Antioxidant activity of alkaloids from Bocconia arborea. A study on six testing methods

Authors

  • RM PÉREZ Laboratorio de Investigación de Productos Naturales. Escuela Superior de Ingeniería Química e Industrias extractivas IPN. Punto fijo 16, col. Torres Lindavista cp 07708, México D.F. México.
  • R VARGAS Laboratorio de Investigación de Fitofarmacología .Universidad Autónoma Metropolitana-Xochimilco A.P. 23- 181 México D.F., México
  • FJ MARTÍNEZ Departamento de Química. Unidad Profesional Interdisciplinaria de Biotecnología. IPN. Av. Acueducto S/N, Barrio la laguna Ticomán, cp 07340, México D.F., México
  • EV GARCÍA Departamento de Química. Unidad Profesional Interdisciplinaria de Biotecnología. IPN. Av. Acueducto S/N, Barrio la laguna Ticomán, cp 07340, México D.F., México
  • B HERNÁNDEZ Departamento de Química. Unidad Profesional Interdisciplinaria de Biotecnología. IPN. Av. Acueducto S/N, Barrio la laguna Ticomán, cp 07340, México D.F., México

Abstract

Antioxidative activity-guided fractionation together with chemical analysis led to the isolation of three benzophenanthridinealkaloids from methanol extract of the bark of Bocconia arborea. Identification was based on spectroscopic methods.The isolated alkaloids 6-acetonyldihydrochelerythrine, chelerythrine and dihydrochelerythrine were tested for antioxidativeactivity on thiocyanate assays, free radical scavenging activity, b-carotene bleaching method, and deoxyribose assay. Allalkaloids exhibited significant antioxidant activities in linoleic acid and b-carotene. Although afforded protection againstthe damage of deoxyribose, liposome peroxidation and microsomial lipid from peroxidation, also exhibited scavengingeffects on the 1,1-diphenyl-2-picrylhydrazyl radicals.

Downloads

References

Djerassi C, Connolly JD, Faulkner DJ, Mori K, Nakanishi K, Ourisson G, Raphael RA, Shamma M, Tamm C. Dictionary

of natural Products London: Chapman & Hall; 1994. p.117-124.

Manske RHF, Brossi A, eds. The alkaloids. New York: Wiley; 1985. p.253-286

Harbone JB, Baxter H. (1993). Phytochemical dictionary. A Handbook of bioactive compounds from plants. London:

Taylor & Francis; 1993. p.203.

Roberts MF, Wink M. Alkaloids: biochemistry, ecology and medicinal applications. New York: Polonium Publishing;

p.397-433.

Vavreeckova C, Gawlik I, Muller K. Benzophenanthridine alkaloids of Chelidonium majus; 1.Inhibition of 5- and 12—

lipoxygenase by a non-Redox mechanism. Planta Med 1996; 62: 397-401.

Cuendet M, Hostettmann K, Potterat O. Iridoid glucosides with free radical scavenging properties from Fagrae blumei.

Helv Chim Acta 1997; 80: 1144-1152.

Burits M, Bucar F. Antioxidant activity of Nigella sativa essential oil. Phytother Res 2000; 14: 323-328.

Miller HEA. A simplified method for the evaluation of antioxidant . J Am Oil Chem Soc 1971; 45: 91-98.

Daglia M, Papetti A, Gregotti C, Berte F, Gazzani G. In vitro antioxidant and ex vivo protective activities of green and

roasted coffe. J Agric Food Chem 2000; 48: 1449-1454.

Nakatani N, Kikuzaki H. A new antioxidative glucoside isolated from Oregano (Origanum vulgare L.). Agric Biol

Chem 1987; 51: 2727-2732.

Blois MS. Antioxidant determination by the use of a stable free radical. Nature 1958; 181: 1199-1200.

Yen G, Chang Y, Sheu F, Chiang H. Isolation and characterization of antioxidant compounds from Aspergillus candidus

Broth filtrate. J Agric Food Chem 2001; 49: 1426-1431.

Pellegrini N, Ying M, Rice-Evans C. Screening of dietary carotenoids and carotenoid-rich fruits extract for antioxidant

activities applying 2,2´-azobis(3-ethylbenzothine-6-surfonic acid) radical cation decolorization assay. Methods Enzymol

; 299: 379-389.

Aruoma OI. Assessment of potential prooxidant and antioxidant actions. J Am Oil Chem Soc 1996; 73: 1617-1625.

Halliwell B, Gutteridge MC, Auroma OI. The deoxyribose method: A simple “test-tube” assay for determination of rate

constants for reactions of hydroxyl radicals. Analytical Bioch 1987; 165: 215-219.

Ratty AK, Sunamoto J, Das NP. Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal

membranes and soybean lipoxygenase-1. Biochem Pharmacol 1988; 37: 989-995.

Duh PD. Antioxidant activity of burdock (Ardium lappa linne): its scavenging effects on free radical and active oxygen.

J Am Oil Chem Soc 1998; 75: 455-461.

Gazzani HG, Papetti A, Daglia M, Berte F, Gregotti C. Protective activity of water soluble components of some

common diet vegetables on rat liver microsome and the effect of thermal treatment. J Agric Food Chem 1998; 46:

-4127.

Ramos A, Piloto J, Visozo A, Garcia A, Lastra H, Ponce de Leon H. Mutagenicity and antioxidant assessment of

Stachitarpheta jamaicensis (L.) Vahl Phytother Res 2001; 15: 360-363.

Oechslin SM, Konig GM, Merkel KO, Wright AD, Kingghorn AD, Sticher O. An NMR study of four benzophenanthridine

alkaloids. J Nat Prod 1991; 54 : 519-524.

Slavik J, Slavikova L. Alkaloide der monhgewachse (Papaveraceae) II. Trenunung des chelerythins und sanguinarins

und auffindung von zwei neuen alkaloiden im schollkraut (Chelidonium majus L.). Colle Czecho Chem Commun

; 20: 21-26.

Slavik J, Dolejs L, Hanus V, Cross AD. Alkaloids of Papaveraceae XL. Chelirubine, chelilutine, sanguinrubine, and

sanguilutine, mass and nuclear magnetic resonance spectra of benzophenanthridine alkaloids. Colle Czecho Chem

Commun 1968; 33: 1619-1623.

Stermitz FR, Chen L, White JI. Alkaloids of the Papaveraceae. Tetrahedron 1966; 22: 1095-1102.

Sharma PN, Shoeb A, Kapil RS, Popli SP. Toddalidimerine, a dimeric benzophenanthridine alkaloids from Toddalia

asiatica. Phytochemistry 1981; 20: 2781-2783.

MacLean DB, Gracey DEF, Saunders JK, Rodrigo R, Manske RHF. Some benzophenanthridine alkaloids from Bocconia

arborea. Can J Chem 1969; 47: 1951-1956.

Manske RHF. Alkaloid from Bocconia arborea. Can J Res B 1943; 21:140-144.

Hanaoka M, Motonishi T, Mukai C. Chemical transformation of protoberberines. Part 9. A biomimetic synthesis of

oxychelerythrine, dihydrochelerythrine, and chelerythrine from berberine. Chem Soc Perkin Trans 1986; 2253-2256.

Holloway GM, Gainer J. The carotenoids crocetin enhances pulmonary oxygenation. J Appl Physiol 1988; 65: 683-686.

Aruoma OI, Grootveld M, Halliwell B. The role of iron in ascorbate-dependent deoxyribose degradation. Evidence

consistent with a site specific hydroxyl radical generation caused by iron bound to deoxyribose molecule. J Inorganic

Bioch 1987; 29: 289-299.

Halliwell B. How to characterize a biological antioxidant. Free Rad Res Comms 1990; 9: 1-32.

Laughton MJ, Evans PJ, Moroney MA, Hoult JRS, Halliwell B. Inhibition of mammalian 5-lipoxygenase and cyclooxygenase

by flavonoids and phenolic dietary additives. Bioch Pharmacol 1991; 42: 1673-1681.

Horie T, Murayama T, Mishima T, Itoh F, Minamide Y, Fuwa T, Awazu S. Identified diallyl polysulfides from an aged

garlic extract which protects the membranes from lipid proxidation. Planta Med 1989; 55: 506-508.

Plaa GL, Hewitt WR. Toxicology of the liver. In target organ toxicology series. New York: Raven Press: 1982. p.217-

Downloads

Published

2002-12-20

How to Cite

1.
PÉREZ R, VARGAS R, MARTÍNEZ F, GARCÍA E, HERNÁNDEZ B. Antioxidant activity of alkaloids from Bocconia arborea. A study on six testing methods. Ars Pharm [Internet]. 2002 Dec. 20 [cited 2025 May 18];44(1):5-21. Available from: https://revistaseug.ugr.es/index.php/ars/article/view/5122

Issue

Vol. 44 No. 1 (2003)

Section

Original Articles

License

The articles, which are published in this journal, are subject to the following terms in relation to the rights of patrimonial or exploitation:

  1. The authors will keep their copyright and guarantee to the journal the right of first publication of their work, which will be distributed with a Creative Commons BY-NC-SA 4.0 license that allows third parties to reuse the work whenever its author, quote the original source and do not make commercial use of it.

b. The authors may adopt other non-exclusive licensing agreements for the distribution of the published version of the work (e.g., deposit it in an institutional telematic file or publish it in a monographic volume) provided that the original source of its publication is indicated.

c. Authors are allowed and advised to disseminate their work through the Internet (e.g. in institutional repositories or on their website) before and during the submission process, which can produce interesting exchanges and increase citations of the published work. (See The effect of open access).