Antioxidant Activity of an Unusual 3-Hydroxyindole Derivative Isolated from Fruits of Aristotelia chilensis (Molina) Stuntz

Abstract

3-Hydroxyindole was isolated from the EtOH extract of fruits of Aristotelia chilensis during analyses by HPLC/MS and GC/MS and identifi ed by its mass fragmentation pattern and spectrophotometric data. Additionally, this extract showed an interesting antioxidant activity in DPPH, crocin and TBARS assays. The presence of this type of compound in this fruit species permits us to explain its strong antioxidant activity and its important part in the biosynthetic pathway of phenolic and alkaloid compounds in this plant. Therefore this compound could be useful for the development of future nutraceutical and antioxidant protective agents.Key words: Hydroxyindole, Antioxidant Activity, Aristotelia chilensis IntroductionAnthocyanins, fl avonoids and phenolic acids are compounds which occur very often in many plant families. Their different biological activities, including antioxidant, antimicrobial, carcinogenic, cytotoxic, anti-infl ammatory and mutagenic properties, make them interesting objects of research (Middleton and Kandaswami, 1993). Recently, attenuation has been payed to the dietary indole amines melatonin and serotonin in different plant foods, including grapes and berries, thus further supporting the hypothesis that health benefi ts associated with Mediterranean dietary style are due to plant food chemical diversity (Iriti and Faoro, 2008). The presence of hydroxyindole in fruits tissues is relevant for their important biological activities. Additionally, the importance of indole moieties in the biosynthesis of phenolics is documented (Applewhite et al., 1994).We have under continuous study different extracts of edible fruits of southern Chile. Recently, we have published the antioxidant and cardioprotective activities of phenolic extracts from fruits of Chilean black berry (Céspedes et al., 2008), which have traditionally been consumed for the treatment of diarrhea and dysentery. Previously, we have reported the alkaloid composition of the leaves of Aristotelia chilensis (Céspedes et al., 1993;Silva et al., 1997). There are some reports about the antioxidant activity and a partial composition of anthocyanidins (Miranda-Rottman et al., 2002;Escribano-Bailon et al., 2006).In continuation of our search for more specifi c antioxidant activities, in the present paper we report the antioxidant activity of an unusual 3-hydroxyindole derivative and of a very interesting fraction obtained during a metabolomic analysis of fruits of A. chilensis. The occurrence of 3-hydroxyindole helps us to explain the antioxidant, chemopreventive, cardiopreventive, and anti-infl ammatory activities of this fruit. Material and Methods Plant materialPlants and fruits of Aristotelia chilensis (Molina) Stuntz (Elaeocarpaceae) were collected from fi elds at the foothills of Los Andes Mountains (900 m, 38°38'57'' S, 71°52'32'' W) on a track at the shore of "Quepe" lake, very near to "Conguillio" National Park, Cherquenco district, near Temuco City, Chile, in January 2006. The samples were identifi ed botanically by Professor Fernando Per...

Usage, biological activity, and safety of selected botanical dietary supplements consumed in the United States

“… 23 , 91 , 98 While most analytical reports have concentrated on the chemical profiling of maqui berry phenolic compounds, mainly anthocyanins, using various analytical techniques coupled in some cases with some biological testing, reports on the isolation of secondary metabolites from the fruits are still scarce. 93 , 94 , 98 , 102 , 103 Among the few such studies is the isolation of 3-hydroxyindole, which was found to possess antioxidant capacity, 104 and the aforementioned bioactive delphinidin-3- O -sambuboside-5- O -glucopyranoside isolated from an anthocyanin-rich extract of maqui berry. 100 …”

Maqui (Aristotelia chilensis): Morpho-phenological characterization to design high-yielding cultivation techniques

“…These results triggered recent studies and development of food, nutraceutical, cosmetical and pharmaceutical products (Avello et al, 2009;Céspedes et al, 2008Céspedes et al, , 2009Céspedes et al, , 2010Gironés-Vilaplana et al, 2012;Rubilar et al, 2011;Schreckinger et al, 2010), all of them based until now on wild crafted maqui berries with increasing exploitation.…”

Antioxidant and anti-inflammatory effects of extracts from Maqui berry Aristotelia chilensis in human colon cancer cells

“…Previously, it has been reported the alkaloid composition of the leaves of A. chilensis [16][17][18][19][20]. On the other hand, in the continuation of the general screening program of Chilean flora with biological activities [20], up-to-date several studies report that fruit extracts of A. chilensis possess several biological activities including antioxidant, cardioprotection, enzymes inhibition and as mediators in inflammation, among other activities [20][21][22][23][24][25][26][27]. It has been enjoyed as an ethno-medicine for many years, it is also used as an anti-inflammatory agent on kidneys pains, diverse digestive ailments (intestinal tumors and stomach ulcers), fever and cicatrization injuries, antiinflammatory effects, antioxidant properties, antiatherogenic, hypoglycemia, antihaemolytic, and inhibit LDL oxidation [28][29][30].…”