TERPENOIDS AND PHYTOSTEROLS ISOLATED FROM PLUMERIA RUBRA L., FORM ACUTIFOLIA (AIT) WOODSON AND ITS FUNGUS PARASITE COLESPORIUM PLUMERIAE

Authors

  • Resende, C. M Institute of Chemistry, Federal University of Rio de Janeiro (UFRJ), University City, Rio de Janeiro. Brazil
  • Barreto A. S Laboratory of Chemical and Biological Analysis (LAQB), Foundation State University Center of the West Zone (UEZO), Avenue Manuel Caldeira de Alvarenga, Campo Grande, Rio de Janeiro, Brazi
  • Pinto, P. R. Laboratory of Chemical and Biological Analysis (LAQB), Foundation State University Center of the West Zone (UEZO), Avenue Manuel Caldeira de Alvarenga, Campo Grande, Rio de Janeiro, Brazil
  • Nascimento C. C. H. C Laboratory of Chemical and Biological Analysis (LAQB), Foundation State University Center of the West Zone (UEZO), Avenue Manuel Caldeira de Alvarenga, Campo Grande, Rio de Janeiro, Brazil.
  • Vasconcelos, S. D. D. De Federal Center of Technological Education Celso Suckow da Fonseca- CEFET-NI, Rio de Janeiro, RJ- Brazil
  • Azevedo, L. A.C. Laboratory of Chemical and Biological Analysis (LAQB), Foundation State University Center of the West Zone (UEZO), Avenue Manuel Caldeira de Alvarenga, Campo Grande, Rio de Janeiro, Brazi
  • Stephens P. R. S. 3Laboratory of Innovations in Therapies, Teaching and Bioproducts/LITEB, OswaldoCruz Institute, IOC/ FIOCRUZ), Rio de Janeiro, Brazil.
  • Nogueira R. I. Empresa Brasileira de Pesquisa Agropecuária (Embrapa), Rio de Janeiro, Brazil.
  • Saranraj, P. Department of Microbiology, Sacred Heart College (Autonomous), Tirupattur, Tami Nadu, India.
  • Diré G. F. Laboratory of Chemical and Biological Analysis (LAQB), Foundation State University Center of the West Zone (UEZO), Avenue Manuel Caldeira de Alvarenga, Campo Grande, Rio de Janeiro, Brazi
  • Pinto, A. C Institute of Chemistry, Federal University of Rio de Janeiro (UFRJ), University City, Rio de Janeiro. Brazil.

DOI:

https://doi.org/10.22270/ajprd.v6i6.428

Keywords:

Plumeria rubra L., form acutifolia, Coleosporium plumeriae Pat, terpenoids, phytosterols GC/ MS, HRGC.

Abstract

The hexane and ethyl acetate extracts of the leaves from Plumeria rubra L., form acutifolia (Ait) Woodson and the methanolic extract from the fungus Coleosporium plumeriae Pat. were analized by high resolution gas chromatography (HRGC) and by high resolution gas chromatography coupled to mass spectrometes (GC-MS). The identification of the chemical constituintes is these extracts has been made by the automatic comparison of the mass spectra obtained standards within the NBS, Wiley and Wiley 275T librarys supplied with the mass spectrometer and by analized of the principal fragmentations. Phytochemical studies of the hexane and ethyl acetate extracts of the leaves showed nine terpenoids (5-ergosten-3b-ol, 5,22-stigmastadien-3b-ol, 4-stigmasten-3-one, 5-stigmasten-3b-ol, 12-ursen-3b-ol, 12-oleanen-3b-ol, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid). The compounds 5-ergosten-3b-ol, 4-stigmasten-3-one, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid have been described for the first time from Plumeria rubra L., forma acutifolia (Ait) Woodson. From the methanolic extract of spores of the fungus Coleosporium plumeriae Pat were isolated 5-stigmasten-3b-ol, methyl esters of long chain fatty acids (C18:0, principally) and one aromatic compound, N-methyl toluenesulfonamide. No previous phytochemical studies of this fungus have been reported.

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References

1. Kupachan, S. M.; Dessetine, A. L.; Blayock, B. T.; Bryan, R. F. Isolation and structural elucidation of allamandin, and antileukemic iridoid lactone from allamanda catártica. J. Org. Chem. 1974;39: 2477- 2482.
2. Adam, G.; Khoi, N. H.; Bergner, C.; Lien, N. T. Plant growth inhibiting properties of plumieride from Plumeria obtusifolia. Phytochemistry Phytochemistry 1979; 18:1399-1400.
3. Pereira, M. M.; Jácome, R. L. R. P.; Alcântara, A. F. de C.; Alves, R. B.; Raslan, D. S. Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae). Quím. Nova. 2007;30(4): 970-983.
4. Barreto, A. S. Carvalho, M. G. de; Gonzaga, L.; Kapplan, M. A. C. Chemical constituents from Himatanthus articulata. J. Braz. Chem. Soc. 1998;9:430-434.
5. Tan GT, Pezzuto JM, Kinghorn D. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1). Reverse transcriptase. J Nat Prod. 1991;54 (1):143-154.
6. Kardono, L. B. S.; Tsauri, S.; Padmawinata, K.; Pezzuto, J.; Kinghorn, A. D.; Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia. J. Nat. Prod. 1990;53:1447-1455.
7. Traquair, J. A. Kokko, G. Spore morphology in Coleosporium plumeriae. Can. J. Bot. 1980;58:2454-2458.
8. Hernández, J. R.; Eboh, D. O.; Rossman, A. Y. New Reports of Rust Fungi (Uredinales) from Nigeria. Caldasia,2005; 27(2):213-221.
9. Ogata, D. Y. First Report of Plumeria Rust, Caused by Coleosporium plumeriae, in Hawaii. Plant Disease 1982; 66: 642.
10. McMillan Jr., R. T. Oxycarboxin a new fungicide for control of frangipani. Proc. Fla. State Hort. Soc. 1984;97: 247-248.
11. McMillan Jr., R. T. Biological Control of Frangipani Rust with Verticillium lecanni. Proc. Fla. State Hort. Soc. 1985;98:328-329.
12. Petit, M. L. Le pétiole des Dicotylédones au point de vue de l'anatomie comparée et de la taxinomie. Mem. Soc. Sci. Phys. Nat. Bordeaux III. 1887;3: 217-404.
13. Siddiqui, S. Shahen, B. Naeed, A. Begum, S. Pentacyclic triterpenoids from the leaves of Plumeria obtusa. Phytochemistry 1989;28:3143-3147.
14. Siddiqui, S. Shahen, B.Begum, S. Naeed, A Pentacyclic triterpenoids from Plumeria obtusa. Phytochemistry 1990; 29: 3615 - 3620.
15. Devprakash, T.R., Gurav, S., Kumar, G.P.S., Mani, T.T. An review of phytochemical constituents and pharmacological activity of Plumeria species. Int. J. Curr. Pharm. Res. 2012;4: 1–6.
16. Wyllie, S. G.; Djerassi, C. Mass spectrometry in structural and stereochemical problems. CXLVI. Mass spectrometric fragmentations typical of sterols wit unsaturated side chains. J. Org. Chem. 1968; 33: 305-313.
17. Itoh, T.; Tamura, T.; Iida, T.; Matsumoto, T. Gas chromatographic differentiation of 4-desmethyl, 4-monomethyl and 4,4-dimethylsterols. Steroids, 1974; 23: 687-698.
18. Lukić, M; Lukić, I; Sladonja, B.; Piližota, V. Variability of 4-Monomethylsterols and 4,4'-Dimethylsterols in Olive Oil and Their Use as Indicators of Olive Variety, Ripening Degree, and Oil Storage Temperature. J Agric Food Chem. 2015 63(22): 5499-508.
19. Veeh, R. H. Inskeep, W. P. Inskeep, F. L. Ferguson, A. H. Transport of Chlorsulfuron through soil columns J. Environ. Qual, 1994; 23: 542-549.
20. Wagenet, R. J. Hutson, J. L. J. Predicting the Fate of Nonvolatile Pesticides in the Unsaturated Zone. Environ. Qual. 1986; 15: 315-322.
21. Colla, L. M. Primaz, A. L. Lima, M. de, Bertolin, T. E. Costa, J. A. V. Isolamento e seleção de fungos para biorremediação a partir de solo contaminado com herbicidas triazínicos. Ciência e Agrotecnologia. 2008; 32(3): 809-813.
22. Wu, S. Gschwend, P. M. Sorption kinetics of hydrophobic organic compounds to natural sediments and soils. Environ. Sci. Tech. 1986;20: 717-725.
23. Santaniello, E. Ferraboschi, P. Grisenti. P. Manzocchi, A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 1992; 92:1071-1140.
24. Moreau, S. P.; Morisseau, c.; Zylber, J.; Archelas, A.; Baratti, J. Microbiological Transformations. 33. Fungal Epoxide Hydrolases Applied to the Synthesis of Enantiopure Para-Substituted Styrene Oxides. A Mechanistic Approach. J. Org. Chem. 1996; 61: 7402-7407.
25. Vasconcelos, D. H. P.; Mafezoli, J.; Uchôa, P. K. S.; Saraiva, N. N.; Lima, M. A. S.; Silva Júnior, J. N.; Barbosa, F. G.; Mattos, M. C.; Oliveira, M. C. F. de; Lima, C. S.; Pessoa, M. N. G. Biotransformation of the Diterpene Ent-18,19-dihydroxytrachylobane by Rhizopus stolonifer. Journal of the Brazilian Chemical Society, 2015; 26(5): 1043-1047.
26. Carvalho, J. M.; Paixão, L. K. O. da; Dolabela, M. F. Marinho, P. S. B.; Marinho. O. A. M. do R. Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides (Melanconiaceae). Acta Amazonica, 2016; 46(1): 69-72.
27. Weeraratne, T. P.; Adikaram, N. K. B. Biology of Plumeria Leaf Rust Disease Caused by Coleosporium Plumeriae. Cey. J. Sci. (Bio. Sci.), 2006; 35 (2):157-162.
28. Ling, Q.; Bogang, L.; Jiafa, G.; Guolin, Z. Chemical study on Aspergillus sp 136. Chinese Journal of Applied and Environmental Biology, 2007; 13: 66-68.
29. Yan, H.; Gao, S.; Li, C.; Li, X.; Wang, B. Chemical constituents of a marine-derived endophytic fungus Penicillium commune G2M. Molecules, 2010; 15: 3270-3275.
30. Tarawneh, A.H.; León, F.; Radwan, M.M.; Rosa, L.H.; Cutler, S.J. Secondary metabolites from the fungus Emericella nidulans. Natural Products Communication. 2013; 8: 1285–1288.
31. Fu, Y.; Wang, J.-Y.; Zhang, D.; Chen, Y.-F.; Gao, S.; Zhao, L.-X.; Ye, F. Solvent-Free Synthesis and Safener Activity of Sulfonylurea Benzothiazolines. Molecules 2017; 22: 1601-1611.
32. Silverstein, R. M.; Webster, F. X. J.; Kiemle, E D. 2006. Identificação Espectrométrica de Compostos Orgânicos, 7ª Edição, Editora LTC, Rio de Janeiro, 490 págs.
33. Barreto, A. S.; Amaral, A. C. F., Silva, J. R. de A.; Schripsema, J.; Rezende, C. M.; Pinto, A. C. Ácido 15-desmetilisoplumierídeo, um novo iridóide isolado das cascas de Plumeria rubra e do látex de Himatanthus sucuuba. Química Nova, 2007;30(5): 1133-1135.
34. Barreto, A. S.; Rezende, C. M.; Pinto, A. C.; Viana, V. R. C.; Tavares, E. :S.; Rev. Bras. Farm. 2001; 82, 9-11.
35. Barreto, A. S.; Carvalho, M. G.; Nery, I. A.; Gonzaga, L.; Kaplan, M. A. C.; J. Braz. Chem. Soc. 1998; 9: 430-434.
36. Silva, J. A.; Silva, A. G.; Reis, R.; Nascimento, C.C.H.C.; Dire, G. F.; Barreto, A. S. Plumeria rubra (Apocynaceae): A good source of ursolic acid. Journal of Medicinal Plant Research 2013; 7: 892-896.

Published

2018-12-12

How to Cite

M, R. C., S, B. A., R., P. P., H. C, N. C. C., De, V. S. D. D., A.C., A. L., … C, P. A. (2018). TERPENOIDS AND PHYTOSTEROLS ISOLATED FROM PLUMERIA RUBRA L., FORM ACUTIFOLIA (AIT) WOODSON AND ITS FUNGUS PARASITE COLESPORIUM PLUMERIAE. Asian Journal of Pharmaceutical Research and Development, 6(6), 15–22. https://doi.org/10.22270/ajprd.v6i6.428