Subscribe to RSS
DOI: 10.1055/s-0033-1351052
Antioxidant Neolignans from Cordia americana
Publication History
received 25 February 2013
revised 15 July 2013
accepted 13 October 2013
Publication Date:
12 November 2013 (online)
![](https://www.thieme-connect.de/media/plantamedica/201318/lookinside/thumbnails/10.1055-s-0033-1351052-1.jpg)
Abstract
Five new neolignans with a bicyclo[2.2.2]octene framework were isolated from an ethanolic extract of the bark of Cordia americana. The structures and relative configurations of the compounds were elucidated by a combination of spectroscopic methods. All the isolated compounds showed good antioxidant activities in the DPPH radical scavenging (0.5–100 µg/mL) and Ferric-reducing antioxidant power (FRAP, 1–100 µg/mL) assays. One of the compounds displayed mild fungistatic activity at 0.1 µmol/spot against Fusarium virguliforme while, at the same time, all compounds were inactive against several strains of Gram (+) and Gram (−) bacteria at all assayed concentrations (10–1000 µg/mL).
Key words
Cordia americana - Boraginaceae - neolignans - bicyclo[2.2.2]octene - yunnaneic acids - rufescenolides - antioxidant activity-
References
- 1 Gottschling M. Clarification of the taxonomic position of Auxemma, Patagonula, and Saccellium (Cordiaceae, Boraginales). J Syst Bot 2006; 31: 361-367
- 2 Ló SMS, Duarte MR. Leaf and stem morpho-anatomy of Cordia americana (L.) Gottschling & J.S. Mill., Boraginaceae. Lat Am J Pharm 2011; 30: 823-828
- 3 Moir M, Thomson RH. Naturally occurring quinones. Part XXIII. Cordiachromes from Patagonula americana L. J Chem Soc [Perkin I] 1973; 15: 1556-1561
- 4 Dai J, Sorribas A, Yoshida WY, Williams PG. Sebestenoids A–D, BACE1 inhibitors from Cordia sebestena . Phytochemistry 2010; 71: 2168-2173
- 5 Geller FC. Isolation, structure elucidation and biological investigation of active compounds in Cordia americana and Brugmansia suaveolens [dissertation]. Tübingen: University of Tübingen; 2010
- 6 Geller FC, Schmidt C, Göttert M, Fronza M, Schattel V, Heinzmann B, Werz O, Flores EMM, Merfort I, Laufer S. Identification of rosmarinic acid as the major active constituent in Cordia americana . J Ethnopharmacol 2010; 128: 561-566
- 7 Yahara S, Satoshiro M, Nishioka I, Nagasawa T, Oura H. Isolation and characterization of phenolic compounds from Coptidis rhizoma . Chem Pharm Bull 1985; 33: 527-531
- 8 do Vale AE, David JM, dos Santos EO, David JP, e Silva LC. Bahia MV, Brandão HN. An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens. Phytochemistry 2012; 76: 158-161
- 9 Tanaka T, Nishimura A, Kouno I, Nonaka G, Young TJ. Isolation and characterization of yunnaneic acids A–D, four novel caffeic acid metabolites from Salvia yunnanensis . J Nat Prod 1996; 59: 843-849
- 10 Tanaka T, Nishimura A, Kouno TI, Nonaka G, Yang CR. Four new caffeic acid metabolites, yunnaneic acids E–H, from Salvia yunnanensis . Chem Pharm Bull 1997; 45: 1596-1600
- 11 Tezuka Y, Terazono M, Kusumoto TI, Kawashima Y, Hatanaka Y, Kadota S, Hattori M, Namba T, Kikuchi T. Helisterculins A and B, two new (7.5′,8.2′)-neolignans, and helisorin, the first (6.4′,7.5′,8.2′)-neolignan, from the indonesian medicinal plant Helicteres isora . Helv Chim Acta 1999; 82: 408-417
- 12 Tapia A, Rodriguez J, Theoduloz C, Lopez S, Feresin G, Schmeda-Hirschmann G. Free radical scavengers and antioxidants from Baccharis grisebachii . J Ethnopharmacol 2004; 95: 155-161
- 13 Oyaizu M. Studies on product of browning reaction prepared from glucose amine. Jpn J Nutr 1986; 44: 307-315
- 14 Gülçin I, Bursal E, Sehitoglu MH, Bilsel M, Gören AC. Polyphenol contents and antioxidant activity of lyophilized aqueous extract of propolis from Erzurum, Turkey. Food Chem Toxicol 2010; 48: 2227-2238
- 15 Jorgensen JH, Turnidge JD, Washington JA. Antibacterial susceptibility tests: dilution and disk diffusion methods. In: Murray PR, Faller MA, Tenover FC, Baron EJ, Yolken RH, editors Manual of clinical microbiology, 7th ed. Washington DC: ASM Press; 1999: 1526-1543
- 16 CLSI. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard-seventh edition. Wayne: Clinical and Laboratory Standards Institute; 2008. CLSI document M100-S18
- 17 Hadacek F, Greger H. Testing of antifungal natural products: methodologies, comparability and assay choice. Phytochem Anal 2000; 11: 137-147
- 18 Jacob MR, Walker LA. Natural products and antifungal drug discovery. In: Ernst EJ, Rogers PD, editors Methods in molecular medicine, Vol. 118: antifungal agents: methods and protocols. 1st edition. Totowa: Humana Press Inc.; 2005: 83-110