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Dimeric aporphine alkaloids from the twigs of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner

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Teerapongpisan, Passakorn, Suthiphasilp, Virayu, Phukhatmuen, Piyaporn, Rujanapun, Narawadee, Chaiyosang, Boonyanoot, Tontapha, Sarawut, Maneerat, Tharakorn, Patrick, Brian O., Duangyod, Thidarat, Charoensup, Rawiwan, Andersen, Raymond J., Laphookhieo, Surat (2023): Dimeric aporphine alkaloids from the twigs of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner. Phytochemistry (113586) 207: 1-11, DOI: 10.1016/j.phytochem.2023.113586, URL: http://dx.doi.org/10.1016/j.phytochem.2023.113586

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urn:lsid:plazi.org:pub:FFD9163CFFC6FFF9FFAEFFEDFFFFFF9F

Cites
Publication: 10.1016/0031-9422(94)00675-J (DOI)
Publication: 10.1016/j.phytol.2018.11.022 (DOI)
Publication: 10.3390/molecules26154521 (DOI)
Publication: 10.1016/j.fitote.2021.104883 (DOI)
Publication: 10.1016/j.phytol.2020.06.009 (DOI)
Publication: 10.1016/0031-9422(96)00219-1 (DOI)
Publication: 10.1021/np50070a013 (DOI)
Publication: 10.1107/S0021889808042726 (DOI)
Publication: 10.1016/j.phytochem.2012.09.011 (DOI)
Publication: 10.1021/np50004a001 (DOI)
Publication: 10.1021/np50030a001 (DOI)
Publication: 10.1021/np50057a001 (DOI)
Publication: 10.1021/np50110a001 (DOI)
Publication: 10.1021/acs.jafc.0c04615 (DOI)
Publication: 10.1021/acs.jafc.1c06106 (DOI)
Publication: 10.1007/s10337-020-03977-x (DOI)
Publication: 10.1021/np070293a (DOI)
Publication: 10.1021/np020498d (DOI)
Publication: 10.1186/1472-6882-13-48 (DOI)
Publication: 10.1016/j.heliyon.2020.e03625 (DOI)
Publication: 10.1107/S2053273314026370 (DOI)
Publication: 10.1107/S2053229614024218 (DOI)
Publication: 10.1021/acs.jnatprod.6b00409 (DOI)
Publication: 10.1016/j.fitote.2010.11.025 (DOI)
Publication: 10.1021/np0102399 (DOI)
Publication: 10.1016/j.tetlet.2020.151890 (DOI)
Publication: 10.3897/phytokeys.94.21553 (DOI)
Publication: 10.1016/j.bioorg.2019.103069 (DOI)
Publication: 10.1016/j.tetlet.2016.07.104 (DOI)
Publication: 10.1016/j.phytol.2018.04.009 (DOI)
Has part
Figure: 10.5281/zenodo.8290487 (DOI)
Figure: 10.5281/zenodo.8290489 (DOI)
Figure: 10.5281/zenodo.8290491 (DOI)
Figure: 10.5281/zenodo.8290493 (DOI)
Figure: 10.5281/zenodo.8290495 (DOI)
Figure: 10.5281/zenodo.8290497 (DOI)

References

  • Achenbach, H., Schwinn, A., 1995. Aporphinoid alkaloids and terpenoids from Piptostigma fugax. Phytochemistry 38, 1037-1048. https://doi.org/10.1016/0031- 9422(94)00675-J.
  • Aldulaimi, A.K.O., Azziz, S.S.S.A., Bakri, Y.M., Nafiah, M.A., Aowda, S.A., Awang, K., Litaudon, M., 2019. Two new isoquinoline alkaloids from the bark of Alphonsea cylindrica King and their antioxidant activity. Phytochem. Lett. 29, 110-114. https:// doi.org/10.1016/j.phytol.2018.11.022.
  • Ali, G., Cuny, G.D., 2021. 8-, 9-, and 11-Aryloxy dimeric aporphines and their pharmacological activities. Molecules 26, 4521. https://doi.org/10.3390/ molecules26154521.
  • Chen, J., Jin, C., Xu, B., Shu, J., Shao, F., Yuan, C., Li, F., Huang, L., Huang, H., 2021. New compounds from the stems of Fissistigma oldhamii var. longistipitatum and their cytotoxic activities. Fitoterapia 151, 104883. https://doi.org/10.1016/j. fitote.2021.104883.
  • Chimeze, V.W.N., Zuhlke, S., Djama, C.M., Eckelmann, D., Wandji, J., 2020. Dimeric dehydroaporphinoids with antiplasmodial properties from the liana of Artabotrys aurantiacus (Annonaceae). Phytochem. Lett. 38, 150-154. https://doi.org/10.1016/ j.phytol.2020.06.009.
  • Connolly, J.D., Haque, M.E., Kadir, A.A., 1996. Two 7, 7'-bisdehydroaporphine alkaloids from Polyalthia bullata. Phytochemistry 43, 295-297. https://doi.org/10.1016/ 0031-9422(96)00219-1.
  • Cortes, D., Davoust, D., Hadi, A.H.A., Myint, S.H., Hocquemiller, R., Cav´e, A., 1990. Trivalvone, une nouvelle bis-aporphine des ecorces de Trivalvaria macrophylla. J. Nat. Prod. 53, 862-866. https://doi.org/10.1021/np50070a013.
  • Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A., Puschmann, H., 2009. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42, 339-341. https://doi.org/10.1107/S0021889808042726.
  • 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, Y.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.
  • Ge, Y.W., Zhu, S., Shang, M.Y., Zang, X.Y., Wang, X., Bai, Y.J., Li, L., Komatsu, K., Cai, S. Q., 2013. Aristololactams and aporphines from the stems of Fissistigma oldhamii (Annonaceae). Phytochemistry 86, 201-207. https://doi.org/10.1016/j. phytochem.2012.09.011.
  • Guinaudeau, H., Leboeuf, M., Cav´e, A., 1979. Aporphine alkaloids, II. J. Nat. Prod. 42, 325-360. https://doi.org/10.1021/np50004a001.
  • Guinaudeau, H., Leboeuf, M., Cav´e, A., 1983. Aporphinoid alkaloids, III. J. Nat. Prod. 46, 761-835. https://doi.org/10.1021/np50030a001.
  • Guinaudeau, H., Leboeuf, M., Cav´e, A., 1988. Aporphinoid alkaloids, IV. J. Nat. Prod. 51, 389-474. https://doi.org/10.1021/np50057a001.
  • Guinaudeau, H., Leboeuf, M., Cav´e, A., 1994. Aporphinoid alkaloids, V. J. Nat. Prod. 57, 1033-1135. https://doi.org/10.1021/np50110a001.
  • He, X.F., Chen, J.J., Li, T.Z., Zhang, X.K., Guo, Y.Q., Zhang, X.M., Hu, J., Geng, C.A., 2020. Nineteen new flavanol-fatty alcohol hybrids with α -glucosidase and PTP1B dual inhibition: one unusual type of antidiabetic constituent from Amomum tsao-ko. J. Agric. Food Chem. 68, 11434-11448. https://doi.org/10.1021/acs.jafc.0c04615.
  • Hou, Z.W., Chen, C.H., Ke, J.P., Zhang, Y.Y., Qi, Y., Liu, S.Y., Yang, Y., Ning, J.M., Bao, G. H., 2021. α -Glucosidase inhibitory activities and the interaction mechanism of novel spiro-flavoalkaloids from YingDe Green Tea. J. Agric. Food Chem. 70, 136-148. https://doi.org/10.1021/acs.jafc.1c06106.
  • Kamto, E.L.D., Mendonca, S.C., Zintchem, A.A., Tiam, E.R., Pegnyemb, D.E., Leitao, G.G., 2021. Aporphine alkaloids from Triclisia dictyophylla Diels by pH-zone refining countercurrent chromatography. Chromatographia 84, 13-20. https://doi.org/ 10.1007/s10337-020-03977-x.
  • Kanokmedhakul, S., Kanokmedhakul, K., Lekphrom, R., 2007. Bioactive constituents of the roots of Polyalthia cerasoides. J. Nat. Prod. 70, 1536-1538. https://doi.org/ 10.1021/np070293a.
  • Kanokmedhakul, S., Kanokmedhakul, K., Yodbuddee, D., Phonkerd, N., 2003. New antimalarial bis-dehydroaporphine alkaloids from Polyalthia debilis. J. Nat. Prod. 66, 616-619. https://doi.org/10.1021/np020498d.
  • Malebo, H.M., Wenzler, T., Cal, M., Swaleh, S.M., Omolo, M.O., Hassanali, A., S´equin, U., H¨aussinger, D., Dalsgaard, P., Hamburger, M., Brun, R., Ndiege, I.O., 2013. Antiprotozoal activity of aporphine and protoberberine alkaloids from Annickia kummeriae (engl. & diels) setten & maas (Annonaceae). BMC Compl. Alternative Med. 13, 1-10. https://doi.org/10.1186/1472-6882-13-48.
  • 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.
  • Sheldrick, G.M., 2015a. SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. A71, 3-8. https://doi.org/10.1107/ S2053273314026370.
  • Sheldrick, G.M., 2015b. Crystal structure refinement with SHELXL. Acta Crystallogr. C71, 3-8. https://doi.org/10.1107/S2053229614024218.
  • Shono, T., Ishikawa, N., Toume, K., Arai, M.A., Masu, H., Koyano, T., Kowithayakorn, T., Ishibashi, M., 2016. Cerasoidine, a bis-aporphine alkaloid isolated from Polyalthia cerasoides during screening for Wnt signal inhibitors. J. Nat. Prod. 79, 2083-2088. https://doi.org/10.1021/acs.jnatprod.6b00409.
  • Sichaem, J., Ruksilp, T., Worawalai, W., Siripong, P., Khumkratok, S., Tip-pyang, S., 2011. A new dimeric aporphine from the roots of Artabotrys spinosus. Fitoterapia 82, 422-425. https://doi.org/10.1016/j.fitote.2010.11.025.
  • Wijeratne, E.M.K., Lankananda, B.D., Tezuka, Y., Nagaoka, T., Gunatilaka, A.L., 2001. Dimeric aporphine alkaloids of Phoenicanthus obliqua from Sri Lanka. J. Nat. Prod. 64, 1465-1467. https://doi.org/10.1021/np0102399.
  • Xiao, B.B., Xia, G.Y., Wang, L.Y., Qiu, B.L., Xia, H., Zhong, W.C., Tian, G.H., Lin, S., 2020. (± )-Bicoryanhunine A, dimeric benzylisoquinoline alkaloid atropo-enantiomers from Corydalis yanhusuo. Tetrahedron Lett. 61, 151890 https://doi.org/10.1016/j. tetlet.2020.151890.
  • Yang, B., Zhou, S.S., Ding, H.B., Li, R., Maung, K.W., Tan, Y.H., 2018. Two new species of Trivalvaria (Annonaceae) from northern Myanmar. PhytoKeys 94, 3-12. https://doi. org/10.3897/phytokeys.94.21553.
  • Yu, Z., Han, C., Song, X., Chen, G., Chen, J., 2019. Bioactive aporphine alkaloids from the stems of Dasymaschalon rostratum. Bioorg. Chem. 90, 103069 https://doi.org/ 10.1016/j.bioorg.2019.103069.
  • Zhou, Q., Fu, Y.H., Zhang, Y.Q., Wu, S.Y., Song, X.P., Cao, C.K., Xu, W., Chen, G.Y., 2016. Fissitungfines A and B, two novel aporphine related alkaloids from Fissistigma tungfangense. Tetrahedron Lett. 57, 4162-4164. https://doi.org/10.1016/j. tetlet.2016.07.104.
  • Zhou, Q., Fu, Y.H., Zhang, Y.Q., Wu, S.Y., Song, X.P., Xu, W., Chen, G.Y., 2018. Bioactive aporphine alkaloids from Fissistigma tungfangense. Phytochem. Lett. 25, 105-108. https://doi.org/10.1016/j.phytol.2018.04.009.