Biodiversity Literature Repository

Submit to community
Liberated Data
Published January 31, 2021 | Version v1
Journal article Restricted

Voacafrines A-N, aspidosperma-type monoterpenoid indole alkaloids from Voacanga africana with AChE inhibitory activity

Authors/Creators

  • 1. ** & * & State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, PR & University of Chinese Academy of Sciences, Beijing, 100049, PR China

Description

Zhao, Qian, Zhu, Wen-Tao, Ding, Xiao, Huo, Zong-Qing, Donkor, Paul O., Adelakun, Tiwalade A., Hao, Xiao-Jiang, Zhang, Yu (2021): Voacafrines A-N, aspidosperma-type monoterpenoid indole alkaloids from Voacanga africana with AChE inhibitory activity. Phytochemistry (112566) 181: 1-9, DOI: 10.1016/j.phytochem.2020.112566, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112566

Files

Restricted

The record is publicly accessible, but files are restricted. <a href="https://zenodo.org/account/settings/login?next=https://zenodo.org/records/8291213">Log in</a> to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFC414379B462201FF886F29FF9EFFEF

Cites
Publication: 10.1016/s0031-9422(96)00645-0 (DOI)
Publication: 10.1016/0031-9422(88)80817-3 (DOI)
Publication: 10.1016/0031-9422(90)89025-5 (DOI)
Publication: 10.1002/anie.201305533 (DOI)
Publication: 10.1016/0031-9422(92)83447-7 (DOI)
Publication: 10.1016/j.fitote.2020.104491 (DOI)
Publication: 10.3109/13880209.2012.658478 (DOI)
Publication: 10.1007/s13659-019-00226-z (DOI)
Publication: 10.1021/np800435c (DOI)
Publication: 10.1016/j.fitote.2019.104347 (DOI)
Publication: 10.1021/np2009169 (DOI)
Publication: 10.1016/0022-1759(83)90303-4 (DOI)
Publication: 10.1016/j.phytol.2016.10.019 (DOI)
Publication: 10.1016/j.phytochem.2015.02.028 (DOI)
Publication: 10.1021/np0200919 (DOI)
Publication: 10.1002/hlca.19830660818 (DOI)
Publication: 10.1186/1752-153x-6-96 (DOI)
Publication: 10.1021/acs.orglett.9b02346 (DOI)
Publication: 10.1021/acs.jnatprod.9b00856 (DOI)
Publication: 10.3390/molecules24071256 (DOI)
Publication: 10.1021/acs.jnatprod.7b00949 (DOI)
Has part
Figure: 10.5281/zenodo.8291216 (DOI)
Figure: 10.5281/zenodo.8291218 (DOI)
Figure: 10.5281/zenodo.8291220 (DOI)
Figure: 10.5281/zenodo.8291222 (DOI)

References

  • Achenbach, H., Benirschke, M., Torrenegra, R., 1997. Alkaloids and other compounds from seeds of Tabernaemontana corymbosa. Phytochemistry 45, 325-335. https://doi. org/10.1016/s0031-9422(96)00645-0.
  • Atta-ur-Rahman, Fatima, T., Khanum, S., 1988. 15β- hydroxyvincadfformine, an alkaloid from the leaves of Rhazya stricta. Phytochemistry 27, 3721-3723. https://doi.org/ 10.1016/0031-9422(88)80817-3.
  • Ellman, G.L., Courtney, K.D., Andres Jr., V., Featherstone, R.M., 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol.
  • Fahn, W., Kaiser, V., Schubel, H., Stockigt ¨, J., Danieli, B., 1990. Catharanthus roseus enzyme mediated synthesis of 3-hydroxyvoafrine-A and 3-hydroxyvoafrine-B, a simple route to the voafrines. Phytochemistry 29, 127-133. https://doi.org/ 10.1016/0031-9422(90)89025-5.
  • Frei, R., Staedler, D., Raja, A., Franke, R., Sasse, F., Gerber-Lemaire, S., Waser, J., 2013. Total synthesis and biological evaluation of jerantinine. E. Angew. Chem. Int. Ed. 52, 1-5. https://doi.org/10.1002/anie.201305533.
  • Furuya, T., Sakamoto, K., Iida, K., Asada, Y., Yoshikawa, T., Sakai, S.L., Aimi, N., 1992. Biotransformation of tabersonine in cell suspension cultures of Catharanthus roseus. Phytochemistry 31, 3065-3068. https://doi.org/10.1016/0031-9422(92)83447-7.
  • Huo, Z.Q., Zhao, Q., Liu, J.W., Zhu, W.T., Hao, X.J., Zhang, Y., 2020. Bousangine A, a novel C-17-nor aspidosperma-type monoterpenoid indole alkaloid from Bousigonia angustifolia. Fitoterapia 142, 104491. https://doi.org/10.1016/j.fitote.2020.104491.
  • Hussain, H., Hussain, J., Al-Harrasi, A., Green, I.R., 2012. Chemistry and biology of the genus Voacanga. Pharm. Biol. 50, 1183-1193. https://doi.org/10.3109/ 13880209.2012.658478.
  • Kitajima, M., Iwai, M., Kogure, N., Kikura-Hanajiri, R., Gode, Y., Takayama, H., 2013. Aspidosperma-aspidosperma-type bisindole alkaloids from Voacanga africana.
  • Li, X.M., Jiang, X.J., Wei, G.Z., Ren, L.H., Wang, L.X., Cheng, X.L., Wang, F., 2019. New iboga-type indole alkaloids from Tabernaemontana divaricata. Nat. Prod. Bioprospect. 9, 425-429. https://doi.org/10.1007/s13659-019-00226-z.
  • Lim, K.H., Hiraku, O., Komiyama T.S., K., 2008. Jerantinines A-G, cytotoxic aspidosperma alkaloids from Tabernaemontana corymbosa. J. Nat. Prod. 71, 1591-1594. https://doi.org/10.1021/np800435c.
  • Liu, J.W., Huo, Z.Q., Zhao, Q., Hao, X.J., He, H.P., Zhang, Y., 2019. Melotenuines A-E, cytotoxic monoterpenoid indole alkaloids from Rhazya stricta. Fitoterapia 138, 104347. https://doi.org/10.1016/j.fitote.2019.104347.
  • Liu, Y.P., Li, Y., Cai, X.H., Li, X.Y., Kong, L.M., Cheng, G.G., Luo, X.D., 2012. Melodinines M-U, cytotoxic alkaloids from Melodinus suaveolens. J. Nat. Prod. 75, 220-224. https://doi.org/10.1021/np2009169.
  • Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63. https://doi.org/10.1016/0022-1759(83)90303-4.
  • Niu, Y., Yang, C., Zhou, J., Huang, S., Liu, J., 2016. Two new compounds with antimicrobial activities from the seeds of Voacanga africana. Phytochemistry Lett 18, 208-212. https://doi.org/10.1016/j.phytol.2016.10.019.
  • Shao, S., Zhang, H., Yuan, C.M., Zhang, Y., Cao, M.M., Zhang, H.Y., Feng, Y., Ding, X., Zhou, Q., Zhao, Q., He, H.P., Hao, X.J., 2015. Cytotoxicity indole alkaloids from the fruits of Melodinus cochinchinensis. Phytochemistry 116, 367-373. https://doi.org/ 10.1016/j.phytochem.2015.02.028.
  • Sheludko, Y., Gerasimenko, I., Kolshorn, H., St¨ockigt, J., 2002. New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture. J. Nat. Prod. 65, 1006-1010. https://doi.org/10.1021/np0200919.
  • Stockigt ¨, J., Pawelka, K.H., Tanahashi, T., Danieli, T., Danieli, B., Hull, W.E., 1983. Voafrine-A and voafrine-B, new dimeric indole alkaloids from cell-suspension cultures of Voacanga africana Stapf. Helv Chem. Acta. 66, 2525-2533. https://doi. org/10.1002/hlca.19830660818.
  • Wang, Y.H., Wan, Q.L., Gu, C.D., Luo, H.R., Long, C.L., 2012. Synthesis and biological evaluation of lycorine derivatives as dual inhibitors of human acetylcholinesterase and butyrylcholinesterase. Chem. Cent. J. 6, 96. https://doi.org/10.1186/1752- 153x-6-96.
  • Xu, H., Huang, H., Zhao, C., Song, C., Song, C., Chang, J., 2019. Total synthesis of (+ )- aspidospermidine. Org. Lett. 21, 6547. https://doi.org/10.1021/acs. orglett.9b02346.
  • Zhang, Y., Ding, X., Yuan, Y.X., Guo, L.L., Hao, X.J., 2020. Cytotoxic monoterpenoid indole alkaloids from Tabernaemontana corymbosa as potent autophagy inhibitors by the attenuation of lysosomal acidification. J. Nat. Prod. 83, 1432-1439. https://doi. org/10.1021/acs.jnatprod.9b00856.
  • Zhang, Y., Goto, M., Oda, A., Hsu, P.L., Guo, L.L., Fu, Y.H., Morris-Natschke, S., Hamel, E., Lee, K.H., Hao, X.J., 2019. Antiproliferative aspidosperma-type monoterpenoid indole alkaloids from Bousigonia mekongensis inhibit tubulin polymerization. Molecules 24, 1256. https://doi.org/10.3390/molecules24071256.
  • Zhang, Y., Yuan, Y.X., Goto, M., Guo, L.L., Li, X.N., Morris-Natschke, S.L., Lee, K.H., Hao, X.J., 2018. Taburnaemins A-I, Cytotoxic vobasinyl-iboga-type bisindole alkaloids from Tabernaemontana corymbosa. J. Nat. Prod. 81, 562-571. https://doi. org/10.1021/acs.jnatprod.7b00949.