larignon, P., Berjeaud, J.-M., 2019. Towards a preventive and/or curative treatment of esca in grapevine trunk disease: general basis in the elaboration of treatments to control plant pathogen attacks. Crop Protect. 116, 156-169. https://doi.org/10.1016/j.cropro.2018.10.016.
- Saboora, A., Sajjadi, S.-T., Mohammadi, P., Fallahi, Z., 2019. Antibacterial activity of different composition of aglycone and glycosidic saponins from tuber of Cyclamen coum Miller. Ind. Crop. Prod. 140, 111662. https://doi.org/10.1016/j. indcrop.2019.111662.
- Saha, S., Walia, S., Kumar, J., Parmar, B.S., 2010. Structure-biological activity relationships in triterpenic saponins: the relative activity of protobassic acid and its derivatives against plant pathogenic fungi. Pest Manag. Sci. 66, 825-831. https:// doi.org/10.1002/ps.1947.
- Saito, S., Sumita, S., Tamura, N., Nagamura, Y., Nishida, K., Ito, M., Ishiguro, I., 1990. Saponins from the leaves of Aralia elata seem. Araliaceae. Chem. Pharm. Bull. 38, 411-414. https://doi.org/10.1248/cpb.38.411.
- Santiago, M.B., Moraes, T. da S., Massuco, J.E., Silva, L.O., Lucarini, R., Silva, D.F. da, Vieira, T.M., Crotti, A.E.M., Martins, C.H.G., 2018. In vitro evaluation of essential oils for potential antibacterial effects against Xylella fastidiosa. J. Phytopathol. 166, 790-798. https://doi.org/10.1111/jph.12762.
- Santos, C., Fragoeiro, S., Oliveira, H., Phillips, A., 2006. Response of Vitis vinifera L. plants inoculated with Phaeoacremonium angustius and Phaeomoniella chlamydospora to thiabendazole, resveratrol and sodium arsenite. Sci. Hortic. 107, 131-136. https://doi.org/10.1016/j.scienta.2005.04.015.
- The Angiosperm Phylogeny Group, 2016. An update of the angiosperm phylogeny group classification for the orders and families of flowering plants: APG IV. Bot. J. Linn. Soc. 181, 1-20. https://doi.org/10.1111/boj.12385.
- Voutquenne, L., Guinot, P., Thoison, O., Sevenet, T., Lavaud, C., 2003. Oleanolic glycosides from Pometia ridleyi. Phytochemistry 64, 781-789. https://doi.org/ 10.1016/s0031-9422(03)00380-7.
- Yu, Q.-T., Qi, L.-W., Li, P., Yi, L., Zhao, J., Bi, Z., 2007. Determination of seventeen main flavonoids and saponins in the medicinal plant huang-qi (Radix astragali) by hplcdad-elsd. J. Separ. Sci. 30, 1292-1299. https://doi.org/10.1002/jssc.200600422.