Triterpenos das folhas de Protium strumosum

A. C. Guimarães; A. C. Siani

doi:10.32712/2446-4775.2007.68

Triterpenes from the leaves of Protium strumosum

Vol. 3 No. 01 (2007)
67-76
17/10/2013
01/03/2007
https://doi.org/10.32712/2446-4775.2007.68

A. C. Guimarães
A. C. Siani

Keywords

Abstract

The present study reports the isolation of triterpenes from the species Protium strumosum (Daly) (Burseraceae). Partitioning of the methanolic extract of the leaves of P. strumosum followed by silica gel chromatographic purification (columns and preparative plates), led to isolation or characterization of the following triterpenes: epifriedelanol, friedeline, lupeol, lupenone, á-amyrin and â-amyrin and also the steroid â-sitosterol 3-O-glucoside. The compounds were characterized by spectroscopic means (1H-RMN, 13C-RMN, CG-EM, IV), co-injection experiments in GC-FID using authenticated patterns, and also by identifying the acetylated derivatives. The isolation of 3-epifridelanol as the majors constituent in the less polar fraction might be related with the anti-inflammatory potential of such Protium species.

References

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ARAGÃO, P.C.A.; TOLEDO, J.B.; MORAIS, A.A.; FILHO, R.B. Substâncias Naturais Isoladas de Stigmaphyllon tomentosum e Byrsonima variabilis. Química Nova, v.13, n.4, p.254-258, 1990.
ARÉVALO, A.G.A. Estudo químico das espécies É T. glaziovii Swartz e T. rhoifolia Willd (Burseraceae), MSc. Thesis, University of Amazon, Manaus, Brazil, 176 pp, 1993.
AWAD, A.B.; CHAN, K.C.; DOWNIE, A.C.; FINK, C.S. Peanuts as a source of â-sitosterol, a sterol with anticancer properties. Nutrition and Cancer, v.36, n.2, p.238-241, 2000.
BRAZ-FILHO, R.; GOTTLIEB, H. E.; MOURÃO, A. P.; MIRANDA, C. A. 3βO-β-Glicopiranosilespinasterol, um novo glicosídio esteroidal de Amarthospermum schomburghinana (Miq.) Baehni. Anais da Academia Brasileira de Ciências, v.58, n.3, p.363-368, 1986.
BUDZIKIEWICZ, H.; WILSON, J. M.; DJERASSI, C. Mass Spectrometry in Structural and Stereochemical Problems. XXXII. Pentacyclic Triterpenes. Journal of the American Chemical Society, v.85, p.3688-3699, 1963.
CHATURVEDI, A. K.; PARAMAR, S. S.; BHATNAGAR, S.C.; MISRA, G.; NIGAM, S. K. Anticonvulsivant and anti-inflammatory activity of natural plant coumarins and triterpenoids. Research Communications in Chemical Pathology and Pharmacology, v.9, n.1, p.11-22, 1974.
CONNOLY, J.D.; HILL, R.A. Triterpenoids. Natural Product Reports v.22, p.487-503, p.487-503, 2005 e revisÃµes precedentes ali citadas.
COSTA, A.F. Farmacognosia, Vol I, 1ª ed., Fundação Calouste Gulbenkian, Lisboa, Portugal, pp. 841-842, 1975.
DALY, C.D. Studies in Neotropical Burseraceae. II. Generic Limits in New World Protieae and Canarieae. Brittonia, v.41, p.17-27, 1989.
GENTRY, A.H. Woody Plants of Northwest South America (Colombia, Ecuador, Peru), Conservation International, Washington DC, pp. 299-304 (1993).
GOETZ, M.A.; HENSENS, O.D.; ZINK, D.L.; BORRIS, R.P.; MORALES, F.; TAMAYO-CASTILLO, G.; SLAUGHTER, R.S.; FELIX, J.; BALL, R.G. Potent Nor-triterpenoid Blockers of the Voltagegated Potassium Channel Kv1.3 from Spachea correae, n.39, p.2895-2898, 1998.
GUEVARA, A.P.; LIM-SYLIANCO, C.Y.; DYRIT, F.M.; FINCH, P. Acylglucosyl sterols from Momordica Charatia. Phytochemistry, v.28, n.6, p.1721-1724, 1989.
GUIMARÃES, A.C. Estudo Químico e Avaliação Biológica das Folhas de Protium strumosum, P. grandifolium, P. llewelynii e P. altsonii, MSc Thesis, University of Amazon, Manaus, Brasil, 1997.
HOENE, F.C. Plantas e substâncias vegetais tóxicas e medicinais, São Paulo Graphicars ed., 355 pp.,1939.
IVORRA, M.D.; PAYA, M.; VILLAR, A. A review of natural products ans plants as potencial antidiabetic drugs. Journal of Ethnopharmacology, v.27, n.3, p.243-275, 1989.
KHALID, S.A. Chemistry of the Burseraceae. In: P.G. Waterman and M. F. Grundon. Ed. Chemistry and Chemical Taxonomy of the Rutales, Academic Press, New York, pp. 281-299, 1983.
KIKUCHI, T.; YOKOI, T.; NIWA, M.; SHINGU, T. Application of Homonuclear Internuclear Double Resonance Technique in the Triterpene Field. II. Assignements of Methyl Ressonances of Triterpenes related to Friedelin. Chemical Pharmaceutical Bulletin, v.28, n.7, p.2014-2023, 1980.
KUNDU, J.K.; ROUF, A.S.S.; HOSSAIN, M.N.; HASAN, C.M.; RASHID, M.A. Antitumor activity of epifriedelanol from Vitis trifolia, Fitoterapia, v.71, n.5, p.577-579, 2000.
LAING, M.; BURKE-LAING, M.; BARTHO, R.; WEEKS, C.M. Crystal and Molecular Structure of Epifriedelinol. Tetrahedron Letters, n. 43, p.3839-3842, 1977.
LIMA, F.V.; MALHEIROS, A.; OTUKI, M.F.; CALIXTO, J.B.; YUNES, R.A.; CECHINEL-FILHO, V.; MONACHE, F.D. Three New Triterpenes from the Resinous Bark of Protium kleinii and their Antinociceptive Activity. Journal of the Brazilian Chemical Society, v.16, n.3B, p.578-582, 2005.
LIU, J. Oleanolic acid and ursolic acid: Research perspectives. Journal of Ethnopharmacology, v.100, n.1-2, p.92-94, 2005.
LOGGIA, R.D.; TUBARO, A.; SOSA, S.; BECKER, H.; SAAR, S.; ISAAC, O. The Role of Triterpenoids in the Topical Anti-Inflammatory Activity of Calendula officinalis Flowers. Planta Medica, v.60, n.6, p.516-520, 1994.
MALDONADO, E.; BELLO, M.; VILLASEÑOR, J.L.; ORTEGA, A. Acyclic diterpenes from Perymenium hintonii. Phytochemistry, v.49, n.4, p.1115-1118, 1998.
MABBERLEY, D.J., The Plant Book - A portable dictionary of the vascular plants. 2nd ed. Cambridge University Press, London, p.241, 1998.
MAHATO, S.B.; KUNDU, A.P. 13C NMR Spectra of Pentacyclic Triterpenoids - A compilation and some salient features. Phytochemistry, v.37, n.6, p.517-1575, 1994.
MAIA, R.M.; BARBOSA, P.R.; CRUZ, F.G.; ROQUE, N.F.; FASCIO, M. Triterpenos da Resina de Protium heptaphyllum March (Burseraceae): Caracterização em Misturas Binárias. Química Nova, v.23, n.3, p.623-626, 2000.
OLIVEIRA, F.A.; VIEIRA-JUNIOR, G.M.; ALMEIDA, F.R.; FLORÃŠNCIO, M.G.; LIMA JR., R.C.; SILVA, R.M.; SANTOS, F.A.; RAO, V.S. Gatroprotective and anti-inflammatory effects of resin from Protium heptaphyllum in mice and rats. Pharmacological Research, n.49, n.2, p.105-111, 2004.
OLIVEIRA, F.A.; CHAVES, M.H.; ALMEIDA, F.R.C.; LIMA JR., R.C.P.; SILVA, R.M.; MAIA, J.L.; BRITO, G.A.A.C.; SANTOS, F.A.; RAO,V.S. Protective effect of of á- and â-amyrin, a triterpene mixture from Protium heptaphyllum (Aubl.) March. trunk wood resin, against acetaminophen-induced liver injury in mice. Journal of Ethnopharmacology, n.98, n.1-2, p.103-108, 2005a.
OLIVEIRA, F.A.; COSTA, C.L.S.; CHAVES, M.H.; ALMEIDA, F.R.C.; CAVALCANTE, I.J.M.; LIMA, A.F.; LIMA JR., R.C.P.; SILVA, R.M.; CAMPOS, A.R.; SANTOS, F.A.; RAO, V.S. Attenuation of capsaicininduced acute and visceral nociceptive pain by á- and â-amyrin, a triterpene mixture isolated from Protium heptaphyllum resin in mice. Life Sciences, v.77, n.23, p.2942-2952, 2005b.
PATRA, A.; MUKHOPADHYAY, A.K.; MITRA, A.K. Carbon-13 Resonance Assignment of some Friedelanes and Taraxasteranes. Organic Magnetic Resonance, v.17, n.3, p.166-168, 1981.
PATRA, A.; CHAUDHURI, S.K. Assignment of Carbon-13 Nuclear Magnetic Resonance Spectra of Some Friedelanes. Magnetic Resonance in Chemistry, v.25, p.95-100, 1987.
PERNET, R. Phytochimie des Burseracees. Lloydia, v.35, n.3, p.280-287, 1972
RAMOS, M.F.S.; SIANI, A.C.; TAPPIN, M.R.R.; GUIMARÃES, A.C.; RIBEIRO, J.E.L.S. Essential oils from oleoresins of Protium spp. Of the Amazon region. Flavour and Fragrance Journal, v.15, p.383-387, 2000.
RIZZINI, C. T.; MORS, W. B. Botânica Econômica Brasileira, 2ª Ed., Âmbito Cultural Edições Ltda., Rio de Janeiro, p.49-50, 1995.
SIANI, A.C., RIBEIRO, M.N.S. Podocarpusflavone A from the leaves of Trattinnickia glazioviiâ€, Biochemical Systematic and Ecology v.23, p.879, n.7-8, 1995.
SIANI, A.C.; RAMOS, M. F.S.; MENEZES-DE-LIMA JR. O.; RIBEIRO-DOS-SANTOS, R.; FERNANDEZFERREIRA, E.; SOARES, R.O.A.; ROSAS, E.C.; SUSUNAGA, G.S.; GUIMARÃES, A.C.; ZOGHBI M.B.; HENRIQUES, M.G.M.O. Journal of Ethnopharmacology, v.66, n.1, p.57-69, 1999a.
SIANI, A.C.; RAMOS, M.S.F.; GUIMARÃES, A.C.; SUSUNAGA, G.S.; ZOGHBI, M.G.B. Volatile Constituents from Oleoresin of Protium heptaphyllum (Aubl.) March. Journal of the Essential Oil Research, v.11, p.72-74, 1999b.
SIANI, A.C.; GARRIDO, I.S.; MONTERIO, S.S.; CARVALHO, E.S.; RAMOS, M.F.S. Protium icicariba as a source of volatile essences. Biochemical Systematic and Ecology, v.32, p.477-489, 2004.
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SUSUNAGA, G.S. Estudo químico e biológico da resina produzida pela espécie Protium heptaphyllum March. (Burseraceae). MSc Thesis, University of Amazon, Manaus, Brazil, 155 pp., 1996.
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A. C. Guimarães
Fundação Centro de Controle de Oncologia do Amazonas, CECON Rua Francisco Orellana nº 215, Conjunto D. Pedro, Planalto, 69040-010 Manaus, AM
A. C. Siani
Departamento de Produtos Naturais, Instituto de Tecnologia em Fármacos, Fundação Oswaldo Cruz, Far-Manguinhos, FIOCRUZ R. Sizenando Nabuco nº 100, 21041-250 Rio de Janeiro, RJ, Brasil

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Triterpenes from the leaves of Protium strumosum. Rev Fitos [Internet]. 2007 Mar. 1 [cited 2024 Nov. 25];3(01):67-76. Available from: https://revistafitos.far.fiocruz.br/index.php/revista-fitos/article/view/68

This work is licensed under a Creative Commons Attribution 4.0 International License.

[1] AIKEN, C.; CHIN, H.C. Betulinic acid derivatives as HIV-1 antivirals. Trends in Molecular Medicine, v.11, n.1, p.31-36, 2005.

[2] ARAGÃO, P.C.A.; TOLEDO, J.B.; MORAIS, A.A.; FILHO, R.B. Substâncias Naturais Isoladas de Stigmaphyllon tomentosum e Byrsonima variabilis. Química Nova, v.13, n.4, p.254-258, 1990.

[3] ARÉVALO, A.G.A. Estudo químico das espécies É T. glaziovii Swartz e T. rhoifolia Willd (Burseraceae), MSc. Thesis, University of Amazon, Manaus, Brazil, 176 pp, 1993.

[4] AWAD, A.B.; CHAN, K.C.; DOWNIE, A.C.; FINK, C.S. Peanuts as a source of â-sitosterol, a sterol with anticancer properties. Nutrition and Cancer, v.36, n.2, p.238-241, 2000.

[5] BRAZ-FILHO, R.; GOTTLIEB, H. E.; MOURÃO, A. P.; MIRANDA, C. A. 3βO-β-Glicopiranosilespinasterol, um novo glicosídio esteroidal de Amarthospermum schomburghinana (Miq.) Baehni. Anais da Academia Brasileira de Ciências, v.58, n.3, p.363-368, 1986.

[6] BUDZIKIEWICZ, H.; WILSON, J. M.; DJERASSI, C. Mass Spectrometry in Structural and Stereochemical Problems. XXXII. Pentacyclic Triterpenes. Journal of the American Chemical Society, v.85, p.3688-3699, 1963.

[7] CHATURVEDI, A. K.; PARAMAR, S. S.; BHATNAGAR, S.C.; MISRA, G.; NIGAM, S. K. Anticonvulsivant and anti-inflammatory activity of natural plant coumarins and triterpenoids. Research Communications in Chemical Pathology and Pharmacology, v.9, n.1, p.11-22, 1974.

[8] CONNOLY, J.D.; HILL, R.A. Triterpenoids. Natural Product Reports v.22, p.487-503, p.487-503, 2005 e revisÃµes precedentes ali citadas.

[9] COSTA, A.F. Farmacognosia, Vol I, 1ª ed., Fundação Calouste Gulbenkian, Lisboa, Portugal, pp. 841-842, 1975.

[10] DALY, C.D. Studies in Neotropical Burseraceae. II. Generic Limits in New World Protieae and Canarieae. Brittonia, v.41, p.17-27, 1989.

[11] GENTRY, A.H. Woody Plants of Northwest South America (Colombia, Ecuador, Peru), Conservation International, Washington DC, pp. 299-304 (1993).

[12] GOETZ, M.A.; HENSENS, O.D.; ZINK, D.L.; BORRIS, R.P.; MORALES, F.; TAMAYO-CASTILLO, G.; SLAUGHTER, R.S.; FELIX, J.; BALL, R.G. Potent Nor-triterpenoid Blockers of the Voltagegated Potassium Channel Kv1.3 from Spachea correae, n.39, p.2895-2898, 1998.

[13] GUEVARA, A.P.; LIM-SYLIANCO, C.Y.; DYRIT, F.M.; FINCH, P. Acylglucosyl sterols from Momordica Charatia. Phytochemistry, v.28, n.6, p.1721-1724, 1989.

[14] GUIMARÃES, A.C. Estudo Químico e Avaliação Biológica das Folhas de Protium strumosum, P. grandifolium, P. llewelynii e P. altsonii, MSc Thesis, University of Amazon, Manaus, Brasil, 1997.

[15] HOENE, F.C. Plantas e substâncias vegetais tóxicas e medicinais, São Paulo Graphicars ed., 355 pp.,1939.

[16] IVORRA, M.D.; PAYA, M.; VILLAR, A. A review of natural products ans plants as potencial antidiabetic drugs. Journal of Ethnopharmacology, v.27, n.3, p.243-275, 1989.

[17] KHALID, S.A. Chemistry of the Burseraceae. In: P.G. Waterman and M. F. Grundon. Ed. Chemistry and Chemical Taxonomy of the Rutales, Academic Press, New York, pp. 281-299, 1983.

[18] KIKUCHI, T.; YOKOI, T.; NIWA, M.; SHINGU, T. Application of Homonuclear Internuclear Double Resonance Technique in the Triterpene Field. II. Assignements of Methyl Ressonances of Triterpenes related to Friedelin. Chemical Pharmaceutical Bulletin, v.28, n.7, p.2014-2023, 1980.

[19] KUNDU, J.K.; ROUF, A.S.S.; HOSSAIN, M.N.; HASAN, C.M.; RASHID, M.A. Antitumor activity of epifriedelanol from Vitis trifolia, Fitoterapia, v.71, n.5, p.577-579, 2000.

[20] LAING, M.; BURKE-LAING, M.; BARTHO, R.; WEEKS, C.M. Crystal and Molecular Structure of Epifriedelinol. Tetrahedron Letters, n. 43, p.3839-3842, 1977.

[21] LIMA, F.V.; MALHEIROS, A.; OTUKI, M.F.; CALIXTO, J.B.; YUNES, R.A.; CECHINEL-FILHO, V.; MONACHE, F.D. Three New Triterpenes from the Resinous Bark of Protium kleinii and their Antinociceptive Activity. Journal of the Brazilian Chemical Society, v.16, n.3B, p.578-582, 2005.

[22] LIU, J. Oleanolic acid and ursolic acid: Research perspectives. Journal of Ethnopharmacology, v.100, n.1-2, p.92-94, 2005.

[23] LOGGIA, R.D.; TUBARO, A.; SOSA, S.; BECKER, H.; SAAR, S.; ISAAC, O. The Role of Triterpenoids in the Topical Anti-Inflammatory Activity of Calendula officinalis Flowers. Planta Medica, v.60, n.6, p.516-520, 1994.

[24] MALDONADO, E.; BELLO, M.; VILLASEÑOR, J.L.; ORTEGA, A. Acyclic diterpenes from Perymenium hintonii. Phytochemistry, v.49, n.4, p.1115-1118, 1998.

[25] MABBERLEY, D.J., The Plant Book - A portable dictionary of the vascular plants. 2nd ed. Cambridge University Press, London, p.241, 1998.

[26] MAHATO, S.B.; KUNDU, A.P. 13C NMR Spectra of Pentacyclic Triterpenoids - A compilation and some salient features. Phytochemistry, v.37, n.6, p.517-1575, 1994.

[27] MAIA, R.M.; BARBOSA, P.R.; CRUZ, F.G.; ROQUE, N.F.; FASCIO, M. Triterpenos da Resina de Protium heptaphyllum March (Burseraceae): Caracterização em Misturas Binárias. Química Nova, v.23, n.3, p.623-626, 2000.

[28] OLIVEIRA, F.A.; VIEIRA-JUNIOR, G.M.; ALMEIDA, F.R.; FLORÃŠNCIO, M.G.; LIMA JR., R.C.; SILVA, R.M.; SANTOS, F.A.; RAO, V.S. Gatroprotective and anti-inflammatory effects of resin from Protium heptaphyllum in mice and rats. Pharmacological Research, n.49, n.2, p.105-111, 2004.

[29] OLIVEIRA, F.A.; CHAVES, M.H.; ALMEIDA, F.R.C.; LIMA JR., R.C.P.; SILVA, R.M.; MAIA, J.L.; BRITO, G.A.A.C.; SANTOS, F.A.; RAO,V.S. Protective effect of of á- and â-amyrin, a triterpene mixture from Protium heptaphyllum (Aubl.) March. trunk wood resin, against acetaminophen-induced liver injury in mice. Journal of Ethnopharmacology, n.98, n.1-2, p.103-108, 2005a.

[30] OLIVEIRA, F.A.; COSTA, C.L.S.; CHAVES, M.H.; ALMEIDA, F.R.C.; CAVALCANTE, I.J.M.; LIMA, A.F.; LIMA JR., R.C.P.; SILVA, R.M.; CAMPOS, A.R.; SANTOS, F.A.; RAO, V.S. Attenuation of capsaicininduced acute and visceral nociceptive pain by á- and â-amyrin, a triterpene mixture isolated from Protium heptaphyllum resin in mice. Life Sciences, v.77, n.23, p.2942-2952, 2005b.

[31] PATRA, A.; MUKHOPADHYAY, A.K.; MITRA, A.K. Carbon-13 Resonance Assignment of some Friedelanes and Taraxasteranes. Organic Magnetic Resonance, v.17, n.3, p.166-168, 1981.

[32] PATRA, A.; CHAUDHURI, S.K. Assignment of Carbon-13 Nuclear Magnetic Resonance Spectra of Some Friedelanes. Magnetic Resonance in Chemistry, v.25, p.95-100, 1987.

[33] PERNET, R. Phytochimie des Burseracees. Lloydia, v.35, n.3, p.280-287, 1972

[34] RAMOS, M.F.S.; SIANI, A.C.; TAPPIN, M.R.R.; GUIMARÃES, A.C.; RIBEIRO, J.E.L.S. Essential oils from oleoresins of Protium spp. Of the Amazon region. Flavour and Fragrance Journal, v.15, p.383-387, 2000.

[35] RIZZINI, C. T.; MORS, W. B. Botânica Econômica Brasileira, 2ª Ed., Âmbito Cultural Edições Ltda., Rio de Janeiro, p.49-50, 1995.

[36] SIANI, A.C., RIBEIRO, M.N.S. Podocarpusflavone A from the leaves of Trattinnickia glazioviiâ€, Biochemical Systematic and Ecology v.23, p.879, n.7-8, 1995.

[37] SIANI, A.C.; RAMOS, M. F.S.; MENEZES-DE-LIMA JR. O.; RIBEIRO-DOS-SANTOS, R.; FERNANDEZFERREIRA, E.; SOARES, R.O.A.; ROSAS, E.C.; SUSUNAGA, G.S.; GUIMARÃES, A.C.; ZOGHBI M.B.; HENRIQUES, M.G.M.O. Journal of Ethnopharmacology, v.66, n.1, p.57-69, 1999a.

[38] SIANI, A.C.; RAMOS, M.S.F.; GUIMARÃES, A.C.; SUSUNAGA, G.S.; ZOGHBI, M.G.B. Volatile Constituents from Oleoresin of Protium heptaphyllum (Aubl.) March. Journal of the Essential Oil Research, v.11, p.72-74, 1999b.

[39] SIANI, A.C.; GARRIDO, I.S.; MONTERIO, S.S.; CARVALHO, E.S.; RAMOS, M.F.S. Protium icicariba as a source of volatile essences. Biochemical Systematic and Ecology, v.32, p.477-489, 2004.

[40] SILVA, J.R.A. Óleo-resinas de Dez Espécies do Gênero Protium. MSc Thesis, University of Amazon, Manaus, Brazil, 120 pp, 1995.

[41] SIQUEIRA, J.B.G. Estudo fitoquímico do gênero Protium: P. unifoliolatum (Engl.) Engl. e P. laxiflorum Engl. MSc Thesis, University of Amazon, Manaus, Brazil, 119 pp, 1991.

[42] SUSUNAGA, G.S. Estudo químico e biológico da resina produzida pela espécie Protium heptaphyllum March. (Burseraceae). MSc Thesis, University of Amazon, Manaus, Brazil, 155 pp., 1996.

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