Login Register Cart 0
Generic placeholder image

Current Topics in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Genus Gelsemium and its Endophytic Fungi - Comprehensive Review of their Traditional Uses, Phytochemistry, Pharmacology, and Toxicology

Author(s): Yun-Lin Peng, Jia-Jun Liang, Yan Xue, Afsar Khan*, Pan-Pan Zhang, Ting-Ting Feng, Da Song, Ying Zhou* and Xin Wei*

Volume 23, Issue 26, 2023

Published on: 22 September, 2023

Page: [2452 - 2487] Pages: 36

DOI: 10.2174/1568026623666230825105233

Price: $65

Abstract

Background: The use of ethnic medicinal plants has revitalized wide popularity in Africa, Asia, and most of the world because of the energy consumption barriers increase of synthetic drugs. Gelsemium is a traditional genus of plants with famous cultural and medicinal significance in Southeast Asia and North America. Three species are reported from the genus Gelsemium, including Gelsemium elegans (Gardn. & Camp.) Benth., Gelsemium sempervirens (L.) J.St.-Hil., and Gelsemium rankinii Small. Among them, G. elegans is well known for its toxicity and is used as a traditional remedy for skin problems, neuralgia, fractures, and cancer. The first record of the toxic medicine G. elegans is the Chinese herbal medicine classically known as Shen-Nong Ben-Cao Jing. In the legend, the Shennong emperor was poisoned by G. elegans, hence, it is also wellknown as Duan Chang Cao in China. In addition, G. sempervirens tincture is also used in the treatment of inflammation of the spinalcolumn, and diminishes blood to the cerebrospinal centers.

Introduction: This review aims to provide up-to-date information on Gelsemium and its endophytic fungi on their traditional uses, phytochemistry, pharmacology, and toxicology. Mechanism studies regarding the detoxification profile of Gelsemium are also reviewed.

Methods: For this updated review, the literature survey and search were performed on the scientific databases PubMed, ScienceDirect, Wiley, China CNKI, Web of Science, SciFinder, and Google Scholar using the relevant keywords.

Results: The plants of the genus Gelsemium are all reported as rich sources of monoterpene indole alkaloids. Previous phytochemical studies published more than 200 alkaloids from Gelsemium and its endophytic fungi, which have attracted considerable attention from pharmaceutists and phytochemists due to their diverse and complex structures. The bioactivities of Gelsemium phytoconstituents studied using various chemical methods are summarized and described herein. Considering the huge influence of Gelsemium regarding its traditional applications, the activities of isolated compounds were focused on the anti-tumor, anti-inflammatory, analgesic and antianxiety, immunostimulatory, and immunosuppressive properties, which provide evidence supporting the ethnopharmacological effectiveness of the genus Gelsemium. Unlike all previous reviews of genus Gelsemium, to the best of our knowledge, the recently reported natural products from its endophytic fungi are first time summarized in this review.

Conclusion: It is clearly suggested from the literature information that the structures and biological activities of Gelsemium have a wide range of attraction from folk to the community of scholars. However, as a highly toxic genus, the work on the detoxification mechanism and toxicology of Gelsemium is urgently needed before entering clinical research. It is noteworthy that the discussion about the relationship between structural and biological activities are a valuable topic of expectation, while the structural modification for active or toxic components may shed light on toxicological breakthrough. Besides the compounds from the plants of genus Gelsemium, the recently reported natural products from its endophytic fungi may provide a supplement for its ethnomedicinal uses and ethnological validity.

« Previous Next »
Graphical Abstract

[1]
Anyamele, T.; Onwuegbuchu, P.N.; Ugbogu, E.A.; Ibe, C. Phytochemical composition, bioactive properties, and toxicological profile of Tetrapleura tetraptera. Bioorg. Chem., 2023, 131, 106288.
[http://dx.doi.org/10.1016/j.bioorg.2022.106288] [PMID: 36470194]
[2]
Jin, G.L.; Su, Y.P.; Liu, M.; Xu, Y.; Yang, J.; Liao, K.J.; Yu, C.X. Medicinal plants of the genus Gelsemium (Gelsemiaceae, Gentianales)—A review of their phytochemistry, pharmacology, toxicology and traditional use. J. Ethnopharmacol., 2014, 152(1), 33-52.
[http://dx.doi.org/10.1016/j.jep.2014.01.003] [PMID: 24434844]
[3]
Ornduff, R. The systematics and breeding system of Gelsemium (Loganiceae). J. Arnold Arbor., 1970, 51(1), 1-17.
[http://dx.doi.org/10.5962/bhl.part.7036]
[4]
Zhang, W.; Zhang, S.Y.; Wang, G.Y.; Li, N.P.; Chen, M.F.; Gu, J.H.; Zhang, D.M.; Wang, L.; Ye, W.C. Five new koumine-type alkaloids from the roots of Gelsemium elegans. Fitoterapia, 2017, 118, 112-117.
[http://dx.doi.org/10.1016/j.fitote.2017.03.004] [PMID: 28300700]
[5]
Editorial Committee of Zhonghua Bencao National Traditional Chinese Herb Administration. Zhonghua Bencao (Chinese Herbal Medicine); Shanghai Science and Technology Publishing House: Shanghai, 1999, pp. 213-215.
[6]
Miranda, F.; Sharp, A.J. Characteristics of the vegetation in certain temperate regions of eastern Mexico. Ecology, 1950, 31(3), 313-333.
[http://dx.doi.org/10.2307/1931489]
[7]
Liang, S.; He, C.Y.; Szab, L.F.; Feng, Y.; Lin, X; Wang, Y. Gelsochalotine, a novel indole ring-degraded monoterpenoid indole alkaloid from Gelsemium elegans. Tetrahedron Lett., 2013, 54(8), 887-890.
[http://dx.doi.org/10.1016/j.tetlet.2012.11.122]
[8]
Sakai, S.; Wongseripipatana, S.; Ponglux, D.; Yokota, M.; Ogata, K.; Takayama, H.; Aimi, N. Indole alkaloids isolated from Gelsemium elegans (Thailand): 19-(Z)-akuammidine, 16-epi-voacarpine, 19-hydroxydihydrogelsevirine, and the revised structure of koumidine. Chem. Pharm. Bull., 1987, 35(11), 4668-4671.
[http://dx.doi.org/10.1248/cpb.35.4668] [PMID: 3442894]
[9]
Kogure, N.; Someya, A.; Urano, A.; Kitajima, M.; Takayama, H. Total synthesis and full NMR assignment of ourouparine, a yohimbane-type indole alkaloid isolated from Gelsemium sempervirens. J. Nat. Med., 2007, 61(2), 208-212.
[http://dx.doi.org/10.1007/s11418-006-0125-4]
[10]
Sun, M.X.; Cui, Y.; Li, Y.; Meng, W.Q.; Xu, Q.Q.; Zhao, J.; Lu, J.C.; Xiao, K. Indole alkaloids from Gelsemium elegans. Phytochemistry., 2019, 162, 232-240.
[http://dx.doi.org/10.1016/j.phytochem.2019.03.016] [PMID: 30953910]
[11]
Xu, Y.K.; Liao, S.G.; Na, Z.; Hu, H.B.; Li, Y.; Luo, H.R. Gelsemium alkaloids, immunosuppressive agents from Gelsemium elegans. Fitoterapia., 2012, 83(6), 1120-1124.
[http://dx.doi.org/10.1016/j.fitote.2012.04.023] [PMID: 22579843]
[12]
Lin, H.; Qiu, H.; Cheng, Y.; Liu, M.; Chen, M.; Que, Y.; Que, W. Gelsemium elegans Benth: Chemical components, pharmacological effects, and toxicity mechanisms. Molecules., 2021, 26(23), 7145.
[http://dx.doi.org/10.3390/molecules26237145] [PMID: 34885727]
[13]
Wang, L.; Chen, S.; Gao, X.; Liang, X.; Lv, W.; Zhang, D.; Jin, X. Recent progress in chemistry and bioactivity of monoterpenoid indole alkaloids from the genus gelsemium : A comprehensive review. J. Enzyme Inhib. Med. Chem., 2023, 38(1), 2155639.
[http://dx.doi.org/10.1080/14756366.2022.2155639] [PMID: 36629436]
[14]
Liu, Y.; Li, Y.; Qu, J.; Ma, S.; Zang, C.; Zhang, Y.; Yu, S. Eremophilane sesquiterpenes and polyketones produced by an endophytic guignardia fungus from the toxic plant gelsemium elegans. J. Nat. Prod., 2015, 78(9), 2149-2154.
[http://dx.doi.org/10.1021/np5009027] [PMID: 26241103]
[15]
Wei, X.; Yang, J.; Ma, H.X.; Ding, C.F.; Yu, H.F.; Zhao, Y.L.; Liu, Y.P.; Khan, A.; Wang, Y.F.; Yang, Z.F.; Huang, W.Y.; Wang, X.H.; Luo, X.D. Antimicrobial indole alkaloids with adductive C9 aromatic unit from Gelsemium elegans. Tetrahedron Lett., 2018, 59(21), 2066-2070.
[http://dx.doi.org/10.1016/j.tetlet.2018.04.041]
[16]
Zhang, W.; Xu, W.; Wang, G.Y.; Gong, X.Y.; Li, N.P.; Wang, L.; Ye, W.C. Gelsekoumidines A and B: Two pairs of atropisomeric bisindole alkaloids from the roots of Gelsemium elegans. Org. Lett., 2017, 19(19), 5194-5197.
[http://dx.doi.org/10.1021/acs.orglett.7b02463] [PMID: 28898085]
[17]
Wang, Z.Y.; Zuo, M.T.; Zhao, X.J.; Li, Y.J.; Sun, Z.L.; Liu, Z.Y. Comparative metabolism of gelsenicine in liver microsomes from humans, pigs, goats and rats. Rapid Commun. Mass Spectrom., 2020, 34(17), e8843.
[http://dx.doi.org/10.1002/rcm.8843] [PMID: 32453886]
[18]
Wu, Y.; Li, Y.; Luo, Y.; Wang, T.; Wang, H.; Chen, S.; Qu, W.; Huang, Z. Gelsemine alleviates both neuropathic pain and sleep disturbance in partial sciatic nerve ligation mice. Acta Pharmacol. Sin., 2015, 36(11), 1308-1317.
[http://dx.doi.org/10.1038/aps.2015.86] [PMID: 26388157]
[19]
Xu, Y.K.; Yang, S.P.; Liao, S.G.; Zhang, H.; Lin, L.P.; Ding, J.; Yue, J.M. Alkaloids from Gelsemium elegans. J. Nat. Prod., 2006, 69(9), 1347-1350.
[http://dx.doi.org/10.1021/np060156y] [PMID: 16989532]
[20]
Chen, Y.; Zhang, Q.; Huang, Y.; Tan, H.; Diao, Y.; Zhang, L. A research progress on the biosynthetic pathways of indole alkaloids. World Sci. Tech. Mod. Trad. Chin. Med., 2016, 18, 1914-1920.
[21]
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. Geleganidines A-C, unusual monoterpenoid indole alkaloids from Gelsemium elegans. J. Nat. Prod., 2015, 78(8), 2036-2044.
[http://dx.doi.org/10.1021/acs.jnatprod.5b00351] [PMID: 26222693]
[22]
Venard, C.; Boujedaini, N.; Mensah-Nyagan, A.G.; Patte-Mensah, C. Comparative analysis of Gelsemine and Gelsemium sempervirens activity on neurosteroid allopregnanolone formation in the spinal cord and limbic system. Evid. Based Complement. Alternat. Med., 2011, 2011, 1-10.
[http://dx.doi.org/10.1093/ecam/nep083] [PMID: 19628662]
[23]
Olioso, D.; Marzotto, M.; Moratti, E.; Brizzi, M.; Bellavite, P. Effects of Gelsemium sempervirens L. on pathway-focused gene expression profiling in neuronal cells. J. Ethnopharmacol., 2014, 153(2), 535-539.
[http://dx.doi.org/10.1016/j.jep.2014.02.048] [PMID: 24613275]
[24]
Bhattacharyya, S.S.; Paul, S.; Khuda-Bukhsh, A.R. Encapsulated plant extract ( Gelsemium sempervirens ) poly (lactide-co-glycolide) nanoparticles enhance cellular uptake and increase bioactivity in vitro. Exp. Biol. Med., 2010, 235(6), 678-688.
[http://dx.doi.org/10.1258/ebm.2010.009338] [PMID: 20511672]
[25]
Zhang, Z.; Liu, G.M.; Xiao, H.; He, H.P. Chemical constituents from Gelsemium ele gans. Chin. Tradit. Herb Drugs, 2011, 42(2), 222-225.
[26]
Schun, Y.; Cordell, G.A.; Garland, M. 21-oxogelsevirine, a new alkaloid from Gelsemium rankinii. J. Nat. Prod., 1986, 49(3), 483-487.
[http://dx.doi.org/10.1021/np50045a017]
[27]
Xue, Q.; Hu, J.; Liu, X.C.; Gu, J. Cytotoxic gelsedine-type indole alkaloids from Gelsemium elegans. J. Asian Nat. Prod. Res., 2020, 22(12), 1138-1144.
[http://dx.doi.org/10.1080/10286020.2019.1694008] [PMID: 31913055]
[28]
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. Six new monoterpenoid indole alkaloids from the aerial part of Gelsemium elegans. Tetrahedron, 2011, 67(26), 4807-4813.
[http://dx.doi.org/10.1016/j.tet.2011.05.026]
[29]
Wang, L.; Sun, L.; Liu, H.Y.; Meng, F.H. Chemical constituents of Gelsemium elegans. Chin. Tradit. Herbal Drugs, 2017, 48(10), 2028-2032.
[30]
Zhang, Z.; Di, Y.T.; Wang, Y.H.; Zhang, Z.; Mu, S.Z.; Fang, X.; Zhang, Y.; Tan, C.; Zhang, Q.; Yan, X.H.; Guo, J.; Li, C.S.; Hao, X.J. Gelegamines A–E: Five new oxindole alkaloids from Gelsemium elegans. Tetrahedron., 2009, 65(23), 4551-4556.
[http://dx.doi.org/10.1016/j.tet.2009.03.086]
[31]
Sun, M.X.; Gao, H.H.; Zhao, J.; Zhang, L.; Xiao, K. New oxindole alkaloids from Gelsemium elegans. Tetrahedron Lett., 2015, 56(45), 6194-6197.
[http://dx.doi.org/10.1016/j.tetlet.2015.09.086]
[32]
Yamada, Y.; Kitajima, M.; Kogure, N.; Takayama, H. Four novel gelsedine-type oxindole alkaloids from Gelsemium elegans. Tetrahedron., 2008, 64(33), 7690-7694.
[http://dx.doi.org/10.1016/j.tet.2008.06.030]
[33]
Kogure, N.; Ishii, N.; Kitajima, M.; Wongseripipatana, S.; Takayama, H. Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans benth. Org. Lett., 2006, 8(14), 3085-3088.
[http://dx.doi.org/10.1021/ol061062i] [PMID: 16805558]
[34]
Wang, H.T.; Yang, Y.C.; Mao, X.; Wang, Y.; Huang, R. Cytotoxic gelsedine-type indole alkaloids from Gelsemium elegans. J. Asian Nat. Prod. Res., 2018, 20(4), 321-327.
[http://dx.doi.org/10.1080/10286020.2017.1342637] [PMID: 28679292]
[35]
Yamada, Y.; Kitajima, M.; Kogure, N.; Wongseripipatana, S.; Takayama, H. Seven new monoterpenoid indole alkaloids from Gelsemium elegans. Chem. Asian J., 2011, 6(1), 166-173.
[http://dx.doi.org/10.1002/asia.201000538] [PMID: 20960496]
[36]
Wei, X.; Huang, X.T.; Zhang, L.Y.; Hu, X.Y.; Zhang, W.; Zhou, Y.Q.; Yu, H.F.; Ding, C.F.; Zhang, L.C.; Liu, X.; Zhou, Y. New oxindole alkaloids with selective osteoclast inhibitory activity from Gelsemium elegans. Nat. Prod. Res., 2022, 36(10), 2630-2636.
[http://dx.doi.org/10.1080/14786419.2021.1913589] [PMID: 33908330]
[37]
Fang, L.; Zhou, J.; Lin, Y.; Wang, X.; Sun, Q.; Li, J.L.; Huang, L. Large-scale separation of alkaloids from Gelsemium elegans by pH-zone-refining counter-current chromatography with a new solvent system screening method. J. Chromatogr. A, 2013, 1307, 80-85.
[http://dx.doi.org/10.1016/j.chroma.2013.07.069] [PMID: 23915643]
[38]
Kitajima, M.; Nakamura, T.; Kogure, N.; Ogawa, M.; Mitsuno, Y.; Ono, K.; Yano, S.; Aimi, N.; Takayama, H. Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of gelsemium alkaloids for A431 epidermoid carcinoma cells. J. Nat. Prod., 2006, 69(4), 715-718.
[http://dx.doi.org/10.1021/np060016o] [PMID: 16643063]
[39]
Kitajima, M.; Urano, A.; Kogure, N.; Takayama, H.; Aimi, N. New oxindole alkaloids and iridoid from Carolina jasmine (Gelsemium sempervirens Ait. f.). Chem. Pharm. Bull., 2003, 51(10), 1211-1214.
[http://dx.doi.org/10.1248/cpb.51.1211] [PMID: 14519934]
[40]
Ponglux, D.; Wongseripipatana, S.; Subhadhirasakul, S.; Takayama, H.; Yokota, M.; Ogata, K.; Phisalaphong, C.; Aimi, N.; Sakai, S. Studies on the indole alkaloids of gelsem1um elegans (thailand): structure elucidation and proposal of biogenetic route. Tetrahedron., 1988, 44(16), 5075-5094.
[http://dx.doi.org/10.1016/S0040-4020(01)86012-9]
[41]
Zhang, B.F.; Chou, G.X.; Wang, Z.T. Two new 11-hydroxy-substituted gelsedine-type indole alkaloids from thestems of Gelsemium elegans. Helv. Chim. Acta, 2009, 92(9), 1889-1894.
[http://dx.doi.org/10.1002/hlca.200900094]
[42]
Takayama, H.; Morohoshi, Y.; Kitajima, M.; Aimi, N.; Wongseripipatana, S.; Ponglux, D.; Sakai, S.I. Two new iridoids from the leaves of Gelsemium elegans Benth. in Thailand. Nat. Prod. Lett., 1994, 5(1), 15-20.
[http://dx.doi.org/10.1080/10575639408043929]
[43]
Takayama, H.; Kitajima, M.; Ogata, K.; Sakai, S. The first and biomimetic construction of the new skeleton of gelselegine-type oxindole alkaloids. J. Org. Chem., 1992, 57(17), 4583-4584.
[http://dx.doi.org/10.1021/jo00043a011]
[44]
Wang, L.; Ye, W-C.; Zhang, W.; Zhang, S-Y.; Yin, Z-Q. New monoterpenoid indole alkaloids from Gelsemium elegans. Heterocycles., 2014, 89(5), 1245-1253.
[http://dx.doi.org/10.3987/COM-14-12970]
[45]
Wang, L.; Wang, J.F.; Mao, X.; Jiao, L.; Wang, X.J. Gelsedine-type oxindole alkaloids from Gelsemium elegans and the evaluation of their cytotoxic activity. Fitoterapia., 2017, 120, 131-135.
[http://dx.doi.org/10.1016/j.fitote.2017.06.005] [PMID: 28596027]
[46]
Liu, D.; Han, Y.; Zhou, H.; Jin, H.; Kang, H.; Huang, F.; Liu, Y.; Liang, X. Offline preparative three-dimensional HPLC for systematic and efficient purification of alkaloids from Gelsemium elegans Benth. J. Chromatogr. A, 2021, 1640, 461935.
[http://dx.doi.org/10.1016/j.chroma.2021.461935] [PMID: 33556681]
[47]
Yamada, Y.; Kitajima, M.; Kogure, N.; Wongseripipatana, S.; Takayama, H. Spectroscopic analyses and chemical transformation for structure elucidation of two novel indole alkaloids from Gelsemium elegans. Tetrahedron Lett., 2009, 50(26), 3341-3344.
[http://dx.doi.org/10.1016/j.tetlet.2009.02.092]
[48]
Liu, Z.J.; Lu, R.R. Chapter 2 Gelsemium alkaloids. Alkaloids Chem. Biol., 1988, 33, 83-140.
[49]
Gu, J.H.; Zhang, W.; Cai, W.Y.; Fu, X.X.; Zhou, H-L.; Li, N-P.; Tian, H-Y.; Liu, J-S.; Ye, W-C.; Wang, L. Gelserancines A–E, monoterpenoid indole alkaloids with unusual skeletons from Gelsemium elegans. Org. Chem. Front., 2021, 8(9), 1918-1925.
[http://dx.doi.org/10.1039/D0QO01559H]
[50]
Qu, J.; Fang, L.; Ren, X.D.; Liu, Y.; Yu, S.S.; Li, L.; Bao, X.Q.; Zhang, D.; Li, Y.; Ma, S.G. Bisindole alkaloids with neural anti-inflammatory activity from Gelsemium elegans. J. Nat. Prod., 2013, 76(12), 2203-2209.
[http://dx.doi.org/10.1021/np4005536] [PMID: 24256496]
[51]
Li, N.P.; Liu, M.; Huang, X.J.; Gong, X.Y.; Zhang, W.; Cheng, M.J.; Ye, W.C.; Wang, L. Gelsecorydines A-E, five gelsedine-corynanthe-type bisindole alkaloids from the fruits of Gelsemium elegans. J. Org. Chem., 2018, 83(10), 5707-5714.
[http://dx.doi.org/10.1021/acs.joc.8b00736] [PMID: 29719959]
[52]
Yin, S.; He, X.F.; Wu, Y.; Yue, J.M. Monoterpenoid indole alkaloids bearing an N4-Iridoid from Gelsemium elegans. Chem. Asian J., 2008, 3(10), 1824-1829.
[http://dx.doi.org/10.1002/asia.200800021] [PMID: 18604820]
[53]
Lin, L.Z.; Hu, S.F.; Cordell, G.A. 19α-hydroxygelsamydine from Gelsemium elegans. Phytochemistry, 1996, 43(3), 723-726.
[http://dx.doi.org/10.1016/0031-9422(96)00280-4] [PMID: 8987583]
[54]
Wichtl, M.; Nikiforov, A.; Schulz, G.; Sponer, S.; Jentzsch, K. Die strukturermittlung von Gelsemium-alkaloid C (14-hydroxygelsemicin) durch NMR-und massenspektrometrie. Monatsh. Chem., 1973, 104(1), 99-104.
[http://dx.doi.org/10.1007/BF00911151]
[55]
Kitajima, M.; Kobayashi, H.; Kogure, N.; Takayama, H. New oxindole and indole alkaloids from Gelsemium rankinii. Tetrahedron, 2010, 66(32), 5987-5992.
[http://dx.doi.org/10.1016/j.tet.2010.06.032]
[56]
Jin, P.; Zhan, G.; Zheng, G.; Liu, J.; Peng, X.; Huang, L.; Gao, B.; Yuan, X.; Yao, G. Gelstriamine A, a triamino monoterpene indole alkaloid with a caged 6/5/7/6/6/5 scaffold and analgesic alkaloids from Gelsemium elegans Stems. J. Nat. Prod., 2021, 84(4), 1326-1334.
[http://dx.doi.org/10.1021/acs.jnatprod.1c00062] [PMID: 33826318]
[57]
Long-Ze, L.; Schun, Y.; Cordell, G.A.; Chou-Zhou, N.; Clardy, J. Three oxindole alkaloids from Gelsemium species. Phytochemistry, 1991, 30(2), 679-683.
[http://dx.doi.org/10.1016/0031-9422(91)83752-7]
[58]
Wu, H.R.; He, X.F.; Jin, X.J.; Pan, H.; Shi, Z.N.; Xu, D.D.; Yao, X.J.; Zhu, Y. New nor-ursane type triterpenoids from Gelsemium elegans. Fitoterapia., 2015, 106, 175-183.
[http://dx.doi.org/10.1016/j.fitote.2015.09.002] [PMID: 26344425]
[59]
Wei, X.; Guo, R.; Wang, X.; Liang, J.J.; Yu, H.F.; Ding, C.F.; Feng, T.T.; Zhang, L.Y.; Liu, X.; Hu, X.Y.; Zhou, Y. New monoterpenoid indoles with osteoclast activities from Gelsemium elegans. Molecules., 2021, 26(24), 7457.
[http://dx.doi.org/10.3390/molecules26247457] [PMID: 34946539]
[60]
Lin, L.Z.; Cordell, G.A.; Ni, C.Z.; Clardy, J. Oxindole alkaloids from Gelsemium elegans. Phytochemistry., 1991, 30(4), 1311-1315.
[http://dx.doi.org/10.1016/S0031-9422(00)95223-3]
[61]
Lin, L.Z.; Cordell, G.A.; Ni, C.Z.; Clardy, J. New humantenine-type alkaloids from Gelsemium elegans. J. Nat. Prod., 1989, 52(3), 588-594.
[http://dx.doi.org/10.1021/np50063a019] [PMID: 2778451]
[62]
Kitajima, M.; Takayama, H.; Sakai, S. Stereoselective transformation of ajmaline into three minor Gelsemium alkaloids, koumidine, (19Z)-anhydrovobasinediol [(19Z)-taberpsychine] and N-demethoxyrankinidine and their absolute configuration. J. Chem. Soc., Perkin Trans. 1, 1991, (8), 1773-1779.
[http://dx.doi.org/10.1039/p19910001773]
[63]
Xu, Y.K.; Yang, L.; Liao, S.G.; Cao, P.; Wu, B.; Hu, H.B.; Guo, J.; Zhang, P. Koumine, humantenine, and yohimbane alkaloids from gelsemium elegans. J. Nat. Prod., 2015, 78(7), 1511-1517.
[http://dx.doi.org/10.1021/np5009619] [PMID: 26103517]
[64]
Kogure, N.; Kobayashi, H.; Ishii, N.; Kitajima, M.; Wongseripipatana, S.; Takayama, H. New humantenine-type indole alkaloids with iridoid unit from Gelsemium species. Tetrahedron Lett., 2008, 49(22), 3638-3642.
[http://dx.doi.org/10.1016/j.tetlet.2008.03.148]
[65]
Zhao, Q.C.; Hua, W.; Zhang, L.; Guo, T.; Zhao, M.H.; Yan, M.; Wu, L.J. Two new alkaloids from Gelsemium elegans. J. Asian Nat. Prod. Res., 2010, 12(4), 273-277.
[http://dx.doi.org/10.1080/10286021003689809] [PMID: 20419537]
[66]
Sun, F.; Xing, Q.Y.; Liang, X.T. Structures of (19R)-kouminol and (19S)-kouminol from Gelsemium elegans. J. Nat. Prod., 1989, 52(5), 1180-1182.
[http://dx.doi.org/10.1021/np50065a049]
[67]
Sun, M.; Hou, X.; Gao, H.; Guo, J.; Xiao, K. Two new koumine-type indole alkaloids from Gelsemium elegans Benth. Molecules., 2013, 18(2), 1819-1825.
[http://dx.doi.org/10.3390/molecules18021819] [PMID: 23434864]
[68]
Lin, L.Z.; Cordell, G.A.; Nit, C-Z.; Clardy, J. N-methoxyanhydrovobasinediol from Gelsemium elegans. Phytochemistry., 1989, 28(10), 2827-2831.
[http://dx.doi.org/10.1016/S0031-9422(00)98099-3]
[69]
Kitajima, M.; Kogure, N.; Yamaguchi, K.; Takayama, H.; Aimi, N. Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Org. Lett., 2003, 5(12), 2075-2078.
[http://dx.doi.org/10.1021/ol0344725] [PMID: 12790532]
[70]
Kogure, N.; Nishiya, C.; Kitajima, M.; Takayama, H. Six new indole alkaloids from Gelsemium sempervirens. Ait. f. Tetrahedron Lett., 2005, 46(35), 5857-5861.
[http://dx.doi.org/10.1016/j.tetlet.2005.06.136]
[71]
Zhang, Q.; Zhang, B.; Chou, G.; Wang, Z. Chemical constituents of aerial parts of Gelsemium elegans. Zhongguo Zhongyao Zazhi, 2011, 36(10), 1305-1310.
[PMID: 21837971]
[72]
Li, N.P.; Liu, J.S.; Liu, J.W.; Tian, H.Y.; Zhou, H.L.; Zheng, Y.R.; Huang, X.J.; Cao, J.Q.; Ye, W.C.; Wang, L. Monoterpenoid indole alkaloids from the fruits of Gelsemium elegans and their anti-inflammatory activities. Bioorg. Chem., 2021, 107, 104624.
[http://dx.doi.org/10.1016/j.bioorg.2020.104624] [PMID: 33465669]
[73]
Zhang, Z.; Zhang, Y.; Wang, Y.H.; Zhang, Q.; Yan, X.H.; Di, Y.T.; He, H.P.; Hao, X.J. Three novel β-carboline alkaloids from Gelsemium elegans. Fitoterapia, 2012, 83(4), 704-708.
[http://dx.doi.org/10.1016/j.fitote.2012.02.007] [PMID: 22406454]
[74]
Liu, Y.; Li, Y.; Liu, Z.; Li, L.; Qu, J.; Ma, S.; Chen, R.; Dai, J.; Yu, S. Sesquiterpenes from the Endophyte Glomerella cingulata. J. Nat. Prod., 2017, 80(10), 2609-2614.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00054] [PMID: 29035525]
[75]
Kogure, N.; Ishii, N.; Kobayashi, H.; Kitajima, M.; Wongseripipatana, S.; Takayama, H. New iridoids from Gelsemium species. Chem. Pharm. Bull., 2008, 56(6), 870-872.
[http://dx.doi.org/10.1248/cpb.56.870] [PMID: 18520100]
[76]
Jensen, S.R.; Kirk, O.; Nielsen, B.J.; Norrestam, R. 9-hydroxy substituted iridoids from Gelsemium sempervirens. Phytochemistry., 1987, 26(6), 1725-1731.
[http://dx.doi.org/10.1016/S0031-9422(00)82277-3]
[77]
Zhang, B.F.; Zhang, Q.P.; Liu, H.; Chou, G.X.; Wang, Z.T. Iridoids from leaves of Gelsemium elegans. Phytochemistry., 2011, 72(9), 916-922.
[http://dx.doi.org/10.1016/j.phytochem.2011.03.021] [PMID: 21497867]
[78]
Zhang, Q.P.; Zhang, B.F.; Chou, G.X.; Wang, Z.T. Two new megastigmane glycosides and a new iridoid glycoside from Gelsemium elegans. Helv. Chim. Acta., 2011, 94(6), 1130-1138.
[http://dx.doi.org/10.1002/hlca.201000399]
[79]
Bai, B.; Peng, S.; Liu, Q.; Shen, J.; Zhu, L.; Wang, D.; Yang, D.; Zhao, Z. A new nonglycosidic iridoid from aerial parts of Gelsemium elegans. Chem. Nat. Compd., 2019, 55(2), 275-277.
[http://dx.doi.org/10.1007/s10600-019-02665-z]
[80]
Hua, W.; Guo, T.; Zhang, L. Chemical constituents of Gelsemium elegans Benth. J. Med. Chem., 2007, 17(2), 108-110.
[81]
Zhang, Z.; Wang, P.; Yuan, W.; Li, S. Steroids, alkaloids, and coumarins from Gelsemium sempervirens. Planta Med., 2008, 74(15), 1818-1822.
[http://dx.doi.org/10.1055/s-0028-1088327] [PMID: 19016214]
[82]
Zhang, B.; Chou, G.; Wang, Z. [Non-alkaloid constituents of Gelsemium elegans.]. Zhongguo Zhongyao Zazhi, 2009, 34(18), 2334-2337.
[PMID: 20030082]
[83]
Zhao, Q.C.; Hua, W.; Fu, Y.H.; Du, Z.Q.; Guo, T.; Wu, L.J. Isolation and identification of the non-alkaloid constituents from whole plant of Gelsemium elegans Benth.(III). J. Shenyang Pharm. Univ., 2010, 27(7), 551-554.
[84]
Zhao, Q.C.; Fu, Y.H.; Du, Z.Q.; Hua, W.; Guo, T.; Jun, L.J. Isolation and identification of the non-alkaloid constituents from Gelsemium elegans Benth. J. Shenyang Pharm. Univ., 2009, 26(9), 694-696.
[85]
Zhao, Q.C.; Hua, W.; Du, Z.Q.; Guo, T.; Wu, L.J. Isolation and identification of non-alkaloid constituents from Gelsemium elegans Benth. J. Shenyang Pharm. Univ., 2007, 24(10), 619-622.
[86]
Cui, Y.; Sun, M.X.; Gao, H.H.; Yang, Y.Y.; Lu, J.C.; Xiao, K. Isolation and identification of the liposoluble constituents from the roots of Gelsemium elegans Benth. J. Shenyang Pharm. Univ., 2014, 31(4), 248-251.
[87]
Liu, B.; Yang, L.; Xu, Y.K.; Liao, S.G.; Luo, H.R.; Na, Z. Two new triterpenoids from Gelsemium elegans and Aglaia odorata. Nat. Prod. Commun., 2013, 8(10), 1934578X1300801.
[http://dx.doi.org/10.1177/1934578X1300801008] [PMID: 24354178]
[88]
Schun, Y.; Cordell, G.A. Cytotoxic steroids of Gelsemium sempervirens. J. Nat. Prod., 1987, 50(2), 195-198.
[http://dx.doi.org/10.1021/np50050a012] [PMID: 3655795]
[89]
Liu, Y.C.; Sun, Z.L.; Liu, Z.Y. Research progress on non-alkaloids analysis for chemical constituents from Gelsemium. Chin. J. Vet. Drug, 2016, 50(10), 55-64.
[90]
Zhao, M.; Guo, T.; Wang, M.; Zhao, Q.; Liu, Y.; Sun, X.; Wang, H.; Hou, Y. The course of uncarinic acid E-induced apoptosis of HepG2 cells from damage to DNA and p53 activation to mitochondrial release of cytochrome c. Biol. Pharm. Bull., 2006, 29(8), 1639-1644.
[http://dx.doi.org/10.1248/bpb.29.1639] [PMID: 16880619]
[91]
Hua, W.; Zhao, Q.C.; Yang, J.; Shi, G.B.; Wu, L.J.; Guo, T. Two new benzofuran lignan glycosides from Gelsemium elegans. Chin. Chem. Lett., 2008, 19(11), 1327-1329.
[http://dx.doi.org/10.1016/j.cclet.2008.09.012]
[92]
Lin, L.; Liu, Y.C.; Liu, Z.Y. The difference in cytotoxic activity between two optical isomers of gelsemine from Gelsemium elegans Benth. on PC12 cells. Molecules., 2019, 24(10), 2004.
[http://dx.doi.org/10.3390/molecules24102004] [PMID: 31130596]
[93]
Zhao, Q.C.; Hua, W.; Zhang, L.; Guo, T.; Zhao, M.H.; Yan, M.; Shi, G.B.; Wu, L.J. Antitumor activity of two gelsemine metabolites in rat liver microsomes. J. Asian Nat. Prod. Res., 2010, 12(9), 731-739.
[http://dx.doi.org/10.1080/10286020.2010.492951] [PMID: 20839118]
[94]
Wang, L.; Xu, H.; Liang, J.; Ding, Y.; Meng, F. An integrated network, RNA sequencing, and experiment pharmacology approach reveals the active component, potential target, and mechanism of Gelsemium elegans in the treatment of colorectal cancer. Front. Oncol., 2020, 10, 616628.
[http://dx.doi.org/10.3389/fonc.2020.616628] [PMID: 33425771]
[95]
Yuan, Z.; Liang, Z.; Yi, J.; Chen, X.; Li, R.; Wu, J.; Sun, Z. Koumine promotes ROS production to suppress hepatocellular carcinoma cell proliferation via NF-κB and ERK/p38 MAPK signaling. Biomolecules., 2019, 9(10), 559.
[http://dx.doi.org/10.3390/biom9100559] [PMID: 31581704]
[96]
Das, S.; Das, J.; Samadder, A.; Bhattacharyya, S.S.; Das, D.; Khuda-Bukhsh, A.R. Biosynthesized silver nanoparticles by ethanolic extracts of Phytolacca decandra, Gelsemium sempervirens, Hydrastis canadensis and Thuja occidentalis induce differential cytotoxicity through G2/M arrest in A375 cells. Colloids Surf. B Biointerfaces, 2013, 101, 325-336.
[http://dx.doi.org/10.1016/j.colsurfb.2012.07.008] [PMID: 23010037]
[97]
Jin, G.; Yue, R.; He, S.; Hong, L.; Xu, Y.; Yu, C. Koumine decreases astrocyte-mediated neuroinflammation and enhances autophagy, contributing to neuropathic pain from chronic constriction injury in rats. Front. Pharmacol., 2018, 9, 989.
[http://dx.doi.org/10.3389/fphar.2018.00989] [PMID: 30214411]
[98]
Luo, Y.; Xiong, B.; Liu, H.; Chen, Z.; Huang, H.; Yu, C.; Yang, J. Koumine suppresses IL-1β secretion and attenuates inflammation associated with blocking ROS/NF-κB/NLRP3 Axis in macrophages. Front. Pharmacol., 2021, 11, 622074.
[http://dx.doi.org/10.3389/fphar.2020.622074] [PMID: 33542692]
[99]
Jin, G.L.; Yang, J.; Chen, W.Q.; Wang, J.; Qiu, H.Q.; Xu, Y.; Yu, C.X. The analgesic effect and possible mechanisms by which koumine alters type II collagen-induced arthritis in rats. J. Nat. Med., 2019, 73(1), 217-225.
[http://dx.doi.org/10.1007/s11418-018-1229-3] [PMID: 30054785]
[100]
Xiong, B.J.; Xu, Y.; Jin, G.L.; Liu, M.; Yang, J.; Yu, C.X. Analgesic effects and pharmacologic mechanisms of the Gelsemium alkaloid koumine on a rat model of postoperative pain. Sci. Rep., 2017, 7(1), 14269.
[http://dx.doi.org/10.1038/s41598-017-14714-0] [PMID: 29079733]
[101]
Zhang, J.Y.; Gong, N.; Huang, J.L.; Guo, L.C.; Wang, Y.X. Gelsemine, a principal alkaloid from Gelsemium sempervirens Ait., exhibits potent and specific antinociception in chronic pain by acting at spinal α3 glycine receptors. Pain, 2013, 154(11), 2452-2462.
[http://dx.doi.org/10.1016/j.pain.2013.07.027] [PMID: 23886522]
[102]
Rujjanawate, C.; Kanjanapothi, D.; Panthong, A. Pharmacological effect and toxicity of alkaloids from Gelsemium elegans Benth. J. Ethnopharmacol., 2003, 89(1), 91-95.
[http://dx.doi.org/10.1016/S0378-8741(03)00267-8] [PMID: 14522437]
[103]
Liu, M.; Shen, J.; Liu, H.; Xu, Y.; Su, Y.P.; Yang, J.; Yu, C.X. Gelsenicine from Gelsemium elegans attenuates neuropathic and inflammatory pain in mice. Biol. Pharm. Bull., 2011, 34(12), 1877-1880.
[http://dx.doi.org/10.1248/bpb.34.1877] [PMID: 22130245]
[104]
Xu, Y.; Qiu, H.Q.; Liu, H.; Liu, M.; Huang, Z.Y.; Yang, J.; Su, Y.P.; Yu, C.X. Effects of koumine, an alkaloid of Gelsemium elegans Benth., on inflammatory and neuropathic pain models and possible mechanism with allopregnanolone. Pharmacol. Biochem. Behav., 2012, 101(3), 504-514.
[http://dx.doi.org/10.1016/j.pbb.2012.02.009] [PMID: 22366214]
[105]
Ling, Q.; Liu, M.; Wu, M.X.; Xu, Y.; Yang, J.; Huang, H.H.; Yu, C.X. Anti-allodynic and neuroprotective effects of koumine, a Benth alkaloid, in a rat model of diabetic neuropathy. Biol. Pharm. Bull., 2014, 37(5), 858-864.
[http://dx.doi.org/10.1248/bpb.b13-00843] [PMID: 24790009]
[106]
Yang, J.; Cai, H.D.; Zeng, Y.L.; Chen, Z.H.; Fang, M.H.; Su, Y.P.; Huang, H.H.; Xu, Y.; Yu, C.X. Effectsof koumine on adjuvant- and collagen-induced arthritis in rats. J. Nat. Prod., 2016, 79(10), 2635-2643.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00554] [PMID: 27657857]
[107]
Liu, M.; Huang, H.H.; Yang, J.; Su, Y.P.; Lin, H.W.; Lin, L.Q.; Liao, W.J.; Yu, C.X. The active alkaloids of Gelsemium elegans Benth. are potent anxiolytics. Psychopharmacology., 2013, 225(4), 839-851.
[http://dx.doi.org/10.1007/s00213-012-2867-x] [PMID: 23052566]
[108]
Dutt, V.; Dhar, V.J.; Sharma, A. Antianxiety activity of Gelsemium sempervirens. Pharm. Biol., 2010, 48(10), 1091-1096.
[http://dx.doi.org/10.3109/13880200903490521] [PMID: 20860436]
[109]
Garg, V.; Dhar, V.J.; Sharma, A.; Dutt, R. Antianxiety Activity of Methanol Extract of Gelsemium sempervirens. J. Stress Physiol. Biochem., 2012, 8(2), 118-124.
[110]
Sun, L.; Lei, L.; Fang, F.; Yang, S.; Jian, W. Inhibitory effects of koumine on splenocyte proliferation and humoral immune response in mice. Pharmacol. Clin. Chin. Mater. Med., 1999, 15, 10-12.
[111]
Wang, Z.R.; Huang, C.Q.; Zhang, Z.Y.; Zhang, L.L.; Lin, J.M. [Effect of koumine on proliferation of murine CD4+ T cells purified by magnetic-activated cell sorting in vitro]. J. First Mil. Med. Univ., 2005, 25(5), 562-564.
[PMID: 15897137]
[112]
Yue, R.; Jin, G.; Wei, S.; Huang, H.; Su, L.; Zhang, C.; Xu, Y.; Yang, J.; Liu, M.; Chu, Z.; Yu, C. Immunoregulatory effect of koumine on nonalcoholic fatty liver disease rats. J. Immunol. Res., 2019, 2019, 1-9.
[http://dx.doi.org/10.1155/2019/8325102] [PMID: 30915371]
[113]
Palit, P.; Mukherjee, D.; Mandal, S.C. Reconstituted mother tinctures of Gelsemium sempervirens L. improve memory and cognitive impairment in mice scopolamine-induced dementia model. J. Ethnopharmacol., 2015, 159, 274-284.
[http://dx.doi.org/10.1016/j.jep.2014.09.008] [PMID: 25459447]
[114]
Chen, L.; Pan, H.; Bai, Y.; Li, H.; Yang, W.; Lin, Z.X.; Cui, W.; Xian, Y.F. Gelsemine, a natural alkaloid extracted from Gelsemium elegans Benth. alleviates neuroinflammation and cognitive impairments in Aβ oligomer-treated mice. Psychopharmacology., 2020, 237(7), 2111-2124.
[http://dx.doi.org/10.1007/s00213-020-05522-y] [PMID: 32363440]
[115]
Yuan, Z.H.; Liang, Z.E.; Wu, J.; Yi, J.E.; Chen, X.J.; Sun, Z.L. A potential mechanism for the anti-apoptotic property of koumine involving mitochondrial pathway in LPS-mediated RAW 264.7 macrophages. Molecules., 2016, 21(10), 1317.
[http://dx.doi.org/10.3390/molecules21101317] [PMID: 27706063]
[116]
Shanghai University. Application of Gelsevirine in the preparation of drugs for the treatment of arthritis. 202211142253.3, 2023-05-05.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy