Chemo-Diversity of Antibacterial Anthraquinones from the Roots of Morinda morindoides

Author(s): Jean-Luc Aboya Moroh, Yannick Fleury, Adama Coulibaly, Roger Labia, Ivan Leguérinel*

Journal Name: The Natural Products Journal

Volume 9 , Issue 4 , 2019

Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Background: Morinda morindoides (Baker) (Rubiaceae) is a medicinal plant with antimicrobial properties currently used in Côte d'Ivoire and other countries. These properties have been described but most of the studies are dealing with crude extracts.

Objective: The chemical structures of the bioactive compounds extracted from Morinda morindoides roots have been characterized.

Methods: The root extracts were analyzed by using HPLC. Fourteen fractions were detected among which 11 compounds have been structurally identified by using a combination of 1H-NMR and 13CNMR and LC-HRMS methodologies.

Results: All these compounds belong to anthraquinone family. The antibacterial activity of the eleven compounds was tested against six strains of microorganisms with ofloxacin as standard (two Gram-negative bacteria, two Gram-positive bacteria and two yeasts). The Minimal Inhibitory Concentrations recorded, varies from 8 to 128 μg / ml. Staphylococcus aureus was the most susceptible organism.

Conclusion: We highlight the chemo-diversity of the antibacterial anthraquinones in the roots of Morinda morindoides.

Keywords: Morinda morindoides, anthraquinones, antibacterial properties, roots, bioactive compounds, Staphylococcus aureus.

Bhatnagar, S.; Das, S.B. Antimalarial activity in tropical plants: A review. J. Herbs Spices Med. Plants, 2007, 13(1), 103-132.
Chaieb, K.; Hajlaoui, H.; Zmantar, T.; Kahla-Nakbi, A.B.; Rouabhia, M.; Mahdouani, K.; Bakhrouf, A. The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): A short review. Phytother. Res., 2007, 21(6), 501-506.
[] [PMID: 17380552]
Magiorakos, A.P.; Srinivasan, A.; Carey, R.B.; Carmeli, Y.; Falagas, M.E.; Giske, C.G.; Harbarth, S.; Hindler, J.F.; Kahlmeter, G.; Olsson-Liljequist, B.; Paterson, D.L.; Rice, L.B.; Stelling, J.; Struelens, M.J.; Vatopoulos, A.; Weber, J.T.; Monnet, D.L. Multidrug-resistant, extensively drug-resistant and pandrug-resistant bacteria: An international expert proposal for interim standard definitions for acquired resistance. Clin. Microbiol. Infect., 2012, 18(3), 268-281.
[] [PMID: 21793988]
Nordmann, P.; Dortet, L.; Poirel, L. Carbapenem resistance in Enterobacteriaceae: Here is the storm! Trends Mol. Med., 2012, 18(5), 263-272.
[] [PMID: 22480775]
Patel, G.; Bonomo, R.A. Stormy waters ahead: Global emergence of carbapenemases. Front. Microbiol., 2013, 4, 48.
[] [PMID: 23504089]
O’Brien, T.F.; Stelling, J. Integrated multilevel surveillance of the world’s infecting microbes and their resistance to antimicrobial agents. Clin. Microbiol. Rev., 2011, 24(2), 281-295.
[] [PMID: 21482726]
West, B.J.; Sabin, R.A. Efficacy of a Morinda citrifolia based skin care regimen. Curr. Res. J. Biol. Sci., 2012, 4, 310-314.
Lee, S.Y.; Park, S.L.; Hwang, J.T.; Yi, S.H. Antidiabetic effect of Morinda citrifolia (noni) fermented by Cheonggukjang in KK-Ay diabetic mice. Evid. Based Complement Alternat. Med, 2012. ID 163280.
Cirillo, C.; Capasso, R. Constipation and botanical medicines: An overview. Phytother. Res., 2015, 29(10), 1488-1493.
[] [PMID: 26171992]
Adesida, G.A.; Adesogan, E.K. Oruwal, a novel dihydroanthraquinone pigment from Morinda lucida Benth. J. Chem. Soc. Chem. Commun., 1972, 1(7), 405-406.
Cimanga, R.K.; Tona, G.L.; Mesia, G.K.; Kambu, O.K.; Bakana, D.P.; Kalenda, P.D.T.; Penge, A.O.; Muyembe, J.J.T.; Totte, J.; Pieters, L.; Vlietinck, A.J. Bioassay-guided isolation of antimalarial triterpenoid acids from the leaves of Morinda lucida. Pharm. Biol., 2006, 44(9), 677-681.
Sivaraman, D.; Muralidharan, P. Evaluation of anti-microbial and anti-inflammatory activity of Morinda tinctoria Roxb. Asian J. Exp. Biol. Sci., 2010, 1, 8-13.
Chang, P.; Lee, K.H.; Shingu, T.; Hirayama, T.; Hall, I.H.; Huang, H.C. Antitumor agents 50. 1 Morindaparvin-A, a new antileukemic anthraquinone, and alizarin-1-methyl ether from Morinda parvifolia, and the antileukemic activity of the related derivatives. J. Nat. Prod., 1982, 45(2), 206-210.
[] [PMID: 7097296]
Ali, A.M.; Ismail, N.H.; Mackeen, M.M.; Yazan, L.S.; Mohamed, S.M.; Ho, A.S.H.; Lajis, N.H. Antiviral, cyototoxic and antimicrobial activities of anthraquinones isolated from the roots of Morinda elliptica. Pharm. Biol., 2000, 38(4), 298-301.
[;1-A;FT298] [PMID: 21214480]
Xiang, W.; Song, Q.S.; Zhang, H.J.; Guo, S.P. Antimicrobial anthraquinones from Morinda angustifolia. Fitoterapia, 2008, 79(7-8), 501-504.
[] [PMID: 18621113]
Cimanga, K.; De Bruyne, T.; Lasure, A.; Van Poel, B.; Pieters, L.; Vanden Berghe, D.; Vlietinck, A.; Kambu, K.; Tona, L. In vitro anticomplementary activity of constituents from Morinda morindoides. J. Nat. Prod., 1995, 58(3), 372-378.
[] [PMID: 7775983]
Bahi, C.; N'Guessan, D.; Guede-Guina, F. Mise en évidence d'une action myorelaxante et cholinergique de Bitter GG (Morinda morindoides), un antidiarrhéique de source végétale Afrique biomédical, 2000, 5, 11-18.
Moroh, J.L.A.; Bahi, C.; Dje, K.; Loukou, Y.G.; Guede-Guina, F. Study of the antibacterial activity of Morinda morindoides (Baker) milne-redheat (rubiaceae) acetatique extract (ACE) on in-vitro growth of Escherichia coli strains. Bull. Soc. R. Sci. Liege, 2008, 77, 44-61.
Ramiarantsoa, H.; Seri, C.S.; Yao-Kouassi, P.A.; Okpekon, T.; Adiko, V.A.; Djakoure, L.A.; Coffy, A.A. A ketosteroid isolated from Morinda morindoides. Eur. J. Sci. Res., 2009, 28, 621-626.
Cimanga, R.K.; Tona, G.L.; Kambu, O.K.; Mesia, G.K.; Muyembe, J.J.T.; Apers, S.; Pieters, L.; Vlietinck, A.J. Antimalarial activity of some extracts and isolated constituents from Morinda morindoides leaves. J. Nat. Rem., 2002, 8(2), 191-202.
Cimanga, K.; Hermans, N.; Apers, S.; Van Miert, S.; Van den Heuvel, H.; Claeys, M.; Pieters, L.; Vlietinck, A. Complement-inhibiting iridoids from Morinda morindoides. J. Nat. Prod., 2003, 66(1), 97-102.
[] [PMID: 12542353]
Moroh, J.L.A.; Bahi, C.; Karamoko, D.; Fleury, Y.; Labia, R.; Leguerinel, I.; Coulibaly, A. Highlighting of the antimicrobial activities of extracts of Morinda morindoides, a medicinal plant used in West and Central Africa. SSRG-IJMS., 2016, 3, 19-25.
Phakhodee, W. Distribution of naturally occurring anthraquinones, iridoids and flavonoids from Morinda genus: Chemistry and biological activity. Walailak J. Sci. Technol., 2012, 9, 173-188.
Kamiya, K.; Hamabe, W.; Tokuyama, S.; Hirano, K.; Satake, T.; Kumamoto-Yonezawa, Y.; Yoshida, H.; Mizushina, Y. Inhibitory effect of anthraquinones isolated from the Noni (Morinda citrifolia) root on animal A-, B- and Y-families of DNA polymerases and human cancer cell proliferation. Food Chem., 2010, 118(3), 725-730.
Sambou, O.; Gassama, A.; Karé, M.; Gambe, D.; Rivard, M.; Martens, T.; Lachaise, I. Antimicrobial anthraquinones and triterpenoid isolated from Morinda geminata DC (Rubiaceae). Med. J. Chem., 2017, 6(5), 191-195.
Rath, G.; Ndonzao, M.; Hostettmann, K. Antifungal anthraquinones from Morinda lucida. Int. J. Pharmacog., 1995, 33(2), 107-114.
Zhang, H.L.; Zhang, Q.W.; Zhang, X.Q.; Ye, W.C.; Wang, Y.T. Chemical constituents from the roots of Morinda officinalis. Chin. J. Nat. Med., 2010, 8(8), 192-195.
Ruksilp, T.; Sichaem, J.; Khumkratok, S.; Siripong, P.; Tip-Pyang, S. Anthraquinones and an iridoid glycoside from the roots of Morinda pandurifolia. Biochem. Syst. Ecol., 2011, 39, 888-892.
Burnett, A.R.; Thomson, R.H. Antharquinone in Morinda umbellata L. Phytochemistry, 1968, 7(8), 1421-1422.
Kamiya, K.; Tanaka, Y.; Endang, H.; Umar, M.; Satake, T. New anthraquinone and iridoid from the fruits of Morinda citrifolia. Chem. Pharm. Bull. (Tokyo), 2005, 53(12), 1597-1599.
[] [PMID: 16327199]
Lv, L.; Chen, H.; Ho, C.T.; Sang, S. Chemical components of the roots of Noni (Morinda citrifolia) and their cytotoxic effects. Fitoterapia, 2011, 82(4), 704-708.
[] [PMID: 21356281]
Pawlus, A.D.; Su, B.N.; Keller, W.J.; Kinghorn, A.D. An anthraquinone with potent quinone reductase-inducing activity and other constituents of the fruits of Morinda citrifolia (noni). J. Nat. Prod., 2005, 68(12), 1720-1722.
[] [PMID: 16378361]
Ismail, N.H.; Ali, A.M.; Aimi, N.; Kitajima, M.; Takayama, H.; Lajis, N.H. Anthraquinones from Morinda elliptica. Phytochemistry, 1997, 45(8), 1723-1725.
Jasril, N.H.L.; Mooi, L.Y.; Abdulla, A.; Sukari, M.A.; Ali, A.M. Antitumor promoting and antioxidant activities of anthraquinones isolated from the cell suspension cultures of Morinda elliptica. Aspac. J. Mol. Biol. Biotechnol., 2003, 11(1), 3-7.
Chang, P.; Lee, K.H. Cytotoxic antileukemic anthraquinones from Morinda parvifolia. Phytochemistry, 1984, 23(8), 1733-1736.
Yoshikawa, M.; Yamaguchi, S.; Nishisaka, H.; Yamahara, J.; Murakami, N. Chemical constituents of Chinese natural medicine, Morindae radix, the dried roots of Morinda officinalis how.: Structures of morindolide and morofficinaloside. Chem. Pharm. Bull. (Tokyo), 1995, 43(9), 1462-1465.
[] [PMID: 7586069]
Wu, Y.B.; Zheng, C.J.; Qin, L.P.; Sun, L.N.; Han, T.; Jiao, L.; Zhang, Q.Y.; Wu, J.Z. Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts. Molecules, 2009, 14(1), 573-583.
[] [PMID: 19169204]
Fraga, B.M.; Quintana, N.; Díaz, C.E. Anthraquinones from natural and transformed roots of Plocama pendula. Chem. Biodivers., 2009, 6(2), 182-192.
[] [PMID: 19235160]
Bouberte, M.Y.; Krohn, K.; Hussain, H.; Gonga, E.; Schulz, B.; Hu, Q. Tithoniaquinone A and tithoniamide B: A new anthraquinone and a new ceramide from leaves of Tithonia diversifolia. Z. Naturforsch., 2006, 61(1), 78-82.
Tao, J.; Morikawa, T.; Ando, S.; Matsuda, H.; Yoshikawa, M. Bioactive constituents from Chinese natural medicines. XI. inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: Structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone. Chem. Pharm. Bull. (Tokyo), 2003, 51(6), 654-662.
[] [PMID: 12808242]
Kalidhar, S.B. Structural elucidation in anthraquinone using 1HNMR glycosilation and alkylation shifts. Phytochemistry, 1989, 28(12), 3459-3463.
Comini, L.R.; Montoya, S.C.; Páez, P.L.; Argüello, G.A.; Albesa, I.; Cabrera, J.L. Antibacterial activity of anthraquinone derivatives from Heterophyllaea pustulata (Rubiaceae). J. Photochem. Photobiol. B, 2011, 102(2), 108-114.
[] [PMID: 20965744]
Quang, D.N. Anthraquinones from the roots of Paederia scandens. Vietnam J. Chem., 2009, 47(1), 95-98.
Ouattara, K.; Doumbia, I.; Touré, A.; Djaman, A.J.; Coulibaly, A. Activité antibactérienne des extraits des feuilles de Morinda morindoides (Morinda, Rubiaceae) sur Staphylococcus aureus et Pseudomonas aeruginosa. Phytotherapie, 2013, 11(3), 172-177.

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2019
Published on: 15 November, 2019
Page: [256 - 261]
Pages: 6
DOI: 10.2174/2210315509666181227100320
Price: $25

Article Metrics

PDF: 38
PRC: 1