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Phlegcarines A-C, three Lycopodium alkaloids from Phlegmariurus carinatus (Desv. ex Poir.) Ching
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- 1. * & Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road Laksi, Bangkok, 10210, Thailand
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Thamnarak, Wanlaya, Thaisaeng, Wachirasak, Batsomboon, Paratchata, Eurtivong, Chatchakorn, Wannarit, Nanthawat, Ruchirawat, Somsak, Thasana, Nopporn (2023): Phlegcarines A-C, three Lycopodium alkaloids from Phlegmariurus carinatus (Desv. ex Poir.) Ching. Phytochemistry (113553) 206: 1-11, DOI: 10.1016/j.phytochem.2022.113553, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113553
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- urn:lsid:plazi.org:pub:FFEC924D1E4DFFFF582DFFFBFF9BFFBA
References
- Anet, F.A.L., Ahmad, M., Khan, N.H., 1962. The alkaloids of Lycopodium annotinum: Part V. The structure and stereochemistry of lycofoline. Can. J. Chem. 40, 236-239. https://doi.org/10.1139/v62-040.
- Ayer, W.A., Fukazawa, Y., Singer, P.P., 1973. Lycoflexine, a new type of lycopodium alkaloid. Tetrahedron Lett. 5045-5048. https://doi.org/10.1016/S0040-4039(01) 87644-9.
- Ayer, W.A., Iverach, G.G., 1964. Lycopodium alkaloids: VII. Lycodoline (alkaloid L. 8). Can. J. Chem. 42, 2514-2522. https://doi.org/10.1139/v64-369.
- Ayer, W.A., Trifonov, L.S., 1994. In: Cordell, G.A., Brossi, A. (Eds.), Lycopodium Alkaloids, th e Alkaloids. Chemistry and Pharmacology. Academic Press, San Diego, pp. 233-266.
- Bruhn, T., Schaumloffel ¨, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249. https://doi.org/10.1002/chir.22138.
- Bruhn, T., Schauml¨offel, A., Hemberger, Y., Pescitelli, G., 2017. SpecDis, ver. 1.71 berlin, Germany. http://specdis-software.jimdo.com.
- Burnell, R.H., Mootoo, B.S., 1961. Lycopodium alaloids: Part IV. Alkaloids of Jamaican Lycopodium clavatum linn. Can. J. Chem. 39, 1090-1093. https://doi.org/10.1139/ v61-135.
- Burnell, R.H., Taylor, D.R., 1962. Lycopodium alkaloids-VII: lycofoline and related bases. Tatrahedron 18, 1467-1469. https://doi.org/10.1016/S0040-4020(01) 99302-0.
- Choo, C.Y., Hirasawa, Y., Karimata, C., Koyama, K., Sekiguchi, M., Kobayashi, J., Morita, H., 2007. Studies directed towards the total synthesis of (+ )-sieboldine A. Bioorg. Med. Chem. 15, 1793, 1707. http://hdl.handle.net/1721.1/43766.
- Christenhusz, M.J.M., Byng, J.W., 2016. The number of known plants species in the world and its annual increase. Phytotaxa 261, 201-217. https://doi.org/10.11646/ phytotaxa.261.3.1.
- CYLview20, Legault, C.Y., 2020. Universite ´de Sherbrooke. http://www.cylview.org.
- Ellman, G.L., Courtney, K.D., Andres, V., Featherstone, R.M., 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7, 88-95. https://doi.org/10.1016/0006-2952(61)90145-9.
- Erra-Balsells, R., Frasca, A.R., 1988. Photochemical reactions of aliphatic-amines in dichloromethane solution. Aust. J. Chem. 41, 103-110. https://doi.org/10.1071/ CH9880103.
- 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.V., 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.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., 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., 2016. Gaussian 16, Revision C.01. Gaussian, Inc., Wallingford CT.
- Grimme, S., 2019. Exploration of chemical compound, conformer, and reaction space with meta-dynamics simulations based on tight-binding quantum chemical calculations. J. Chem. Theor. Comput. 15, 2847-2862. https://doi.org/10.1021/acs. jctc.9b00143.
- Halldorsdottir, E.S., Jaroszewski, J.W., Olafsdottir, E.S., 2010. Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. Alpestre. Phytochemistry 71, 149-157. https://doi.org/10.1016/j.
- Hirasawa, Y., Morita, H., Shiro, M., Kobayashi, J., 2003. Sieboldine A, a novel tetracyclic alkaloid from Lycopodium sieboldii, inhibiting acetylcholinesterase. Org. Lett. 5, 3991-3993. https://doi.org/10.1021/ol035560s.
- Hirasawa, Y., Kobayashi, J., Morita, H., 2009. The Lycopodium alkaloids. Heterocycles 77, 679-729.
- Ishiuchi, K., Kubota, T., Morita, H., Kobayashi, J., 2006. Lycopladine A, a new C16N alkaloid from Lycopodium complanatum. Tetrahedron Lett. 47, 3287-3289. https:// doi.org/10.1016/j.tetlet.2006.03.027.
- Kartha, V.B., Mantscha, H.H., Jones, R.N., 1973. The vibrational analysis of cyclopentanone. Can. J. Chem. 51, 1749-1766. https://doi.org/10.1139/v73-263.
- Katakawa, K., Mito, H., Kogure, N., Kitajima, M., Wongseripipatana, S., Arisawa, M., Takayama, H., 2011. Ten new fawcettimine-related alkaloids from three species of Lycopodium. Tetrahedron 67, 6561-6567. https://doi.org/10.1016/j.
- Kitajima, M., Takayama, H., 2012. Lycopodium alkaloids: isolation and asymmetric synthesis. Top. Curr. Chem. 309, 1-31. https://doi.org/10.1007/128_2011_126.
- Kogure, N., Maruyama, M., Wongseropipatana, S., Kitajima, M., Takayama, H., 2016.
- Linghu, X., Kennedy-Smith, J.J., Toste, F.D., 2007. Total synthesis of (+ )-fawcettimine. Angew. Chem., Int. Ed. 46, 7671-7673. https://doi.org/10.1002/ange.200702695.
- Liu, F., Liu, Y.-C., Jiang, W.-W., He, J., Wu, X.-D., Peng, L.-Y., Su, J., Cheng, X., Zhao, Q.- S., 2014. Carinatines A and B, lycopodium alkaloids from Phlegmariurus carinatus. Nat. Prod. Bioprospect. 4, 221-225. https://doi.org/10.1007/s13659-014-0030-6.
- Liu, J., Zhu, Y., Yu, C., Zhou, Y., Han, Y., Wu, F., Qi, B., 1986. The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity. Can. J.
- Liu, Y., Wang, Q., Zheng, D.K., Zhang, D., Xie, Z., Hu, J.W., Xie, X.H., Li, J., Jian, S.P., 2022. Abietane diterpenoids with neuroprotective activities from Phlegmariurus carinatus. Nat. Prod. Res. https://doi.org/10.1080/14786419.2022.2059662.
- Ma, X., Gang, D.R., 2004. The Lycopodium alkaloids. Nat. Prod. Rep. 21, 752-772. https://doi.org/10.1039/B409720N.
- Morita, H., Hirasawa, Y., Kobayashi, J., 2005. Lycopodatines A C, C16N alkaloids from Lycopodium inundatum. J. Nat. Prod. 68, 1809-1812. https://doi.org/10.1021/ np050389+ .
- Ndongo, J.T., Mbing, J.M., Tara, M.F., Monteillier, A., Pegnyemb, D.E., Cuendet, M., Laatsch, H., 2017. Indoline alkaloids from Tabernaemontana contorta with cancer chemopreventive activity. Phytochemistry 144, 189-196. https://doi.org/10.1016/ j.phytochem.2017.09.013.
- Nilsu, T., Thorroad, S., Ruchirawat, S., Thasana, N., 2016. Squarrosine A and pyrrolhuperzine A, new Lycopodium alkaloids from Thai and Philippine Huperzia squarrosa. Planta Med. 82, 1046-1050. https://doi.org/10.1055/s-0042-106904.
- Nilsu, T., Thaisaeng, W., Thamnarak, W., Eurtivong, C., Jumraksa, A., Thorroad, S., Khunnawutmanotham, N., Ruchirawat, S., Thasana, N., 2018. Three Lycopodium alkaloids from Thai club mosses. Phytochemistry 156, 83-88. https://doi.org/ 10.1016/j.phytochem.2018.09.001.
- Pan, G., Williams, R.M., 2012. Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B. J. Org. Chem. 77, 4801-4811. https://doi.org/10.1021/jo3006045.
- Pongpamorn, P., Wan-erlor, S., Ruchirawat, S., Thasana, N., 2016. Lycoclavatumide and 8β,11α- dihydroxylycopodine, a new fawcettimine and lycopodine-type alkaloid from Lycopodium clavatum. Tetrahedron 72, 7065-7069. https://doi.org/10.1016/j.
- Pracht, P., Bohle, F., Grimme, S., 2020. Automated exploration of the low-energy chemical space with fast quantum chemical methods. Phys. Chem. Chem. Phys. 22, 7169-7192. https://doi.org/10.1039/C9CP06869D.
- Sangster, A.W., Stuart, K.L., 1965. Ultraviolet spectra of alkaloids. Chem. Rev. 65, 69-130. https://doi.org/10.1021/cr60233a003.
- Siengalewicz, P., Mulzer, J., Rinner, U., 2013. Chapter 1: lycopodium Alkaloids - synthetic highlights and recent developments, the alkaloids. Chemistry and pharmacology 72, 1-151. https://doi.org/10.1016/B978-0-12-407774-4.00001-7.
- Tagawa, M., Iwatsuki, K., 1979. In: Smitinand, T., Larson, K. (Eds.), Pteridophytes. Part 1: Psilotaceae to Dennstaedtiaceae. Flora of Thailand, vol. 3, pp. 1-128.
- Takayama, H., Katakawa, K., Kitajima, M., Yamaguchi, K., Aimi, N., 2002. Seven new Lycopodium alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, from Lycopodium serratum Thunb. Tetrahedron Lett. 43, 8307-8311. https://doi.org/10.1016/S0040- 4039(02)02026-9.
- Tan, C., Zhu, D., 2004. Lycopodine-type lycopodium alkaloids from Huperzia serrata. Helv. Chim. Acta 87, 1963-1967. https://doi.org/10.1002/hlca.200490178.
- The Pteridophyte Phylogeny Group, 2016. A community-derived classification for extant lycophytes and ferns. J. Systemat. Evol. 54, 563-603. https://doi.org/10.1111/ jse.12229.
- Jumruksa, A., Ruchirawat, S., Thasana, N., 2014. Three new Lycopoium alkaloids from Huperzia carinata and Huperzia squarrosa. Tetrahedron 70, 8017-8022. https:// doi.org/10.1016/j.tet.2014.08.042.
- Tong, X.-T., Tan, C.-H., Ma, X.-Q., Wang, B.-D., Jiang, S.-H., Zhu, D.-Y., 2003. Miyoshianines A and B, two new Lycopodium alkaloids from Huperzia miyoshiana. Planta Med. 69, 576-579. https://doi.org/10.1055/s-2003-40648.
- Wang, C., Yang, X., Mellick, G.D., Feng, Y., 2022. Phlegmacaritones A and B, a pair of serratane-related triterpenoid epimers with an unprecedented carbon skeleton from Phlegmariurus carinatus. J. Nat. Prod. 85, 899-909. https://doi.org/10.1021/acs. jnatprod.1c01021.
- Weigend, F., 2006. Accurate coulomb-fitting basis sets for H to Rn. Phys. Chem. Chem. Phys. 8, 1057-1065. https://doi.org/10.1039/B515623H.
- Weigend, F., Ahlrichs, R., 2005. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys. Chem. Chem. Phys. 7, 3297-3305. https://doi.org/10.1039/B508541A. Xiong, J., Meng, W.-J., Zhang, H.-Y., Zou, Y., Wang, W.-X., Xin-Yi Wang, X.-Y., Yang, Q.- L., Osman, E.E.A., Hua, J.-F., 2019. Lycofargesiines A-F, further Lycopodium alkaloids from the club moss Huperzia fargesii. Phytochemistry 162, 183-192. https://doi.org/10.1016/j.phytochem.2019.03.015.
- Zhao, Y., Truhlar, D.G., 2008. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06- class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215-241. https:// doi.org/10.1007/s00214-007-0310-x.