Biodiversity Literature Repository

Submit to community
Liberated Data
Published June 30, 2019 | Version v1
Journal article Restricted

Indole alkaloids from Gelsemium elegans

Authors/Creators

  • 1. ∗ & Lab of Toxicology and Pharmacology, Faculty of Naval Medicine, Second Military Medical University, Shanghai, 200433, China & -demethoxy-gelsemamide is an open-loop indole alkaloid and 11-demethoxy-gelsemazonamide is an aromatic azo-linked dimeric indole alkaloid. Among the five alkaloids, (4R)-19-oxo-gelsevirine N & - demethoxy-gelsemamide exhibited significant inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells, with IC values of 6.18 ± 1.07 and 12.2 ± 1.02 μM, respectively.

Description

Sun, Ming-Xue, Cui, Yan, Li, Yu, Meng, Wen-Qi, Xu, Qing-Qiang, Zhao, Jie, Lu, Jin-Cai, Xiao, Kai (2019): Indole alkaloids from Gelsemium elegans. Phytochemistry 162: 232-240, DOI: 10.1016/j.phytochem.2019.03.016, URL: http://dx.doi.org/10.1016/j.phytochem.2019.03.016

Files

Restricted

The record is publicly accessible, but files are restricted. <a href="https://zenodo.org/account/settings/login?next=https://zenodo.org/records/10482294">Log in</a> to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:FFB05768FFFD3E28D97AFFD0FFA5FF50

Has part
Figure: 10.5281/zenodo.10482296 (DOI)
Figure: 10.5281/zenodo.10482298 (DOI)
Figure: 10.5281/zenodo.10482300 (DOI)
Figure: 10.5281/zenodo.10482302 (DOI)
Figure: 10.5281/zenodo.10482304 (DOI)
Figure: 10.5281/zenodo.10482306 (DOI)
Figure: 10.5281/zenodo.10482308 (DOI)
Figure: 10.5281/zenodo.10482310 (DOI)
Figure: 10.5281/zenodo.10482312 (DOI)

References

  • Kitajima, M., 2007. Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources Gelsemium and Ophiorrhiza. J. Nat. Med. 61, 14-23.
  • Kitajima, M., Kobayashi, H., Kogure, N., Takayama, H., 2010. New oxindole and indole alkaloids from Gelsemium rankinii. Tetrahedron 66, 5987-5992.
  • Kitajima, M., Kogure, N., Yamaguchi, K., Takayama, H., Aimi, N., 2003a. Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Org. Lett. 5, 2075-2078.
  • Kitajima, M., Urano, A., Kogure, N., Takayama, H., Aimi, N., 2003b. New oxindole alkaloids and iridoid from Carolina jasmine (Gelsemium sempervirens Ait. f.). Chem. Pharm. Bull. 51, 1211-1214.
  • Kogure, N., Ishii, N., Kitajima, M., Wongseripipatana, S., Takayama, H., 2006. Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans benth. Org. Lett. 8, 3085-3088.
  • Lin, L.Z., Cordell, A., G, Ni, C.Z., Clardy, J., 1989. Gelsemamide and 11-methoxygelsemamide, two novel secoindole alkaloids from gelsemium elegans. Tetrahedron Lett. 30, 1177-1180.
  • Lin, L.Z., Cordell, G.A., Ni, C.Z., Clardy, J., 1991. Oxindole alkaloids from Gelsemium elegans. Phytochemistry 30, 1311-1315.
  • Liu, M., Huang, H.H., Yang, J., Su, Y.P., Lin, H.W., Lin, L.Q., Liao, W.J., Yu, C.X., 2013. The active alkaloids of Gelsemium elegans Benth. are potent anxiolytics. Psychopharmacology 225, 839-851.
  • Meng, W., Pei, Z., Feng, Y., Zhao, J., Chen, Y., Shi, W., Xu, Q., Lin, F., Sun, M., Xiao, K., 2017. Neglected role of hydrogen sulfide in sulfur mustard poisoning: keap 1 Ssulfhydration and subsequent Nrf 2 pathway activation. Sci. Rep. 7, 9433.
  • Ouyang, S., Wang, L., Zhang, Q.W., Wang, G.C., Wang, Y., Huang, X.J., Zhang, X.Q., Jiang, R.W., Yao, X.S., Che, C.T., Ye, W.C., 2011. Six new monoterpenoid indole alkaloids from the aerial part of Gelsemium elegans. Tetrahedron 67, 4807-4813.
  • Ponglux, D., Wongseripipatana, S., Subhadhirasakul, S., Takayama, H., Yokota, M., Ogata, K., Phisalaphong, C., Aimi, N., Sakai, S.-i., 1988a. Studies on the indole alkaloids of gelsemium elegans (Thailand): structure elucidation and proposal of biogenetic route. Tetrahedron 44, 5075-5094.
  • Ponglux, D., Wongseripipatana, S., Takayama, H., Ogata, K., Aimi, N., Sakai, S.-i., 1988b. A new class of indole alkaloid 'elegansamine' constructed from a monoterpenoid indole alkaloid and an iridoid. Tetrahedron Lett. 29, 5395-5396.
  • Rujjanawate, C., Kanjanapothi, D., Panthong, A., 2003. Pharmacological effect and toxicity of alkaloids from Gelsemium elegans Benth. J. Ethnopharmacol. 89, 91-95.
  • Schun, Y., Cordell, G.A., 1986. 21-Oxogelsevirine, a new alkaloid from Gelsemium Rankinii. J. Nat. Prod. 49, 483-487.
  • Sun, M.X., Gao, H.H., Zhao, J., Zhang, L., Xiao, K., 2015. New oxindole alkaloids from Gelsemium elegans. Tetrahedron Lett. 56, 6194-6197.
  • Wu, Y.E., Li, Y.D., Luo, Y.J., Wang, T.X., Wang, H.J., Chen, S.N., Qu, W.M., Huang, Z.L., 2015. Gelsemine alleviates both neuropathic pain and sleep disturbance in partial sciatic nerve ligation mice. Acta Pharmacol. Sin. 36, 1308-1317.
  • Xu, Y.K., Yang, S.P., Liao, S.G., Zhang, H., Lin, L.P., Ding, J., Yue, J.M., 2006. Alkaloids from Gelsemium elegans. J. Nat. Prod. 69, 1347-1350.
  • Yamada, Y., Kitajima, M., Kogure, N., Wongseripipatana, S., Takayama, H., 2011. Seven new monoterpenoid indole alkaloids from Gelsemium elegans. Chem. Asian J. 6, 166-173.
  • Yin, S., He, X.F., Wu, Y., Yue, J.M., 2008. Monoterpenoid indole alkaloids bearing an N4- Iridoid from Gelsemium elegans. Chem. Asian J. 3, 1824-1829.
  • Zhang, J.Y., Gong, N., Huang, J.L., Guo, L.C., Wang, Y.X., 2013a. Gelsemine, a principal alkaloid from Gelsemium sempervirens Ait., exhibits potent and specific antinociception in chronic pain by acting at spinal a3 glycine receptors. Pain 154, 2452-2462.
  • Zhang, L., Du, L., Lv, W.W., Zhao, Q.C., Hua, W., An, Y., Guo, T., Wu, L.J., 2013b. Four new koumine metabolites in rat liver microsomes. J. Asian Nat. Prod. Res. 15, 46-52.
  • Zhang, W., Huang, X.J., Zhang, S.Y., Zhang, D.M., Jiang, R.W., Hu, J.Y., Zhang, X.Q., Wang, L., Ye, W.C., 2015. Geleganidines A-C, unusual monoterpenoid indole alkaloids from Gelsemium elegans. J. Nat. Prod. 78, 2036-2044.
  • Zhang, W., Xu, W., Wang, G.Y., Gong, X.Y., Li, N.P., Wang, L., Ye, W.C., 2017. Gelsekoumidines a and B: two pairs of atropisomeric bisindole alkaloids from the roots of gelsemium elegans. Org. Lett. 19, 5194-5197.
  • Zhang, Z., Di, Y.T., Wang, Y.H., Zhang, Z., Mu, S.Z., Fang, X., Zhang, Y., Tan, C.J., Zhang, Q., Yan, X.H., Guo, J., Li, C.S., Hao, X.J., 2009. Gelegamines A-E: five new oxindole alkaloids from Gelsemium elegans. Tetrahedron 65, 4551-4556.