Antioxidant phenylethanoid glycosides and a neolignan from Jacaranda caucana.
Extracts from several plants of the family Bignoniaceae from Panama were submitted to a rapid DPPH TLC test for the detection of radical-scavenging activity. The MeOH extract of the stems of Jacaranda caucana, a tree that grows from Costa Rica to Colombia, was selected due to its interesting activity and the lack of phytochemical studies on the polar extract. This extract was partitioned between ethyl acetate, butanol, and water. The EtOAc fraction afforded two new phenylethanoid glycosides (1, 2), along with protocatechuic acid, acteoside, and jionoside D. Further purifications yielded isoacteoside and martynoside. The BuOH fraction afforded a new rhamnosyl derivative of sisymbrifolin (8), a neolignan. The structures were determined by means of spectrometric methods, including 1D and 2D NMR experiments and MS analysis.
Laboratory of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland.
Frédéric
F
Martin
Anne-Emmanuelle
AE
Hay
Valentin R
VR
Quinteros Condoretty
Delphine
D
Cressend
Marianne
M
Reist
Mahabir P
MP
Gupta
Pierre-Alain
PA
Carrupt
Kurt
K
Hostettmann
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029402:Bignoniaceae / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D059808:Polyphenols
D000975:Antioxidants; D016166:Free Radical Scavengers; D005960:Glucosides; D006027:Glycosides; D017705:Lignans; D010636:Phenols; C550788:4-O-rhamnosyl-7S,8R-7',8'-erythro-sisymbrifolin; C550789:6'-O-(1-hydroxy-4-oxo-cyclohexanacetyl)acteoside; C550790:6'-O-(cis-1,4-dihydroxycyclohexanacetyl)acteoside; C058956:acteoside; D059808:Polyphenols