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Chemical constituents of Antidesma bunius aerial parts and the anti-AGEs activity of selected compounds
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- 1. * & Institute of Pharmacy, Pharmacognosy, Center for Molecular Biosciences (CMBI), University of Innsbruck, Innrain 80-82/IV, 6020, Innsbruck, Austria & Faculty of Pharmacy, PHENIKAA University, Hanoi, 12116, Viet Nam
- 2. SONAS, EA921, UNIV Angers, SFR QUASAV, Faculty of Health Sciences, Dpt Pharmacy, 16 Bd Daviers, 49045, Angers cedex 01, France
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Nguyen-Ngoc, Hieu, Alilou, Mostafa, S, Derbr, everine, e, Blanchard, Patricia, Pham, Giang Nam, Nghiem, Duc Trong, Richomme, Pascal, Stuppner, Hermann, Ganzera, Markus (2022): Chemical constituents of Antidesma bunius aerial parts and the anti-AGEs activity of selected compounds. Phytochemistry (113300) 202: 1-13, DOI: 10.1016/j.phytochem.2022.113300, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113300
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- urn:lsid:plazi.org:pub:FFD5FF9F4564B1017747A45769622E19
References
- Abdullaeva, R.K., Bobakulov, K.M., Nishanbaev, C.Z., Sham 'yanov, I.D., Abdullaev, N.D., 2016. Flavonoids and other constituents from the aerial part of Anaphalis racemifera. Chem. Nat. Compd. 52, 503-504. https://doi.org/10.1007/s10600-016-1688-2.
- An, J.P., Ha, T.K., Kim, J., Cho, T.O., Oh, W.K., 2016. Protein tyrosine phosphatase 1B inhibitors from the stems of Akebia quinata. Molecules 21, 1091. https://doi.org/ 10.3390/molecules21081091.
- Asia Foundation, 2012. Guide to Medicinal Plants of Daos in Ba Vi. https://asiafoundatio n.org/resources/pdfs/MedicinalPlantIndexoftheDaosinBaVi.pdf.
- Bicker, J., Petereit, F., Hensel, A., 2009. Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia 80, 483-495. https://doi.org/10.1016/ j.fitote.2009.08.015.
- Bouzergoune, F., Ciavatta, M.L., Bitam, F., Carbone, M., Aberkane, M.C., Gavagnin, M., 2016. Phytochemical study of Eryngium triquetrum: isolation of polyacetylenes and lignans. Planta Med. 82, 1438-1445. https://doi.org/10.1055/s-0042-110316.
- Bozzo, C., Pujol, M.D., Solans, X., Font-Bardia, M., 2003. A new synthesis of 3-hydroxy- 2,3-dihydro-1,4-benzodioxin-2-carboxamides and 3-aminomethylene-1,4-benzodioxin-2(3H)-one derivatives. Tetrahedron 59, 1227-1236. https://doi.org/ 10.1016/S0040-4020(03)00025-5.
- Bringmann, G., Rischer, H., Wohlfarth, M., Schlauer, J., 2000a. Biosynthesis of antidesmone in cell cultures of Antidesma membranaceum (Euphorbiaceae): an unprecedented class of glycine-derived alkaloids. J. Am. Chem. Soc. 122, 9905-9910. https://doi.org/10.1021/ja001391k.
- Bringmann, G., Schlauer, J., Rischer, H., Wohlfarth, M., Muhlbacher, J., Buske, A., Porzel, A., Schmidt, J., Adam, G., 2000b. Revised structure of antidesmone, an unusual alkaloid from tropical Antidesma plants (Euphorbiaceae). Tetrahedron 56, 3691-3695. https://doi.org/10.1016/S0040-4020(00)00289-1.
- Bruhn, T., Schauml¨offel, A., Hemberger, Y., Pecitelli, G., 2017. In: SpecDis, Version 1.70. Berlin, Germany.
- Buske, A., Schmidt, J., Porzel, A., Adam, G., 2001. Alkaloidal, megastigmane and lignan glucosides from Antidesma membranaceum (Euphorbiaceae). Eur. J. Org Chem. 18, 3537-3543. https://doi.org/10.1002/1099-0690(200109)2001:18%3C3537::AID- EJOC3537%3E3.0.CO;2-A.
- Cai, Y., Cai, T.-G., 2010. Two new aristolochic acid derivatives from the roots of Aristolochia fangchi and their cytotoxicities. Chem. Pharm. Bull. 58, 1093-1095. https://doi.org/10.1248/cpb.58.1093.
- Caro, M.S.B., de Oliveira, L.H., Ilha, V., Burrow, R.A., Dalcol, I.I., Morel, A.F., 2012. Absolute configuration of franganine. J. Nat. Prod. 75, 1220-1222. https://doi.org/ 10.1021/np300206x.
- Chen, Y.-C., Cheng, M.-J., Lee, S.-J., Dixit, A.K., Ishikawa, T., Tsai, I.-L., Chen, I.-S., 2004. Coumarinolignans from the root of Formosan Antidesma pentandrum var. barbatum. Helv. Chim. Acta 87, 2805-2811. https://doi.org/10.1002/hlca.200490251.
- Chen, Y.-C., Cheng, M.-J., Lee, S.-J., Tsai, I.-L., Chen, I.-S., 2007. Chemical constituents from the root of Antidesma pentandrum var. barbatum. J. Chin. Chem. Soc. 54, 1325-1332. https://doi.org/10.1002/jccs.200700187.
- Cretton, S., Breant, L., Pourrez, L., Ambuehl, C., Marcourt, L., Ebrahimi, S.N., Hamburger, M., Perozzo, R., Karimou, S., Kaiser, M., Cuendet, M., Christen, P., 2014. Antitrypanosomal quinoline alkaloids from the roots of Waltheria indica. J. Nat. Prod. 77, 2304-2311. https://doi.org/10.1021/np5006554.
- Dariya, B., Nagaraju, G.P., 2020. Advanced glycation end products in diabetes, cancer and phytochemical therapy. Drug Discov. Today 25, 1614-1623. https://doi.org/ 10.1016/j.drudis.2020.07.003.
- Darwish, F.M.M., Reinecke, M.G., 2003. Ecdysteroids and other constituents from Sida spinosa L. Phytochemistry 62, 1179-1184. https://doi.org/10.1016/S0031-9422(03) 00021-9.
- De Groot, L., Posthumus, M.D., Kallenberg, C.G.M., Bijl, M., 2010. Risk factors and early detection of atherosclerosis in rheumatoid arthritis. Eur. J. Clin. Invest. 40, 835-842. https://doi.org/10.1111/j.1365-2362.2010.02333.x.
- eFloras, 2008. Published on the Internet. Missouri Botanical Garden, St. Louis, MO & Harvard University Herbaria, Cambridge, MA. http://www.efloras.org. (Accessed January 2022).
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, J.A., J., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian 16. Gaussian, Inc., Wallingford CT.
- Gerards, M., Snatzke, G., 1990. Circular dichroism, XCIII determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their "in situ" complexes with [Rh2(O2CCF3)4]. Tetrahedron: Asymmetry 1, 221-236. https://doi. org/10.1016/S0957-4166(00)86328-4.
- Grimblat, N., Zanardi, M.M., Sarotti, A.M., 2015. Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts. J. Org. Chem. 80, 12526-12534. https://doi.org/ 10.1021/acs.joc.5b02396.
- Han, B.H., Park, M.H., Han, Y.N., 1990. Cyclic peptide and peptide alkaloids from seeds of Zizyphus vulgaris. Phytochemistry 29, 3315-3319. https://doi.org/10.1016/0031- 9422(90)80207-W.
- Hiltunen, E., Pakkanen Tuula, T., Alvila, L., 2006. Phenolic compounds in silver birch (Betula pendula Roth) wood. Holzforschung 60, 519-527. https://doi.org/10.1515/ HF.2006.086.
- Khan, M., Liu, H., Wang, J., Sun, B., 2020. Inhibitory effect of phenolic compounds and plant extracts on the formation of advance glycation end products: a comprehensive review. Food Res. Int. 130, 108933 https://doi.org/10.1016/j.foodres.2019.108933.
- Kiyekbayeva, L., Mohamed, N.M., Yerkebulan, O., Mohamed, E.I., Ubaidilla, D., Nursulu, A., Assem, M., Srivedavyasasri, R., Ross, S.A., 2018. Phytochemical constituents and antioxidant activity of Echinops albicaulis. Nat. Prod. Res. 32, 1203-1207. https://doi.org/10.1080/14786419.2017.1323213.
- Krongyut, O., Sutthanut, K., 2019. Phenolic profile, antioxidant activity, and antiobesogenic bioactivity of Mao Luang fruits (Antidesma bunius L.). Molecules 24, 4109. https://doi.org/10.3390/molecules24224109.
- Lee, S.-J., Jang, H.-J., Kim, Y., Oh, H.-M., Lee, S., Jung, K., Kim, Y.-H., Lee, W.-S., Lee, S.- W., Rho, M.-C., 2016. Inhibitory effects of IL-6-induced STAT3 activation of bioactive compounds derived from Salvia plebeia R. Br. Process Biochem. 51, 2222-2229. https://doi.org/10.1016/j.procbio.2016.09.003.
- Lomchoey, N., Panseeta, P., Boonsri, P., Apiratikul, N., Prabpai, S., Kongsaeree, P., Suksamrarn, S., 2018. New bioactive cyclopeptide alkaloids with rare terminal unit from the root bark of Ziziphus cambodiana. RSC Adv. 8, 18204-18215. https://doi. org/10.1039/C7RA13050C.
- Lu, Y., Xue, Y., Liu, J., Yao, G., Li, D., Sun, B., Zhang, J., Liu, Y., Qi, C., Xiang, M., Luo, Z., Du, G., Zhang, Y., 2015. (± )-Acortatarinowins A-F, norlignan, neolignan, and lignan enantiomers from Acorus tatarinowii. J. Nat. Prod. 78, 2205-2214. https://doi.org/ 10.1021/acs.jnatprod.5b00328.
- Martin, F., Hay, A.-E., Cressend, D., Reist, M., Vivas, L., Gupta, M.P., Carrupt, P.-A., Hostettmann, K., 2008. Antioxidant C-glucosylxanthones from the leaves of Arrabidaea patellifera. J. Nat. Prod. 71, 1887-1890. https://doi.org/10.1021/ np800406q.
- Mauldina, M.G., Sauriasari, R., Elya, B., 2017. α- Glucosidase inhibitory activity from ethyl acetate extract of Antidesma bunius (L.) Spreng stem bark containing triterpenoids. Phcog. Mag. 13, 590-594. https://doi.org/10.4103/pm.pm_25_17.
- Nagaraj, R.H., Shipanova, I.N., Faust, F.M., 1996. Protein cross-linking by the Maillard reaction. Isolation, characterization, and in vivo detection of a lysine-lysine crosslink derived from methylglyoxal. J. Biol. Chem. 271, 19338-19345. https://doi.org/ 10.1074/jbc.271.32.19338.
- Ngamlerst, C., Udomkasemsab, A., Kongkachuichai, R., Kwanbunjan, K., Chupeerach, C., Prangthip, P., 2019. The potential of antioxidant-rich Maoberry (Antidesma bunius) extract on fat metabolism in liver tissues of rats fed a high-fat diet. BMC Compl. Alternative Med. 19, 294. https://doi.org/10.1186/s12906-019-2716-0.
- Owen, R.W., Haubner, R., Hull, W.E., Erben, G., Spiegelhalder, B., Bartsch, H., Haber, B., 2003. Isolation and structure elucidation of the major individual polyphenols in carob fibre. Food Chem. Toxicol. 41, 1727-1738. https://doi.org/10.1016/S0278- 6915(03)00200-X.
- Peng, W.C., 2011. Constituents from charred Cirsium japonicum. Chem. Nat. Compd. 47, 279. https://doi.org/10.1007/s10600-011-9904-6.
- Rouger, C., Derbr´e, S., Charreau, B., Pabois, A., Cauchy, T., Litaudon, M., Awang, K., Richomme, P., 2015. Lepidotol A from Mesua lepidota inhibits inflammatory and immune mediators in human endothelial cells. J. Nat. Prod. 78, 2187-2197. https:// doi.org/10.1021/acs.jnatprod.5b00222.
- S´ero, L., Sanguinet, L., Blanchard, P., Dang, B.T., Morel, S., Richomme, P., S´eraphin, D., Derbr´e, S., 2013. Tuning a 96-well microtiter plate fluorescence-based assay to identify AGE inhibitors in crude plant extracts. Molecules 18, 14320-14339. https:// doi.org/10.3390/molecules181114320.
- Shao, S.-Y., Yang, Y.-N., Feng, Z.-M., Jiang, J.-S., Zhang, P.-C., 2018. An efficient method for determining the relative configuration of furofuran lignans by 1H NMR spectroscopy. J. Nat. Prod. 81, 1023-1028. https://doi.org/10.1021/acs. jnatprod.8b00044.
- Tanaka, T., Nonaka, G.-I., Nishioka, I., 1985. Punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry 24, 2075-2078. https://doi.org/10.1016/ S0031-9422(00)83125-8.
- Tanaka, T., Fujisaki, H., Nonaka, G.-i., Nishioka, I., 1992. Tannins and related compounds. CXVIII. Structures, preparation, high-performance liquid chromatography and some reactions of dehydroellagitannin-acetone condensates. Chem. Pharm. Bull. 40, 2937-2944. https://doi.org/10.1248/cpb.40.2937.
- Tawali, S., As' ad, S., Hatta, M., Bukhari, A., Khairi, N., Rifai, Y., R, D., 2019. Anthocyanin-rich buni-berry (Antidesma bunius) extract increases paraoxonase 1 gene expression in BALB/c mice fed with a high-fat diet. J. Young Pharm. 11, 46-50. https://doi.org/10.5530/jyp.2019.11.10.
- Torres-Tapia, L.W., Sosa-Espinosa, T., Peraza-S´anchez, S.R., 2013. Isolation of a phydroxyphenyl anhydride from the leaves of Diphysa carthagenensis. Nat. Prod. Res. 27, 286-289. https://doi.org/10.1080/14786419.2012.668689.
- Trang, D.T., Huyen, L.T., Nhiem, N.X., Quang, T.H., Hang, D.T.T., Yen, P.H., Tai, B.H., Anh, H.L.T., Binh, N.Q., Van Minh, C., Van Kiem, P., 2016. Tirucallane glycoside from the leaves of Antidesma bunius and inhibitory NO production in BV2 cells and RAW264.7 macrophages. Nat. Prod. Commun. 11, 935-937. https://doi.org/ 10.1177/1934578X1601100717.
- Ueno, Y., Kato, Y., Okatani, S., Ishida, N., Nakanishi, M., Kitade, Y., 2003. Synthesis of antisense oligonucleotides carrying modified 2-5A molecules at their 5'-termini and their properties. Bioconjugate Chem. 14, 690-696. https://doi.org/10.1021/ bc020072a.
- Xiong, L., Zhu, C., Li, Y., Tian, Y., Lin, S., Yuan, S., Hu, J., Hou, Q., Chen, N., Yang, Y., Shi, J., 2011. Lignans and neolignans from Sinocalamus affinis and their absolute configurations. J. Nat. Prod. 74, 1188-1200. https://doi.org/10.1021/np200117y. Yoshida, T., Hatano, T., Okuda, T., Memon, M.U., Shingu, T., Inoue, K., 1984. Spectral and chromatographic analyses of tannins. I. 13C Nuclear Magnetic Resonance spectra of hydrolyzable tannins. Chem. Pharm. Bull. 32, 1790-1799. https://doi. org/10.1248/cpb.32.1790.