Picrolemma sprucei Hook. f.: Uso Tradicional, Princípios Ativos e seus Derivados Semi-sintéticos, Exploração Comercial e Econômica

A.M. Pohlit; R.C.N. Amorim

doi:10.32712/2446-4775.2006.38

Picrolemma sprucei Hook. f.: Traditional Use, Active Principles and their Semisynthetic Derivatives, Commercial and Economic Uses

Vol. 2 No. 01 (2006)
19-26
15/10/2013
01/06/2006
https://doi.org/10.32712/2446-4775.2006.38

A.M. Pohlit
R.C.N. Amorim

Keywords

Picrolemma sprucei

Picrolemma pseudocoffea

quassinoid

isobrucein B

neosergeolide

15-deacetylsergeolide

Abstract

In this review of the botanical, ethnobotanical, ethnopharmacological, chemical and pharmacological literature available concernig the Amazonian plant Picrolemma sprucei Hook. f. (Simaroubaceae), the different biological activities attributed by traditional medicine and scientific studies are emphasized. Special emphasis is given to the status emphasis is given to the status of knowledge of the principal chemical components (quassinoids) found in this plant species: sergeolide (1), neosergeolide (5), isobrucein B (2) and 15-deacetylsergeolide which include antimalarial, acute toxic, antitumor, cytotoxic, antifeedant, larvicidal/insecticidal and phytotoxic properties. A discussion of the important derivatives (natural and semi-synthetic) and their biological activities intends to reveal the potential of this plant as a source of highly bioactive quassinoids for structural and activity medicinal chemistry studies, as well as the potential of P. sprucei as a source of extracts for phytotherapeutic use.

References

BERTANI, S.; BOURDY, G.; LANDAU, I.; ROBINSON, J.C.; ESTERRE, PH.; DEHARO, E. Evaluation of French Guiana traditional antimalarial remedies. Journal of Ethnopharmacology, v.98, p.45-54, 2005.
BHATNAGAR, S.C.; CARUSO, A.J.; POLONSKY, J. Biologically active quassinoids: synthetic methodology for the conversion of chaparranin into glaucarubolone esters and quassinoid analogs. Tetrahedron, v.43 n.15, p.3471-3480, 1987.
BHATNAGAR, S.C.; POLONSKY, J.; SEVENT, T.; PRANCÉ, T. Isolation and structure of 15-O-benzoyl-brucein D, a new quassinoid from Soulamea amara (X-ray analysis). Tetrahedron Letters, v.26, n.9, p.1225-1228, 1985.
DAIDO, M.; OHNO, N.; IMAMURA, K.; FUKAMIYA, N.; HATAKOSHI, M.; YAMAZAKI, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Antifeedant and inseticidal activity of quassinoids against the Diamondblack moth (Plutella xylostella) and structure-Activity Relationships. Bioscience, Biotechnology, and Biochemistry, v.59 n.6, p.974-979, 1995.
DUKE, J.A.; VASQUEZ, R. Amazonian Ethnobotanical Dictionary. USA, CRC Press, p. 137, 1994.
FANDEUR, T.; MORETTI, C.; POLONSKY, J. In vitro and in vivo assessement of the antimalarial activity of Sergeolide. Planta Medica, v.51, p.20-23, 1985.
FERREIRA, M.C. O Mercado de plantas medicinais em Manaus. In: A floresta em jogo. O extrativismo na Amazônia Central. São Paulo, Laure Emperaire, tradução brasileira: Editora da UNESP, p.177-181, 2000.
FUKAMIYA, N.; LEE, K.; MUHAMMAD, I.; MURAKAMI, C.; OKANO, M.; HARVEY, I.; PELLETIER, J. Structure-activity relationships of quassinoids for eukaryotic protein synthesis. Cancer Letters, v.220, p.37-48, 2005.
GRENAND, P.; MORETTI, C.; JACQUEMIN, H. Pharmacopées Traditionnelles de Guyane. Edições de l’Orstom, Institut Français de recherce scientifique pour le développment en coopération, Paris, França, p.397-399, 1987.
KUBOTA, K.; FUKAMIYA, N.; TOKUDA, H.; NISHINO, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Quassinoids as inhibitors of Epstein-Barr virus early antigen activation. Cancer Letters, v.113, p.165-168, 1997.
KUPCHAN, S.M.; BRITTON, R.W.; LACADIE, J.A.; ZIEGLER, M.F.; SIGEL, C.W. The isolation and structural elucidation of Bruceantin and Bruceantinol, new potent antileukemic quassinoids from Brucea antidysenterica. Journal of Organic Chemistry, v.40, n.5, p.648-654, 1975
LE COINTE, P. Árvores e plantas úteis (Amazônia brasileira III). Companhia Editora Nacional, São Paulo, SP, p.92, 1947.
LIDERT, Z.; WING, K.; POLONSKY, J.; IMAKURA, Y.; OKANO, M.; TANI, S.; LIN, Y.; KIYOKAWA, H.; LEE, K. Insect antifeedant and growth inhibitory activity of forty-six quassinoids on two species of agricultural pests. Journal of Natural Products, v.50, n.3, p.442-448, 1987.
MILLIKEN, W. Plants for Malaria, Plants for Fever. Medicinal species in Latin America - a bibliographic survey. Editora Royal Botanic Garden, Kew, p.99, 1997.
MOBOT - Missouri Botanical Garden: http://mobot.mobot.org/cgi-bin/search_vast. Current specimen List for Picrolemma sprucei. Acesso em 07 de dezembro de 2005.
MORETTI, C.; POLONSKY, J.; VUILHORGNE, M.; PRANGE, T. Isolation and structure of sergeolide, a potent cytotoxic quassinoid from Piclolemma pseudocoffea. Tetrahedron Letters, v.23 n.6, p.647-650, 1982.
MORS, W.B.; RIZZINI, C.T.; PEREIRA, N.A.; DEFILIPPS, R.A. Medicinal plants of Brazil. Editora Reference Publications, p.314, 2000.
NYBG - New York Botanical Garden: http://www.nybg.org/. Acesso em 21 de novembro de 2005.
OKANO, M.; FUKAMIYA, N.; TAGAHARA, K.; TOKUDA, H.; IWASHIMA, A.; NISHINO, H.; LEE, H. Inhiitory effects of quassinoids on Epstein-Barr virus activation. Cancer Letters, v.94, p.139-146, 1995.
PIO CORRÊA, M. Dicionário das Plantas Úteis do Brasil e das Exóticas Cultivadas. Rio de Janeiro, Ministério da Agricultura-IBDF, v.1-6, il., 1984.
POHLIT, A.M.; QUIGNARD, E.L.J.; NUNOMURA, S.M.; TADEI, W.P.; HIDALGO, A.F.; PINTO, A.C.S.; SANTOS, E.V.M.; ALECRIM, A.M.; FERRAZ, A.B.; PEDROSO, A.C.S.; DINIZ, E.V.; FINNEY, E.K.; GOMES, E.O.; DON, L.C.; QUEIROZ, M.M.A.; HENRIQUE, M.C.; SANTOS, M.; LACERDA JUNIOR, O.S.; PINTO, P.S.; SILVA, S.G.; GRAÇA, Y.R. Screening of
plants found in Amazonas State, Brazil for activity against Aedes aegypti larvae. Acta Amazonica, v.34, n.1, p.97-105, 2004.
POLONSKY, J.; BHATNAGAR, S.; MORETTI, C. 15-deacetylsergeolide, a potent antileukemic quassinoid from Picrolemma pseudocoffea. Journal of Natural Products, v.47, n.6, p.994-996, 1984.
POLONSKY, J.; BHATNAGAR, S.C.; GRIFFITHS, D.C.; PICKETT, J.A.; WOODCOCK, C.M. Activity of quassinoids as antifeedants against aphids. Journal of Chemical Ecology, v.15, n.3, p.993-999, 1989.
RAHMAN, S.; FUKAMIYA, N.; OHNO, N.; TOKUDA, H.; NISHINO, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Inhibitory effects of quassinoid derivates on Epstein-Barr virus early antigen activation. Chemical & Pharmaceutical Bulletin, v.45, n.4, p.675-677, 1997.
RIBEIRO, J.E.L.; HOPKINS, M.J.G.; VICENTINI, A.; SOTHERS, C.A.; COSTA, M.A.S.; BRITO, J.M.; SOUZA, M.A.D.; MARTINS, L.H.P.; LOHMANN, L.G.; ASSUNÇÃO, P.A.C.L.; PEREIRA, E.C.; SILVA, C.F.; MESQUITA, M.R.; PROCÓPIO, L.C. Flora da Reserva Ducke – Guia de identificação das plantas vasculares de uma floresta de terrafirme
na Amazônia Central. Manaus-AM, INPA, p.547-549, 1999.
SARAIVA, R. C. G. Estudo fitoquímico de Picrolemma sprucei Hook. (Simaroubaceae) e dosagem dos princípios antimaláricos nos chás do caule e raiz. Manaus. Dissertação de Mestrado, Universidade Federal do Amazonas, 2001.
SARAIVA, R. C. G.; BARRETO, A.S.; SIANI, A.C.; FERREIRA, J.L.P.; ARAÃšJO, R.B.; NUNOMURA, S.M.; POHLIT, A.M. Anatomia Foliar e Caulinar de Picrolemma sprucei Hook
(Simaroubaceae). Acta Amazônica, v.33, n.2, p.213-220, 2003.
SCHPECTOR, J.Z.; CASTELLANO, E.E.; FHO, E.R.; VIEIRA, I.J.C. A new quassinoid isolated from Piclolemma pseudocoffea. Acta Crystallographica C, v.50, p.794-797,
SILVA, M.F.; LISBÔA, P.L.B.; LISBOA, R.C.L. Nomes vulgares de plantas amazônicas. Brasil, Instituto Nacional de Pesquisas da Amazônia – INPA, p.46, 1977
SPOHN, R.F.; GRIECO, P.A.; NARGUND, R.P.; Chemical transformations in the quassinoid series: Construction of the sensitive hidroxy enone functionality present in ring A of quassimarin and related quassinoids. Tetrahedron Letters, v.28 n.22, p.2491-2494, 1987.
TISCHLER, M.; CARDELLINA II, J.H.; BOYD, M.R.; CRAGG, G.M. Cytotoxic quassinoids from Cedronia granatensis. Journal of Natural Products, v.55 n.5, p.667-671, 1992.
THOMAS, W.W. the American genera of Simaroubaceae and their distribution. Acta Botanica Brasilica, v.4 n.1, p.11-18, 1990.
VIEIRA, I.J.C.; RODRIGUES-FILHO, E.; FERNANDES, J.B.; DA SILVA, M.F.G.F.; VIEIRA, P.C. Complete 1H and 13C chemical shift assignments of a new C22-quassinoid isolated from Picrolemma sprucei Hook by NMR spectroscopy. Magnetic Resonance in Chemistry, v.38, p.805-808, 2000.
VIGNERON, M.; DEPARIS, X.; DEHARO, E.; BOURDY, G. Antimalarial remedies in French Guiana: A knowledge attitudes and practices study. Journal of Ethnopharmacology, v.98, p.351-360, 2005.

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Author(s)

A.M. Pohlit
Laboratório de Princípios Ativos da Amazônia LAPAAM, Coordenação de Pesquisas em Produtos Naturais - CPPN Instituto Nacional de Pesquisas da Amazônia – INPA Avenida André Araújo, 2936, Petrópolis Manaus, AM, Brasil Tel.: +55 92 36433177; Fax: +55 92 36433177
R.C.N. Amorim
Laboratório de Princípios Ativos da Amazônia LAPAAM, Coordenação de Pesquisas em Produtos Naturais - CPPN Instituto Nacional de Pesquisas da Amazônia – INPA Avenida André Araújo, 2936, Petrópolis Manaus, AM, Brasil Tel.: +55 92 36433177; Fax: +55 92 36433177

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Picrolemma sprucei Hook. f.: Traditional Use, Active Principles and their Semisynthetic Derivatives, Commercial and Economic Uses. Rev Fitos [Internet]. 2006 Jun. 1 [cited 2025 Feb. 10];2(01):19-26. Available from: https://revistafitos.far.fiocruz.br/index.php/revista-fitos/article/view/38

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

[1] BERTANI, S.; BOURDY, G.; LANDAU, I.; ROBINSON, J.C.; ESTERRE, PH.; DEHARO, E. Evaluation of French Guiana traditional antimalarial remedies. Journal of Ethnopharmacology, v.98, p.45-54, 2005.

[2] BHATNAGAR, S.C.; CARUSO, A.J.; POLONSKY, J. Biologically active quassinoids: synthetic methodology for the conversion of chaparranin into glaucarubolone esters and quassinoid analogs. Tetrahedron, v.43 n.15, p.3471-3480, 1987.

[3] BHATNAGAR, S.C.; POLONSKY, J.; SEVENT, T.; PRANCÉ, T. Isolation and structure of 15-O-benzoyl-brucein D, a new quassinoid from Soulamea amara (X-ray analysis). Tetrahedron Letters, v.26, n.9, p.1225-1228, 1985.

[4] DAIDO, M.; OHNO, N.; IMAMURA, K.; FUKAMIYA, N.; HATAKOSHI, M.; YAMAZAKI, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Antifeedant and inseticidal activity of quassinoids against the Diamondblack moth (Plutella xylostella) and structure-Activity Relationships. Bioscience, Biotechnology, and Biochemistry, v.59 n.6, p.974-979, 1995.

[5] DUKE, J.A.; VASQUEZ, R. Amazonian Ethnobotanical Dictionary. USA, CRC Press, p. 137, 1994.

[6] FANDEUR, T.; MORETTI, C.; POLONSKY, J. In vitro and in vivo assessement of the antimalarial activity of Sergeolide. Planta Medica, v.51, p.20-23, 1985.

[7] FERREIRA, M.C. O Mercado de plantas medicinais em Manaus. In: A floresta em jogo. O extrativismo na Amazônia Central. São Paulo, Laure Emperaire, tradução brasileira: Editora da UNESP, p.177-181, 2000.

[8] FUKAMIYA, N.; LEE, K.; MUHAMMAD, I.; MURAKAMI, C.; OKANO, M.; HARVEY, I.; PELLETIER, J. Structure-activity relationships of quassinoids for eukaryotic protein synthesis. Cancer Letters, v.220, p.37-48, 2005.

[9] GRENAND, P.; MORETTI, C.; JACQUEMIN, H. Pharmacopées Traditionnelles de Guyane. Edições de l’Orstom, Institut Français de recherce scientifique pour le développment en coopération, Paris, França, p.397-399, 1987.

[10] KUBOTA, K.; FUKAMIYA, N.; TOKUDA, H.; NISHINO, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Quassinoids as inhibitors of Epstein-Barr virus early antigen activation. Cancer Letters, v.113, p.165-168, 1997.

[11] KUPCHAN, S.M.; BRITTON, R.W.; LACADIE, J.A.; ZIEGLER, M.F.; SIGEL, C.W. The isolation and structural elucidation of Bruceantin and Bruceantinol, new potent antileukemic quassinoids from Brucea antidysenterica. Journal of Organic Chemistry, v.40, n.5, p.648-654, 1975

[12] LE COINTE, P. Árvores e plantas úteis (Amazônia brasileira III). Companhia Editora Nacional, São Paulo, SP, p.92, 1947.

[13] LIDERT, Z.; WING, K.; POLONSKY, J.; IMAKURA, Y.; OKANO, M.; TANI, S.; LIN, Y.; KIYOKAWA, H.; LEE, K. Insect antifeedant and growth inhibitory activity of forty-six quassinoids on two species of agricultural pests. Journal of Natural Products, v.50, n.3, p.442-448, 1987.

[14] MILLIKEN, W. Plants for Malaria, Plants for Fever. Medicinal species in Latin America - a bibliographic survey. Editora Royal Botanic Garden, Kew, p.99, 1997.

[15] MOBOT - Missouri Botanical Garden: http://mobot.mobot.org/cgi-bin/search_vast. Current specimen List for Picrolemma sprucei. Acesso em 07 de dezembro de 2005.

[16] MORETTI, C.; POLONSKY, J.; VUILHORGNE, M.; PRANGE, T. Isolation and structure of sergeolide, a potent cytotoxic quassinoid from Piclolemma pseudocoffea. Tetrahedron Letters, v.23 n.6, p.647-650, 1982.

[17] MORS, W.B.; RIZZINI, C.T.; PEREIRA, N.A.; DEFILIPPS, R.A. Medicinal plants of Brazil. Editora Reference Publications, p.314, 2000.

[18] NYBG - New York Botanical Garden: http://www.nybg.org/. Acesso em 21 de novembro de 2005.

[19] OKANO, M.; FUKAMIYA, N.; TAGAHARA, K.; TOKUDA, H.; IWASHIMA, A.; NISHINO, H.; LEE, H. Inhiitory effects of quassinoids on Epstein-Barr virus activation. Cancer Letters, v.94, p.139-146, 1995.

[20] PIO CORRÊA, M. Dicionário das Plantas Úteis do Brasil e das Exóticas Cultivadas. Rio de Janeiro, Ministério da Agricultura-IBDF, v.1-6, il., 1984.

[21] POHLIT, A.M.; QUIGNARD, E.L.J.; NUNOMURA, S.M.; TADEI, W.P.; HIDALGO, A.F.; PINTO, A.C.S.; SANTOS, E.V.M.; ALECRIM, A.M.; FERRAZ, A.B.; PEDROSO, A.C.S.; DINIZ, E.V.; FINNEY, E.K.; GOMES, E.O.; DON, L.C.; QUEIROZ, M.M.A.; HENRIQUE, M.C.; SANTOS, M.; LACERDA JUNIOR, O.S.; PINTO, P.S.; SILVA, S.G.; GRAÇA, Y.R. Screening of

[22] plants found in Amazonas State, Brazil for activity against Aedes aegypti larvae. Acta Amazonica, v.34, n.1, p.97-105, 2004.

[23] POLONSKY, J.; BHATNAGAR, S.; MORETTI, C. 15-deacetylsergeolide, a potent antileukemic quassinoid from Picrolemma pseudocoffea. Journal of Natural Products, v.47, n.6, p.994-996, 1984.

[24] POLONSKY, J.; BHATNAGAR, S.C.; GRIFFITHS, D.C.; PICKETT, J.A.; WOODCOCK, C.M. Activity of quassinoids as antifeedants against aphids. Journal of Chemical Ecology, v.15, n.3, p.993-999, 1989.

[25] RAHMAN, S.; FUKAMIYA, N.; OHNO, N.; TOKUDA, H.; NISHINO, H.; TAGAHARA, K.; LEE, K.; OKANO, M. Inhibitory effects of quassinoid derivates on Epstein-Barr virus early antigen activation. Chemical & Pharmaceutical Bulletin, v.45, n.4, p.675-677, 1997.

[26] RIBEIRO, J.E.L.; HOPKINS, M.J.G.; VICENTINI, A.; SOTHERS, C.A.; COSTA, M.A.S.; BRITO, J.M.; SOUZA, M.A.D.; MARTINS, L.H.P.; LOHMANN, L.G.; ASSUNÇÃO, P.A.C.L.; PEREIRA, E.C.; SILVA, C.F.; MESQUITA, M.R.; PROCÓPIO, L.C. Flora da Reserva Ducke – Guia de identificação das plantas vasculares de uma floresta de terrafirme

[27] na Amazônia Central. Manaus-AM, INPA, p.547-549, 1999.

[28] SARAIVA, R. C. G. Estudo fitoquímico de Picrolemma sprucei Hook. (Simaroubaceae) e dosagem dos princípios antimaláricos nos chás do caule e raiz. Manaus. Dissertação de Mestrado, Universidade Federal do Amazonas, 2001.

[29] SARAIVA, R. C. G.; BARRETO, A.S.; SIANI, A.C.; FERREIRA, J.L.P.; ARAÃšJO, R.B.; NUNOMURA, S.M.; POHLIT, A.M. Anatomia Foliar e Caulinar de Picrolemma sprucei Hook

[30] (Simaroubaceae). Acta Amazônica, v.33, n.2, p.213-220, 2003.

[31] SCHPECTOR, J.Z.; CASTELLANO, E.E.; FHO, E.R.; VIEIRA, I.J.C. A new quassinoid isolated from Piclolemma pseudocoffea. Acta Crystallographica C, v.50, p.794-797,

[33] SILVA, M.F.; LISBÔA, P.L.B.; LISBOA, R.C.L. Nomes vulgares de plantas amazônicas. Brasil, Instituto Nacional de Pesquisas da Amazônia – INPA, p.46, 1977

[34] SPOHN, R.F.; GRIECO, P.A.; NARGUND, R.P.; Chemical transformations in the quassinoid series: Construction of the sensitive hidroxy enone functionality present in ring A of quassimarin and related quassinoids. Tetrahedron Letters, v.28 n.22, p.2491-2494, 1987.

[35] TISCHLER, M.; CARDELLINA II, J.H.; BOYD, M.R.; CRAGG, G.M. Cytotoxic quassinoids from Cedronia granatensis. Journal of Natural Products, v.55 n.5, p.667-671, 1992.

[36] THOMAS, W.W. the American genera of Simaroubaceae and their distribution. Acta Botanica Brasilica, v.4 n.1, p.11-18, 1990.

[37] VIEIRA, I.J.C.; RODRIGUES-FILHO, E.; FERNANDES, J.B.; DA SILVA, M.F.G.F.; VIEIRA, P.C. Complete 1H and 13C chemical shift assignments of a new C22-quassinoid isolated from Picrolemma sprucei Hook by NMR spectroscopy. Magnetic Resonance in Chemistry, v.38, p.805-808, 2000.

[38] VIGNERON, M.; DEPARIS, X.; DEHARO, E.; BOURDY, G. Antimalarial remedies in French Guiana: A knowledge attitudes and practices study. Journal of Ethnopharmacology, v.98, p.351-360, 2005.