Quinones and Benzophenones from the Medicinal Plants of Africa

Medicinal Plant Research in Africa: Pharmacology and Chemistry

Volumn , Issue , 2013, Pages 351-391

  Eyong, Kenneth O ^a   Kuete, Victor ^b   Efferth, Thomas ^c  

^a UNIVERSITY OF YAOUNDÉ I   (Cameroon)

^b UNIVERSITY OF DSCHANG   (Cameroon)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Africa; Benzophenone; Plants; Quinones

Indexed keywords

EID: 84902926424     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-405927-6.00010-2     Document Type: Chapter

References (93)

1. Gorman R., Kaloga M., Li X.C., Ferreira D., Bergenthal D., Kolodziej H. Furanonaphthoquinones, atraric acid and a benzofuran from the stem barks of Newbouldia laevis. Phytochemistry 2003, 64:583-587.
2. Moss G.P. Nomenclature of quinones with isoprenoid side-chain 1973, Department of Chemistry, Queen Mary University of London, London.
3. Abegaz B.M. Novel phenylanthraquinones, isofuranonaphthoquinones, homoisoflavonoids and biflavonoids from African plants in the genus Bulbine, Scilla, Ledebouria and Rhus. Phytochem Rev 2002, 1:299-310.
4. Eyong K.O., Kumar S.P., Kuete V., Folefoc G.N., Nkengfack E.A., Baskaran S. Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol. Bioorg Med Chem Lett 2008, 18:5387-5390.
5. Pérez-Sacau E., Díaz-Peñate R.G., Estévez-Braun A., Ravelo A.G., García-Castellano J.M., Pardo L., et al. Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line. J Med Chem 2007, 50:696-706.
6. Herbert R.B. The biosynthesis of secondary metabolites 1989, Chapman and Hall, London, p. 33-80. 2nd ed.
7. Gafner S., Wolfender J.L., Nianga M., Stoeckli E.H., Hostettmann K. Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots. Phytochemistry 1996, 42(5):1315-1320.
8. Ashiralieva A., Kleiner D. Polyhalogenated benzo- and naphthoquinones are potent inhibitors of plant and bacterial ureases. FEBS Lett 2003, 555:367-370.
9. Turner W.B. Fungal metabolites 1971, Academic Press, London, p. 93-4.
10. David O.H. The polyketides metabolites 1991, Ellis Horwood, England, p. 78-100.
11. Stöckigt J., Srocka U., Zenk M.H. Structure and biosynthesis of a new anthraquinone from Streptocarpus dunnii. Phytochemistry 1973, 12:2389-2391.
12. Gill M. Pigments of fungi (Macromycetes). Nat Prod Rep 1994, 11:67-90.
13. Beerhues L., Liu B. Biosynthesis of biphenyls and benzophenones-evolution of benzoic acid-specific type III polyketide synthases in plants. Phytochemistry 2009, 70:1719-1727.
14. Gafner S., Wolfender J.L., Nianga M., Hostettmann K. A naphthoquinone from Newbouldia laevis root. Phytochemistry 1998, 48:215-216.
15. Gafner S., Wolfender J.L., Nianga M., Evans H.S., Hostettmann K. Antifungal and antibacterial naphthoquinone from Newbouldia laevis root. Phytochemistry 1996, 42:1315-1320.
16. Singh P., Singh A. Quinonoid constituents of the bark of Markhamia stipulata Wall. Pharmazie 1980, 35(11):701-702.
17. Joshi K.C., Singh P., Pardasani R.T. Chemical constituents of the stem heart wood of Markhamia stipulata. Planta Med 1978, 34(2):219-221.
18. Houghton P.J., Pandey R., Hawkes J.E. Naphthoquinones and an alkaloid from the roots of Newbouldia laevis. Phytochemistry 1994, 35:1602-1603.
19. El-Naggar L.J., Beal J.L. Iridoids. A review. J Nat Prod 1980, 43(6):649-707.
20. Fotsing M.T., Yankep E., Njamen D., Tanee Fomum Z., Nyasse B., Bodo B., et al. Identification of an anti-inflammatory principle from the stem bark of Millettia versicolor. Planta Med 2003, 69:767-770.
21. Duarte D.S., Dolabela M.F., Salas C.E., Raslan D.S., Oliveira A.B., Nenninger A., et al. Chemical characterization and biological activity of Macfadyena unguis-cati (Bignoniaceae). J Pharm Pharmacol 2000, 52(3):347-352.
22. Williams R.B., Norris A., Miller J.S., Razafitsalama L.J., Andriantsiferana R., Rasamison V.E., et al. Two new cytotoxic naphthoquinones from Mendoncia cowanii from the rainforest of Madagascar. Planta Med 2006, 72(6):564-566.
23. Kuete V., Efferth T. Pharmacogenomics of Cameroonian traditional herbal medicine for cancer therapy. J Ethnopharmacol 2011, 137:752-766.
24. Bapela N.B., Lall N., Fourie P.B., Franzblau S.G., Van Rensburg C.E.J. Activity of 7-methyljuglone in combination with antituberculous drugs against Mycobacterium tuberculosis. Phytomedicine 2006, 13:630-635.
25. McGaw L.J., Lall N., Hlokwe T.M., Michel A.L., Meyer J.J.M., Eloff J.N. Purified compounds and extracts from Euclea species with antimycobacterial activity against Mycobacterium bovis and fast-growing mycobacteria. Biol Pharm Bull 2008, 31(7):1429-1433.
26. Induli M., Cheloti M., Wasuna A., Wekesa I., Wanjohi J.M., Byamukama R., et al. Naphthoquinones from the roots of Aloe secundiflora. Phytochem Lett 2012, 5(3):506-509.
27. Van der Kooy F., Meyer J.J.M., Lall N. Antimycobacterial activity and possible mode of action of newly isolated neodiospyrin and other naphthoquinones from Euclea natalensis. S Afr J Bot 2006, 72:349-352.
28. McGaw L.J., Lall N., Meyer J.J.M., Eloff J.N. The potential of South African plants against Mycobacterium infections. J Ethnopharmacol 2008, 119:482-500.
29. Kuete V., Tangmouo J.G., Marion Meyer J.J., Lall N. Diospyrone, crassiflorone and plumbagin: three antimycobacterial and antigonorrhoeal naphthoquinones from two Diospyros spp. Int J Antimicrob Agents 2009, 34:322-325.
30. Tangmouo J.G., Meli A.L., Komguem J., Kuete V., Ngounou F.N., Lontsi D., et al. Crassiflorone, a new naphthoquinone from Diospyros crassiflora (Hien). Tetrahedron Lett 2006, 47:3067-3070.
31. Zhong S.M., Waterman P.G., Jeffrey J.A.D. Naphthoquinones and triterpenes species. Phytochemistry 1984, 23(5):1067-1072.
32. Wabo H.K., Tatsimo S.N., Tane P., Connolly J.D. Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis. Planta Med 2007, 73:187-189.
33. Endale M., Alao J.P., Akala H.M., Rono N.K., Eyase F.L., Derese S., et al. Antiplasmodial quinones from Pentas longiflora and Pentas lanceolata. Planta Med 2012, 78:31-35.
34. El-Hady S., Bukuru J., Kesteleyn B., Van Puyvelde L., Nguyen Van T., De Kimpe N. New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora. J Nat Prod 2002, 65:1377-1379.
35. Kuete V., Eyong O.K., Folefoc N.G., Penlap Beng V., Hussain H., Krohn K., et al. Antimicrobial screening of methanolic extract and chemical constituents isolated from Newbouldia laevis seem. Pharmazie 2007, 62:552-556.
36. Drewes S.E., Khan F., van Vuuren S.F., Viljoen A.M. Simple 1,4-benzoquinones with antibacterial activity from stems and leaves of Gunnera perpensa. Phytochemistry 2005, 66:1812-1816.
37. Burnett A.R., Thomson R.H. Naturally occurring quinones. Part XIV. The quinonoid constituents of Pyrola media. J Chem Soc C 1968, 857-860.
38. Thomson R.H. Naturally occurring quinones 1971, Academic Press, London, 41-74. 2nd ed.
39. Arot Manguroa L.O., Midiwo J.O., Kraus W., Ugi I. Benzoquinone derivatives of Myrsine africana and Maesa lanceolata. Phytochemistry 2003, 64:855-862.
40. Mahmoud A.A., AL-Shihry S.S., Son B.W. Diterpenoid quinones from rosemary (Rosmarinus officinalis L.). Phytochemistry 2005, 66:1685-1690.
41. Eyong K.O., Folefoc G.N., Kuete V., Penlap Beng V., Hussain H., Krohn K., et al. Newbouldiaquinone A: a naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis. Phytochemistry 2006, 67:605-609.
42. Vouffo B., Hussain H., Eyong O.K., Dongo E., Folefoc G.N., Krohn K. Chemical constituents of Dorstenia picta and Newbouldia laevis. Biochem Syst Ecol 2008, 32:730-732.
43. Kambou G., Bolleddula J., Dalavoy S.S., Muraleedharan G., Nair B. Pest-managing activities of plant extracts and anthraquinones from Cassia nigricans from Burkina Faso. Biores Technol 2008, 99:2037-2045.
44. Ben-Erik Van W.Y.K., Abiy Y., Dagne E. The chemotaxonomic significance of root anthraquinones and pre-anthraquinones in the genus Lomatophyllum (Asphodelaceae). Biochem Syst Ecol 1995, 23(7-8):806-808.
45. Dagne E., Yenesew A., Asmellash A., Demissew S., Maw S. Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species. Phytochemistry 1994, 35(2):401-406.
46. Dagne E., Knipholone W.S. A unique anthraquinone derivative from Kniphofia foliosa. Phytochemistry 1984, 23(8):1729-1731.
47. Mutanyatta J., Bezabih M., Abegaz B.M., Dreyer M., Brun R., Kocher N., et al. The first 6'-O-sulfated phenylanthraquinones: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis. Tetrahedron 2005, 61:8475-8484.
48. Bezabih M., Motlhagodi S., Abegaz B.M. Isofuranonaphthoquinones and phenolic and knipholone derivatives from the roots of Bulbine capitata. Phytochemistry 1997, 46(6):1063-1067.
49. Abegaz B.M., Bezabih M., Msuta T., Brun R., Menche D., Mühlbacher J., et al. Gaboroquinones A and B and 4'-O-demethylknipholone-4'-Oβ-d-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens. J Nat Prod 2002, 65:1117-1121.
50. Berhanu E., Fetene M., Dagne E. Anthraquinones as taxonomic markers in Ethiopian Kniphofia species. Phytochemistry 1986, 25(4):847-850.
51. Ali M.I.A., Shalaby N.M.M., Elgamal M.H.A., Mousa A.S.M. Antifungal effects of different plant extracts and their major components of selected Aloe species. Phytother Res 1999, 13:401-407.
52. Lenta B.N., Weniger B., Antheaume C., Noungoue D.T., Ngouela S., Assob J.C.N., et al. Anthraquinones from the stem bark of Stereospermum zenkeri with antimicrobial activity. Phytochemistry 2007, 68:1595-1599.
53. Tamokou J.D.D., Tala M.F., Wabo H.K., Kuiate J.R., Tane P. Antimicrobial activities of methanol extract and compounds from stem bark of Vismia rubescens. J Ethnopharmacol 2009, 124:571-575.
54. Fournier G., Ludwig Bercht C.A., Paris R.R., Paris M.R. 3-methoxychrysazin, a new anthraquinone from Xyris semifuscata. Phytochemistry 1975, 14:2099.
55. Ngamga D., Awouafack M.D., Tane P., Bezabih M., Abegaz B.M. Two new anthraquinones from Gladiolus psittascinus. Biochem Syst Ecol 2007, 35:709-713.
56. Hou Y., Cao S., Brodie P.J., Callmander M.W., Ratovoson F., Rakotobe E.A., et al. Antiproliferative and antimalarial anthraquinones of Scutia myrtina from the Madagascar forest. Bioorg Med Chem 2009, 17:2871-2876.
57. Alemayehu G., Hailu A., Abegaz B.M. Bianthraquinones from Senna didymobotrya. Phytochemistry 1996, 42(5):1423-1425.
58. Wanjohi J.M., Yenesew A., Midiwo J.O., Heydenreich M., Peter M.G., Dreyer M., et al. Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica. Tetrahedron 2005, 61:2667-2674.
59. Saleh N.A.M., El-Hadidi M.N., Arafa R.F.M. Flavonoids and anthraquinones of some Egyptian Rumex species (Polygonaceae). Biochem Syst Ecol 1993, 21(2):301-303.
60. El-Gamal A.A., Takeya K., Itokawa H., Halim A.F., Amer M.M., Saad H.E.A., et al. Anthraquinones from Galium sinaicum. Phytochemistry 1995, 40(1):245-251.
61. El-Gamal A.A., Takeya K., Itokawa H., Halim A.F., Amer M.M., Saad H.E.A., et al. Anthraquinones from the polar fractions of Galium sinaicum. Phytochemistry 1996, 42(4):1149-1155.
62. El-Emary N.A., Backheet E.Y. Three hydroxymethyl anthraquinone glycosides from Rubia tinctorum. Phytochemistry 1998, 49(1):277-279.
63. Sob S.V.T., Wabo H.K., Tchinda A.T., Tane P., Ngadjui B.T., Ye Y. Anthraquinones, sterols, triterpenoids and xanthones from Cassia obtusifolia. Biochem Syst Ecol 2010, 38:342-345.
64. Halim A.F., Abd EI-Fattah H., El-Gamal A.A., Thomson R.H. Anthraquinones from Galium sinaicum. Phytochemistry 1992, 31:355-356.
65. Esmat A.Y., Tomasetto C., Rio M.C. Cytotoxicity of a natural anthraquinone (aloin) against human breast cancer cell lines with and without ErbB-2-topoisomerase IIα coamplification. Cancer Biol Ther 2006, 5(1):97-103.
66. Noungoue D.T., Antheaume C., Chaabi M., Ndjakou B.L., Ngouela S., Lobstein A., et al. Anthraquinones from the fruits of Vismia laurentii. Phytochemistry 2008, 69:1024-1028.
67. Kumar U.S., Aparna P., Rao R.J., Rao T.P., Rao J.M. 1-Methyl anthraquinones and their biogenetic precursors from Stereospermum personatum. Phytochemistry 2003, 63:925-929.
68. Kuete V., Nguemeving J.R., Penlap Beng V., Azebaze A.G.B., Etoa F.X., Meyer M., et al. Antimicrobial activity of the methanolic extracts and compounds from Vismia laurentii De Wild (Guttiferae). J Ethnopharmacol 2007, 109:372-379.
69. Kouam S.F., Khan S.N., Krohn K., Ngadjui B.T., Kapche D.G.W.F., Yapna D.B., et al. Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis. J Nat Prod 2006, 69:229-233.
70. Tih A.E., Ghogomu R.T., Sondengam B.L., Caux C., Bodo B. Minor constituents of Harungana madagascariensis stem bark. Biochem Syst Ecol 2006, 34:267-269.
71. Tsaffack M., Nguemeving J.R., Kuete V., Ndejouong Tchize B.L.S., Mkounga P., Penlap Beng V., et al. Two new antimicrobial dimeric compounds: febrifuquinone, a vismione-anthraquinone coupled pigment and adamabianthrone, from two Psorospermum species. Chem Pharm Bull 2009, 57(10):1113-1118.
72. Sob S.V.T., Wabo H.K., Tang C.-P., Tane P., Ngadjui B.T., Ye Y. Phenol esters and other constituents from the stem barks of Stereospermum acuminatissimum. J Asian Nat Prod Res 2011, 13(12):1128-1134.
73. Wabo H.K., Kouam S.F., Krohn K., Hussain H., Tala M.F., Tane P., et al. Prenylated anthraquinones and other constituents from the seeds of Vismia laurentii. Chem Pharm Bull 2007, 55(11):1640-1642.
74. Mammo W., Dagne E., Casser I., Steglich W. Unusual anthraquinone lactones from Araliorhamnus vaginata. Phytochemistry 1990, 29(8):2637-2640.
75. Eyong K.O., Krohn K., Hussain H., Folefoc G.N., Nkengfack A.E., Schulz B., et al. Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis. Chem Pharm Bull 2005, 53(6):616-619.
76. Magadula J.J., Kapingu M.C., Bezabih M., Abegaz B.M. Polyisoprenylated benzophenones from Garcinia semseii (Clusiaceae). Phytochem Lett 2008, 1:215-218.
77. Wabo H.K., Kikuchi H., Katou Y., Tane P., Oshima Y. Xanthones and a benzophenone from the roots of Pentadesma butyracea and their antiproliferative activity. Phytochem Lett 2010, 3:104-107.
78. Ngouela S., Lenta B.N., Noungoue D.T., Ngoupayo J., Boyom F.B., Tsamo E., et al. Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn. f. Phytochemistry 2006, 67:302-306.
79. Gafner S., Wolfender J.L., Nianga M., Evans H.S., Hostettmann K. Antifungal and antibacterial naphthoquinone from Newbouldia laevis root. Phytochemistry 1996, 42:1315-1320.
80. Kuete V., Efferth T. Cameroonian medicinal plants: pharmacology and derived natural products. Front Pharmacol 2010, 1:123.
81. Kuete V. Potential of Cameroonian plants and derived products against microbial infections: a review. Planta Med 2010, 76(14):1479-1491.
82. Kuete V., Alibert-Franco S., Eyong K.O., Ngameni B., Folefoc G.N., Nguemeving J.R., et al. Antibacterial activity of some natural products against bacteria expressing. Int J Antimicrob Agents 2011, 37(2):156-161.
83. Gu J.Q., Graf T.N., Lee D., Chai H.B., Mi Q., Kardono L.B., et al. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. J Nat Prod 2004, 67(7):1156-1161.
84. Cai L., Wei G.X., van der Bijl P., Wu C.D. Namibian chewing stick, Diospyros lycioides, contains antibacterial compounds against oral pathogens. J Agric Food Chem 2000, 48:909-914.
85. Mahapatra A., Mativandlela S.P., Binneman B., Fourie P.B., Hamilton C.J., Meyer J.J., et al. Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase. Bioorg Med Chem 2007, 15:7638-7646.
86. Emodin. <> [accessed 19.11.12]. http://en.wikipedia.org/wiki/Emodin/.
87. Feng Y., Huang S.L., Dou W., Zhang S., Chen J.H., Shen Y., et al. Emodin, a natural product, selectively inhibits 11beta-hydroxysteroid dehydrogenase type 1 and ameliorates metabolic disorder in diet-induced obese mice. Br J Pharmacol 2010, 161(1):113-126.
88. Dorsey J.F., Kao G.D. Aloe(-emodin) for cancer? More than just a comforting salve. Cancer Biol Ther 2007, 6(1):89-90.
89. Sun Y. Chemosensitization by emodin, a plant-derived anti-cancer agent: mechanism of action. Cancer Biol Ther 2008, 7(3):476-478.
90. Liu A., Chen H., Wei W., Ye S., Liao W., Gong J., et al. Antiproliferative and antimetastatic effects of emodin on human pancreatic cancer. Oncol Rep 2011, 26(1):81-89.
91. Badgwell D.B., Walker C.M., Baker W.T., Strickland F.M. Ethanol and aloe emodin alter the p53 mutational spectrum in ultraviolet radiation-induced murine skin tumors. Mol Carcinog 2004, 39(3):127-138.
92. Singh J., Singh J. A bianthraquinone and a triterpenoid from the seeds of Cassia hirsute. Phytochemistry 1986, 25(8):1985-1987.
93. Pedersen J.A. Naturally occurring quinols and quinones studied as semiquinones by electron spin resonance. Phytochemistry 1978, 17:775-778.