Symphonia globulifera, a widespread source of complex metabolites with potent biological activities

Planta Medica

Volumn 81, Issue 2, 2015, Pages 95-107

  Fromentin, Yann ^a   Cottet, Kevin ^a   Kritsanida, Marina ^a   Michel, Sylvie ^a   Gaboriaud Kolar, Nicolas ^a,b   Lallemand, Marie Christine ^a,c  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITY OF ATHENS   (Greece)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

biological activities; biosynthesis; Clusiaceae; ethnomedicine; secondary metabolites; Symphonia globulifera

Indexed keywords

BIFLAVONOID; DRUG METABOLITE; HERBACEOUS AGENT; HUMAN IMMUNODEFICIENCY VIRUS ANTIBODY; METHYL NERVONATE; PHLOROGLUCINOL DERIVATIVE; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOL; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE; ANTIINFECTIVE AGENT; PLANT EXTRACT;

AFRICA; ANTIMALARIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BIOSYNTHESIS; CHOLINESTERASE INHIBITION; MEDICINAL PLANT; METABOLITE; NONHUMAN; REVIEW; SOUTH AMERICA; SYMPHONIA GLOBULIFERA; TRADITIONAL MEDICINE; CHEMICAL STRUCTURE; CHEMISTRY; CLUSIACEAE; ISOLATION AND PURIFICATION; METABOLOMICS; SECONDARY METABOLISM;

CLUSIACEAE; SYMPHONIA GLOBULIFERA;

ANTI-INFECTIVE AGENTS; BIOSYNTHETIC PATHWAYS; CLUSIACEAE; MEDICINE, TRADITIONAL; METABOLOMICS; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANTS, MEDICINAL; SECONDARY METABOLISM;

EID: 84921778072     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0034-1396148     Document Type: Review

References (76)

1. Harvey A. Natural products in drug discovery. Drug Discov Today: 2008; 13 894 901
2. Balick M. J., Mendelsohn R. Assessing the economic value of traditional medicines from tropical rain forests. Conser Biol: 1992; 6 128 130
3. Lopez A., Hudson J. B., Towers G. HN. Antiviral and antimicrobial activities of Colombian medicinal plants. J Ethnopharmacol: 2001; 77 189 196
4. Ssegawa P., Kasenene J. M. Medicinal plant diversity and uses in the Sango bay area, Southern Uganda. J Ethnopharmacol: 2007; 113 521 540
5. Gupta M. P., Solís P. N., Calderón A. I., Guionneau-Sinclair F., Correa M., Galdames C., Guerra C., Espinosa A., Alvenda G. I., Robles G., Ocampo R. Medical ethnobotany of the Teribes of Bocas del Toro, Panama. J Ethnopharmacol: 2005; 96 389 401
6. Gustafson K. R., Blunt J. W., Munro M. HG, Fuller R. W., Mckee T. C., Cardellina J. H., Mcmahon J. B., Cragg G. M., Boyd M. R. The guttiferones, HIV-Inhibitory Benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea. Tetrahedron: 1992; 48 10093 10102
7. Kumar S., Sharma S., Chattopadhyay S. K. The potential health benefit of polyisoprenylated benzophenones from Garcinia and related genera: ethno botanical and therapeutic importance. Fitoterapia: 2013; 89 86 125
8. Dick C. W., Abdul-Salim K., Bermingham E. Molecular systematic analysis reveals cryptic tertiary diversification of a widespread tropical rain forest tree. Am Nat: 2003; 162 691 703
9. Tropicos database, Missouri Botanical Garden. Available at http://www.tropicos.org Accessed October 1, 2014
10. Dick C. W., Heuertz M. The complex biogeographic histrory of widespread tropical tree species. Evolution: 2008; 62 2760 2774
11. Lemée A. Flore de la Guyane française. Vol. 4. Paris Lechevallier: 1952; -: 1956
12. Gill G. E., Fowler R. T., Mori S. A. Pollination biology of Symphonia globulifera (Clusiaceae) in central French Guiana. Biotropica: 1998; 30 139 144
13. The International Plant Names Index 2013. Available at http://www.ipni.org Accessed October 1, 2014
14. Budde K. B., González-Martínez S. C., Hardy O. J., Heuertz M. The ancient tropical rainforest tree Symphonia globulifera L. f. (Clusiaceae) was not restricted to postulated Pleistocene refugia in Atlantic Equatorial Africa. Heredity: 2013; 111 66 76
15. Akendengué B., Louis A. M. Medicinal plants used by the Masango people in Gabon. J Ethnopharmacol: 1994; 41 193 200
16. Ajibesin K., Ekpo B., Bala D., Essien E., Adesanya S. Ethnobotanical survey of Akwa Ibom State of Nigeria. J Ethnopharmacol: 2008; 115 387 408
17. Lenta B. N., Vonthron-Sénécheau C., Weniger B., Devkota K. P., Ngoupayo J., Kaiser M., Naz Q., Choudhary M. I., Tsamo E., Sewald N. Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds from Allanblackia monticola and Symphonia globulifera. Molecules: 2007; 12 1548 1557
18. Coelho-Ferreira M. Medicinal knowledge and plant utilization in an Amazonian coastal community of Marudá, Pará State (Brazil). J Ethnopharmacol: 2009; 126 159 175
19. Kadiri A. B. Evaluation of medicinal herbal trade (Paraga) in Lagos State of Nigeria. Ethno Leaflets: 2008; 12 677 681
20. Ciochina R., Grossman R. B. Polycyclic polyprenylated acylphloroglucinols. Chem Rev: 2006; 106 3963 3986
21. Ngouela S., Lenta B. N., Noungoue D. T., Ngoupayo J., Boyom F. F., Tsamo E., Gut J., Rosenthal P. J., Connolly J. D. Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f. Phytochemistry: 2006; 67 302 306
22. Marti G., Eparvier V., Moretti C., Prado S., Grellier P., Hue N., Thoison O., Delpech B., Guéritte F., Litaudon M. Antiplasmodial benzophenone derivatives from the root barks of Symphonia globulifera (Clusiaceae). Phytochemistry: 2010; 71 964 974
23. Nkengfack A. E., Mkounga P., Meyer M., Fomum Z. T., Bodo B. Globulixanthones C, D and E: three prenylated xanthones with antimicrobial properties from the root bark of Symphonia globulifera. Phytochemistry: 2002; 61 181 187
24. Nkengfack A. E., Mkounga P., Fomum Z. T., Meyer M., Bodo B. Globulixanthones A and B, two new cytotoxic xanthones with isoprenoid groups from the root bark of Symphonia globulifera. J Nat Prod: 2002; 65 734 736
25. Bayma J. C., Arruda M. SP, Neto M. S. A prenylated xanthone from the bark of Symphonia globulifera. Phytochemistry: 1998; 38 1159 1160
26. Locksley H. D., Moore I., Scheinmann F. Extractives from Guttiferae. Part II. The isolation and structure of four polyhydroxyxanthones in Symphonia globulifera L. J Chem Soc C: 1966; 430 432
27. Mkounga P., Fomum Z. T., Meyer M., Bodo B., Nkengfack A. E. Globulixanthone F, a new polyoxygenated xanthone with an isoprenoid group and two antimicrobial biflavonoids from the stem bark of Symphonia globulifera. Nat Prod Comm: 2009; 4 803 808
28. Locksley H. D., Moore I., Scheinmann F. Extractives from Guttiferae. Part III. The isolation and structure of symphoxanthone and globuxanthone from Symphonia globulifera L. J Chem Soc C: 1966; 2186 2190
29. Locksley H. D., Moore I., Scheinmann F. Extractives from Guttiferae. Part IV. Isolation and structure of ugaxanthone and M barraxanthone from Symphonia globulifera L. J Chem Soc C: 1966; 2265 2269
30. Locksley H. D., Moore I., Scheinmann F. Extractives from guttiferae-VI: the significance of maclurin in xanthone biosynthesis. Tetrahedron: 1967; 23 2229 2234
31. Li X. C., Joshi A. S., ElSohly H. N., Khan S. I., Jacob M. R., Zhang Z., Khan I. A., Ferreira D., Walker L. A., Broedel S. E. jr., Raulli R. E., Cihlar R. L. Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. J Nat Prod: 2002; 65 1909 1914
32. Hamed W., Brajeul S., Mahuteau-Betzer F., Thoison O., Mons S., Delpech B., Nguyen V. H., Sévenet T., Marazano C. Oblongifolins A-D, polyprenylated benzoylphloroglucinol derivatives from Garcinia oblongifolia. J Nat Prod: 2006; 69 774 777
33. Huang S. X., Feng C., Zhou Y., Xu G., Han Q. B., Qiao C. F., Chang D. C., Luo K. Q., Xu H. X. Bioassay-guided isolation of xanthones and polycyclic prenylated acylphloroglucinols from Garcinia oblongifolia. J Nat Prod: 2009; 72 130 135
34. Xu G., Feng C., Zhou Y., Han Q. B., Qiao C. F., Huang S. X., Chang D. C., Zhao Q. S., Luo K. Q., Xu H. X. Bioassay and ultraperformance liquid chromatography/mass spectrometry guided isolation of apoptosis-inducing benzophenones and xanthone from the pericarp of Garcinia yunnanensis Hu. J Agric Food Chem: 2008; 56 11144 11150
35. Yang H., Figueroa M., To S., Baggett S., Jiang B., Basile M. J., Weinstein I. B., Kennelly E. J. Benzophenones and biflavonoids from Garcinia livingstonei fruits. J Agric Food Chem: 2010; 58 4749 4755
36. Acuña U. M., Figueroa M., Kavalier A., Jancovski N., Basile M. J., Kennelly E. J. Benzophenones and biflavonoids from Rheedia edulis. J Nat Prod: 2010; 73 1775 1779
37. Williams R. B., Hoch J., Glass T. E., Evans R., Miller J. S., Wisse J. H., Kingston D. G. A novel cytotoxic guttiferone analogue from Garcinia macrophylla from the Suriname rainforest. Planta Med: 2003; 69 864 866
38. Merza J., Mallet S., Litaudon M., Dumontet V., Séraphin D., Richomme P. New cytotoxic guttiferone analogues from Garcinia virgata from New Caledonia. Planta Med: 2006; 72 87 89
39. Pereira I. O., Marques M. J., Pavan A. L., Codonho B. S., Barbiéri C. L., Beijo L. A., Doriguetto A. C., DMartin E. C., dos Santos M. H. Leishmanicidal activity of benzophenones and extracts from Garcinia brasiliensis Mart. Fruits. Phytomedicine: 2010; 17 339 345
40. Sang S., Liao C. H., Pan M. H., Rosen R. T., Lin-Shiau S. Y., Lin J. K., Ho C. T. Chemical studies on antioxidant mechanism of garcinol: analysis of radical reaction products of garcinol with peroxyl radicals and their antitumor activities. Tetrahedron: 2002; 58 10095 10102
41. Fromentin Y., Grellier P., Wansi J. D., Lallemand M. C., Buisson D. Yeast-mediated xanthone synthesis through oxidative intramolecular cyclization. Org Lett: 2012; 14 5054 5057
42. Ren Y., Yuan C., Chai H. B., Ding Y., Li X. C., Ferreira D., Kinghorn A. D. Absolute configuration of (-)-gambogic acid, an antitumor agent. J Nat Prod: 2011; 74 460 463
43. Zhang X., Li X., Sun H., Wang X., Zhao L., Gao Y., Liu X., Zhang S., Wang Y., Yang Y., Zeng S., Guo Q., You Q. Garcinia xanthones as orally active antitumor agents. J Med Chem: 2013; 56 276 292
44. Baslas R. K., Kumar P. Isolation and characterization of biflavanone and xanthones in the fruits of Garcinia xanthochymus. Acta Ciencia Indica Chemistry: 1981; 7 31 34
45. Bittrich V., Nascimento-Junior J. E., Amaral M. CE, Nogueira P. C. The anther oil of Symphonia globulifera L.f. (Clusiaceae). Biochem Syst Ecol: 2013; 49 131 134
46. Atkinson J. E., Gupta P., Lewis J. R. Benzophenone participation in xanthone biosynthesis (Gentianaceae). Chem Comm: 1968; 1386 1387
47. Camm E. L., Towers G. HN. Phenylalanine ammonia lyase. Phytochemistry: 1973; 12 961 973
48. Sutter A., Grisebach H. Biosynthesis of flavonoids - XXXIV. Occurrence of the NIH-SHIFT in flavonoid biosynthesis. Phytochemistry: 1969; 8 101 106
49. Ali M. A., Kagan J. The biosynthesis of flavonoid pigments: on the incorporation of phloroglucinol and phloroglucinol cinnamate into rutin in Fagopyrum esculentum. Phytochemistry: 1974; 13 1479 1482
50. Schröder J., Raiber S., Berger T., Schmidt A., Schmidt J., Soares-Sello A. M., Bardshiri E., Strack D., Simpson T. J., Veit M., Schröder G. Plant polyketide synthases: a chalcone synthase-type enzyme which performs a condensation reaction with methylmalonyl-CoA in the biosynthesis of C-methylated chalcones. Biochemistry: 1998; 37 8417 8425
51. Li X., Park N. I., Xu H., Woo S. H., Park C. H., Park S. U. Differential expression of flavonoid biosynthesis genes and accumulation of phenolic compounds in common buckwheat (Fagopyrum esculentum). J Agric Food Chem: 2010; 58 12176 12181
52. Halbwirth H., Puhl I., Haas U., Jezik K., Treutter D., Stich K. Two-phase flavonoid formation in developing strawberry (Fragaria x ananassa) fruit. J Agric Food Chem: 2006; 54 1479 1485
53. Yamaguchi L. F., Kato M. J. Diurnal and seasonal changes in biflavonoids biosynthesis in Araucaria angustifolia needles. Glob J Biochem: 2012; 3 9 12
54. Molyneux R. J., Waiss A. CJ, Haddon W. F. Oxidative coupling of apigenin. Tetrahedron: 1970; 26 1409 1416
55. 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
56. Fujita M., Inoue T. Biosynthesis of mangiferin in Anemarrhena asphodeloides: intact incorporation of C6-C3 precursor into xanthone. Tet Lett: 1977; 51 4503 4506
57. Fujita M., Inoue T. Further studies on the biosynthesis of mangiferin in Anemarrhena asphodeloides: hydroxilation of the shikimate-derived ring. Phytochemistry: 1981; 20 2183 2185
58. Nualkaew N., Morita H., Shimokawa Y., Kinjo K., Kushiro T., De-Eknamkul W., Ebizuka Y., Abe I. Benzophenone synthase from Garcinia mangostana L. pericarps. Phytochemistry: 2012; 77 60 69
59. Masters K. S., Bräse S. Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis. Chem Rev: 2012; 112 3717 3776
60. Hill J. G., Nakashima T. T., Vederas J. C. Fungal xanthone biosynthesis. Distribution of acetate-derived oxygens in ravenelin. J Am Chem Soc: 1982; 104 1745 1748
61. Peters S., Schmidt W., Beerhues L. Regioselective oxidative phenol couplings of 2, 3′,4, 6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L. Planta: 1998; 204 64 69
62. Atkinson J. E., Lewis J. R. Oxidative coupling. Part VII. Biogenetic type synthesis of naturally occurring xanthones. J Chem Soc C: 1969; 281 287
63. Adam P., Arigoni D., Bacher A., Eisenreich W. Biosynthesis of hyperforin in Hypericum perforatum. J Med Chem: 2002; 45 4786 4793
64. Boubakir Z., Beuerle T., Liu B., Beerhues L. The first prenylation step in hyperforin biosynthesis. Phytochemistry: 2005; 66 51 57
65. Karppinen K., Hokkanen J., Tolonen A., Mattila S., Hohtola A. Biosynthesis of hyperforin and adhyperforin from amino acid precursors in shoot cultures of Hypericum perforatum. Phytochemistry: 2007; 68 1038 1045
66. George J. H., Hesse M. D., Baldwin J. E., Adlington R. M. Biomimetic synthesis of polycyclic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum. Org Lett: 2010; 12 3532 3535
67. Nguyen L. TT, Nguyen H. T., Barbič M., Brunner G., Heilmann J., Pham H. D., Nguyen D. M., Nguyen L. HD. Polyisoprenylated acylphloroglucinols and a polyisoprenylated tetracyclic xanthone from the bark of Calophyllum thorelii. Tet Lett: 2012; 53 4487 4493
68. Sang S., Liao C. H., Pan M. H., Rosen R. T., Lin-Shiau S. Y., Lin J. K., Ho C. T. Chemical studies on antioxidant mechanism of garcinol: analysis of radical reaction products of garcinol and theirs antitumor activities. Tetrahedron: 2001; 57 9931 9938
69. Lenta B. N., Vonthron-Sénécheau C., Fongang Soh R., Tantangmo F., Ngouela S., Kaiser M., Tsamo E., Anton R., Weniger B. In vitro antiprotozoal activities and cytotoxicity of some selected Cameroonian medicinal plants. J Ethnopharmacol: 2007; 11 8 12
70. Wang J., Hudson R., Sintim H. O. Inhibitors of fatty acid synthesis in prokaryotes and eukaryotes as anti-infective, anticancer and anti-obesity drugs. Future Med Chem: 2012; 4 1113 1151
71. Zhao X. J., McElhaney-Feser G. E., Sheridan M. J., Broedel SE J. R., Cihlar R. L. Avirulence of Candida albicans FAS2 mutants in a mouse model of systemic candidiasis. Infect Immun: 1997; 65 829 832
72. Liu H., Liu J. Y., Wu X., Zhang J. T. Biochemistry, molecular biology, and pharmacology of fatty acid synthase, an emerging therapeutic target and diagnosis/prognosis marker. Int J Biochem Mol Biol: 2010; 1 69 89
73. Smith S. The animal fatty acid synthase: one gene, one polypeptide, seven enzymes. FASEB J: 1994; 8 1248 1259
74. Lin S. K. Rapid detoxification of benzodiazepine or Z-drugs dependence using acetylcholinesterase inhibitors. Med Hypotheses: 2014; 83 108 110
75. Silva T., Reis J., Teixeira J., Borges F. Alzheimers disease, enzyme targets and drug discovery struggles: from natural products to drug prototypes. Ageing Res Rev: 2014; 15 116 145
76. Fromentin Y., Gaboriaud-Kolar N., Lenta B. N., Wansi J. D., Buisson D., Mouray E., Grellier P., Loiseau P. M., Lallemand M. C., Michel S. Synthesis of novel guttiférone A derivatives: in-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani. Eur J Med Chem: 2013; 65 284 294