Biflavonoid toxicarine, rotenoids and a flavanone from the roots of Tephrosia toxicaria

Biflavonoid toxicarine, rotenoids and a flavanone from the roots of Tephrosia toxicaria

Authors

DOI:

https://doi.org/10.5433/1679-0375.2020v41n1p71

Keywords:

Tephrosia toxicaria, Fabaceae, Flavonoids, Roots.

Abstract

For the first time the structural determination of the biflavonoid, 4-H-2,3-dihydro-1-benzopyran-4-one-6-[2-phenyl-8-(3-methyl-2-butenyl)-5,7-dimethoxy-2-H-3,4-dihydro-1-benzopiran-4-yl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl, named toxicarine (1) is presented, joined the isolation of the flavanone 7-O-methylglabranine (2) and a mixture of the rotenoids tephrosin (3) and rotenolone (4) from the roots of Tephrosia toxicaria (Sw.) Pers. Their structures were established by spectroscopic methods, meanly spectral data obtained by analysis of 1H and 13C NMR (1D and 2D) spectra.

Downloads

Download data is not yet available.

Author Biographies

Cesar Cornélio Andrei, Universidade Estadual de Londrina

PhD in Chemistry from the Universidade Federal de São Carlos. Retired professor at the Universidade Estadual de Londrina

Terezinha de Jesus Faria, Universidade Estadual de Londrina

PhD in Organic Chemistry from the Universidade Federal de Minas Gerais. Professor of the Department of Chemistry, Universidade Estadual de Londrina

Adriana Aparecida Bosso Tomal, Universidade Estadual de Londrina

PhD in Food Science from the Universidade Estadual de Londrina. Visiting Professor at Universidade Estadual de Londrina

Pedro Renato Anizelli, Instituto Federal de Paraná - Campus Jacarezinho

PhD in Chemistry / Physical Chemistry from the Universidade Estadual de Londrina. Professor at the Instituto Federal de Paraná, Jacarezinho campus

Raimundo Braz-Filho, Universidade Federal Rural do Rio de Janeiro

PhD at the Universidade Federal Rural do Rio de Janeiro

References

AGRAWAL, P. K.; THAKUR, R. S.; BANSAL, M. C. Flavonoides. In: AGRAWAL, P. K. (ed.). Carbon-13 of flavonoids. Amsterdam: Elesvier Science Publishers B. V., 1989. p. 95-173.

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

Downloads

Published

2020-06-20

How to Cite

Andrei, C. C., Faria, T. de J., Tomal, A. A. B., Anizelli, P. R., & Braz-Filho, R. (2020). Biflavonoid toxicarine, rotenoids and a flavanone from the roots of Tephrosia toxicaria. Semina: Ciências Exatas E Tecnológicas, 41(1), 71–78. https://doi.org/10.5433/1679-0375.2020v41n1p71

Issue

Section

Original Article

Most read articles by the same author(s)

Similar Articles

You may also start an advanced similarity search for this article.

Loading...