Published April 30, 2022
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Serrulatane diterpenoids from the leaves of Eremophila glabra and their potential as antihyperglycemic drug leads
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- 1. * & Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100, Copenhagen,
Description
Petersen, Malene J., Liang, Chao, Kjaerulff, Louise, Ndi, Chi, Semple, Susan, Buirchell, Bevan, Coriani, Sonia, Møller, Birger Lindberg, Staerk, Dan (2022): Serrulatane diterpenoids from the leaves of Eremophila glabra and their potential as antihyperglycemic drug leads. Phytochemistry (113072) 196: 1-11, DOI: 10.1016/j.phytochem.2021.113072, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113072
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- urn:lsid:plazi.org:pub:5341FFF63E3F3E38FFE65440FF88BF10
References
- Algreiby, A.A., Hammer, K.A., Durmic, Z., Vercoe, P., Flematti, G.R., 2018. Antibacterial compounds from the Australian native plant Eremophila glabra. Fitoterapia 126, 45-52. https://doi.org/10.1016/j.fitote.2017.11.008.
- Atanasov, A.G., Zotchev, S.B., Dirsch, V.M., Supuran, C.T., 2021. Natural products in drug discovery: advances and opportunities. Nat. Rev. Drug Discov. 20, 200-216. https://doi.org/10.1038/s41573-020-00114-z.
- Botirov, E.K., Karimov, A.M., 2018. Flavonoids from roots of Scutellaria intermedia. Chem. Nat. Compd. 54, 577-578. https://doi.org/10.1007/s10600-018-2412-1.
- Brown, A., Buirchell, B.J., 2011. A Field Guide to the Eremophilas of Western Australia. Simon Nevill Publications, York.
- Bruhn, T., Schauml¨offel, A., Hemberger, Y., Pecitelli, G., 2017. SpecDis Version 1.71; Berlin, Germany. https://specdis-software.jimdo.com.
- Callari, R., Fischer, D., Heider, H., Weber, N., 2018. Biosynthesis of angelyl-CoA in Saccharomyces cerevisiae. Microb. Cell Factories 17, 72. https://doi.org/10.1186/ s12934-018-0925-8.
- Chatterjee, S., Khunti, K., Davies, M.J., 2017. Type 2 diabetes. Lancet 389, 2239-2251. https://doi.org/10.1016/S0140-6736(17)30058-2.
- Croft, K.D., Ghisalberti, E.L., Jefferies, P.R., Proudfoot, G.M., 1981. The chemistry of Eremophila spp. XVI. New serrulatanes from Eremophila spp. Aust. J. Chem. 34, 1951-1957. https://doi.org/10.1071/CH9811951.
- Forster, P.G., Ghisalberti, E.L., Jefferies, P.R., Poletti, V.M., Whiteside, N.J., 1986. Serrulatane diterpenes from Eremophila spp. Phytochemistry 25, 1377-1383. https://doi.org/10.1016/S0031-9422(00)81293-5.
- 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., et al., 2016. Gaussian 16, Revision C.01. Gaussian, Inc., Wallingford CT.
- Galic, S., Hauser, C., Kahn, B.B., Haj, F.G., Neel, B.G., Tonks, N.K., Tiganis, T., 2005. Coordinated regulation of insulin signaling by the protein tyrosine phosphatases PTP1B and TCPTP. Mol. Cell Biol. 25, 819-829. https://doi.org/10.1128/ MCB.25.2.819-829.2005.
- Gericke, O., Hansen, N.L., Pedersen, G.B., Kjaerulff, L., Lou, D., Staerk, D., Moller, B.L., Pateraki, I., Heskes, A.M., 2020. Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species. BMC Plant Biol. 20, 91. https://doi.org/10.1186/s12870-020-2293-x.
- Gericke, O., Fowler, R.M., Heskes, A.M., Bayly, M.J., Semple, S.J., Ndi, C.P., Staerk, D., Loland, C.J., Murphy, D.J., Buirchell, B.J., Moller, B.L., 2021. Navigating through chemical space and evolutionary time across the Australian continent in plant genus Eremophila. Plant J. 108, 555-578. https://doi.org/10.1111/tpj.15448.
- Ghisalberti, E.L., 1994. The ethnopharmacology and phytochemistry of Eremophila species (Myoporaceae). J. Ethnopharmacol. 44, 1-9. https://doi.org/10.1016/0378- 8741(94)90092-2.
- Habgood, M.J., James, T., Heifetz, A., 2020. Conformational searching with quantum mechanics. In: Heifetz, A. (Ed.), Quantum Mechanics in Drug Discovery. Springer Science+Business Media, LLC, part of Springer Nature, New York, p. 207. https:// doi.org/10.1007/978-1-0716-0282-9_14.
- Hansen, C.C., Nelson, D.R., Moller, B.L., Werck-Reichhart, D., 2021. Plant cytochrome P450 plasticity and evolution. Mol. Plant 14, 1244-1265. https://doi.org/10.1016/j. molp.2021.06.028.
- Hjortness, M.K., Riccardi, L., Hongdusit, A., Ruppe, A., Zhao, M., Kim, E.Y., Zwart, P.H., Sankaran, B., Arthanari, H., Sousa, M.C., De Vivo, M., Fox, J.M., 2018. Abietane-type diterpenoids inhibit protein tyrosine phosphatases by stabilizing an inactive enzyme conformation. Biochemistry 57, 5886-5896. https://doi.org/10.1021/acs. biochem.8b00655.
- International Diabetes Federation, 2019. IDF Diabetes Atlas, ninth ed. Brussels, Belgium. https://diabetesatlas.org/atlas/ninth-edition/.
- Kjaerulff, L., Jensen, A.B.J., Ndi, C., Semple, S., Moller, B.L., Staerk, D., 2020. Isolation, structure elucidation and PTP1B inhibitory activity of serrulatane diterpenoids from the roots of Myoporum insulare. Phytochem. Lett. 39, 49-56. https://doi.org/ 10.1016/j.phytol.2020.07.001.
- Kumar, R., Duffy, S., Avery, V.M., Carroll, A.R., Davis, R.A., 2018. Microthecaline A, a quinoline serrulatane alkaloid from the roots of the Australian desert plant Eremophila microtheca. J. Nat. Prod. 81, 1079-1083. https://doi.org/10.1021/acs. jnatprod.7b00992.
- Luo, D., Callari, R., Hamberger, B., Wubshet, S.G., Nielsen, T.N., Andersen-Ranberg, J., Hallstr¨om, B.M., Cozzi, F., Heider, H., Moller, B.L., Staerk, D., Hamberger, B., 2016. In: Proc. Natl. Acad. Sci. U.S.A., vol. 113, pp. E5082-E5089. https://doi.org/ 10.1073/pnas.1607504113.
- Ndi, C.P., Semple, S.J., Griesser, H.J., Pyke, S.M., Barton, M.D., 2007. Antimicrobial compounds from Eremophila serrulata. Phytochemistry 68, 2684-2690. https://doi. org/10.1016/j.phytochem.2007.05.039.
- Newman, D.J., Cragg, G.M., 2020. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J. Nat. Prod. 83, 770-803. https:// doi.org/10.1021/acs.jnatprod.9b01285.
- Padhi, S., Nayak, A.K., Behera, A., 2020. Type II diabetes mellitus: a review on recent drug based therapeutics. Biomed. Pharmacother. 131, 110708. https://doi.org/ 10.1016/j.biopha.2020.110708.
- Pedersen, H.A., Ndi, C., Semple, S.J., Buirchell, B., Moller, B.L., Staerk, D., 2020. PTP1Binhibiting branched-chain fatty acid dimers from Eremophila oppositifolia subsp. angustifolia identified by high-resolution PTP1B inhibition profiling and HPLC-PDA- HRMS-SPE-NMR analysis. J. Nat. Prod. 83, 1598-1610. https://doi.org/10.1021/ acs.jnatprod.0c00070.
- Pescitelli, G., Bruhn, T., 2016. Good computational practice in the assignment of absolute configurations by TDDFT calculations of ECD spectra. Chirality 28, 466-474. https://doi.org/10.1002/chir.22600.
- Reinhardt, J.K., Klemd, A.M., Danton, O., De Mieri, M., Smiesko, M., Huber, R., Burgi, T., Grundemann, C., Hamburger, M., 2019. Sesquiterpene lactones from Artemisia argyi: absolute configuration and immunosuppressant activity. J. Nat. Prod. 82, 1424-1433. https://doi.org/10.1021/acs.jnatprod.8b00791.
- Semple, S.J., Reynolds, G.D., O' Leary, M.C., Flower, R.L., 1998. Screening of Australian medicinal plants for antiviral activity. J. Ethnopharmacol. 60, 163-172. https://doi. org/10.1016/s0378-8741(97)00152-9.
- Singab, A.N., Youssef, F.S., Ashour, M.L., Wink, M., 2013. The genus Eremophila (Scrophulariaceae): an ethnobotanical, biological and phytochemical review. J. Pharm. Pharmacol. 65, 1239-1279. https://doi.org/10.1111/jphp.12092.
- Smith, J.E., Tucker, D., Watson, K., Jones, G.L., 2007. Identification of antibacterial constituents from the indigenous Australian medicinal plant Eremophila duttonii F. Muell. (Myoporaceae). J. Ethnopharmacol. 112, 386-393. https://doi.org/10.1016/ j.jep.2007.03.031.
- Tahtah, Y., Wubshet, S.G., Kongstad, K.T., Heskes, A.M., Pateraki, I., Moller, B.L., J¨ager, A.K., Staerk, D., 2016. High-resolution PTP1B inhibition profiling combined with high-performance liquid chromatography-high-resolution mass spectrometry-solid-phase extraction-nuclear magnetic resonance spectroscopy: proof-of-concept and antidiabetic constituents in crude extract of Eremophila lucida. Fitoterapia 110, 52-58. https://doi.org/10.1016/j.fitote.2016.02.008.
- Tomasi, J., Mennucci, B., Cammi, R., 2005. Quantum mechanical continuum solvation models. Chem. Rev. 105, 2999-3093. https://doi.org/10.1021/cr9904009.
- Wang, L., Chen, K., Zhang, M., Ye, M., Qiao, X., 2021. Catalytic function, mechanism, and application of plant acyltransferases. Crit. Rev. Biotechnol. https://doi.org/ 10.1080/07388551.2021.1931015.
- Wubshet, S.G., Tahtah, Y., Heskes, A.M., Kongstad, K.T., Pateraki, I., Hamberger, B., Moller, B.L., Staerk, D., 2016. Identification of PTP1B and α- glucosidase inhibitory serrulatanes from Eremophila spp. by combined use of dual high-resolution PTP1B and α- glucosidase inhibition profiling and HPLC-HRMS-SPE-NMR. J. Nat. Prod. 79, 1063-1072. https://doi.org/10.1021/acs.jnatprod.5b01128.
- Zabolotny, J.M., Bence-Hanulec, K.K., Stricker-Krongrad, A., Haj, F., Wang, Y., Minokoshi, Y., Kim, Y.B., Elmquist, J.K., Tartaglia, L.A., Kahn, B.B., Neel, B.G., 2002. PTP1B regulates leptin signal transduction in vivo. Dev. Cell 2, 489-495. https://doi. org/10.1016/s1534-5807(02)00148-x.
- Zahran, E.M., Abdelmohsen, U.R., Hussein, A.S., Salem, M.A., Khalil, H.E., Yehia Desoukey, S., Fouad, M.A., Kamel, M.S., 2019. Antiulcer potential and molecular docking of flavonoids from Ocimum forskolei Benth., family Lamiaceae. Nat. Prod. Res. 35, 1-5. https://doi.org/10.1080/14786419.2019.1645662.