Login Register Cart 0
Generic placeholder image

The Natural Products Journal

Editor-in-Chief

ISSN (Print): 2210-3155
ISSN (Online): 2210-3163

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

Xanthones from Securidaca inappendiculata and Securidaca longepedunculata: Chemistry and Biological Activity

Author(s): Gomotsang Bojase and Japheth O. Ombito*

Volume 14, Issue 1, 2024

Published on: 05 July, 2023

Article ID: e100523216763 Pages: 16

DOI: 10.2174/2210315513666230510123728

Price: $65

Abstract

The genus Securidaca (Polygalaceae) comprises 49 taxonomically accepted species distributed in Asia and Africa. The roots, barks, and leaves of Securidaca species are famous for medicinal purposes, especially in Africa and Asia. In this paper, we review the xanthones isolated from S. inappendiculata and S. longepedunculata, the two main species that have been investigated and the bioactivities of these compounds to evaluate the traditional use of these plant species and future development. The references regarding Securidaca species were retrieved from Scopus, Web of Science, PubMed, ScienceDirect, Google Scholar, and SciFinder between 1990 and 2022. Chemical structures of more than 70 xanthones isolated mainly from the stems and roots of S. inappendiculata and S. longepedunculata are presented. These xanthones might be responsible for the ethnomedicinal uses reported in the literature based on the exhibited biological properties such as cytotoxic, antidiabetic, antiviral, and erectile dysfunction of these compounds. Reviewing the research progress made on the isolated xanthones from the genus Securidaca lays a foundation for the future utilization and development of this genus.

Graphical Abstract

[1]
The Plant List Available Fromhttp://www.theplantlist.org/[Accesed on: June 2022]
[2]
Wallnöfer, B. A new species of Securidaca L.(Polygalaceae) from Peru. Ann. Nat. Hist. Mus. Wien. Ser. B. Bot. Zool., 1998, 709-714.
[3]
Global Biodiversity Information Facility Available Fromhttps://www.gbif.org/occurrence/3384565103[Accessed on: June 2022].
[4]
Yunnan Institute of Botany. Flora of Yunnan; Science Press Peking: China, 1983.
[5]
Mongalo, N.I.; McGaw, L.J.; Finnie, J.F.; Staden, J.V. Securidaca longipedunculata Fresen (Polygalaceae): A review of its ethnomedicinal uses, phytochemistry, pharmacological properties and toxicology. J. Ethnopharmacol., 2015, 165, 215-226.
[http://dx.doi.org/10.1016/j.jep.2015.02.041] [PMID: 25724970]
[6]
Rakuambo, N.C.; Meyer, J.J.M.; Hussein, A.; Huyser, C.; Mdlalose, S.P.; Raidani, T.G. In vitro effect of medicinal plants used to treat erectile dysfunction on smooth muscle relaxation and human sperm. J. Ethnopharmacol., 2006, 105(1-2), 84-88.
[http://dx.doi.org/10.1016/j.jep.2005.10.008] [PMID: 16309865]
[7]
PhytoImages Available Fromhttp://www.phytoimages.siu.edu/imgs/pelserpb/r/Polygalaceae_Securidaca_inappendiculata_50228.html[Accessed on: March 2023]
[8]
Remali, J.; Sahidin, I.; Aizat, W.M. Xanthone biosynthetic pathway in plants: A review. Front. Plant Sci., 2022, 13, 809497.
[http://dx.doi.org/10.3389/fpls.2022.809497] [PMID: 35463410]
[9]
Pinto, M.M.M.; Palmeira, A.; Fernandes, C.; Resende, D.I.S.P.; Sousa, E.; Cidade, H.; Tiritan, M.E.; Correia-da-Silva, M.; Cravo, S. From natural products to new synthetic small molecules: A journey through the world of xanthones. Molecules, 2021, 26(2), 431.
[http://dx.doi.org/10.3390/molecules26020431] [PMID: 33467544]
[10]
El-Seedi, H.; El-Barbary, M.; El-Ghorab, D.; Bohlin, L.; Borg-Karlson, A.K.; Göransson, U.; Verpoorte, R. Recent insights into the biosynthesis and biological activities of natural xanthones. Curr. Med. Chem., 2010, 17(9), 854-901.
[http://dx.doi.org/10.2174/092986710790712147] [PMID: 20156171]
[11]
Hagel, J.M.; Krizevski, R.; Kilpatrick, K.; Sitrit, Y.; Marsolais, F.; Lewinsohn, E.; Facchini, P.J. Expressed sequence tag analysis of khat (Catha edulis) provides a putative molecular biochemical basis for the biosynthesis of phenylpropylamino alkaloids. Genet. Mol. Biol., 2011, 34(4), 640-646.
[http://dx.doi.org/10.1590/S1415-47572011000400017] [PMID: 22215969]
[12]
Boatright, J.; Negre, F.; Chen, X.; Kish, C.M.; Wood, B.; Peel, G.; Orlova, I.; Gang, D.; Rhodes, D.; Dudareva, N. Understanding in vivo benzenoid metabolism in petunia petal tissue. Plant Physiol., 2004, 135(4), 1993-2011.
[http://dx.doi.org/10.1104/pp.104.045468] [PMID: 15286288]
[13]
Pinto, M.M.M.; Sousa, M.E.; Nascimento, M.S.J. Xanthone derivatives: new insights in biological activities. Curr. Med. Chem., 2005, 12(21), 2517-2538.
[http://dx.doi.org/10.2174/092986705774370691] [PMID: 16250875]
[14]
Vieira, L.M.M.; Kijjoa, A. Naturally-occurring xanthones: recent developments. Curr. Med. Chem., 2005, 12(21), 2413-2446.
[http://dx.doi.org/10.2174/092986705774370682] [PMID: 16250871]
[15]
Yang, X.D.; Xu, L.Z.; Yang, S.L. Xanthones from the stems of Securidaca inappendiculata. Phytochemistry, 2001, 58(8), 1245-1249.
[http://dx.doi.org/10.1016/S0031-9422(01)00356-9] [PMID: 11738416]
[16]
Meli Lannang, M. A.; Lontsi, D.; Ngounou, F.N.; Sondengam, B.L.; Nkengfack, A.E.; van Heerden, F.R.; Assob, J.C.N.; Securidacaxanthone, A. Securidacaxanthone A, a heptaoxygenated xanthone from Securidaca longepedunculata. Fitoterapia, 2006, 77(3), 199-202.
[http://dx.doi.org/10.1016/j.fitote.2006.01.006] [PMID: 16564647]
[17]
Dibwe, D.F.; Awale, S.; Kadota, S.; Morita, H.; Tezuka, Y. Heptaoxygenated xanthones as anti-austerity agents from Securidaca longepedunculata. Bioorg. Med. Chem., 2013, 21(24), 7663-7668.
[http://dx.doi.org/10.1016/j.bmc.2013.10.027] [PMID: 24216090]
[18]
Meli, A.L.; Ngninzeko, F.N.; Castilho, P.C.; Wansi, J.D.; Kuete, V.; Lontsi, D.; Beng, V.P.; Choudhary, M.I.; Sondengam, B.L.; Securidacaxanthones, B. Securidacaxanthones B and C, xanthones from Securidaca longepedunculata (Polygalaceae). Planta Med., 2007, 73, 411.
[19]
Kang, W.Y.; Xu, X.J. Structure of a new xanthone from Securidaca inappendiculata. Chem. Nat. Compd., 2008, 44(4), 432-434.
[http://dx.doi.org/10.1007/s10600-008-9089-9]
[20]
Zuo, J.; Ji, C.L.; Xia, Y.; Li, X.; Chen, J.W. Xanthones as α-glucosidase inhibitors from the antihyperglycemic extract of Securidaca inappendiculata. Pharm. Biol., 2014, 52(7), 898-903.
[http://dx.doi.org/10.3109/13880209.2013.872673] [PMID: 24621306]
[21]
Zuo, J.; Mao, K.; Yuan, F.; Li, X.; Chen, J. Xanthones with anti-tumor activity isolated from Securidaca inappendiculata. Med. Chem. Res., 2014, 23(11), 4865-4871.
[http://dx.doi.org/10.1007/s00044-014-1051-8]
[22]
Wang, Q.; Ma, C.; Ma, Y.; Li, X.; Chen, Y.; Chen, J. Structure–activity relationships of diverse xanthones against multidrug resistant human tumor cells. Bioorg. Med. Chem. Lett., 2017, 27(3), 447-449.
[http://dx.doi.org/10.1016/j.bmcl.2016.12.045] [PMID: 28065566]
[23]
Wedajo, F.; Gure, A.; Meshesha, M.; Kedir, K.; Frese, M.; Sewald, N.; Abdissa, N. Cytotoxic compounds from the root bark of Securidac alongipedunculata. Bull. Chem. Soc. Ethiop., 2022, 36(2), 417-422.
[http://dx.doi.org/10.4314/bcse.v36i2.14]
[24]
Galeffi, C.; Federici, E.; Msonthi, J.D.; Marini-Bettolo, G.B.; Nicoletti, M. New xanthones from Ectiadiopsis oblongifolia and Securidaca longependunculata. Fitoterapia, 1990, 61, 79-81.
[25]
Rakuambo, N.C.; Meyer, J.J.M.; Hussein, A. Xanthone isolated from Securidaca longependunculata with activity against erectile dysfunction. Fitoterapia, 2004, 75(5), 497-499.
[http://dx.doi.org/10.1016/j.fitote.2004.03.010] [PMID: 15261388]
[26]
Bo, T.; Yang, X.; Gao, F.; Liu, H.; Li, K.A.; Xiu, L. Optimized separation of pharmacologically active xanthones from Securidaca inappendiculata by capillary electrophoresis. Chromatographia, 2002, 55(3-4), 217-223.
[http://dx.doi.org/10.1007/BF02492145]
[27]
Bo, T.; Huang, Y.; Yang, X.; Li, K.A.; Liu, H.; Xu, L. Capillary electrophoretic behaviors of pharmacologically active xanthones from Securidaca inappendiculata with β-cyclodextrin as a buffer additive. J. Chromatogr. Sci., 2003, 41(4), 182-186.
[http://dx.doi.org/10.1093/chromsci/41.4.182] [PMID: 12803804]
[28]
Bo, T.; Liu, F.; An Li, K.; Liu, H. Comparison of different capillary electrophoresis modes and HPLC for the separation of xanthones. J. Liq. Chromatogr. Relat. Technol., 2003, 26(6), 993-1003.
[http://dx.doi.org/10.1081/JLC-120018899]
[29]
Zuo, J.; Zhang, W.; Xia, Y.; Li, X.; Luan, J.J.; Chen, J.W. PEGylated niosomes as delivery systems efficiently prolonged the clearance time of 2-hydroxy-1, 7-dimethoxyxanthone in vivo. Lat. Am. J. Pharm., 2015, 34, e14.
[30]
Bo, T.; Yang, X.; Liu, F.; Li, K.A.; Xiu, L.; Liu, H. Optimized separation of pharmacologically active xanthones from Securidaca inappendiculata by micellar electrokinetic chromatography and microemulsion electrokinetic chromatography. Anal. Chim. Acta, 2002, 474(1-2), 37-48.
[http://dx.doi.org/10.1016/S0003-2670(02)01027-9]
[31]
Bo, T.; Yang, X.; Li, K.A.; Xu, L.; Liu, H. Comparison of micellar electrokinetic chromatography and microemulsion electrokinetic chromatography for separation of pharmacologically active xanthones from Securidaca inappendiculata. J. Sep. Sci., 2003, 26(1-2), 133-136.
[http://dx.doi.org/10.1002/jssc.200390004]
[32]
Wu, X.; Gong, S.; Bo, T.; Liao, Y.; Liu, H. Determination of dissociation constants of pharmacologically active xanthones by capillary zone electrophoresis with diode array detection. J. Chromatogr. A, 2004, 1061(2), 217-223.
[http://dx.doi.org/10.1016/j.chroma.2004.10.085] [PMID: 15641365]
[33]
Joseph, C.C.; Moshi, M.J.; Sempombe, J.; Nkunya, M.H.H. (4-Methoxy-benzo[1,3]dioxol-5-yl)- Phenylmethanone: an antibacterial benzophenone from securidaca longepedunculata. Afr. J. Tradit. Complement. Altern. Med., 2006, 3(3), 80-86.
[http://dx.doi.org/10.4314/ajtcam.v3i3.31169]
[34]
Xue-Dong, Y.; Li-Zhen, X.; Shi-Lin, Y. Two new xanthones from the stems of Securidaca inappendiculata. J. Integr. Plant Biol., 2003, 45, 365.
[35]
Kang, W.Y.; Wang, Z.M.; Li, Z.Q.; Xu, X.J. Three New Compounds from Securidaca inappendiculata. Helv. Chim. Acta, 2005, 88(10), 2771-2776.
[http://dx.doi.org/10.1002/hlca.200590217]
[36]
Zhang, L.; Yang, X.; Xu, L.; Yang, S. Three new xanthones from the roots of Securidaca inappendiculata. Heterocycles, 2005, 65(7), 1685-1690.
[http://dx.doi.org/10.3987/COM-05-10392]
[37]
Zuo, J.; Xia, Y.; Li, X.; Ou-Yang, Z.; Chen, J. Selective modulation of MAPKs contribute to the anti-proliferative and anti-inflammatory activities of 1,7-dihydroxy-3,4-dimethoxyxanthone in rheumatoid arthritis-derived fibroblast-like synoviocyte MH7A cells. J. Ethnopharmacol., 2015, 168, 248-254.
[http://dx.doi.org/10.1016/j.jep.2015.03.069] [PMID: 25862966]
[38]
Tao, M.; Ji, C.; Wu, Y.; Dong, J.; Li, Y.; Olatunji, O.J.; Zuo, J. 1, 7-Dihydroxy-3, 4-dimethoxyxanthone inhibits lipopolysaccharide-induced inflammation in raw264. 7 macrophages by suppressing TLR4/NF-κB signaling cascades. Inflammation, 2020, 43(5), 1821-1831.
[http://dx.doi.org/10.1007/s10753-020-01256-3] [PMID: 32468498]
[39]
Kang, W.Y.; Ji, Z.Q.; Wang, J.M. A new xanthone from the roots of Securidaca inappendiculata. Chem. Pap., 2009, 63(1), 102-104.
[http://dx.doi.org/10.2478/s11696-008-0087-y]
[40]
Meyer, J.J.M.; Rakuambo, N.C.; Hussein, A.A. Novel xanthones from Securidaca longepedunculata with activity against erectile dysfunction. J. Ethnopharmacol., 2008, 119(3), 599-603.
[http://dx.doi.org/10.1016/j.jep.2008.06.018] [PMID: 18638534]
[41]
Dibwe, D.F.; Awale, S.; Kadota, S.; Tezuka, Y.; Muchimangins, A-D. Muchimangins A–D: novel diphenylmethyl-substituted xanthones from Securidaca longepedunculata. Tetrahedron Lett., 2012, 53(46), 6186-6190.
[http://dx.doi.org/10.1016/j.tetlet.2012.08.115]
[42]
Dibwe, D.F.; Awale, S.; Kadota, S.; Morita, H.; Tezuka, Y. Muchimangins E and F: novel diphenylmethyl-substituted xanthones from Securidaca longepedunculata. Tetrahedron Lett., 2014, 55(11), 1916-1919.
[http://dx.doi.org/10.1016/j.tetlet.2014.01.149]
[43]
Dibwe, D.F.; Awale, S.; Kadota, S.; Morita, H.; Tezuka, Y.; Muchimangins, G-J. Muchimangins G-J, fully substituted xanthones with a diphenylmethyl substituent, from Securidaca longepedunculata. J. Nat. Prod., 2014, 77(5), 1241-1244.
[http://dx.doi.org/10.1021/np5000445] [PMID: 24779644]
[44]
Dibwe, D.F.; Awale, S.; Kadota, S.; Morita, H.; Tezuka, Y. Two new diphenylmethyl-substituted xanthones from Seicuridaca longepedunculata. Nat. Prod. Commun., 2014, 9(5), 1934578X1400900.
[http://dx.doi.org/10.1177/1934578X1400900517] [PMID: 25026713]
[45]
Yang, X.D.; An, N.; Xu, L.Z.; Yang, S.L. New xanthone glycosides from Securidaca inappendiculata. J. Asian Nat. Prod. Res., 2002, 4(2), 141-145.
[http://dx.doi.org/10.1080/10286020290027434] [PMID: 12067160]
[46]
Suffness, M.; Douros, J. Current status of the NCI plant and animal product program. J. Nat. Prod., 1982, 45(1), 1-14.
[http://dx.doi.org/10.1021/np50019a001] [PMID: 7069421]
[47]
Bischoff, H. The mechanism of alpha-glucosidase inhibition in the management of diabetes. Clin. Invest. Med., 1995, 18(4), 303-311.
[PMID: 8549017]
[48]
Carrascosa, J.M.; Molero, J.C.; Fermín, Y.; Martínez, C.; Andrés, A.; Satrústegui, J. Effects of chronic treatment with acarbose on glucose and lipid metabolism in obese diabetic Wistar rats. Diabetes Obes. Metab., 2001, 3(4), 240-248.
[http://dx.doi.org/10.1046/j.1463-1326.2001.00102.x] [PMID: 11520303]

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