[Further acylated chalcones from Bidens pilosa]
1Institut für Pharmazeutische Biologie der Universität Marburg, Deutschhausstr. Marburg/L., Federal Republic of Germany.
Planta Medica
|October 1, 1988
Summary
Three new acylated chalcone glucosides were identified in Bidens pilosa leaves. These compounds were structurally characterized using advanced spectroscopic techniques, contributing to natural product chemistry.
Area of Science:
- Phytochemistry
- Natural Product Chemistry
- Organic Chemistry
Context:
- Bidens pilosa (Asteraceae) is a plant species known for its diverse secondary metabolites.
- Acylated chalcone glucosides represent a class of compounds with potential biological activities.
- Isolation and characterization of novel compounds are crucial for understanding plant chemical diversity.
Purpose:
- To isolate and elucidate the structures of new acylated chalcone glucosides from Bidens pilosa leaves.
- To contribute to the phytochemical knowledge of the Asteraceae family.
- To provide characterized compounds for potential further biological evaluation.
Summary:
- Three novel acylated chalcone glucosides were successfully isolated from the leaves of Bidens pilosa L.
- The structures of these compounds were determined using comprehensive spectroscopic analyses, including 1D and 2D NMR (1H-NMR, 2D-1H-NMR, 13C-NMR).
- The identified compounds are okanin 4'- O-beta- D-(4''-acetyl-6''- TRANS- P-coumaroyl)-glucoside, okanin 4'- O-beta- D-(2'',4''-diacetyl-6''- TRANS- P-coumaroyl)-glucoside, and okanin 4'- O-beta- D-(3'',4''-diacetyl-6''- TRANS- P-coumaroyl)-glucoside.
Impact:
- Expands the known chemical constituents of Bidens pilosa.
- Provides new molecular entities for natural product research.
- Enhances the understanding of chalcone glucoside biosynthesis and structure-activity relationships.
Related Concept Videos
02:05Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
02:41Formation of Halohydrin from Alkenes
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
01:01Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
02:46Halogenation of Alkenes
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.