Published January 31, 2021
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Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities
Creators
- 1. ** & * & Key Laboratory of Chemical Biology (Ministry of Education), Institute of Pharmacognosy, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong,
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Hu, Shuiyao, Chai, Wern Chern, Xu, Lintao, Li, Shaoqiang, Jin, Cuirong, Zhu, Rongxiu, Yang, Luping, Zhang, Ranran, Tang, Kaijun, Li, Ping, Yang, Erlan, Chang, Wenqiang, Shen, Tao, Semple, Susan, Venter, Henrietta, Xiang, Lan (2021): Catecholic alkaloid sulfonates and aromatic nitro compounds from Portulaca oleracea and screening of their anti-inflammatory and anti-microbial activities. Phytochemistry (112587) 181: 1-11, DOI: 10.1016/j.phytochem.2020.112587, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112587
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- urn:lsid:plazi.org:pub:FFEFFFEEF40DFFC0FFDBFFC1AC7CFFA9
References
- Alam, M.A., Juraimi, A.S., Rafii, M.Y., Hamid, A.A., Aslani, F., 2014. Screening of Purslane (Portulaca oleracea L.) accessions for high salt tolerance. Sci. World J. 627916, 2014.
- Al-Zereini, W., Schuhmann, I., Laatsch, H., Helmke, E., 2007. New aromatic nitro compounds from Salegentibacter sp. T436, an arctic sea ice bacterium: taxonomy, fermentation, isolation and biological activities. J. Antibiot. 60, 301-308.
- Budzikiewicz, H., 2006. Bacterial aromatic sulfonates - a Bucherer reaction in nature. Mini-Reviews Org. Chem. 3, 93-97.
- Chen, Q.W., Tian, Y., Chen, H.W., Gao, T., Dong, J.X., 2014. Nitrogenous chemical constituents of Weiceng. Mil. Med. Sci. 38, 62-66.
- Chinese Pharmacopeia Committee, 2015. Pharmacopeia of People' s Republic of China. China Medical Science and Technology Press, Beijing.
- Clinical and Laboratory Standards Institute (CLSI), 2006. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically: Approved Standard, seventh ed. CLSI M7-A7, Wayne, PA.
- Dweck, A.C., 2001. Purslane (Portulaca oleracea) - the global panacea. Pers. Care Mag. 2, 7-15.
- El-Bakatoushi, R., Alframawy, A.M., Samer, M., El-Sadek, L., Botros, W., 2013. Evolution of the Portulaca oleracea L. aggregate in Egypt on molecular and phenotypic levels revealed by morphology, inter-simple sequence repeat (ISSR) and 18S rDNA gene sequence markers. Flora 208, 464-477.
- Epifano, F., Sosa, S., Tubaro, A., Marcotullio, M.C., Curini, M., Genovese, S., 2011. Topical anti-inflammatory activity of boropinic acid and its natural and semisynthetic derivatives. Bioorg. Med. Chem. Lett 21, 769-772.
- European Committee on Antimicrobial Susceptibility Testing (EUCAST), 2017. Method for the Determination of Broth Dilution Minimum Inhibitory Concentrations of Antifungal Agents for Yeast. EUCAST Definitive Document E.DEF 7.3.1, Copenhagen, Denmark.
- Frank, J., Chafetz, L.J., 1977. IR spectrophotometric assay of carbachol solutions. Pharmaceut. Sci. 66, 439.
- Freire, P.T.C., Melo, F.E.A., Filho, J.M., 1996. Polarized Raman and infrared spectra of taurine crystals. J. Raman Spectrosc. 27, 507-512.
- Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J.A., 2004. Gaussian 03, Revision A.1. Gaussian, Inc., Pittsburgh, PA.
- Fung, K.P., Han, Q.B., Ip, M., Yang, X.S., Lau, C.B.S., Chan, B.C.L., 2017. Synergists from Portulaca oleracea with macrolides against methicillin-resistant Staphylococcus aureus and related mechanism. Hong Kong Med. J. 23, 38-42.
- Ganbaatar, J., Osadchii, S.A., Shults, E.E., Tolstikov, G.A., 2002. Study of alkaloids of the Siberian and Altai flora 9.* synthesis of amino derivatives of elatidine. Russ. Chem. Bull. 51, 2290-2294.
- Ge, L., Lan, L.F., Bao, H.B., Yang, K.D., 2014. Study on the chemical constituents of Peristrophe roxburghiana. Guihaia 34, 155-159.
- Geng, Z.L., Wang, H.X., Zhao, P.J., Hao, X.J., Zeng, Y., 2009. Research development on halogenases and biological halogenation. Acta Bot. Yunnanica 31, 269-278.
- Gribble, G.W., 2004. Natural organohalogens: a new frontier for medicinal agents. J. Chem. Educ. 81, 1441-1449.
- Gritzer, R.F., Moffitt, K., Godchaux, W., Leadbetter, E.R., 2003. Sulfoacetaldehyde bisulfite adduct is a substrate for enzymes presumed to act on sulfoacetaldehyde. J. Microbiol. Methods 53, 423-425.
- Huang, Q.Q., Bi, J.L., Sun, Q.Y., Yang, F.M., Wang, Y.H., Tang, G.H., Zhao, F.W., Wang, H., Xu, J.J., Kennelly, E.J., Long, C.L., Yin, G.F., 2012. Bioactive isoquinoline alkaloids from Corydalis saxicola. Planta Med. 78, 65-70.
- Iranshahy, M., Javadi, B., Iranshahi, M., Jahanbakhsh, S.P., Mahyari, S., Hassani, F.V., Karimi, G., 2017. A review of traditional uses, phytochemistry and pharmacology of Portulaca oleracea L. J. Ethnopharmacol. 205, 158-172.
- Jain, T., Kaiser, C., Ackerman, D.M., Ladd, D.L., Fong, K.L., Roberts, G.D., Staiger, D.B., Davis, L.L., Webb, R.L., 1986. Sulfoconjugation of dopamine: a critical examination of the reaction between dopamine and concentrated sulfuric acid. Can. J. Chem. 64, 2418-2422.
- Jiao, Z.Z., Yue, S., Sun, H.X., Jin, T.Y., Wang, H.N., Zhu, R.X., Xiang, L., 2015. Indoline amide glucosides from Portulaca oleracea: isolation, structure, and DPPH radical scavenging activity. J. Nat. Prod. 78, 2588-2597.
- Jin, T.Y., Li, S.Q., Jin, C.R., Shan, H., Wang, R.M., Zhou, M.X., Li, A.L., Li, L.Y., Hu, S.Y., Shen, T., Xiang, L., 2018. Catecholic isoquinolines from Portulaca oleracea and their antiinflammatory and β2-adrenergic receptor agonist activity. J. Nat. Prod. 81, 768-777.
- Johnson, T.B., Kohmann, E.F., 1915. 3-nitro-4-hydroxycinnamic acid and its methyl ether. J. Am. Chem. Soc. 37, 162-167.
- Kim, H.Y., Kim, H.V., Yoon, J.H., Kang, B.R., Cho, S.M., Lee, S., Kim, J.Y., Kim, J.W., Cho, Y., Woo, J., Kim, Y.S., 2014. Taurine in drinking water recovers learning and memory in the adult APP/PS1 mouse model of Alzheimer' s disease. Sci. Rep. 4, 7467.
- Kim, Y., Lim, H.J., Jang, H.J., Lee, S., Jung, K., Lee, S.W., Lee, S.J., Rho, M.C., 2018. Portulaca oleracea extracts and their active compounds ameliorate inflammatory bowel diseases in vitro and in vivo by modulating TNF-α, IL-6 and IL-1β signaling. Food Res. Int. 106, 335-343.
- Lara, M.V., Disante, K.B., Podest´a, F.E., Andreo, C.S., Drincovich, M.F., 2003. Induction of a crassulacean acid like metabolism in the C4 succulent plant, Portulaca oleracea L.: physiological and morphological changes are accompanied by specific modifications in phosphoenolpyruvate carboxylase. Photosynth. Res. 77, 241-254.
- Lei, X., Li, J.M., Liu, B., Zhang, N., Liu, H.Y., 2015. Separation and identification of four new compounds with antibacterial activity from Portulaca oleracea L. Molecules 20, 16375-16387.
- Li, C.Y., Meng, Y.H., Ying, Z.M., Xu, N., Hao, D., Gao, M.Z., Zhang, W.J., Xu, L., Gao, Y. C., Ying, X.X., 2016. Three novel alkaloids from Portulaca oleracea L. and their anti-inflammatory effects. J. Agric. Food Chem. 64, 5837-5844.
- Meng, Y.H., Ying, Z.M., Xiang, Z., Hao, D., Zhang, W.J., Zheng, Y., Gao, Y.C., Ying, X.X., 2016. The anti-inflammation and pharmacokinetics of a novel alkaloid from Portulaca oleracea L. J. Pharm. Pharmacol. 68, 397-405.
- Mitchell, S.C., 2018. Xenobiotic C-sulfonate derivatives: metabolites or metabonates. Xenobiotica 48, 211-218.
- Napolitano, A., Pezzella, A., Prota, G., 1999. 6,7-Dihydroxy-1,2,3,4- tetrahydroisoquinoline formation by iron mediated dopamine oxidation: a novel route to endogenous neurotoxins under oxidative stress conditions. Tetrahedron Lett. 40, 2833-2836.
- Parry, R., Nishino, S., Spain, J., 2011. Naturally-occurring nitro compounds. Nat. Prod. Rep. 28, 152-167.
- Pesnot, T., Gershater, M.C., Ward, J.M., Hailes, H.C., 2011. Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids. Chem. Commun. 47, 3242-3244.
- Philip, J.S., Nobuyuki, H., 2010. ECD cotton effect approximated by the Gaussian curve and other methods. Chirality 22, 229-233.
- Potapov, V.M., Dem' yanovich, V.M., Skvortsova, T.V., 1987. Circular dichroism and configuration of ( )-1-methyl-1,2,3,4,tetrahydroisoquinoline. Chem. Heterocycl. Compd. 23, 990-992.
- Ringdahl, B., Chan, R.P.K., Craig, J.C., Manske, R.H.F., 1981. Proterberine alkaloids: chiroptical properties and absolute configuration. J. Nat. Prod. 44, 75-79. Schmidt, B., H¨olter, F., Berger, R., Jessel, S., 2010. Mizoroki-Heck reactions with 4- phenoldiazonium salts. Adv. Synth. Catal. 352, 2463-2473.
- Schuhmann, I., Yao, C.B., Al-Zereini, W., Anke, H., Helmke, E., Laatsch, H., 2009. Nitro derivatives from the Arctic ice bacterium Salegentibacter sp. isolate T436*. J. Antibiot. 62, 453-460.
- Sheldrick, G.M., 2015a. SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. A71, 3-8.
- Sheldrick, G.M., 2015b. Crystal structure refinement with SHELXL. Acta Crystallogr. C71, 3-8.
- Ibrahim, A.S., 2017. Assessment of herbal drugs for promising anti- Candida activity. BMC Compl. Alternative Med. 17, 257-265.
- Sun, H.X., He, X.Q., Liu, C.J., Li, L.Y., Zhou, R.Y., Jin, T.Y., Yue, S., Feng, D., Gong, J., Sun, J.W., Ji, J.B., Xiang, L., 2016. Effect of oleracein E, a neuroprotective tetrahydroisoquinoline, on rotenone-induced Parkinson' s disease cell and animal models. ACS Chem. Neurosci. 8, 155-164.
- 13 Tian, J.P., Yin, Y.W., Sun, H.B., Luo, X.F., 2002. Magnesium chloride: an efficient C NMR relaxation agent for amino acids and some carboxylic acids. J. Magn. Reson. 159, 137-144.
- Wang, B., Yang, H., 2018. Study on the synthesis of sodium dodecyl benzene sulfonate. Shandong Chem. Ind. 47, 49-51.
- Wang, C.J., Li, K., Zhang, X.J., Wang, Y.S., Zhang, H.J., 2016. Study on the synthesis of o - nitrophenoxyacetic acid. Zhoukou Norm. Univ. 33, 102-103, 110.
- Xie, Z.F., Chen, Y., Dai, Y.J., Tong, Z.F., 2007. Adsorption of sulfosalicylic acid on 717 anion exchange resin. Chin. J. Process Eng. 7, 278-282.
- Xiu, F., Li, X.T., Zhang, W.J., He, F., Ying, X.X., Stien, D., 2018. A new alkaloid from Portulaca oleracea L. and its antiacetylcholinesterase activity. Nat. Prod. Res. 18, 1-8. Yang, Y., Chen, J.H., Liu, Q., Ben, C., Todd, C.D., Shi, J., Yang, Y.P., Hu, X.Y., 2012. Comparative proteomic analysis of the thermotolerant plant Portulaca oleracea acclimation to combined high temperature and humidity stress. J. Proteome Res. 11, 3605-3623.
- Zhou, Y.X., Xin, H.L., Rahman, K., Wang, S.J., Peng, C., Zhang, H., 2015. Portulaca oleracea L.: a review of phytochemistry and pharmacological effects. BioMed Res. Int. 2015, 925631.