Simple Phenols, Phenolic Acids, and Related Esters from the Medicinal Plants of Africa

Medicinal Plant Research in Africa: Pharmacology and Chemistry

Volumn , Issue , 2013, Pages 225-249

  Kougan, Guy B ^a   Tabopda, Turibio ^a   Kuete, Victor ^b   Verpoorte, Robert ^c  

^a UNIVERSITY OF YAOUNDÉ I   (Cameroon)

^b UNIVERSITY OF DSCHANG   (Cameroon)

^c LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Africa; Biosynthesis; Medicinal plants; Phenylpropanoids

Indexed keywords

EID: 84902941177     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-405927-6.00006-0     Document Type: Chapter

References (103)

1. Pridham J.B. Low molecular weight phenols in higher plants. Annu Rev Plant Physiol 1965, 16(1):13-36.
2. Bruneton J. Pharmacognosy: phytochemistry medicinal plants 1999, Intercept Ltd, Hampshire. 2nd ed.
3. Manach C., Scalbert A., Morand C., Remesy C., Jimenez L. Polyphenols: food sources and bioavailability. Am J Clin Nutr 2004, 79(5):727-747.
4. Cheynier V. Polyphenols in foods are more complex than often thought. Am J Clin Nutr 2005, 81(1):223S-229S.
5. De la Rosa E., Gonzalez-Aguilar G.A. Fruit and vegetable, phytochemicals: chemistry, nutritional value, and stability 2010, Wiley-Blackwell, Ames, IA. 1st ed.
6. Cai Y., Sun M., Xing J., Corke H. Antioxidant phenolic constituents in roots of Rheum officinale and Rubia cordifolia: structure-radical scavenging activity relationships. J Agric Food Chem 2004, 52(26):7884-7890.
7. Murkovic M. Phenolic compounds. Encyclopedia of food sciences and nutrition 2003, 4507-4514. Academic Press, Oxford. 2nd ed. C. Benjamin (Ed.).
8. Fruits phenolics 1990, CRC Press, Boca Raton, FL. J.-J. Macheix, A. Fleuriet, J. Billot (Eds.).
9. Bendini A., Cerretani L., Carrasco-Pancorbo A., Gomez-Caravaca A.M., Segura-Carretero A., Fernandez-Gutierrez A., et al. Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade. Molecules 2007, 12(8):1679-1719.
10. Sircar D., Mitra A. Accumulation of p-hydroxybenzoic acid in hairy roots of Daucus carota 2: confirming biosynthetic steps through feeding of inhibitors and precursors. J Plant Physiol 2009, 166(13):1370-1380.
11. Adesanya S.A., Sofowora A. Biological standardisation of Zanthoxylum roots for antisickling activity. Planta Med 1983, 48(5):27-33.
12. Gruz J., Ayaz F.A., Torun H., Strnad M. Phenolic acid content and radical scavenging activity of extracts from medlar (Mespilus germanica L.) fruit at different stages of ripening. Food Chem 2011, 124(1):271-277.
13. Yip E.C., Chan A.S., Pang H., Tam Y.K., Wong Y.H. Protocatechuic acid induces cell death in HepG2 hepatocellular carcinoma cells through a c-Jun N-terminal kinase-dependent mechanism. Cell Biol Toxicol 2006, 22(4):293-302.
14. Fukuji T.S., Tonin F.G., Tavares M.F. Optimization of a method for determination of phenolic acids in exotic fruits by capillary electrophoresis. J Pharm Biomed Anal 2010, 51(2):430-438.
15. Robbins R.J. Phenolic acids in foods: an overview of analytical methodology. J Agric Food Chem 2003, 51(10):2866-2887.
16. Ellis B.E., Towers G.H. Biogenesis of rosmarinic acid in Mentha. Biochem J 1970, 118(2):291-297.
17. Stafford H.A. Biosynthesis of phenolic compounds in first internodes of Sorghum: lignin and related products. Plant Physiol 1967, 42:450-455.
18. Stevanovic T., Diouf P.N., Garcia-Perez M.E. Bioactive polyphenols from healthy diets and forest biomass. Curr Nutr Food Sci 2009, 5(4):264-295.
19. Clifford M.N. Chlorogenic acids and other cinnamates- nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agric 2000, 80(7):1033-1043.
20. Kaminaga Y., Schnepp J., Peel G., Kish C.M., Ben-Nissan G., Weiss D., et al. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation. J Biol Chem 2006, 281(33):23357-23366.
21. Bartels D. Targeting detoxification pathways: an efficient approach to obtain plants with multiple stress tolerance?. Trends Plant Sci 2001, 6(7):284-286.
22. Barclay K.D., McKersie B.D. Peroxidation reactions in plant membranes: effects of free fatty acids. Lipids 1994, 29(12):877-883.
23. García E., Chacón J.L., Martínez J., Izquierdo P.M. Changes in volatile compounds during ripening in grapes of airén, macabeo and chardonnay white varieties grown in La Mancha region (Spain). Food Sci Technol Int 2003, 9(1):33-41.
24. Mustafa N., Verpoorte R. Phenolic compounds in Catharanthus roseus. Phytochem Rev 2007, 6(2):243-258.
25. Khadem S., Marles R.J. Monocyclic phenolic acids; hydroxy- and polyhydroxybenzoic acids: occurrence and recent bioactivity studies. Molecules 2010, 15(11):7985-8005.
26. Lattanzio V, Lattanzio VMT, Cardinali A. Role of phenolics in the resistance mechanisms of plants against fungal pathogens and insects. In: Imperato F, editor. Phytochemistry: advances in research. Trivandrum, India: Research Signpost. 2006; p. 23-67.
27. Adesina S.K. The Nigerian Zanthoxylum; chemical and biological values. Review. Afr J Tradit Complement Altern Med 2005, 2(3):282-301.
28. Cowan M.M. Plant products as antimicrobial agents. Clin Microbiol Rev 1999, 12(4):564-582.
29. Baidez A.G., Gomez P., Del Rio J.A., Ortuno A. Dysfunctionality of the xylem in Olea europaea L. Plants associated with the infection process by Verticillium dahliae Kleb. Role of phenolic compounds in plant defense mechanism. J Agric Food Chem 2007, 55(9):3373-3377.
30. Owen R.W., Giacosa A., Hull W.E., Haubner R., Spiegelhalder B., Bartsch H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur J Cancer 2000, 36(10):1235-1247.
31. Duke J.A. Handbook of medicinal herbs 1985, CRC Press, Boca Raton, FL.
32. Pugazhendhi D., Pope G.S., Darbre P.D. Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J Appl Toxicol 2005, 25(4):301-309.
33. Khim Phin Chong S.R., Atong M. In vitro antimicrobial activity and fungitoxicity of syringic acid, caffeic acid and 4-hydroxybenzoic acid against ganoderma boninense. J Agric Sci 2009, 1(2):15-20.
34. Sroka Z., Cisowski W. Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem Toxicol 2003, 41(6):753-758.
35. Guan S., Jiang B., Bao Y.M., An L.J. Protocatechuic acid suppresses MPP+-induced mitochondrial dysfunction and apoptotic cell death in PC12 cells. Food Chem Toxicol 2006, 44(10):1659-1666.
36. Liu Y.M., Jiang B., Bao Y.M., An L.J. Protocatechuic acid inhibits apoptosis by mitochondrial dysfunction in rotenone-induced PC12 cells. Toxicol In Vitro 2008, 22(2):430-437.
37. Yin M.C., Lin C.C., Wu H.C., Tsao S.M., Hsu C.K. Apoptotic effects of protocatechuic acid in human breast, lung, liver, cervix, and prostate cancer cells: potential mechanisms of action. J Agric Food Chem 2009, 57(14):6468-6473.
38. An L.J., Guan S., Shi G.F., Bao Y.M., Duan Y.L., Jiang B. Protocatechuic acid from Alpinia oxyphylla against MPP+-induced neurotoxicity in PC12 cells. Food Chem Toxicol 2006, 44(3):436-443.
39. Hur J.M., Park J.G., Yang K.H., Park J.C., Park J.R., Chun S.S., et al. Effect of methanol extract of Zanthoxylum piperitum leaves and of its compound, protocatechuic acid, on hepatic drug metabolizing enzymes and lipid peroxidation in rats. Biosci Biotechnol Biochem 2003, 67(5):945-950.
40. Herrmann K.M., Weaver L.M. The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 1999, 50:473-503.
41. Klaus M.H. The shikimate pathways: early steps in the biosynthesis of aromatic compounds. Plant Cell 1995, 7:907-917.
42. Queiroz E.F., Kuhl C., Terreaux C., Mavi S., Hostettmann K. New dihydroalkylhexenones from Lannea edulis. J Nat Prod 2003, 66(4):578-580.
43. Chaaib F., Queiroz E.F., Ndjoko K., Diallo D., Hostettmann K. Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides. Planta Med 2003, 69(4):316-320.
44. Hsiao J.-J., Chiang H.-C. Phenylpropanoids from Aralia bipinnata. Phytochemistry 1995, 39(4):825-827.
45. Ishii H., Ishikawa T., Tohojoh T., Murakami K., Kawanabe E., Lu S.-T., et al. Studies on the chemical constituents of Rutaceous plants. Part 45. Novel phenyl propanoids: cuspidiol, boninenal, and methyl boninenalate. J Chem Soc Perkin Trans 1 1982, 2051-2058.
46. Okorie D.A. A new phthalide and xanthones from Anthocleista djalonensis and Anthocleista vogelii. Phytochemistry 1976, 15(11):1799-1800.
47. Ezoubeiri A., Gadhi C.A., Fdil N., Benharref A., Jana M., Vanhaelen M. Isolation and antimicrobial activity of two phenolic compounds from Pulicaria odora L. J Ethnopharmacol 2005, 99(2):287-292.
48. Elujoba A.A., Nagels L. Chromatographic isolation and estimation of zanthoxylol: an antisickling agent from the roots of Zanthoxylum species. J Pharm Biomed Anal 1985, 3(5):447-451.
49. Jakupovic J., Kuhnke J., Schuster A., Metwally M.A., Bohlmann F. Phloroglucinol derivatives and other constituents from South African Helichrysum species. Phytochemistry 1986, 25(5):1133-1142.
50. Lourens A.C.U., Van Vuuren S.F., Viljoen A.M., Davids H., Van Heerden F.R. Antimicrobial activity and in vitro cytotoxicity of selected South African Helichrysum species. S Afr J Bot 2011, 77(1):229-235.
51. Mathekga A.D.M., Meyer J.J.M. Antimicrobial activity of South African Helichrysum species. S Afr J Bot 1998, 64(5):293-295.
52. Dekker T.G., Fourie T.G., Snyckers F.O., van der Schyf C.J. Studies of South African medicinal plants. Part 2. Caespitin, a new phloroglucinol derivative with antimicrobial properties from Helichrysum caespititium. S Afr J Chem 1983, 36:114-116.
53. Mathekga A.D.M., Meyer J.J.M., Horn M.M., Drewes S.E. An acylated phloroglucinol with antimicrobial properties from Helichrysum caespititium. Phytochemistry 2000, 53(1):93-96.
54. Mutanyatta-Comar J., Phale O.J.K., Abegaz B.M., Croft K. Phloroglucinol derivatives and flavones from Helichrysum paronychioides. Bull Chem Soc Ethiop 2006, 20(1):61-68.
55. Es-Safi N.E., Kollmann A., Khifi S., Ducrot P.H. Antioxidative effect of compounds isolated from Globularia alypum L. structure-activity relationships. LWT-Food Sci Technol 2007, 40(7):1246-1252.
56. Hostettmann K., Marston A. Search for new antifungal compounds from higher plants. Pure Appl Chem 1994, 66(10-11):2231-2234.
57. Drewes S.E., Van Vuuren S.F. Antimicrobial acylphloroglucinols and dibenzyloxy flavonoids from flowers of Helichrysum gymnocomum. Phytochemistry 2008, 69(8):1745-1749.
58. Tabopda T.K., Ngoupayo J., Liu J., Ali M.S., Khan S.N., Ngadjui B.T., et al. Alpha-glucosidase inhibitors ellagic acid derivatives with immunoinhibitory properties from Terminalia superba. Chem Pharm Bull 2008, 56(6):847-850.
59. Mazimba O., Majinda R.R., Modibedi C., Masesane I.B., Cencic A., Chingwaru W. Tylosema esculentum extractives and their bioactivity. Bioorg Med Chem 2011, 19(17):5225-5230.
60. Kuete V., Nana F., Ngameni B., Mbaveng A.T., Keumedjio F., Ngadjui B.T. Antimicrobial activity of the crude extract, fractions and compounds from stem bark of Ficus ovata (Moraceae). J Ethnopharmacol 2009, 124(3):556-561.
61. Kuete V., Metuno R., Ngameni B., Tsafack A.M., Ngandeu F., Fotso G.W., et al. Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae). J Ethnopharmacol 2007, 112(3):531-536.
62. Teke G.N., Kuiate J.R., Kuete V., Teponno R.B., Tapondjou L.A., Tane P., et al. Bio-guided isolation of potential antimicrobial and antioxidant agents from the stem bark of Trilepisium madagascariense. S Afr J Bot 2011, 77(2):319-327.
63. Yagi S., Chrétien F., Duval R.E., Fontanay S., Maldini M., Piacente S., et al. Antibacterial activity, cytotoxicity and chemical constituents of Hydnora johannis roots. S Afr J Bot 2012, 78:228-234.
64. Tabopda T.K., Ngoupayo J., Liu J., Mitaine-Offer A.C., Tanoli S.A., Khan S.N., et al. Bioactive aristolactams from Piper umbellatum. Phytochemistry 2008, 69(8):1726-1731.
65. Kubo I., Kinst-Hori I. 2-Hydroxy-4-methoxybenzaldehyde: a potent tyrosinase inhibitor from African medicinal plants. Planta Med 1999, 65(1):19-22.
66. Ngameni B., Kuete V., Simo I.K., Mbaveng A.T., Awoussong P.K., Patman R., et al. Antibacterial and antifungal activities of the crude extract and compounds from Dorstenia turbinata (Moraceae). S Afr J Bot 2009, 75:256-261.
67. Mukonyi K.W., Ndiege I.O. 2-Hydroxy-4-methoxybenzaldehyde: aromatic taste modifying compound from Mondia whitei skeels. Bull Chem Soc Ethiop 2001, 15(2):137-141.
68. Ouattara B., Angenot L., Guissou P., Fondu P., Dubois J., Frederich M., et al. LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam. Phytochemistry 2004, 65(8):1145-1151.
69. Aladesanmi A.J., Odediran S.A. Antimicrobial activity of Trichilia heudelotii leaves. Fitoterapia 2000, 71(2):179-182.
70. Tanee Fomum Z., Foyere Ayafor J., Wandji J., Gana Fomban W., Ephrem Nkengfack A. Erythrinasinate, an ester from three Erythrina species. Phytochemistry 1986, 25(3):757-779.
71. Tanee Fomum Z., Ayafor J.F., Ifeadike P.N., Nkengfack A.E., Wandji J. Erythrina studies. Part 3. Isolation of an isoflavone from Erythrina senegalensis and Erythrina excelsa. Planta Med 1986, 52(4):341.
72. Nkengfack A.E., Vouffo T.W., Vardamides J.C., Kouam J., Fomum Z.T., Meyer M., et al. Phenolic metabolites from Erythrina species. Phytochemistry 1997, 46(3):573-578.
73. Hussain H.A.B., Elshazly A., Elsayed A., Krohn K., Riaz M., Schulz B. Chemical constituents and antimicrobial activity of Salix subserrata. Rec Nat Prod 2011, 5(2):133-137.
74. Dosumu O.O., Idowu P.A., Onocha P.A., Ekundayo O. Isolation of 3-(4-hydroxyphenyl) methylpropenoate and bioactivity evaluation of Gomphrena celosioides extracts. EXCLI J 2010, 9:173-180.
75. Mayaka R.K., Langat M.K., Omolo J.O., Cheplogoi P.K. Antimicrobial prenylated acetophenones from berries of Harrisonia abyssinica. Planta Med 2012, 78(4):383-386.
76. Mbaze L.M., Lado J.A., Wansi J.D., Shiao T.C., Chiozem D.D., Mesaik M.A., et al. Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae). Phytochemistry 2009, 70(11-12):1442-1447.
77. 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 Trad CAM 2006, 3(3):80-86.
78. Lenta B.N., Vonthron-Senecheau C., Weniger B., Devkota K.P., Ngoupayo J., Kaiser M., et al. Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds from Allanblackia monticola and Symphonia globulifera. Molecules 2007, 12(8):1548-1557.
79. Ayoub N.A. Unique phenolic carboxylic acids from Sanguisorba minor. Phytochemistry 2003, 63(4):433-436.
80. Mahmoud A.A., Ahmed A.A., Iinuma M., Tanaka T. Further monoterpene 5-methylcoumarins and an acetophenone derivative from Ethulia conyzoides. Phytochemistry 1998, 48(3):543-546.
81. Achenbach H., Waibel R., Addae-Mensah I. Lignans and other constituents from Carissa edulis. Phytochemistry 1983, 22(3):749-753.
82. Latte K.P., Kaloga M., Schafer A., Kolodziej H. An ellagitannin, n-butyl gallate, two aryltetralin lignans, and an unprecedented diterpene ester from Pelargonium reniforme. Phytochemistry 2008, 69(3):820-826.
83. Thabti I., Elfalleh W., Hannachi H., Ferchichi A., Campos M.D.G. Identification and quantification of phenolic acids and flavonol glycosides in Tunisian Morus species by HPLC-DAD and HPLC-MS. J Funct Foods 2012, 4(1):367-374.
84. Muchuweti M., Ndhlala A.R., Kasiamhuru A. Analysis of phenolic compounds including tannins, gallotannins and flavanols of Uapaca kirkiana fruit. Food Chem 2006, 94(3):415-419.
85. Adjé F.A., Lozano Y.F., Le Gernevé C., Lozano P.R., Meudec E., Adima A.A., et al. Phenolic acid and flavonol water extracts of Delonix regia red flowers. Ind Crops Prod 2012, 37(1):303-310.
86. Salem M.M., Davidorf F.H., Abdel-Rahman M.H. In vitro anti-uveal melanoma activity of phenolic compounds from the Egyptian medicinal plant Acacia nilotica. Fitoterapia 2011, 82(8):1279-1284.
87. Abdel-Kader M.S. Two new norphenylpropanoid glucosides and hemipholin from the flowers of Ononis vaginalis. J Braz Chem Soc 1997, 8(6):637-679.
88. Bezabih M., Abegaz B.M. 4'-Demethylknipholone from aerial parts of Bulbine capitata. Phytochemistry 1998, 48(6):1071-1073.
89. Zaghloul A.M., Gohar A.A., Ahmad M.M., Baraka H.N., El-Bassuony A.A. Phenylpropanoids from the stem bark of Jacaranda mimosifolia. Nat Prod Res 2011, 25(1):68-76.
90. Gouda Y.G., Abdel-Baky A.M., Mohamed K.M., Darwish F.M., Kasai R., Yamasaki K. Phenylpropanoid and phenylethanoid derivatives from Kigelia pinnata DC. fruits. Nat Prod Res 2006, 20(10):935-939.
91. Helene T., Kouam S.F., Ngadjui B.T., Dongo E., Abegaz B.M. Phenolic metabolites from the seeds of Canarium schweinfurthii. Bull Chem Soc Ethiop 2000, 14(2):155-160.
92. Munkombwe N.M., Galebotswe P., Modibesane K., Morebodi N. Phenylpropanoid glycosides of Gnidia polycephala. Phytochemistry 2003, 64(8):1401-1404.
93. Fokou PA. Chemical investigation of three plants used in Cameroonian traditional medicine: Maesopsis eminii (Rhamnaceae), Autranella congolensis (Sapotaceae) and Pentadesma grandifolia (Guttiferae). PhD Thesis. University of Bielefeld: Bielefeld, Germany; 2006.
94. Kamara B.I., Brandt E.V., Ferreira D., Joubert E. Polyphenols from honeybush tea (Cyclopia intermedia). J Agric Food Chem 2003, 51(13):3874-3879.
95. Mbosso E.J.T., Ngouela S., Nguedia J.C.A., Beng V.P., Rohmer M., Tsamo E. Spathoside, a cerebroside and other antibacterial constituents of the stem bark of Spathodea campanulata. Nat Prod Res 2008, 22(4):296-304.
96. Mueller-Harvey I., Hartley R.D., Reed J.D. Characterisation of phenolic compounds, including flavonoids and tannins, of ten ethiopian browse species by high performance liquid chromatography. J Sci Food Agric 1987, 39(1):1-14.
97. Jakupovic J., Zdero C., Grenz M., Tsichritzis F., Lehmann L., Hashemi-Nejad S.M., et al. Twenty-one acylphloroglucinol derivatives and further constituents from South African Helichrysum species. Phytochemistry 1989, 28(4):1119-1131.
98. Bohlmann F., Zdero C. Neue geranylphloroglucin-derivatives aus Helichrysum monticola. Phytochemistry 1980, 19(4):683-684.
99. Bohlmann F., Mahanta P.K. Weitere phloroglucin-derivate aus Helichrysum gymnocomum. Phytochemistry 1979, 18(2):348-350.
100. Bohlmann F., Zdero C. Neue phloroglucin-derivate aus Helichrysum natalitium und Helichrysum bellum. Phytochemistry 1979, 18(4):641-644.
101. Bohlmann F., Suwita A. Neue phloroglucin-derivate aus Leontonyx-arten sowie weitere verbindungen aus vertretern der tribus inuleae. Phytochemistry 1978, 17(11):1929-1934.
102. Kouam S.F., Ngadjui B.T., Krohn K., Wafo P., Ajaz A., Choudhary M.I. Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis. Phytochemistry 2005, 66:1174-1179.
103. Vouffo B., Hussain H., Eyong E.K., Dongo E., Folefock G.N., Nkengfack A.E., et al. Chemical constituents of Dorstenia picta and Newbouldia laevis. Biochem Syst Ecol 2008, 36:730-732.