Published September 30, 2020 | Version v1

Natural sucrose esters: Perspectives on the chemical and physiological use of an under investigated chemical class of compounds

  • 1. ∗ & São Paulo State University (UNESP), Institute of Biosciences, Humanities and Exact Sciences, São Jose do Rio Preto, SP, Brazil

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Vargas, Jorge Andrés Mora, Ortega, Julieth Orduña, Metzker, Gustavo, Larrahondo, Jesus Eliecer, Boscolo, Mauricio (2020): Natural sucrose esters: Perspectives on the chemical and physiological use of an under investigated chemical class of compounds. Phytochemistry (112433) 177: 1-21, DOI: 10.1016/j.phytochem.2020.112433, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112433

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References

  • Adia, M.M., Anywar, G., Byamukama, R., Kamatenesi-Mugisha, M., Sekagya, Y., Kakudidi, E.K., Kiremire, B.T., 2014. Medicinal plants used in malaria treatment by Prometra herbalists in Uganda. J. Ethnopharmacol. 155, 580-588. https://doi.org/ 10.1016/j.jep.2014.05.060.
  • Ahsan, F., Arnold, J.J., Meezan, E., Pillion, D.J., 2003. Sucrose cocoate, a component of cosmetic preparations, enhances nasal and ocular peptide absorption. Int. J. Pharm. 251, 195-203. https://doi.org/10.1016/S0378-5173(02)00597-5.
  • Ashraf-Khorassani, M., Nazem, N., Taylor, L.T., Coleman, W.M., 2008. Isolation, fractionation, and identification of sucrose esters from various oriental tobaccos employing supercritical fluids. Beitrage zur Tab. Int. Contrib. to Tob. Res. 23, 32-45. https://doi.org/10.2478/cttr-2013-0846.
  • Ashraf-Khorassani, M., Taylor, L.T., Nazem, N., Coleman, W.M., 2005. Isolation of tetraacyl sucrose esters from Turkish tobacco using supercritical fluid CO2and comparison with conventional solvent extraction. J. Agric. Food Chem. 53, 1866-1872. https:// doi.org/10.1021/jf040417e.
  • Ashraf-Khorassani, N., Nazem, N., Taylor, L., Coleman, W., 2016. Identification and quantification of sucrose esters in various Turkish tobaccos. Beitrage zur Tab. Int. to Tob. Res. 21, 441-450. https://doi.org/10.2478/cttr-2013-0812.
  • Barros, M.T., Petrova, K.T., 2009. Ziegler-Natta catalysed polymerisation for the preparation of copolymers with pendant sucrose moieties. Eur. Polym. J. 45, 295-301. https://doi.org/10.1016/j.eurpolymj.2008.10.013.
  • Barros, M.T., Petrova, K.T., Singh, R.P., 2010. Synthesis of hydrophilic and amphiphilic acryl sucrose monomers and their copolymerisation with styrene, methylmethacrylate and α- and β- pinenes. Int. J. Mol. Sci. 11, 1792-1807. https://doi.org/10.3390/ ijms11041792.
  • Becerra, N., Toro, C., Zanocco, A.L., Lemp, E., Gunther, G., 2008. Characterization of micelles formed by sucrose 6-O-monoesters. Colloids Surfaces A Physicochem. Eng. Asp. 327, 134-139. https://doi.org/10.1016/j.colsurfa.2008.06.012.
  • Bernal, C.A., Castellanos, L., Aragon, D.M., Martinez-Matamoros, D., Jimenez, C., Baena, Y., Ramos, F.A., 2018. Peruvioses A to F, sucrose esters from the exudate of Physalis peruviana fruit as α- amylase inhibitors. Carbohydr. Res. 461, 4-10. https://doi.org/ 10.1016/j.carres.2018.03.003.
  • Bernet, B., Vasella, A., 2000. Intra- and intermolecular H-bonds of alcohols in DMSO 1 H- NMR analysis of inter-residue H-bonds in selected oligosaccharides: cellobiose, lactose, N,N'-Diacetylchitobiose, maltose, sucrose, agarose, and hyaluronates. Helv. Chim. Acta 83, 2055-2071.
  • Bharati, D., Rawat, S., Sharma, P., 2015. Evaluation of in vivo efficacy of aqueous leaf extract of Phyllanthus niruri in diabetic hypertensive rats. Ann. Clin. Exp. Hypertens. 3, 1-7.
  • Buta, J.G., Lusby, W.R., Neal, J.W., Waters, R.M., Pittarelli, G.W., 1993. Sucrose esters from Nicotiana gossei active against the greenhouse whitefly Trialeuroides vaporariorum. Phytochemistry 32, 859-864. https://doi.org/10.1016/0031-9422(93) 85220-L.
  • Chang, C.L., Zhang, L.J., Chen, R.Y., Kuo, L.M.Y., Huang, J.P., Huang, H.C., Lee, K.H., Wu, Y.C., Kuo, Y.H., 2010. Antioxidant and anti-inflammatory phenylpropanoid derivatives from calamus quiquesetinervius. J. Nat. Prod. 73, 1482-1488. https://doi.org/ 10.1021/np100181c.
  • Chang, H.T., Tu, P.F., 2007. New oligosaccharide esters and xanthone C-glucosides from Polygala telephioides. Helv. Chim. Acta 90, 944-950. https://doi.org/10.1002/hlca. 200790095.
  • Chen, J., Park, K., 2000. Synthesis of fast-swelling, superporous sucrose hydrogels. Carbohydr. Polym. 41, 259-268. https://doi.org/10.1016/S0144-8617(99)00144-7.
  • Chen, T., Li, J.X., Xu, Q., 2000. Phenylpropanoid glycosides from Smilax glabra. Phytochemistry 53, 1051-1055. https://doi.org/10.1016/S0031-9422(99)00522-1.
  • Cheng, J.T., Li, Y., He, J., Li, X.Y., Wu, X. De, Shao, L.D., Dong, L. Bin, Deng, X., Gao, X., Peng, L.Y., Cheng, X., Zhao, Q.S., 2012. Three new sucrose fatty acid esters from Equisetum hiemale L. Helv. Chim. Acta 95, 1158-1163. https://doi.org/10.1002/ hlca.201100515.
  • Cho, J.G., Cha, B.J., Minlee, S., Shrestha, S., Jeong, R.H., Sunglee, D., Kim, Y.C., Lee, D.G., Kang, H.C., Kim, J., Baek, N.I., 2015a. Diterpenes from the roots of Oryza sativa L. And their inhibition activity on NO production in LPS-stimulated RAW264.7 macrophages. Chem. Biodivers. 12, 1356-1364. https://doi.org/10.1002/cbdv. 201400239.
  • Cho, J.G., Cha, B.J., Seo, W.D., Jeong, R.H., Shrestha, S., Kim, J.Y., Kang, H.C., Baek, N.I., 2015b. Feruloyl sucrose esters from Oryza sativa roots and their tyrosinase inhibition activity. Chem. Nat. Compd. 51, 1094-1098. https://doi.org/10.1007/s10600-015- 1500-8.
  • Choi, J.K., Murillo, G., Su, B.N., Pezzuto, J.M., Kinghorn, A.D., Mehta, R.G., 2006. Ixocarpalactone A isolated from the Mexican tomatillo shows potent antiproliferative and apoptotic activity in colon cancer cells. FEBS J. 273, 5714-5723. https://doi.org/ 10.1111/j.1742-4658.2006.05560.x.
  • Chortyk, O.T., Kays, S.J., Teng, Q., 1997. Characterization of insecticidal sugar esters of Petunia. J. Agric. Food Chem. 45, 270-275. https://doi.org/10.1021/jf960322f.
  • Chortyk, O.T., Pomonis, J.G., Johnson, A.W., 1996. Syntheses and characterizations of insecticidal sucrose esters. J. Agric. Food Chem. 44, 1551-1557. https://doi.org/10. 1021/jf950615t.
  • Chouhan, H.S., Singh, S.K., 2011. Phytochemical analysis, antioxidant and anti-inflammatory activities of Phyllanthus simplex. J. Ethnopharmacol. 137, 1337-1344. https://doi.org/10.1016/j.jep.2011.07.069.
  • Christiansen, A., Backensfeld, T., Kuhn, S., Weitschies, W., 2011. Investigating the stability of the nonionic surfactants tocopheryl polyethylene glycol succinate and sucrose laurate by HPLC-MS, DAD, and CAD. J. Pharm. Sci. 100, 1773-1782. https:// doi.org/10.1002/jps.22408.
  • Cicchetti, E., Duroure, L., Le Borgne, E., Laville, R., 2018. Upregulation of skin-aging biomarkers in aged NHDF cells by a sucrose ester extract from the agroindustrial waste of physalis peruviana calyces. J. Nat. Prod. 81, 1946-1955. https://doi.org/10. 1021/acs.jnatprod.7b01069.
  • Crucho, C.C., Petrova, K.T., Pinto, R.C., Barros, M.T., 2008. Novel unsaturated sucrose ethers and their application as monomers. Molecules 13, 762-770. https://doi.org/ 10.3390/molecules13040762.
  • Davies, D.B., Christofides, J.C., 1987. Comparison of intramolecular hydrogen-bonding conformations of sucrose-containing oligosaccharides in solution and the solid state. Carbohydr. Res. 163, 269-274. https://doi.org/10.1016/0008-6215(87)80188-X.
  • de Koster, C.G., Pajarron, A.M., Heerma, W., Haverkamp, J., 1993. Fast atom bombardment mass spectrometry of sucrose monocaprate and sucrose monolaurate. Biol. Mass Spectrom. 22, 277-284. https://doi.org/10.1002/bms.1200220503.
  • Deshpande, P.S., Deshpande, T.D., Kulkarni, R.D., Mahulikar, P.P., 2013. Synthesis of sucrose-coconut fatty acids esters: reaction kinetics and rheological analysis. Ind. Eng. Chem. Res. 52, 15024-15033. https://doi.org/10.1021/ie401524g.
  • Ding, L., Xie, F., Zhao, M., Xie, J., Xu, G., 2006. Rapid characterization of the sucrose esters from oriental tobacco using liquid chromatography/ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 20, 1816-2822. https://doi.org/10.1002/ rcm.2664 Rapid.
  • Donfack, A.R.N., Toyang, N.J., Wabo, H.K., Tane, P., Awouafack, M.D., Kikuchi, H., Tamokou, J.D.D., Kuiate, J.R., Oshima, Y., 2012. Stigmastane derivatives from the roots of Vernonia guineensis and their antimicrobial activity. Phytochem. Lett. 5, 596-599. https://doi.org/10.1016/j.phytol.2012.06.002.
  • Dong, X.Z., Huang, C.L., Yu, B.Y., Hu, Y., Mu, L.H., Liu, P., 2014. Effect of Tenuifoliside A isolated from Polygala tenuifolia on the ERK and PI3K pathways in C6 glioma cells. Phytomedicine 21, 1178-1188. https://doi.org/10.1016/j.phymed.2014.04.022.
  • Eggleston, G., 2010. Future sustainability of the sugar and sugar - ethanol industries. Sustain. Sugar Sugar-Ethanol Ind. 1-19. https://doi.org/10.1021/bk-2010-1058. ch001.
  • El-Rokh, A.R., Negm, A., El-Shamy, M., El-Gindy, M., Abdel-Mogib, M., 2018. Sucrose diester of aryldihydronaphthalene-type lignans from Echium angustifolium Mill. and their antitumor activity. Phytochemistry 149, 155-160. https://doi.org/10.1016/j. phytochem.2018.02.014.
  • El Sheikha, A., Zaki, M., Bakr, A., El Habashy, M., Montet, D., 2008. Physico-chemical Properties and Biochemical Composition of Physalis (Physalis Pubescens L.) Fruits, vol. 2. Glob. Sci. Books Ltd., pp. 124-130.
  • Erickson, W.R., Fields, S.C., 2014. Low Temperature, Vacuum Assisted Chlorination of Sucrose-6-Esters Free of Overchlorinated By-Products as Intermediates for the Production of the Artificial Sweetener. sucralose US8729255B2.
  • Fabre, N., Urizzi, P., Souchard, J., Frechard, A., Claparols, C., Fouraste, I., Moulis, C., 2000. An antioxidant sinapic acid ester isolated from Iberis amara. Fitoterapia 71, 425-428. https://doi.org/10.1016/S0367-326X(00)00127-1.
  • Ferrer, M., Pastor, E., Parra, J.L., 2000. Chemical versus enzymatic catalysis for the regioselective synthesis of sucrose esters of fatty acids. Glass 509-514. https://doi.org/ 10.1016/s0167-2991(00)81008-3.
  • Ferrer, M., Soliveri, J., Plou, F.J., Lopez-Cortes, N., Reyes-Duarte, D., Christensen, M., Copa-Patino, J.L., Ballesteros, A., 2005. Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida Antarctica B, and their antimicrobial properties. Enzym. Microb. Technol. 36, 391-398. https://doi.org/10. 1016/j.enzmictec.2004.02.009.
  • Feuge, R.O., Zeringue, H.J., Weiss, T.J., Brown, M., 1970. Preparation of sucrose esters by interesterification. J. Am. Oil Chem. Soc. 47, 56-60. https://doi.org/10.1007/ BF02541458.
  • Fitremann, J., Queneau, Y., Maitre, J.P., Bouchu, A., 2007. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Lett. 48, 4111-4114. https://doi.org/10.1016/j.tetlet.2007.04.015.
  • Franco, L.A., Ocampo, Y.C., Gomez, H.A., De La Puerta, R., Espartero, J.L., Ospina, L.F., 2014. Sucrose esters from Physalis peruviana calyces with anti-inflammatory activity. Planta Med. 80, 1605-1614. https://doi.org/10.1055/s-0034-1383192.
  • Georgopoulou, C., Aligiannis, N., Fokialakis, N., Mitaku, S., 2005. Acretoside, a new sucrose ester from Aristolochia cretica. J. Asian Nat. Prod. Res. 7, 799-803. https://doi. org/10.1080/1028602042000191617.
  • Ghosh, B., Jones, A.D., 2017. Profiling, characterization, and analysis of natural and synthetic acylsugars (sugar esters). Anal. Methods 9, 892-905. https://doi.org/10. 1039/c6ay02944b.
  • Gumel, A.M., Annuar, M.S.M., Heidelberg, T., Chisti, Y., 2011. Lipase mediated synthesis of sugar fatty acid esters. Process Biochem. 46, 2079-2090. https://doi.org/10.1016/ j.procbio.2011.07.021.
  • Halinski, L.P., Stepnowski, P., 2013. GC-MS and MALDI-TOF MS profiling of sucrose esters from Nicotiana tabacum and N. rustica[1] L.P. Halinski, P. Stepnowski, GC-MS and MALDI-TOF MS profiling of sucrose esters from Nicotiana tabacum and N. rustica. Zeitschrift Fur Naturforsch. - Sect. C J. B. Zeitschrift fur Naturforsch. - Sect. C J. Biosci. 68, 210-222. https://doi.org/10.1515/znc-2013-5-607.
  • Hali n ski, L.P., Stepnowski, P., 2016. Cuticular hydrocarbons and sucrose esters as chemotaxonomic markers of wild and cultivated tomato species (Solanum section Lycopersicon). Phytochemistry 132, 57-67. https://doi.org/10.1016/j.phytochem. 2016.09.011.
  • Hang, F., Shi, C., Xu, Y., Lu, H., Xie, C., Li, K., 2017. Green synthesis of sucrose laurate under different ultrasonic frequencies. Sugar Tech 19, 241-247. https://doi.org/10. 1007/s12355-016-0460-z.
  • Hu, Y., Liao, H.B., Dai-Hong, G., Liu, P., Wang, Y.Y., Rahman, K., 2010. Antidepressantlike effects of 3,6'-disinapoyl sucrose on hippocampal neuronal plasticity and neurotrophic signal pathway in chronically mild stressed rats. Neurochem. Int. 56, 461-465. https://doi.org/10.1016/j.neuint.2009.12.004.
  • Huang, D., Jiang, X., Zhu, H., Fu, X., Zhong, K., Gao, W., 2010. Improved synthesis of sucrose fatty acid monoesters under ultrasonic irradiation. Ultrason. Sonochem. 17, 352-355. https://doi.org/10.1016/j.ultsonch.2009.08.009.
  • Huang, Z., Bi, Y.J., Sha, Y.F., Xie, W.Y., Wu, D., Liu, B.Z., 2018. Separation and analysis of sucrose esters in tobacco by online liquid chromatography-gas chromatography/mass spectrometry. Anal. Sci. 34, 887-891. https://doi.org/10.2116/analsci.18P076.
  • Januario, A.H., Rodrigues Filho, E., Pietro, R.C.L.R., Kashima, S., Sato, D.N., Franca, S.C., 2002. Antimycobacterial physalins from physalis angulata L. (Solanaceae). Phyther. Res. 16, 445-448. https://doi.org/10.1002/ptr.939.
  • Ji, L., Yuan, Y., Luo, L., Chen, Z., Ma, X., Ma, Z., Cheng, L., 2012. Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors. Steroids 77, 441-447. https://doi.org/10. 1016/j.steroids.2011.11.016.
  • Jiang, B., Liu, Y., Bhandari, B., Zhou, W., 2008. Impact of caramelization on the glass transition temperature of several caramelized sugars. Part II: mathematical modeling. J. Agric. Food Chem. 56, 5148-5152. https://doi.org/10.1021/jf703792x.
  • Jiang, Y., Tu, P., Chen, X., Zhang, T., 2005. Isolation of two sucrose esters from Polygala tenuifolia by high speed countercurrent chromatography. J. Liq. Chromatogr. Relat. Technol. 28, 1583-1592. https://doi.org/10.1081/JLC-200058371.
  • Kandra, L., Severson, R., Wagner, G.J., 1990. Modified branched-chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes. Eur. J. Biochem. 188, 385-391. https://doi.org/10.1111/j.1432-1033.1990. tb15415.x.
  • Kandra, L., Wagner, G.J., 1988. Studies of the site and mode of biosynthesis of tobacco trichome exudate components. Arch. Biochem. Biophys. 265, 425-432. https://doi. org/10.1016/0003-9861(88)90145-2.
  • Karrer, R., Herberg, H., 1992. Analysis of sucrose fatty acid esters by high temperature gc. J.HR.Chrom. 15, 585-589.
  • Khan, N.R., Rathod, V.K., 2015. Enzyme catalyzed synthesis of cosmetic esters and its intensification: a review. Process Biochem. 50, 1793-1806. https://doi.org/10.1016/ j.procbio.2015.07.014.
  • Kharchafi, G., Jerome, F., Adam, I., Pouilloux, Y., Barrault, J., 2005. Design of well balanced hydrophilic-lipophilic catalytic surfaces for the direct and selective monoesterification of various polyols. New J. Chem. 29, 928. https://doi.org/10.1039/ b418509a.
  • Kiem, P. Van, Nhiem, N.X., Cuong, N.X., Hoa, T.Q., Huong, H.T., Huong, L.M., Minh, C. Van, Kim, Y.H., 2008. New phenylpropanoid esters of sucrose from Polygonum hydropiper and their antioxidant activity. Arch Pharm. Res. (Seoul) 31, 1477-1482. https://doi.org/10.1007/s12272-001-2133-y.
  • Kim, K.H., Chang, S.W., Lee, K.R., 2010. Feruloyl sucrose derivatives from Bistorta manshuriensis. Can. J. Chem. 88, 519-523. https://doi.org/10.1139/V10-037.
  • Kim, K.H., Kim, C.S., Park, Y.J., Moon, E., Choi, S.U., Lee, J.H., Kim, S.Y., Lee, K.R., 2015. Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus. Bioorg. Med. Chem. Lett 25, 96-99. https://doi.org/10.1016/j. bmcl.2014.11.001.
  • Kobayashi, W., Miyase, T., Suzuki, S., Noguchi, H., Chen, X.M., 2000. Oligosaccharide esters from the roots of Polygala arillata. J. Nat. Prod. 63, 1066-1069. https://doi. org/10.1021/np0000567.
  • Li, S., Song, Z., Liu, Z., Bai, S., 2008. Characterization and insecticidal activity of sucrose octanoates. Agron. Sustain. Dev. 28, 239-245. https://doi.org/10.1051/ agro:2007037.
  • Lie, A., Stensballe, A., Pedersen, L.H., 2015. Structural analyses of sucrose laurate regioisomers by mass spectrometry techniques. J. Carbohydr. Chem. 34, 206-214. https://doi.org/10.1080/07328303.2015.1021475.
  • Lin, Y., Wagner, G.J., 1994. Surface disposition and stability of pest-interactive, trichomeexuded diterpenes and sucrose esters of tobacco. J. Chem. Ecol. 20, 1907-1921. https://doi.org/10.1007/BF02066232.
  • Liu, Q.B., Huang, X.X., Bai, M., Chang, X.B., Yan, X.J., Zhu, T., Zhao, W., Peng, Y., Song, S.J., 2014. Antioxidant and anti-inflammatory active dihydrobenzofuran neolignans from the seeds of prunus tomentosa. J. Agric. Food Chem. 62, 7796-7803. https:// doi.org/10.1021/jf502171z.
  • Liu, T., Yip, Y.M., Song, L., Feng, S., Liu, Y., Lai, F., Zhang, D., Huang, D., 2013. Inhibiting enzymatic starch digestion by the phenolic compound diboside A: a mechanistic and in silico study. Food Res. Int. 54, 595-600. https://doi.org/10.1016/j.foodres.2013. 07.062.
  • Lu, Y., Yin, L.L., Gray, D.L., Thomas, L.C., Schmidt, S.J., 2017. Impact of sucrose crystal composition and chemistry on its thermal behavior. J. Food Eng. 214, 193-208. https://doi.org/10.1016/j.jfoodeng.2017.06.016.
  • Maier, C., Conrad, J., Steingass, C.B., Beifuss, U., Carle, R., Schweiggert, R.M., 2015. Quillajasides A and B: new phenylpropanoid sucrose esters from the inner bark of Quillaja saponaria molina. J. Agric. Food Chem. 63, 8905-8911. https://doi.org/10. 1021/acs.jafc.5b03532.
  • Maldonado, E., Torres, F.R., Martinez, M., Perez-Castorena, A.L., 2006. Sucrose esters from the fruits of Physalis nicandroides var. attenuata. J. Nat. Prod. 69, 1511-1513. https://doi.org/10.1021/np060274l.
  • Masum, M.N., Choodej, S., Yamauchi, K., Mitsunaga, T., 2019. Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis. Med. Chem. Res. 28, 623-632. https://doi.org/10.1007/ s00044-019-02312-w.
  • Miller, H.E., Rigelhof, F., Marquart, L., Prakash, A., Kanter, M., 2000. Antioxidant content of whole grain breakfast cereals, fruits and vegetables. J. Am. Coll. Nutr. 19, 312S-319S. https://doi.org/10.1080/07315724.2000.10718966.
  • Miyase, T., Noguchi, H., Chen, X.M., 1999. Sucrose esters and xanthone C-glycosides from the roots of Polygala sibirica. J. Nat. Prod. 62, 993-996. https://doi.org/10.1021/ np990084t.
  • Moh, M.H., Tang, T.S., Tan, G.H., 2000. Improved separation of sucrose ester isomers using gradient high performance liquid chromatography with evaporative light scattering detection. Food Chem. 69, 105-110. https://doi.org/10.1016/S0308- 8146(99)00226-5.
  • Molinier, V., Wisniewski, K., Bouchu, A., Fitremann, J., Queneau, Y., 2003. Transesterification of sucrose in organic medium: study of acyl group migrations. J. Carbohydr. Chem. 22, 657-669. https://doi.org/10.1081/CAR-120026466.
  • Mora Vargas, J.A., Orduna Ortega, J., Bernardo Correia dos santos, M., Metzker, G., Gomes, E., Boscolo, M., 2020. A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains. Carbohydr. Res., 107957. https://doi.org/10.1016/j.carres.2020.107957.
  • Nakamura, S., 1999. Application of Sucrose Fatty Acid Esters as Food Emulsifiers, Industrial Applications of Surfactants IV. The Royal Society of Chemistryhttps://doi. org/10.1533/9781845698614.73.
  • Neal, J.W., Buta, J.G., Pittarelli, G.W., Lusby, W.R., Bentz, J.A., 1994. Novel sucrose esters from nicotiana-gossei - effective biorationals against selected horticultural insect pests. J. Econ. Entomol. 87, 1600-1607.
  • Neta, N., do, A.S., dos Santos, J.C.S., Sancho, S. de O., Rodrigues, S., Goncalves, L.R.B., Rodrigues, L.R., Teixeira, J.A., 2012. Enzymatic synthesis of sugar esters and their potential as surface-active stabilizers of coconut milk emulsions. Food Hydrocolloids 27, 324-331. https://doi.org/10.1016/j.foodhyd.2011.10.009.
  • Ocampo, Y.C., Caro, D.C., Rivera, D.E., Franco, L.A., 2017. Safety of sucrose esters from Physalis peruviana L. in a 28-day repeated-dose study in mice. Biomed. Pharmacother. 90, 850-862. https://doi.org/10.1016/j.biopha.2017.04.046.
  • Ohkawabata, S., Kanemaru, M., Kuawahara, S.Y., Yamamoto, K., Kadokawa, J.I., 2012. Synthesis of 6-O-hexadecyl-and 6-O-octylsucroses and their self-assembling properties under aqueous conditions. J. Carbohydr. Chem. 31, 659-672. https://doi.org/10. 1080/07328303.2012.702250.
  • Okumura, H., Kitazawa, N., Wada, S., Hotta, H., 2011. Stability of sucrose fatty acid esters under acidic and basic conditions. J. Oleo Sci. 60, 313-320. https://doi.org/10.5650/ jos.60.313.
  • Ono, M., Takamura, C., Sugita, F., Masuoka, C., Yoshimitsu, H., Ikeda, T., Nohara, T., 2007. Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum. Chem. Pharm. Bull. (Tokyo) 55, 551-556. https://doi.org/10.1248/cpb.55.551.
  • Ovenden, S.P.B., Yu, J., Bernays, J., Wan, S.S., Christophidis, L.J., Sberna, G., Tait, R.M., Wildman, H.G., Lebeller, D., Lowther, J., Walsh, N.G., Meurer-Grimes, B.M., 2005. Physaloside A, an acylated sucrose ester from Physalis viscosa. J. Nat. Prod. 68, 282-284. https://doi.org/10.1021/np049746r.
  • Panda, P., Appalashetti, M., Natarajan, M., Mary, C.P., Venkatraman, S.S., Judeh, Z.M.A., 2012. Synthesis and antiproliferative activity of helonioside A, 3',4',6'-tri-O-feruloylsucrose, lapathoside C and their analogs. Eur. J. Med. Chem. 58, 418-430. https://doi.org/10.1016/j.ejmech.2012.10.034.
  • Pedersen, N.R., Wimmer, R., Matthiesen, R., Pedersen, L.H., Gessesse, A., 2003. Synthesis of sucrose laurate using a new alkaline protease. Tetrahedron Asymmetry 14, 667-673. https://doi.org/10.1016/S0957-4166(03)00086-7.
  • Perez-Castorena, A.L., Luna, M., Martinez, M., Maldonado, E., 2012. New sucrose esters from the fruits of Physalis solanaceus. Carbohydr. Res. 352, 211-214. https://doi. org/10.1016/j.carres.2012.02.003.
  • Perez-Castorena, A.L., Martinez, M., Maldonado, E., 2010. Labdanes and sucrose esters from physalis sordida. J. Nat. Prod. 73, 1271-1276. https://doi.org/10.1021/ np100127k.
  • Perez-Victoria, I., Zafra, A., Morales, J.C., 2007. Determination of regioisomeric distribution in carbohydrate fatty acid monoesters by LC-ESI-MS. Carbohydr. Res. 342, 236-242. https://doi.org/10.1016/j.carres.2006.11.019.
  • Perez, B., Anankanbil, S., Guo, Z., 2017. Chapter 10. Synthesis of sugar fatty acid esters and their industrial utilizations. Fat. Acids 329-354. https://doi.org/10.1016/B978- 0-12-809521-8.00010-6.
  • Peris, M., 2016. Sucrose: properties and determination. In: Encyclopedia of Food and Health, first ed. Elsevier Ltd. https://doi.org/10.1016/B978-0-12-384947-2.00669-3.
  • Petkova, N., Vassilev, D., Grudeva, R., Koleva, M., Denev, P., 2015. Ultrasound-Assisted synthesis of undecylenoyl sucrose esters. Int. Sci. Conf. - Gabrovo I 517-521. https:// doi.org/10.13140/RG.2.1.4149.7048.
  • Plat, T., Linhardt, R.J., 2001. Syntheses and applications of sucrose-based esters. J. Surfactants Deterg. 4, 415-421. https://doi.org/10.1007/s11743-001-0196-y.
  • Polat, T., Linhardt, R.J., 2001. Syntheses and applications of sucrose-based esters. J. Surfactants Deterg. 4, 415-421. https://doi.org/10.1007/s11743-001-0196-y.
  • Potier, P., Bouchu, A., Gagnaire, J., Queneau, Y., 2001. Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides. Tetrahedron Asymmetry 12, 2409-2419. https://doi.org/10.1016/S0957-4166(01)00424-4.
  • Qian-Cutrone, J., Huang, S., Trimble, J., Li, H., Lin, P.F., Alam, M., Klohr, S.E., Kadow, K.F., 1996. Niruriside, a new HIV REV/RRE binding inhibitor from Phyllanthus niruri. J. Nat. Prod. 59, 196-199. https://doi.org/10.1021/np9600560.
  • Queneau, Y., Fitremann, J., Trombotto, S., 2004. The chemistry of unprotected sucrose: the selectivity issue. Compt. Rendus Chem. 7, 177-188. https://doi.org/10.1016/j. crci.2003.10.014.
  • Queneau, Y., Jarosz, S., Lewandowski, B., Fitremann, J., 2007a. Sucrose chemistry and applications of sucrochemicals. In: Advances in Carbohydrate Chemistry and Biochemistry, https://doi.org/10.1016/S0065-2318(07)61005-1.
  • Queneau, Y., Jarosz, S., Lewandowski, B., Fitremann, J., 2007b. Sucrose chemistry and applications of sucrochemicals. In: Advances in Carbohydrate Chemistry and Biochemistry, https://doi.org/10.1016/S0065-2318(07)61005-1.
  • Richel, A., Laurent, P., Wathelet, B., Wathelet, J.P., Paquot, M., 2011. Microwave-assisted conversion of carbohydrates. State of the art and outlook. Compt. Rendus Chem. 14, 224-234. https://doi.org/10.1016/j.crci.2010.04.004.
  • Rodriguez-Diaz, M., Delporte, C., Cartagena, C., Cassels, B.K., Gonzalez, P., Silva, X., Leon, F., Wessjohann, L.A., 2011. Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. J. Pharm. Pharmacol. 63, 718-724. https://doi.org/10.1111/j.2042-7158.2011.01263.x.
  • Rolls, B.J., Pirraglia, P.A., Jones, M.B., Peters, J.C., 1992. Effects of olestra, a noncaloric fat substitute, on daily energy and fat intakes in lean men. Am. J. Clin. Nutr. 56, 84-92. https://doi.org/10.1093/ajcn/56.1.84.
  • Ruiz-Matute, A.I., Hernandez-Hernandez, O., Rodriguez-Sanchez, S., Sanz, M.L., Martinez-Castro, I., 2011. Derivatization of carbohydrates for GC and GC-MS analyses. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 879, 1226-1240. https://doi. org/10.1016/j.jchromb.2010.11.013.
  • Saeed, S., Rashid, N., Jones, P.G., Ali, M., Hussain, R., 2010. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents. Eur. J. Med. Chem. 45, 1323-1331. https://doi.org/10.1016/j.ejmech.2009.12.016.
  • Sallaud, C., Giacalone, C., Topfer, R., Goepfert, S., Bakaher, N., Rosti, S., Tissier, A., 2012. Characterization of two genes for the biosynthesis of the labdane diterpene Z-abienol in tobacco (Nicotiana tabacum) glandular trichomes. Plant J. 72, 1-17. https://doi. org/10.1111/j.1365-313X.2012.05068.x.
  • San Martin, R., Briones, R., 1999. Industrial uses and sustainable supply of. Econ. Bot. 53, 302-311. https://doi.org/10.1007/BF02866642.
  • Sarin, B., Verma, N., Martin, J.P., Mohanty, A., 2015. An overview of important ethnomedicinal herbs of Phyllanthus Species : present status and future. Prospects 1-10 2014.
  • Sasayama, T., Kamikanda, Y., Shibasaki-Kitakawa, N., 2018. Process design for green and selective production of bio-based surfactant with heterogeneous resin catalyst. Chem. Eng. J. 334, 2231-2237. https://doi.org/10.1016/j.cej.2017.11.132.
  • Sato, J., Goto, K., Nanjo, F., Kawai, S., Murata, K., 2000. Antifungal activity of plant extracts against Arthrinium sacchari and Chaetomium funicola. J. Biosci. Bioeng. 90, 442-446. https://doi.org/10.1016/S1389-1723(01)80016-5.
  • Sauthier, M., Mortreux, A., Suisse, I., 2014. From conventional to greener catalytic approaches for carbohydrates etherification. In: Rauter, A.P., Lindhorst, T.K.L., Queneau, Y. (Eds.), Carbohydrate Chemistry Chemical and Biological Approache. The Royal Society of Chemistry, pp. 73-98. https://doi.org/10.1039/9781849739986- 00073.
  • Schilmiller, A.L., Charbonneau, A.L., Last, R.L., 2012. Identification of a BAHD acetyltransferase that produces protective acyl sugars in tomato trichomes. Proc. Natl. Acad. Sci. Unit. States Am. 109, 16377-16382. https://doi.org/10.1073/pnas. 1207906109.
  • Scientific Panel on Food Additives, Flavourings, P.A. and M. in C. with F., 2004. Opinion of the scientific Panel on food Additives, Flavourings, processing aids and materials in contact with food on sucrose esters of fatty acids, E 473 and sucroglycerides, E 474 based on a request from the commission related to sucrose esters of fatty. EFSA J 2, 1-23.
  • Severson, R.F., Arrendale, R.F., Chortyk, O.T., Green, C.R., Thome, F.A., Stewart, J.L., Johnson, A.W., 1985. Isolation and characterization of the sucrose esters of the cuticular waxes of green tobacco leaf. J. Agric. Food Chem. 33, 870-875. https://doi. org/10.1021/jf00065a026.
  • Shah, R., Kolanos, R., DiNovi, M.J., Mattia, A., Kaneko, K.J., 2017. Dietary exposures for the safety assessment of seven emulsifiers commonly added to foods in the United States and implications for safety. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 34, 905-917. https://doi.org/10.1080/19440049.2017.1311420.
  • Simonovska, B., Srbinoska, M., Vovk, I., 2006. Analysis of sucrose esters - insecticides from the surface of tobacco plant leaves. J. Chromatogr. A 1127, 273-277. https:// doi.org/10.1016/j.chroma.2006.05.103.
  • Sook Yun, Y., Satake, M., Katsuki, S., Kunugi, A., 2004. Phenylpropanoid derivatives from edible canna, Canna edulis. Phytochemistry 65, 2167-2171. https://doi.org/10. 1016/j.phytochem.2004.06.003.
  • Sun, X., Zimmermann, M.L., Campagne, J.M., Sneden, A.T., 2000. New sucrose phenylpropanoid esters from Polygonum perfoliatum. J. Nat. Prod. 63, 1094-1097. https:// doi.org/10.1021/np000055e.
  • Tachrim, Z.P., Wang, L., Yoshida, T., Muto, M., Nakamura, T., Masuda, K., Hashidoko, Y., Hashimoto, M., 2016. Comprehensive structural analysis of halogenated sucrose derivatives: revisiting the reactivity of sucrose primary alcohols. Chemistry 1, 58-63. https://doi.org/10.1002/slct.201500003.
  • Takasaki, M., Konoshima, T., Kuroki, S., Tokuda, H., Nishino, H., 2001. Cancer chemopreventive activity of phenylpropanoid esters of sucrose, vanicoside B and lapathoside A, from Polygonum lapathifolium. Canc. Lett. 173, 133-138. https://doi.org/10. 1016/S0304-3835(01)00670-X.
  • Thevenet, S., Descotes, G., Bouchu, A., Queneau, Y., 1997. Hydrophobic effect driven esterification of sucrose in aqueous medium. J. Carbohydr. Chem. 16, 691-696. https://doi.org/10.1080/07328309708007347.
  • Thevenet, S., Wernicke, A., Belniak, S., Descotes, G., Bouchu, A., Queneau, Y., 1999. Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity versus acyl- or alkyloxycarbonyl-group migrations. Carbohydr. Res. 318, 52-66. https://doi.org/10.1016/S0008-6215(99)00079-8.
  • Tian, S., Nakamura, K., Kayahara, H.K., 2004. Analysis of phenolic compounds in white rice, brown rice. J. Agric. Food Chem. 52, 4808-4813. https://doi.org/10.1021/ jf049446f.
  • Tona, L., Ngimbi, N.P., Tsakala, M., Mesia, K., Cimanga, K., Apers, S., De Bruyne, T., Pieters, L., Totte, J., Vlietinck, A.J., 1999. Antimalarial activity of 20 crude extracts from nine African medicinal plants used in Kinshasa, Congo. J. Ethnopharmacol. 68, 193-203. https://doi.org/10.1016/S0378-8741(99)00090-2.
  • Toyang, N.J., Ateh, E.N., Keiser, J., Vargas, M., Bach, H., Tane, P., Sondengam, L.B., Davis, H., Bryant, J., Verpoorte, R., 2012a. Toxicity, antimicrobial and anthelmintic activities of Vernonia guineensis Benth. (Asteraceae) crude extracts. J. Ethnopharmacol. 144, 700-704. https://doi.org/10.1016/j.jep.2012.10.016.
  • Toyang, N.J., Krause, M.A., Fairhurst, R.M., Tane, P., Bryant, J., Verpoorte, R., 2013. Antiplasmodial activity of sesquiterpene lactones and a sucrose ester from Vernonia guineensis Benth. (Asteraceae). J. Ethnopharmacol. 147, 618-621. https://doi.org/ 10.1016/j.jep.2013.03.051.
  • Toyang, N.J., Wabo, H.K., Ateh, E.N., Davis, H., Tane, P., Kimbu, S.F., Sondengam, L.B., Bryant, J., 2012b. In vitro anti-prostate cancer and ex vivo antiangiogenic activity of Vernonia guineensis Benth. (Asteraceae) tuber extracts. J. Ethnopharmacol. 141, 866-871. https://doi.org/10.1016/j.jep.2012.03.021.
  • Wagner, G.J., Wang, E., Shepherd, R.W., 2004. New approaches for studying and exploiting an old protuberance, the plant trichome. Ann. Bot. 93, 3-11. https://doi.org/ 10.1093/aob/mch011.
  • Wang, N., Yao, X., Ishii, R., Kitanaka, S., 2003. Bioactive sucrose esters from Bidens parviflora. Phytochemistry 62, 741-746. https://doi.org/10.1016/S0031-9422(02) 00454-5.
  • Wang, N.L., Wang, J., Yao, X.S., Kitanaka, S., 2006. Two neolignan glucosides and antihistamine release activities from Bidens parviflora WILLD. Chem. Pharm. Bull. 54, 1190-1192 JST.JSTAGE/cpb/54.1190 [pii].
  • Wei, T., Yu, X., Wang, Y., Zhu, Y., Du, C., Jia, C., Mao, D., 2014. Purification and evaluation of the enzymatic properties of a novel fructosyltransferase from Aspergillus oryzae: a potential biocatalyst for the synthesis of sucrose 6-acetate. Biotechnol. Lett. 36, 1015-1020. https://doi.org/10.1007/s10529-014-1457-x.
  • Yan, L.L., Gao, W.Y., Zhang, Y.J., Wang, Y., 2008. A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis. Fitoterapia 79, 306-307. https://doi.org/10. 1016/j.fitote.2007.11.029.
  • Yoshinari, K., Sashida, Y., Mimaki, Y., Shimomura, H., 1990. New polyacylated sucrose derivatives from the bark of Prunus padus. Chem. Pharm. Bull. (Tokyo) 38, 415-417. https://doi.org/10.1248/cpb.38.415.
  • Zhang, C.-Y., Luo, J.-G., Liu, R.-H., Lin, R., Yang, M.-H., Kong, L.-Y., 2016a. 1 H NMR spectroscopy-guided isolation of new sucrose esters from Physalis alkekengi var. franchetii and their antibacterial activity. Fitoterapia 114, 138-143. https://doi.org/ 10.1016/j.fitote.2016.09.007.
  • Zhang, C.R., Khan, W., Bakht, J., Nair, M.G., 2016b. New antiinflammatory sucrose esters in the natural sticky coating of tomatillo (Physalis philadelphica), an important culinary fruit. Food Chem. 196, 726-732. https://doi.org/10.1016/j.foodchem.2015. 10.007.
  • Zhang, C.Y., Luo, J.G., Liu, R.H., Lin, R., Yang, M.H., Kong, L.Y., 2017. Physakengoses K- Q, seven new sucrose esters from Physalis alkekengi var. franchetii. Carbohydr. Res. 449, 120-124. https://doi.org/10.1016/j.carres.2017.07.010.
  • Zhang, D., Miyase, T., Kuroyanagi, M., Umehara, K., Noguchi, H., 1998. Oligosaccharide polyesters from roots of Polygala glomerata. Phytochemistry 47, 45-52. https://doi. org/10.1016/S0031-9422(97)00490-1.
  • Zhang, D., Miyase, T., Kuroyanagi, M., Umehara, K., Ueno, A., 1996. Five new triterpene saponins, polygalasaponins XXVIII-XXXII from the root of Polygala japonica HOUTT. Chem. Pharm. Bull. (Tokyo) 44, 810-815. https://doi.org/10.1248/cpb.44.810.
  • Zhang, L., Liao, C.C., Huang, H.C., Shen, Y.C., Yang, L.M., Kuo, Y.H., 2008. Antioxidant phenylpropanoid glycosides from Smilax bracteata. Phytochemistry 69, 1398-1404. https://doi.org/10.1016/j.phytochem.2008.01.002.
  • Zhao, J.-Q., Wang, Y.-M., Wang, D., Yang, C.-R., Xu, M., Zhang, Y.-J., 2013. Five new sucrose esters from the whole plants of Phyllanthus cochinchinensis. Nat. Products Bioprospect. 3, 61-65. https://doi.org/10.1007/s13659-013-0026-7.
  • Zhao, L., Zhang, H., Hao, T., Li, S., 2015. In vitro antibacterial activities and mechanism of sugar fatty acid esters against five food-related bacteria. Food Chem. 187, 370-377. https://doi.org/10.1016/j.foodchem.2015.04.108.
  • Zhao, W., Huang, X.X., Yu, L.H., Liu, Q.B., Li, L.Z., Sun, Q., Song, S.J., 2014. Tomensides A-D, new antiproliferative phenylpropanoid sucrose esters from Prunus tomentosa leaves. Bioorg. Med. Chem. Lett 24, 2459-2462. https://doi.org/10.1016/j.bmcl. 2014.04.018.
  • Zheng, Y., Zheng, M., Ma, Z., Xin, B., Guo, R., Xu, X., 2015. Sugar Fatty Acid Esters, Polar Lipids: Biology, Chemistry, and Technology. AOCS Presshttps://doi.org/10.1016/ B978-1-63067-044-3.50012-1.
  • Zhu, H., Feng, Y., Yang, J., Pan, W., Li, Z., Tu, Y., Zhu, X., Huang, G., 2013. Separation and characterization of sucrose esters from Oriental tobacco leaves using accelerated solvent extraction followed by SPE coupled to HPLC with ion-trap. J. Separ. Sci. 36, 2486-2495. https://doi.org/10.1002/jssc.201300294.
  • Zhu, J., Tang, Y., Li, J., Zhang, S., 2009. Analysis of sucrose esters with long acyl chain by coupling of HPLC-ELSD with ESI-MS system. Chin. J. Chem. Eng. 17, 1032-1037. https://doi.org/10.1016/S1004-9541(08)60313-4.