Tags

Type your tag names separated by a space and hit enter

A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.
Arch Pharm Res. 2011 Apr; 34(4):543-50.AP

Abstract

The aerial part of Rubus rigidus var. camerunensis (Rosaceae) is used to treat respiratory and cardiovascular disorders in the Cameroonian traditional medicine. The ethanol extract exhibited more potent antioxidant activity (E(max)s of 119% and 229% activity on DPPH and β-carotene test) than aqueous extract. Bioactivity-guided fractionation of the ethanol extract based on free radical-scavenging assay (DPPH assay) afforded five flavonoid glycosides (four flavonol glycosides and an anthocyanin) and three glucosides of 19α-hydroxyursane-type triterpenoid (two monomeric and one dimeric triterpenoids). The flavonoids were identified as kaempferol 3-O-(2″-O-E-p-coumaroyl)-β-D-glucopyranoside (1), kaempferol-3-O-β-D-glucopyranoside (astragalin, 2), kaempferol-3-O-α-L-arabinofuranoside (juglanin, 3), quercetin-3-O-β-D-glucopyranoside (isoquercitrin, 4), pelargonidin-3-O-β-D-glucopyranoside (callistephin, 5). The three triterpenoids were 2α, 3β, 19α, 23-tetrahydroxyurs-12-ene-28-O-β-D-glucopyranosyl ester (nigaichigoside F(1), 6), 2α, 3β, 19α-trihydroxyurs-12-ene-23-carboxyl-28-O-β-D-glucopyranosyl ester (suavissimoside R(1), 7) as monomeric triterpenoids and coreanoside F(1) (8) as a dimeric triterpenoid. The flavonoids exhibited potent antioxidant activities (66 to 93.56% against DPPH radical) and they were also active on β-carotene test. Coreanoside F(1) exhibited a 63% antioxidant activity, meanwhile the other two triterpenoids showed a weak activity. Three important facts on structure-activity relationship were observed: Compound 8, a dimeric triterpenoid glycoside, strongly enhanced antioxidant activity of its monomers, compound 3 with 3-O-α-L-arabinofuranyl has much more potent activity than compound 2 with 3-O-β-D-glucopyranosyl, and antocyanin (5) is more potent than its corresponding flavonol glycosides.

Links

Aggregator Full Text

Authors+Show Affiliations

Nguelefack TB
Laboratory of Animal Physiology and Phytopharmacology, Faculty of Science, University of Dschang, Dschang, Cameroon.
Mbakam FH
No affiliation info available
Tapondjou LA
No affiliation info available
Watcho P
No affiliation info available
Nguelefack-Mbuyo EP
No affiliation info available
Ponou BK
No affiliation info available
Kamanyi A
No affiliation info available
Park HJ
No affiliation info available

MeSH

Biphenyl CompoundsDimerizationFlavonoidsFree Radical ScavengersFree RadicalsGlycosidesMolecular StructurePicratesPlant Components, AerialPlant ExtractsRosaceaeTriterpenes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21544719

Citation

Nguelefack, Télesphore Benoît, et al. "A Dimeric Triterpenoid Glycoside and Flavonoid Glycosides With Free Radical-scavenging Activity Isolated From Rubus Rigidus Var. Camerunensis." Archives of Pharmacal Research, vol. 34, no. 4, 2011, pp. 543-50.
Nguelefack TB, Mbakam FH, Tapondjou LA, et al. A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis. Arch Pharm Res. 2011;34(4):543-50.
Nguelefack, T. B., Mbakam, F. H., Tapondjou, L. A., Watcho, P., Nguelefack-Mbuyo, E. P., Ponou, B. K., Kamanyi, A., & Park, H. J. (2011). A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis. Archives of Pharmacal Research, 34(4), 543-50. https://doi.org/10.1007/s12272-011-0404-9
Nguelefack TB, et al. A Dimeric Triterpenoid Glycoside and Flavonoid Glycosides With Free Radical-scavenging Activity Isolated From Rubus Rigidus Var. Camerunensis. Arch Pharm Res. 2011;34(4):543-50. PubMed PMID: 21544719.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis. AU - Nguelefack,Télesphore Benoît, AU - Mbakam,Félicité Hermine Kamga, AU - Tapondjou,Léon Azéfack, AU - Watcho,Pierre, AU - Nguelefack-Mbuyo,Elvine Pami, AU - Ponou,Beaudelaire Kemvoufo, AU - Kamanyi,Albert, AU - Park,Hee-Juhn, Y1 - 2011/05/05/ PY - 2010/10/13/received PY - 2010/12/29/accepted PY - 2010/12/28/revised PY - 2011/5/6/entrez PY - 2011/5/6/pubmed PY - 2011/9/13/medline SP - 543 EP - 50 JF - Archives of pharmacal research JO - Arch Pharm Res VL - 34 IS - 4 N2 - The aerial part of Rubus rigidus var. camerunensis (Rosaceae) is used to treat respiratory and cardiovascular disorders in the Cameroonian traditional medicine. The ethanol extract exhibited more potent antioxidant activity (E(max)s of 119% and 229% activity on DPPH and β-carotene test) than aqueous extract. Bioactivity-guided fractionation of the ethanol extract based on free radical-scavenging assay (DPPH assay) afforded five flavonoid glycosides (four flavonol glycosides and an anthocyanin) and three glucosides of 19α-hydroxyursane-type triterpenoid (two monomeric and one dimeric triterpenoids). The flavonoids were identified as kaempferol 3-O-(2″-O-E-p-coumaroyl)-β-D-glucopyranoside (1), kaempferol-3-O-β-D-glucopyranoside (astragalin, 2), kaempferol-3-O-α-L-arabinofuranoside (juglanin, 3), quercetin-3-O-β-D-glucopyranoside (isoquercitrin, 4), pelargonidin-3-O-β-D-glucopyranoside (callistephin, 5). The three triterpenoids were 2α, 3β, 19α, 23-tetrahydroxyurs-12-ene-28-O-β-D-glucopyranosyl ester (nigaichigoside F(1), 6), 2α, 3β, 19α-trihydroxyurs-12-ene-23-carboxyl-28-O-β-D-glucopyranosyl ester (suavissimoside R(1), 7) as monomeric triterpenoids and coreanoside F(1) (8) as a dimeric triterpenoid. The flavonoids exhibited potent antioxidant activities (66 to 93.56% against DPPH radical) and they were also active on β-carotene test. Coreanoside F(1) exhibited a 63% antioxidant activity, meanwhile the other two triterpenoids showed a weak activity. Three important facts on structure-activity relationship were observed: Compound 8, a dimeric triterpenoid glycoside, strongly enhanced antioxidant activity of its monomers, compound 3 with 3-O-α-L-arabinofuranyl has much more potent activity than compound 2 with 3-O-β-D-glucopyranosyl, and antocyanin (5) is more potent than its corresponding flavonol glycosides. SN - 0253-6269 UR - https://www.unboundmedicine.com/medline/citation/21544719/A_dimeric_triterpenoid_glycoside_and_flavonoid_glycosides_with_free_radical_scavenging_activity_isolated_from_Rubus_rigidus_var__camerunensis_ L2 - https://dx.doi.org/10.1007/s12272-011-0404-9 DB - PRIME DP - Unbound Medicine ER -