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Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria.
J Nat Prod. 2003 Aug; 66(8):1061-4.JN

Abstract

Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays.

Authors+Show Affiliations

Cioffi G
Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy.
Morales Escobar L
No affiliation info available
Braca A
No affiliation info available
De Tommasi N
No affiliation info available

MeSH

AntioxidantsBoliviaChalconeElectron Spin Resonance SpectroscopyFlavanonesGlycosidesMacluraMolecular StructureOxidation-ReductionPlant BarkPlant StemsPlants, MedicinalStereoisomerismbeta Carotene

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12932124

Citation

Cioffi, Giuseppina, et al. "Antioxidant Chalcone Glycosides and Flavanones From Maclura (Chlorophora) Tinctoria." Journal of Natural Products, vol. 66, no. 8, 2003, pp. 1061-4.
Cioffi G, Morales Escobar L, Braca A, et al. Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. J Nat Prod. 2003;66(8):1061-4.
Cioffi, G., Morales Escobar, L., Braca, A., & De Tommasi, N. (2003). Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. Journal of Natural Products, 66(8), 1061-4.
Cioffi G, et al. Antioxidant Chalcone Glycosides and Flavanones From Maclura (Chlorophora) Tinctoria. J Nat Prod. 2003;66(8):1061-4. PubMed PMID: 12932124.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. AU - Cioffi,Giuseppina, AU - Morales Escobar,Luis, AU - Braca,Alessandra, AU - De Tommasi,Nunziatina, PY - 2003/8/23/pubmed PY - 2003/12/25/medline PY - 2003/8/23/entrez SP - 1061 EP - 4 JF - Journal of natural products JO - J Nat Prod VL - 66 IS - 8 N2 - Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/12932124/Antioxidant_chalcone_glycosides_and_flavanones_from_Maclura__Chlorophora__tinctoria_ DB - PRIME DP - Unbound Medicine ER -