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Antioxidant and Antimutagenic Polyisoprenylated Benzophenones and Xanthones from Rheedia acuminata

Almanza, Giovanna R.; Quispe, Raul; Mollinedo, Patricia LU ; Rodrigo, Gloria LU ; Fukushima, Odette; Villagomez, Rodrigo LU ; Åkesson, Björn LU and Sterner, Olov LU (2011) In Natural Product Communications 6(9). p.1269-1274
Abstract
Dichloromethane extract of the stem bark of Rheedia acuminata yielded three benzophenones with antioxidant activity, the new one named acuminophenone A (1), guttiferone K (2) and isoxanthochymol (3), along with the known xanthones formoxanthone C (4) and macluraxanthone (5). The structures were established through interpretation of their spectroscopic data, the stereochemistry of compounds (1) and (2) were resolved by experimental and computational experiments and their antioxidant activities were measured using the DPPH, ABTS and TEAC assays. The antioxidant results showed that metabolites 1, 4 and 5 had a better antioxidant activity than the reference compound quercetin. In addition, we evaluate the mutagenicity and antimutagenicity of... (More)
Dichloromethane extract of the stem bark of Rheedia acuminata yielded three benzophenones with antioxidant activity, the new one named acuminophenone A (1), guttiferone K (2) and isoxanthochymol (3), along with the known xanthones formoxanthone C (4) and macluraxanthone (5). The structures were established through interpretation of their spectroscopic data, the stereochemistry of compounds (1) and (2) were resolved by experimental and computational experiments and their antioxidant activities were measured using the DPPH, ABTS and TEAC assays. The antioxidant results showed that metabolites 1, 4 and 5 had a better antioxidant activity than the reference compound quercetin. In addition, we evaluate the mutagenicity and antimutagenicity of the CH2Cl2 extract as well as of the free radical scavenger compounds 1, 4 and 5 by the AMES Salmonella/microsomal test. No mutagenicity was found in the CH2Cl2 extract using Salmonella typhimurium strains TA98, TA100, TA102, TA1537 and TA1538, with or without S9 metabolic activation. The pure compounds neither showed mutagenicity in TA 102 strain and the most important result was the strong reduction of mutagenic effect induced by hydrogen peroxide in S. typhimurium TA 102, with or without S9, showed by the compounds 1 (more than 93%) and 4 (more than 88%) at 0.02 mu g/plate. (Less)
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published
subject
keywords
Rheedia acuminata, polyisoprenylated benzophenones, prenylated, xanthones, acuminophenone A, guttiferone K, isoxanthochymol, formoxanthone C, macluraxanthone, antioxidant capacity, mutagenicity, antimutagenicity
in
Natural Product Communications
volume
6
issue
9
pages
1269 - 1274
publisher
Natural Products Inc
external identifiers
  • wos:000294381500016
  • scopus:80155169009
ISSN
1934-578X
language
English
LU publication?
yes
id
cc8c2b87-ad34-4822-9072-1f29cb0e3da8 (old id 2159218)
date added to LUP
2011-09-22 16:00:03
date last changed
2017-05-28 03:14:56
@article{cc8c2b87-ad34-4822-9072-1f29cb0e3da8,
  abstract     = {Dichloromethane extract of the stem bark of Rheedia acuminata yielded three benzophenones with antioxidant activity, the new one named acuminophenone A (1), guttiferone K (2) and isoxanthochymol (3), along with the known xanthones formoxanthone C (4) and macluraxanthone (5). The structures were established through interpretation of their spectroscopic data, the stereochemistry of compounds (1) and (2) were resolved by experimental and computational experiments and their antioxidant activities were measured using the DPPH, ABTS and TEAC assays. The antioxidant results showed that metabolites 1, 4 and 5 had a better antioxidant activity than the reference compound quercetin. In addition, we evaluate the mutagenicity and antimutagenicity of the CH2Cl2 extract as well as of the free radical scavenger compounds 1, 4 and 5 by the AMES Salmonella/microsomal test. No mutagenicity was found in the CH2Cl2 extract using Salmonella typhimurium strains TA98, TA100, TA102, TA1537 and TA1538, with or without S9 metabolic activation. The pure compounds neither showed mutagenicity in TA 102 strain and the most important result was the strong reduction of mutagenic effect induced by hydrogen peroxide in S. typhimurium TA 102, with or without S9, showed by the compounds 1 (more than 93%) and 4 (more than 88%) at 0.02 mu g/plate.},
  author       = {Almanza, Giovanna R. and Quispe, Raul and Mollinedo, Patricia and Rodrigo, Gloria and Fukushima, Odette and Villagomez, Rodrigo and Åkesson, Björn and Sterner, Olov},
  issn         = {1934-578X},
  keyword      = {Rheedia acuminata,polyisoprenylated benzophenones,prenylated,xanthones,acuminophenone A,guttiferone K,isoxanthochymol,formoxanthone C,macluraxanthone,antioxidant capacity,mutagenicity,antimutagenicity},
  language     = {eng},
  number       = {9},
  pages        = {1269--1274},
  publisher    = {Natural Products Inc},
  series       = {Natural Product Communications},
  title        = {Antioxidant and Antimutagenic Polyisoprenylated Benzophenones and Xanthones from Rheedia acuminata},
  volume       = {6},
  year         = {2011},
}