Chemical Constituents of Adesmia Boronioides and Evaluation of their Antioxidant Activity

DOI:

https://doi.org/10.37285/ijpsn.2015.8.3.5

Authors

  • Orlando Muñoz
  • C Delporte

Abstract

As part of our ongoing research into the pharmacologically active compounds of Chilean flora, here we did phytochemical investigation of Adesmia boronioides Hook.f (fabaceae). (Papilonaceae) leaves. This effort has led to isolation and identification of liqueritigenin, isoliquiritigenin, sesamin, isodrimenin and a kaempferol glycoside, kaempferol 3-O-β-D-[galactopyranosyl  (1–2) rhamnoside]-7-O –α-L-rhamnopyranoside.Compound structures were identified by 1D- and 2D-NMR experiments, mass and UV spectrometry and comparison with data from the literature. This is the first time these compounds have been isolated from this plant’s leaves.These active constituents have been studied further pharmacologically. Antioxidant properties in A. boronioides leaves were determined.

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Keywords:

Adesmiaboronioides, flavonoids, flavonoid glycosides, isodrimenin, sesamin

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Published

2015-08-30

How to Cite

1.
Muñoz O, Delporte C. Chemical Constituents of Adesmia Boronioides and Evaluation of their Antioxidant Activity. Scopus Indexed [Internet]. 2015 Aug. 30 [cited 2024 May 18];8(3):2919-223. Available from: http://www.ijpsnonline.com/index.php/ijpsn/article/view/783

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Research Articles

References

Ahmed A, Gohar, Galal T, Maatooqa and Niwa M. (2000) Two- Flavonoid Glycosides from Chenopodium Murale, Phytochemistry. 53; 299-303.

Appel HJ, Conolly K, Overton R. and Bond J. (1960). Sesquiter-penoids. Part II. The Constitution and Stereochemistry of Drimenin. Isotrimenin and Confertifolin. J. Chem. Soc, 82: 4685-4692.

Agnese A M and Cabrera J. L. (1996). Hydrophilic Components in two Adesmia Species. Biochemical Systematics and Ecology, 24(2); 171-172.

Agnese A M, Pérez C and Cabrera J. L. (2001). Adesmiaaegiceras: Antimicrobial activity and Chemical study. Phytomedicine, 8(5); 389-394.

Benzie FF and Strain JJ. (1996). The Ferric Reducing Ability of Plasma (FRAP) as A Measure of “Antioxidant Power”. The FRAP Assay. Analytical Biochemistry, 239: 70-76.

Faini F, Castillo M, Torres R, DelleMonache G and Gacs-Baitz E. (1995). Malabaricane Triterpene Glucosides from Adesmia aconcaguensis. Phytochemistry, 40(3): 885-890.

Feldman M, Santos J and Grenier D. (2011). Comparative Evaluation of Two Structurally Related Flavonoids, Isoliquiritigen in and Liquiritigenin, for their Oral Infection Therapeutic Potential. J.Nat.Prod, 74; 1862-1867.

Gomez P, Sotes G, Hahn S, Becerra J. and San Martin J. (2013). Chemical composition of the Essential Oil from the Leaves of adesmia bijuga phil., Fabaceae, one critically Endangered species in Central Chile. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, 12(6): 622-626.

Gonzalez S, Bandoni A, van Baren C, Leo Lira P, Cerda-Garcia C and Nathan P.J. (2002) Structure, Conformation and absolute Configuration of Novel Bisnorsesquiterpenes from the Adesmia-boronioides essential oil. Tetrahedron, 58: 3065-3071.

Gonzalez SB, Houghton PJ and Hoult RS. (2003). The Activity Against Leucocyte Eicosanoid Generation of Essential Oil and Polar Fractions of Adesmiaboronoides Hook. F. Phytotherapy Research, 17: 290-293.

Harborne, JF. (Ed.) (1994). The flavonoids–Advances in research since 1986 Chapman and Hall, London, U.K., p.483.

Henriquez C, Almonacid S, Chiffelle I, Valenzuela T, Araya M, Cabezas L. Simpson R and Speisky H. (2010). Determination of Antioxidant Capacity, Total Phenolic Content and Mineral Compo- sition of Different Fruit Tissue Of Five Apple Cultivars Grown In Chile. Chilean Journal of Agricultural Research, 7(4): 523-536.

Hueso-Rodríguez J and Rodríguez B. (1989). A new and efficient route to Optically Active Drimanes. Synthesis of (+)-Winterin, (+)-Conferti-folin, (+)-Isodrimenin, and (+)- Bicyclofarnesol. Tetrahedron, 45: 1567-1576.

Lee JY, Lee J-H, Park JH, Kim SY, Choi JY, Lee SH, Kim YS, Kang SS, Jang Ch and Han Y (2009). Liquiritigenin, a Licorice Flavonoid, Helps Mice Resist Disseminated Candidiasis due to Candida Albicans by Th1 Immune Response, Whereas Liquiritin, its Glycoside form, does not International Immunopharmacology, 9: 632-638.

Lee YS, Kim SH, Jung SH, Kim JK, Pan CH and Lim SS (2010). Aldose Reductase Inhibitory Compounds from Glycyrrhiza Uralensis. Biol Pharm Bull, 33: 917-921.

Lee Ch. and Chim Yen G. (2006). Antioxidant Activity and Bioactive Compounds of Tea Seed (Camellia oleifera Abel.) Oil. J. Agric. Food Chem, 54; 779 -784.

Liu X, Ye W, Yu B, Zhao S, Wua H and Chec Ch. (2004). Two new Flavonol Glycosides from Gymnema Sylvestre and Euphorbia Ebracteolata. Carbohydrate Research, 339: 891-895.

Lyu H, Kwak H, Lee D, Kim K, Kim S and Baek N. (2008) Isolation of Flavonoids from Processed Aconiti Tuber. J.Appl. Biol. Chem, 51: 165-168.

Ma Ch, G. Li, Zhang D, L.Ke, F and Xiao. (2005). One step Isolation and Purification of Liquiritigenin and Isoliquiritigenin from Gycyrrhiza Uralensis Risch. Using High-speed. Journal of Chromatography A, 1078; 188-192.

Marticorena C. and Quezada M.(1985). Flora vascular de Chile. Gayana Bot. 42; 13-114.

Meselhy M. (2003). Constituents from Moghat, the Roots of Glossostemon bruguieri. Molecules, 8; 614-621.

Moazzami A, Andersson R and Kamal-Eldin A. (2007). Quantitative NMR Analysis of a Sesamin Catechol Metabolite in Human Urine.The Journal of Nutrition, 137; 940-944.

Montes M and Wilkomirsky T. (1985). Medicina Tradicional Chilena. Santiago de Chile: Edit. Universidad de Concepcion Simirgiotis M, Silva M, Becerra J and Schmeda-Hirschmann G.(2012). Direct Characterisation of Phenolic Antioxidants In Infusions from Four Mapuche Medicinal Plants by Liquid Chromatography with Diode Array Detection (Hplc-Dad) and Electrospray Ionisation Tandem Mass Spectrometry (HPLC-ESI–MS). Food Chem, 131; 318-327.

Shibano M. Ozaki K. Watanabe H. Tabata A. Taniguchi M. Baba K. (2010). Planta Med, 76;729-733.

Su Y, Koike K, Nikaido T, Liu, J. Zheng J., and Guo D. (2003). Conyzasaponins I-Q, Nine New Triterpenoid Saponins from Conyza blinii. J. Nat. Prod. 66, 1593-1599.

Tiap-ling A. (2004). Estuduio Quimico Bioguiado De Los Extractos Con Actividad Analgésica Y Antiinflamatoria De Adesmia Atacamensis Phil. PhD Thesis. Facultad de Ciencias Quimicas y Farmaceutica. Universidad de Chile.

Ulibarri E. and Burkart A. (2000). Sinopsis de lase species de Adesmia (leguminosae, adesmieae) de Argentina. Darwiniana 38; 59-126.

Villaño D, Fernández-Pachón MS, Moyá ML, Troncoso AM, García-Parrilla MC. (2007). Radical Scavenging Ability of Pholyfenolic Compounds towards dphh free Radical. Talanta, 71: 230.

White J. and Burton J. (1985). Syntheses of the Insect Antifeedant (±)-Cinnamodial and the Drimane Sesquiterpenoids (±)-Isodrimenin and ( ±)-Fragrolide J. Org. Chem, 50: 357-364.

Zheng Z, Wing Cheng K, Chao J, Wu J and Wang M. (2008). Tyrosinase inhibitors from paper mulberry (Broussonetia papyrifera) Food Chemistry, 106; 529-535.

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