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Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their α-glucosidase inhibitory activity

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  • 1. The Research Unit of Natural Product Utilization, School of Science, Walailak University, Thasala, Nakhon Si Thammarat, 80160, Thailand

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Tantapakul, Cholpisut, Suthiphasilp, Virayu, Payaka, Apirak, Chaiyosang, Boonyanoot, Harding, David J., Phuphong, Worrapong, Tontapha, Sarawut, Laphookhieo, Surat (2022): Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their α-glucosidase inhibitory activity. Phytochemistry (113168) 198: 1-7, DOI: 10.1016/j.phytochem.2022.113168, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113168

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urn:lsid:plazi.org:pub:FFA6BB0F6378FFF83E02FFAB2F30B949

Cites
Publication: 10.1016/j.ejmech.2018.07.017 (DOI)
Publication: 10.1139/v07-120 (DOI)
Publication: 10.1016/S0031-9422(00)91494-8 (DOI)
Publication: 10.1016/j.phytol.2017.05.004 (DOI)
Publication: 10.1107/S0021889808042726 (DOI)
Publication: 10.1021/acs.jnatprod.9b00262 (DOI)
Publication: 10.1039/jr9420000181 (DOI)
Publication: 10.2217/nnm-2016-0388 (DOI)
Publication: 10.1016/j.phytochem.2018.10.014 (DOI)
Publication: 10.1016/0040-4020(72)88159-6 (DOI)
Publication: 10.1007/s13659-015-0078-y (DOI)
Publication: 10.1080/10286020802514002 (DOI)
Publication: 10.1055/s-0044-100797 (DOI)
Publication: 10.1021/acschemneuro.9b00232 (DOI)
Publication: 10.1016/j.heliyon.2020.e03625 (DOI)
Publication: 10.1080/14786419.2018.1457667 (DOI)
Publication: 10.1016/j.bmc.2009.05.051 (DOI)
Publication: 10.1080/10286020.2017.1317750 (DOI)
Publication: 10.1107/S2053229614024218 (DOI)
Publication: 10.1107/S2053273314026370 (DOI)
Publication: 10.5935/0103-5053.20130231 (DOI)
Publication: 10.1016/j.phytol.2012.03.007 (DOI)
Publication: 10.1016/S0367-326X(00)00210-0 (DOI)
Publication: 10.1016/j.bmc.2020.115462 (DOI)
Publication: 10.1016/j.phymed.2008.12.015 (DOI)
Publication: 10.1007/s13659-013-0062-3 (DOI)
Publication: 10.1007/s13659-016-0090-x (DOI)
Publication: 10.1080/10286020.2015.1042370 (DOI)
Publication: 10.1016/j.fitote.2014.03.015 (DOI)
Has part
Figure: 10.5281/zenodo.8236380 (DOI)
Figure: 10.5281/zenodo.8236382 (DOI)
Figure: 10.5281/zenodo.8236384 (DOI)
Figure: 10.5281/zenodo.8236386 (DOI)

References

  • Alfonsi, R., Caimano, M., Botta, B., Mori, M., Di Marcotullio, L., 2018. Synergistic inhibition of the Hedgehog pathway by newly designed Smo and Gli antagonists bearing the isoflavone scaffold. Eur. J. Med. Chem. 156, 554-562. https://doi.org/ 10.1016/j.ejmech.2018.07.017.
  • Cheenpracha, S., Karalai, C., Ponglimanont, C., Chantrapromma, K., 2007. Cytotoxic rotenoids from the stems of Derris trifoliata. Can. J. Chem. 85, 1019-1022. https:// doi.org/10.1139/v07-120.
  • Chibber, S.S., Sharma, R.P., 1979. Robustigenin, a new isoflavone from Derris robusta seed shells. Phytochemistry 18, 1082. https://doi.org/10.1016/S0031-9422(00) 91494-8.
  • Chien, S., Chen, C., Wang, S., Wu, J., Shih, C., Chao, L.K., Chao, C., Chiu, H., Kuo, Y., 2017. Two new flavonoids from Derris laxiflora Benth. Phytochem. Lett. 21, 29-31. https://doi.org/10.1016/j.phytol.2017.05.004.
  • Dolomanov, O.V., Bourhis, R.J., Gildea, R.J., Howard, J.A.K., Puschmann, H., 2009. Olex2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42, 339-341. https://doi.org/10.1107/S0021889808042726.
  • Fan, J., Kuang, Y., Dong, Z., Yi, Y., Zhou, Y., Li, B., Qiao, X., Ye, M., 2020. Prenylated phenolic compounds from the ariel parts of Glycyrrhiza uralensis as PTP1B and α- glucosidase inhibitor. J. Nat. Prod. 83, 814-824. https://doi.org/10.1021/acs. jnatprod.9b00262.
  • 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 Jr., J.A., 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., 2009. Gaussian 09 (Revision A.02. Gaussian, Inc., Wallingford, CT.
  • Harper, S.H., 1942. The active principles of leguminous fish-poison plants. Part VI. Robustic acid. J. Chem. Soc. 181-182. https://doi.org/10.1039/jr9420000181.
  • Ingallina, C., Costa, P.M., Ghirga, F., Klippstein, R., Wang, J.T., Berardozzi, S., Hodgins, N., Infante, P., Pollard, S.M., Botta, B., Al-Jamal, K.T., 2017. Polymeric glabrescione B nanocapsules for passive targeting of Hedgehog-dependent tumor therapy in vitro. Nanomedicine 12, 711-728. https://doi.org/10.2217/nnm-2016- 0388.
  • Jaidee, W., Andersen, R.J., Patrick, B.O., Stephen, G.P., Muanprasat, C., Borwornpinyo, S., Laphookhieo, S., 2019. Alkaloids and styryllactones from Goniothalamus cheliensis. Phytochemistry 157, 8-20. https://doi.org/10.1016/j. phytochem.2018.10.014.
  • Jain, A.C., Jain, S.M., 1972. Synthesis of derrubone and robustone. Tetrahedron 28, 5063-5067. https://doi.org/10.1016/0040-4020(72)88159-6.
  • Li, X., Mao, M., Ren, F., Jiang, X., Hai, P., Wang, F., 2015. Pterocarpadiols A-D, rare 6a,11b-dihydroxypterocarpans from Derris robusta. Nat. Prod. Bioprospect. 5, 287-291. https://doi.org/10.1007/s13659-015-0078-y.
  • Lu, H., Liang, J., 2009. Novel N-containing rotenoid and seco-rotenoid from the root of Derris elliptica. J. Asian Nat. Prod. Res. 11, 58-62. https://doi.org/10.1080/ 10286020802514002.
  • Mittraphab, Y., Ngamrojanavanich, N., Shimizu, K., Matsubara, K., Pudhom, K., 2018. Anti-angiogenic activity of rotenoids from the stems of Derris trifoliata. Planta Med. 84, 779-785. https://doi.org/10.1055/s-0044-100797.
  • Nam, G., Ji, Y., Lee, H.J., Kang, J., Yi, Y., Kim, M., Lin, Y., Lee, Y., Lim, M.H., 2019. Orobol: an isoflavone exhibiting regulatory multifunctionality against four pathological features of Alzheimer' s disease. ACS Chem. Neurosci. 10, 3386-3390. https://doi.org/10.1021/acschemneuro.9b00232.
  • Phukhatmuen, P., Raksat, A., Laphookhieo, S., Charoensup, R., Duangyod, T., Maneerat, W., 2020. Bioassay-guided isolation and identification of antidiabetic compounds from Garcinia cowa leaf extract. Heliyon 6, e03625. https://doi.org/ 10.1016/j.heliyon.2020.e03625.
  • Posri, P., Suthiwong, J., Takomthong, P., Wongsa, C., Chuenban, C., Boonyarat, C., Yenjai, C., 2019. A new flavonoid from the leaves of Atalantia monophylla (L.) DC. Nat. Prod. Res. 33, 1115-1121. https://doi.org/10.1080/14786419.2018.1457667.
  • Rao, R.R., Tiwari, A.K., Reddy, P.P., Babu, K.S., Ali, A.Z., Madhusudana, K., Rao, J.M., 2009. New furanoflavonoids, intestinal α- glucosidase inhibitory and free-radical (DPPH) scavenging, activity from antihyperglycemic root extract of Derris indica (Lam.). Bioorg. Med. Chem. 17, 5170-5175. https://doi.org/10.1016/j. bmc.2009.05.051.
  • Saraphon, C., Boonloh, K., Kukongviriyapan, V., Yenjai, C., 2017. Cytotoxic flavonoids from the fruits of Derris indica. J. Asian Nat. Prod. Res. 19, 1198-1203. https://doi. org/10.1080/10286020.2017.1317750.
  • Sheldrick, G.M., 2015a. Crystal structure refinement with SHELXL. Acta Crystallogr. C71, 3-8. https://doi.org/10.1107/S2053229614024218.
  • Sheldrick, G.M., 2015b. SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. A71, 3-8. https://doi.org/10.1107/ S2053273314026370.
  • Souza, R.F.D., Marinho, V.H.S., Silva, G.A.D., Costa-Jr, L.M., Silva, J.K.R.D., Bastos, G.N. T., Arruda, A.C., Silva, M.N.D., Arruda, M.S.P., 2013. New isoflavones from the leaves of Vatairea guianensis Aubl´e. J. Braz. Chem. Soc. 24, 1857-1863. https://doi. org/10.5935/0103-5053.20130231.
  • Phakhodee, W., Cheenpracha, S., Laphookhieo, S., 2012. Glycopentaphyllone: the first isolation of hydroperoxyquinolone from the fruits of Glycosmis pentaphylla. Phytochem. Lett. 5, 379-381. https://doi.org/10.1016/j.phytol.2012.03.007.
  • Stewart, M., Bartholomew, B., Currie, F., Abbiw, D.K., Latif, Z., Sarker, S.D., Nash, R.J., 2000. Pyranoisoflavones from Rinorea welwitschii. Fitoterapia 71, 595-597. https:// doi.org/10.1016/S0367-326X(00)00210-0.
  • Suthiphasilp, V., Maneerat, W., Rujanapun, N., Duangyod, T., Charoensup, R., Deachathai, S., Andersen, R.J., Patrick, B.O., Pyne, S.G., Laphookhieo, S., 2020. α- Glucosidase inhibitory and nitric oxide production inhibitory activities of alkaloids isolated from a twig extract of Polyalthia cinnamomea. Bioorg. Med. Chem. 28, 115462. https://doi.org/10.1016/j.bmc.2020.115462.
  • Tewtrakul, S., Cheenpracha, S., Karalai, C., 2009. Nitric oxide inhibitory principles from Derris trifoliata stems. Phytomedicine 16, 568-572. https://doi.org/10.1016/j. phymed.2008.12.015.
  • Wang, F., Li, X.L., Wei, G.Z., Ren, F.C., Liu, J.K., 2013. New isoflavonoids from Erythrina arborescen s and structure revision of anagyroidisoflavone A. Nat. Prod. Bioprospect. 3, 238-242. https://doi.org/10.1007/s13659-013-0062-3.
  • Wei, G.Z., Mao, M.F., Li, X.M., Ren, F.C., Wang, F., 2016. Derrisisoflavones H-K and one isoflavan derivative from Derris robusta. Nat. Prod. Bioprospect. 6, 111-116. https:// doi.org/10.1007/s13659-016-0090-x.
  • Yang, L.F., Wang, K., Jiang, M.G., Liu, H.C., Wang, X., Qin, P.Y., Ouyang, Q.L., 2015. Isolation and characterization of a new bioactive isoflavone from Derris eriocarpa. J. Asian Nat. Prod. Res. 17, 1002-1009. https://doi.org/10.1080/ 10286020.2015.1042370.
  • Zhang, H., Lunga, P., Li, Z., Dai, Q., Du, Z., 2014. Flavonoids and stilbenoids from Derris eriocarpa. Fitoterapia 95, 147-153. https://doi.org/10.1016/j.fitote.2014.03.015.