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Manage software rollouts and standards compliance. Use Adobe and Microsoft tools to manage and deploy updates. Get support for a wide range of document security standards. Pick and choose additional services to do even more with Reader. Customize your Reader to fit your needs. Assay- guided isolation led to seven p-coumaric acid derivatives and six flavonoids as the main active constituents of the crude drug.
The activity towards the superoxide anion was mainly due to the flavonoid constituents. Both p-coumaric acid derivatives and flavonoids inhibited lipoperoxidation in erythrocytes. The results support the use of Baccharis grisebachii in Argentinian traditional medicine. All rights reserved.
Keywords: Baccharis grisebachii; Asteraceae; p-Coumaric acid derivatives; Flavonoids; Labdane diterpenes; Antioxidants 1. Introduction Decoctions from the aerial parts of some Baccharis species such as Baccharis articulata, B. Recently, it has been in Argentina, are recommended in infusion to treat gastric ul- reported that a crude extract of Baccharis illinita, used for its cers, as a digestive, local antiseptic and cicatrizant. The plant protective action to relieve stomach ulcers, showed gastro- is a bush, which grows in sandy soils in northern Argentina, protective effects in rats Baggio et al.
Rodriguez , gferesin unsj. Feresin , schmeda utalca. Tapia et al. Several gastrointestinal tract diseases seem to be 2. Isolation induced by oxidative stress Oh et al. On the other hand, the traditional use of many Baccharis species are as The resinous exudate of the aerial parts was obtained by hepatoprotective and digestive crude drugs.
The CH2 Cl2 solution was American crude drugs, we now report the isolation and iden- filtered and taken to dryness under reduced pressure to give tification of free radical scavengers and antioxidants from the a semisolid yellow-orange residue g.
After TLC compari- 2. Compounds 1—11, 13 and 14 were isolated from Province, Argentina, during the flowering time in Decem- the exudate by extensive chromatography. While compounds ber The plant was identified by Dr. Sephadex LH 20 45 cm length, 8 cm i.
Fraction 7 afforded 30 mg 3.
For and MeOH extract, respectively. For the UV spectra of the flavonoids see respectively. Each extract was tested for free radical scav- Mabry et al.
The remaining aqueous phase was was assessed by the decoloration of a methanolic so- lyophilized 40 g. The isolation of the free radical scavenging lution of 1,1,-diphenylpicrylhydrazyl radical DPPH, compounds was monitored by the DPPH autographic assay. Some 30 pounds. Fractions were pooled of three determinations. The formic acid to yield mg of compound 9 Nevandensin degree of decoloration indicates the free radical scavenging Rt: 33 min.
The combined fractions 22—23 afford 30 mg of efficiency of the substances. Catechin was used as a refer- quercetin The same compounds were isolated and iden- ence free radical scavenger. Superoxide anion scavengers reduce the speed of 3,5-Diprenyl-p-coumaric acid 4: 5. The activity was measured 4-Acetyl-3,5-diprenylcinnamic acid 5: 1. Xanthine oxidase activity The XO A.
Most of the com- spectronic Genesys 10 UV-scanning equipment Schmeda- pounds were previously reported in an article on the antimi- Hirschmann et al. Extracts and products were evalu- crobial effect of the crude drug Feresin et al. The crude exudate showed a moderate effect towards the 2.
The unpolar extracts of the tions. Human red blood cells obtained from healthy donors plant hexane and DCM-soluble were devoid of activity in were washed three times in cold phosphate buffered saline the superoxide and XO assays with a moderate effect as an PBS by centrifugation at rpm. After the last wash- inhibitor of lipoperoxidation in erythrocytes. The final cell sus- ether and EtOAc extracts obtained by partition of the defatted pensions were incubated with different concentrations of the methanol extract with Et2 O and EtOAc, respectively.
The final concentration of DMSO in the samples due to the flavonoid constituents of the crude drug.
The xanthine oxidase inhibitory effect of the der vigorous shaking.
Results are expressed Both p-coumaric acid derivatives and flavonoids inhibited as percentage of inhibition compared to controls. Each deter- lipoperoxidation in erythrocytes.
The highest activity was mination was repeated four times. For the p- 2. Cells were plated were the p-coumaric acid derivatives 1, 4 and 5 and the at a density of 2. Con- flavonoid 9.
It can be estimated that the content of p-coumaric fluent cultures of MRC-5 cells were treated with medium acid derivatives and flavonoids in the crude drug are about containing the compounds at concentrations ranging from 0. Cells Several biological activities were reported for 3-prenyl were exposed for 24 hours to test medium with or without hydroxycinnamic acid 1, also known as drupanin as well as the compound control. Each drug concentration was for 3,5-diprenylhydroxycinnamic acid 4.
The compounds tested in quadruplicate, and repeated three times in separate have been shown to display tripanocidal activity towards experiments. Drupanin inhib- Haun To calculate the IC50 values the results were ited cell growth in human tumor cells Akao et al.
Results and discussion acid in a micelle solution Aga et al.
In a study on the antioxidant compounds from corn steep From the exudate and polar extracts of Baccharis grise- liquor, Niwa et al. The activity was mainly affected by A. Structure of the compounds isolated from the resinous exudate and methanolic extract of Baccharis grisebachii.
The p-coumaric acid derivatives were more chloride in a better way than caffeic acid. The authors found that o- The aromatic ortho-dihydroxy groups of the cinnamic dihydroxy derivatives of cinnamic and benzoic acids caffeic, acid derivatives combined with a lipophilic residue seems chlorogenic, and protocatechuic acids , in a molar ratio of 1 to be a prerequisite for an optimal binding within the ac- to metmyoglobin, efficiently blocked LDL oxidation initiated tive site of the human neutrophil elastase Siedle et al.
Furthermore, the replacement of one OH In a study on the structure-hepatoprotective effect of group from catecholic structure with an H p-coumaric acid 3,4-dihydroxycinnamic acid caffeic acid derivatives, Perez- or methoxy group ferulic acid decreased the antioxidant Alvarez et al.
The 4-hydroxy play antioxidant activity measured by the decoloration of the substituent, however, proved to be very important for hepato- DPPH radical and correlated with the methyl linoleate assay protective activity because the 4-hydroxy analogue improved Kikuzaki et al. Ferulic acid was the most effective A. The crushed leaves and flowers are recommended as an antisep- results indicated that lipophilicity of the antioxidants might tic and wound healing agent.
The plant exudate as well as be an important feature in their activity. Hydroxycinnamic some of its main compounds have been shown to display an- acids such as ferulic acid, sinapic acid, and p-coumaric acid timicrobial effect towards dermatophytic fungi and bacteria linked to the plant cell wall polymers can be released by in- Feresin et al.
Flavonoids and phenolics of higher plants are known to In an in vitro investigation of the inhibitory effect of be excellent antioxidants in vitro and numerous studies sug- phenylpropanoids on copper-induced protein oxidative mod- gest that dietary intake of plant polyphenol antioxidants may ification of mice brain homogenate, Toda found that have positive effects in oxidative-stress related pathologies phenolic carboxylic acids with 3,4-dihydroxy or 4-hydroxy- Urquiaga and Leighton, Several diseases of the gas- 3-methoxy substituents and benzo-alpha-pyrons with 6,7- trointestinal tract seem to be induced by oxidative stress Oh dihydroxy or 7-hydroxymethoxy substituents in phenyl- et al.
This compound has been reported as anti- coumaric acid derivatives, giving support to its use as a medic- inflammatory Reddy et al. Quercetin is a well-known free radical scavenger medicine of San Juan Province in Argentina.
It is well known that antioxidant activity is com- Several biological activities have been reported so far for monly related with gastroprotective El-Abhar et al. Their role in oxidative stress is well known and re- Kahraman et al.
More- Kostyuk, ; Mahakunakorn et al.
Extracts and compounds from B. Our results support the traditional use of infusions of organism with natural antioxidant compounds derived from Baccharis grisebachii by the Andean population in western plants may have beneficial effects since it has been shown that Argentina.
Tapia thanks the Universidad de Talca for a grant.