Mass Spectra of the Hydroxyindole-3-carboxylic Acids and the Hydroxyskatoles

Marchelli, Rosangela; Jamieson, W. D.; Safe, S.; Hutzinger, O.; Heacock, R. A.

doi:10.1139/v71-211

Cited by 9 publications

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“…The electron impact fragmentations of indole, hydroxyindole and oxindol have been extensively investigated and documented (Powers, 1968;Marchelli et al, 1971;Evans et al, 1990 …”

Section: Resultsmentioning

confidence: 99%

“…The electron impact fragmentations of indole, hydroxyindole and oxindol have been extensively investigated and documented (Powers, 1968;Marchelli et al, 1971;Evans et al, 1990 +· ) correspond to typical fragmentations of these indole compounds. Finally, the study of these fragmentations, UV and NMR spectral data and comparison with those of an authentic sample led us to a 3-hydroxyindole.…”

Section: Resultsmentioning

confidence: 99%

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

Céspedes

Alarcón

Valdez‐Morales

et al. 2009

Zeitschrift Für Naturforschung C

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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...

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“…The electron impact fragmentations of indole, hydroxyindole and oxindol have been extensively investigated and documented (Powers, 1968;Marchelli et al, 1971;Evans et al, 1990 …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%