Toxicarina, um biflavonóide inédito das raízes de Tephrosia toxicaria.
DOI:
https://doi.org/10.5433/1679-0375.2020v41n1p71Palavras-chave:
Tephrosia toxicaria, Fabaceae, Flavonoids, Roots.Resumo
O biflavonóide inédito 4-H-2,3-diidro-1-benzopiran-4-ona-6-[2-fenil-8-(3-metil-2-butenil)-5,7-dimetoxi-2-H-3,4-diidro-1-benzopiran-4-il]-5,7-diidroxy-8-(3-metil-2-butenil)-2-fenil, denominada toxicarina (1), a flavanona 7-O-metil glabranina (2) e a mistura de rotenóides tefrosina (3) e rotenolona (4) foram isolados e caracterizados, das raízes de Tephrosia toxicaria (Sw.) Pers. As estruturas foram determinadas por métodos espectroscópicos principalmente pelos espectros de 1H e 13C uni e bidimensionais.Referências
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ARROIO, A.; HONORIO, K. M.; WEBER, K. C.; HOMEM-DE-MELLO, P.; SILVA, A. B. F. A theoretical study on the chemopreventive activity of flavonoid compounds. Internet Electronic Journal of Molecular Design, [S. l.], v. 3, p. 781-788, 2004.
BABA, K.; TAKEUCHI, K.; HAMASAKI, F.; KOZAWA, M. Chemical studies on the constituents of the thymelaeaceous plants. I. Structures of two new flavans from Daphne odora Thunb. Chemical & pharmaceutical bulletin, Tokyo, v. 34, p 595-602, 1986 DOI: https://doi.org/10.1248/cpb.34.595
CUCA-SUAREZ, L.; DELLE-MONACHE, F.; MARINIBETTOLO, G.; MENICHINI, F. Three new prenylated flavanones from Tephrosia sp. II Farmaco, Pávia, v. 35. p. 796-800, 1980.
DAYAL, R. An alternative synthesis of 7-Omethylglabranine. Current science, Faisalabad, v. 49, p. 427, 1980.
DIAS, J. C.; REBELO, M. M.; ALVES, C. N. A semiempirical study of biflavonoid compounds with biological activity against tuberculosis. Journal of molecular structure, Amsterdam, v. 676, p. 83-87, 2004.
DOI: https://doi.org/10.1016/j.theochem.2004.03.001
DOMINGUES, H. A.; QUEIROZ, R. T.; ROSSI, M. L; MARTINELLI, A. P.; LUZ, C. F. P. Pollen morphology and ultrastructure of Tephrosia Pers. (Leguminosae – Papilionoideae – Millettieae): a taxonomic
approach for native and cultivated species in Brazil. Grana, Stockholm, v. 58, p. 159-173, 2019. DOI: https://doi.org/10.1080/00173134.2019.1571626
GOMEZ, F.; QUIJANO, L.; GARCIA, G.; CALDERON, J. S.; RIOS, T. A prenylated flavan from Tephrosia madrensis. Phytochemistry. v. 22, p. 1305-1306, 1983. DOI: https://doi.org/10.1016/0031-9422(83)80255-6
GOMEZ-GARIBAY, F.; CALDERON, J. S.; QUIJANO, L.; TELLEZ, O.; OLIVARES, M. S.; RIOS, T. An unusual prenylbiflavanol from Tephrosia tepicana. Phytochemistry, London, v. 46, p. 1285-1287, 1997. DOI: https://doi.org/10.1016/S0031-9422(97)80029-5
JANG, D.S.; PARK, E. J.; KANG, Y.; HAWTHORNE, M. E.; VIGO, J. S.; GRAHAM, J. G.; CABIESES, F.; FONG, H. H. S.; MEHTA, R. G.; PEZZUTO, J. M.; KINGHORN, A. D. Potential cancer chemopreventive flavonoids from the stems of Tephrosia toxicaria. Journal of Natural Products, [Gorakhpur], v. 66, p. 1166-1170,
2003. DOI: https://doi.org/10.1021/np0302100
KISHORE, P. H.; REDDY, M. V. B.; GUNASEKAR, D.; MURTHY, M. M.; CAUX, C.; BODO, B. A new coumestan from Tephrosia calophylla. Chemical & pharmaceutical bulletin, Tokyo, v. 51, p, 194-196, 2003. DOI: https://doi.org/10.1002/chin.200332170
LIM, H.; KIM, S. B.; PARK, H.; CHANG, H. W.; KIM, H. P. New anti-inflammatory synthetic biflavonoid with C-C (6-6") linkage: Differential effects on cyclooxygenase-2 and inducible nitric oxide synthase. Archives of pharmacal research, Seoul, v. 32, p. 1525-
1531, 2009. DOI: https://doi.org/10.1007/s12272-009-2104-2
MAHJOUB, M. A.; AMMAR, S.; EDZIRI, H.; MIGHRI, N.; BOURAOUI, A.; MIGHRI, Z. Anti-inflammatory and antioxidant activities of some extracts and pure natural products isolated from Rhus tripartitum (Ucria). Medicinal Chemistry Research, Cambridge, v. 19, p. 271-282, 2010. DOI: https://doi.org/10.1007/s00044-009-9190-z
MARTINEZ, R.; ZARPELON, A. C.; DOMICIANO, T.P.; GEORGETTI, S.R.; BARACAT, M.M.; MOREIRA, I.C.; ANDREI, C.C.; VERRI Jr, W. A.; CASAGRANDE, R. Antinociceptive effect of Tephrosia sinapou extract in the acetic acid, phenyl-p-benzoquinone, formalin, and
complete Freund’s adjuvant models of overt pain-like behavior
in mice. Scientifica, Cairo, v. 2016, p. 1-8, 2016. DOI: https://doi.org/10.1155/2016/8656397
MARTINEZ, R. M.; ZARPELON, A. C.; CARDOSO, R. D.; VICENTINI, F. T. M. C.; GEORGETTI, S, R.; BARACAT, M. M.; ANDREI, C. C.; MOREIRA, I. C.; VERRI JUNIOR, W. A.; CASAGRANDE, R. Ethyl acetate extract inhibits inflammatory pain in mice: opioid receptor
dependent inhibition of TNF and IL-1 production. Pharmaceutical
Biology, Lisse, v. 51, p. 1262-1271, 2013. DOI: https://doi.org/10.3109/13880209.2013.786099
PEREIRA, A. S.; PINTO, A. C.; CARDOSO, J. N.; AQUINO-NETO, F. R.; VIEIRA, P. C.; FERNANDES, J. B.; SILVA, M. F. G. F.; ANDREI, C. C. Analysis of rotenoids by high temperature high resolution
gas chromatography-mass spectrometry. Journal of high resolution chromatography, Weinheim, v. 21, p. 513-518, 1998. DOI: https://doi.org/10.1002/(SICI)1521-168(19980901)21:9<513::AID-HRC513>3.0.CO;2-F
RIBEIRO, W. H. F.; VASCONCELOS, J. N.; ARRIAGA, A. M. C.; OLIVEIRA, M. C. F.; ANDRADE-NETO, M.; LEMOS, T. L. G.; SANTIAGO, G. M. P.; NASCIMENTO, R. F.; MAFEZOLI, J. Tephrosia
toxicaria Pers essential oil: Chemical composition and larvicidal activity. Natural Product Communications, Westerville, v.1, p. 391-393, 2006. DOI: https://doi.org/10.1177/1934578X0600100509
TANAKA, T.; IINUMA, M. A. F.; OHYAMA, M.; BURANDT, C. L. Flavonoids from the root and stem of Sophora tomentosa. Phytochemistry, Oxford, v. 46, p.1431-1437, 1997. DOI: http://doi.org/10.1016/S0031-9422(97)00474-3
TOUQEER, S.; SAEED, M. A.; AJAIB, M. A Review on the phytochemistry and pharmacology of genus Tephrosia.
Phytopharmacology, Jena, v. 4, p. 598-637, 2013.
VASCONCELOS, J. N.; LIMA, J. Q.; LEMOS, T. L. G.; OLIVEIRA, M. F.; BESERRA, A. M. M.; ANDRADE-NETO, M.; MAFEZOLI, J.; ARRIAGA, A. M. C.; SANTIAGO, G. M. P.; BRAZ-FILHO, R. Estudo
químico e biológico de Tephrosia toxicaria Pers. Química Nova, São Paulo, v. 32, p.382-386, 2009.DOI: https://doi.org/10.1590/S0100-40422009000200021
WILMSEN, P. K.; DALLA SANTA, S; SALVADOR, M. Antioxidant activity of the flavonoid hesperidin in chemical and biological systems. Journal of agricultural and food chemistry, Washington, v. 53. p. 4757-4761, 2005. DOI: https://doi.org/org/10.1021/jf0502000
ARROIO, A.; HONORIO, K. M.; WEBER, K. C.; HOMEM-DE-MELLO, P.; SILVA, A. B. F. A theoretical study on the chemopreventive activity of flavonoid compounds. Internet Electronic Journal of Molecular Design, [S. l.], v. 3, p. 781-788, 2004.
BABA, K.; TAKEUCHI, K.; HAMASAKI, F.; KOZAWA, M. Chemical studies on the constituents of the thymelaeaceous plants. I. Structures of two new flavans from Daphne odora Thunb. Chemical & pharmaceutical bulletin, Tokyo, v. 34, p 595-602, 1986 DOI: https://doi.org/10.1248/cpb.34.595
CUCA-SUAREZ, L.; DELLE-MONACHE, F.; MARINIBETTOLO, G.; MENICHINI, F. Three new prenylated flavanones from Tephrosia sp. II Farmaco, Pávia, v. 35. p. 796-800, 1980.
DAYAL, R. An alternative synthesis of 7-Omethylglabranine. Current science, Faisalabad, v. 49, p. 427, 1980.
DIAS, J. C.; REBELO, M. M.; ALVES, C. N. A semiempirical study of biflavonoid compounds with biological activity against tuberculosis. Journal of molecular structure, Amsterdam, v. 676, p. 83-87, 2004.
DOI: https://doi.org/10.1016/j.theochem.2004.03.001
DOMINGUES, H. A.; QUEIROZ, R. T.; ROSSI, M. L; MARTINELLI, A. P.; LUZ, C. F. P. Pollen morphology and ultrastructure of Tephrosia Pers. (Leguminosae – Papilionoideae – Millettieae): a taxonomic
approach for native and cultivated species in Brazil. Grana, Stockholm, v. 58, p. 159-173, 2019. DOI: https://doi.org/10.1080/00173134.2019.1571626
GOMEZ, F.; QUIJANO, L.; GARCIA, G.; CALDERON, J. S.; RIOS, T. A prenylated flavan from Tephrosia madrensis. Phytochemistry. v. 22, p. 1305-1306, 1983. DOI: https://doi.org/10.1016/0031-9422(83)80255-6
GOMEZ-GARIBAY, F.; CALDERON, J. S.; QUIJANO, L.; TELLEZ, O.; OLIVARES, M. S.; RIOS, T. An unusual prenylbiflavanol from Tephrosia tepicana. Phytochemistry, London, v. 46, p. 1285-1287, 1997. DOI: https://doi.org/10.1016/S0031-9422(97)80029-5
JANG, D.S.; PARK, E. J.; KANG, Y.; HAWTHORNE, M. E.; VIGO, J. S.; GRAHAM, J. G.; CABIESES, F.; FONG, H. H. S.; MEHTA, R. G.; PEZZUTO, J. M.; KINGHORN, A. D. Potential cancer chemopreventive flavonoids from the stems of Tephrosia toxicaria. Journal of Natural Products, [Gorakhpur], v. 66, p. 1166-1170,
2003. DOI: https://doi.org/10.1021/np0302100
KISHORE, P. H.; REDDY, M. V. B.; GUNASEKAR, D.; MURTHY, M. M.; CAUX, C.; BODO, B. A new coumestan from Tephrosia calophylla. Chemical & pharmaceutical bulletin, Tokyo, v. 51, p, 194-196, 2003. DOI: https://doi.org/10.1002/chin.200332170
LIM, H.; KIM, S. B.; PARK, H.; CHANG, H. W.; KIM, H. P. New anti-inflammatory synthetic biflavonoid with C-C (6-6") linkage: Differential effects on cyclooxygenase-2 and inducible nitric oxide synthase. Archives of pharmacal research, Seoul, v. 32, p. 1525-
1531, 2009. DOI: https://doi.org/10.1007/s12272-009-2104-2
MAHJOUB, M. A.; AMMAR, S.; EDZIRI, H.; MIGHRI, N.; BOURAOUI, A.; MIGHRI, Z. Anti-inflammatory and antioxidant activities of some extracts and pure natural products isolated from Rhus tripartitum (Ucria). Medicinal Chemistry Research, Cambridge, v. 19, p. 271-282, 2010. DOI: https://doi.org/10.1007/s00044-009-9190-z
MARTINEZ, R.; ZARPELON, A. C.; DOMICIANO, T.P.; GEORGETTI, S.R.; BARACAT, M.M.; MOREIRA, I.C.; ANDREI, C.C.; VERRI Jr, W. A.; CASAGRANDE, R. Antinociceptive effect of Tephrosia sinapou extract in the acetic acid, phenyl-p-benzoquinone, formalin, and
complete Freund’s adjuvant models of overt pain-like behavior
in mice. Scientifica, Cairo, v. 2016, p. 1-8, 2016. DOI: https://doi.org/10.1155/2016/8656397
MARTINEZ, R. M.; ZARPELON, A. C.; CARDOSO, R. D.; VICENTINI, F. T. M. C.; GEORGETTI, S, R.; BARACAT, M. M.; ANDREI, C. C.; MOREIRA, I. C.; VERRI JUNIOR, W. A.; CASAGRANDE, R. Ethyl acetate extract inhibits inflammatory pain in mice: opioid receptor
dependent inhibition of TNF and IL-1 production. Pharmaceutical
Biology, Lisse, v. 51, p. 1262-1271, 2013. DOI: https://doi.org/10.3109/13880209.2013.786099
PEREIRA, A. S.; PINTO, A. C.; CARDOSO, J. N.; AQUINO-NETO, F. R.; VIEIRA, P. C.; FERNANDES, J. B.; SILVA, M. F. G. F.; ANDREI, C. C. Analysis of rotenoids by high temperature high resolution
gas chromatography-mass spectrometry. Journal of high resolution chromatography, Weinheim, v. 21, p. 513-518, 1998. DOI: https://doi.org/10.1002/(SICI)1521-168(19980901)21:9<513::AID-HRC513>3.0.CO;2-F
RIBEIRO, W. H. F.; VASCONCELOS, J. N.; ARRIAGA, A. M. C.; OLIVEIRA, M. C. F.; ANDRADE-NETO, M.; LEMOS, T. L. G.; SANTIAGO, G. M. P.; NASCIMENTO, R. F.; MAFEZOLI, J. Tephrosia
toxicaria Pers essential oil: Chemical composition and larvicidal activity. Natural Product Communications, Westerville, v.1, p. 391-393, 2006. DOI: https://doi.org/10.1177/1934578X0600100509
TANAKA, T.; IINUMA, M. A. F.; OHYAMA, M.; BURANDT, C. L. Flavonoids from the root and stem of Sophora tomentosa. Phytochemistry, Oxford, v. 46, p.1431-1437, 1997. DOI: http://doi.org/10.1016/S0031-9422(97)00474-3
TOUQEER, S.; SAEED, M. A.; AJAIB, M. A Review on the phytochemistry and pharmacology of genus Tephrosia.
Phytopharmacology, Jena, v. 4, p. 598-637, 2013.
VASCONCELOS, J. N.; LIMA, J. Q.; LEMOS, T. L. G.; OLIVEIRA, M. F.; BESERRA, A. M. M.; ANDRADE-NETO, M.; MAFEZOLI, J.; ARRIAGA, A. M. C.; SANTIAGO, G. M. P.; BRAZ-FILHO, R. Estudo
químico e biológico de Tephrosia toxicaria Pers. Química Nova, São Paulo, v. 32, p.382-386, 2009.DOI: https://doi.org/10.1590/S0100-40422009000200021
WILMSEN, P. K.; DALLA SANTA, S; SALVADOR, M. Antioxidant activity of the flavonoid hesperidin in chemical and biological systems. Journal of agricultural and food chemistry, Washington, v. 53. p. 4757-4761, 2005. DOI: https://doi.org/org/10.1021/jf0502000
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2020-06-20
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Andrei, C. C., Faria, T. de J., Tomal, A. A. B., Anizelli, P. R., & Braz-Filho, R. (2020). Toxicarina, um biflavonóide inédito das raízes de Tephrosia toxicaria. Semina: Ciências Exatas E Tecnológicas, 41(1), 71–78. https://doi.org/10.5433/1679-0375.2020v41n1p71
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