Antioxidant principles from Bauhinia tarapotensis.
A new cyclohexenone (1) and a new caffeoyl ester derivative (2), together with the known compounds (-)-isolariciresinol 3-alpha-O-beta-D-glucopyranoside (3), (+)-1-hydroxypinoresinol 1-O-beta-D-glucopyranoside (4), isoacteoside (5), luteolin 4'-O-beta-D-glucopyranoside (6), and indole-3-carboxylic acid (7), were isolated from the leaves of Bauhinia tarapotensis. The structures of these new compounds were determined by spectroscopic data analysis. The antioxidant activities of 1-7 were determined by measuring their free radical scavenging effects, using the 1,1-diphenyl-2-dipicrylhydrazyl free radical (DPPH) and Trolox equivalent antioxidant activity (TEAC) methods, and the coupled oxidation of beta-carotene and linoleic acid. Compounds 3-5 showed good activities in the DPPH and TEAC tests, while compounds 1 and 2 were active in the coupled oxidation of beta-carotene and linoleic acid bioassay.
Braca
A
A
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno, 33, 56126 Pisa, Italy. braca@farm.unipi.it
De Tommasi
N
N
Di Bari
L
L
Pizza
C
C
Politi
M
M
Morelli
I
I
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D052160:Benzothiazoles; D015764:Bepridil / Q000031:analogs & derivatives* / Q000494:pharmacology; D001713:Biphenyl Compounds; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002839:Chromans / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004484:Ecuador; D007887:Fabaceae / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D047311:Luteolin; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols; D010851:Picrates; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry
C435257:1-hydroxypinoresinol 1-O-glucopyranoside; D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002109:Caffeic Acids; D002839:Chromans; D003512:Cyclohexanones; D005419:Flavonoids; D016166:Free Radical Scavengers; D005960:Glucosides; D007211:Indoles; D010636:Phenols; D010851:Picrates; D013451:Sulfonic Acids; C435255:cyclohexanone, caffeoyl ester; C435256:isolariciresinol 3-O-glucopyranoside; C120646:luteolin 4'-O-glucoside; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C064683:isoacteoside; C012382:indole-3-carboxylic acid; C036468:cyclohexanone; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl; D047311:Luteolin; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid