Related Experiment Video
Updated: Oct 24, 2025
07:59
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
10.1K
Phenanthrene Dimers: Promising Source of Biologically Active Molecules
Antonino De Natale1, Antonino Pollio1, Anna De Marco2
1Department of Biology, University of Napoli, Federico II, via Cinthia, Napoli I-80126, Italy.
Current Topics in Medicinal Chemistry
|August 16, 2021
Summary
Phenanthrene dimers, natural compounds from plants like orchids, exhibit diverse biological activities. Their structures serve as valuable chemotaxonomic markers and offer insights into plant biogenesis.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Medicinal Chemistry
Background:
- Over a hundred phenanthrenoid dimers have been identified, with forty-two being completely phenanthrenic.
- These compounds are sourced from fourteen plant genera across five families, notably Orchidaceae.
- Semi-synthesis of acetylated and methylated dimers aids in structural elucidation of natural products.
Purpose of the Study:
- To review the occurrence of phenanthrene dimers in various natural sources.
- To provide a comprehensive overview of their structural characteristics.
- To summarize the diverse biological activities associated with these compounds.
Main Methods:
- Literature review of isolated phenanthrenoid dimers.
- Analysis of structural features and semi-synthetic modifications.
- Compilation of reported biological activities.
Main Results:
- Phenanthrene dimers are found in diverse plant families, with specific substituents potentially acting as chemotaxonomic markers (e.g., vinyl group in Juncaceae).
- Biogenetic pathways suggest formation via radical coupling of phenanthrenes or dehydrogenation of dihydro-analogs.
- These compounds display a wide range of biological activities, including antiproliferative, antimicrobial, anti-inflammatory, and antioxidant effects.
Conclusions:
- Phenanthrene dimers represent a significant class of natural products with potential applications in medicine and chemotaxonomy.
- Further research into their biogenesis and biological activities is warranted.
- Their structural diversity and biological relevance underscore their importance in natural product chemistry.
![Chemical-Induced Skin Carcinogenesis Model Using Dimethylbenz[a]Anthracene and 12-O-Tetradecanoyl Phorbol-13-Acetate DMBA-TPA](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60445.jpg&w=3840&q=50)
Related Concept Videos
01:25Aromatic Compounds: Overview
12.1K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
In 1825, Faraday...
12.1K
01:24Diels–Alder Reaction: Characteristics of Dienophiles
6.6K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.6K
01:29Diels–Alder Reaction: Characteristics of Dienes
4.6K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.6K
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
3.3K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.3K
01:26Physical Properties of Amines
3.6K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.6K
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
3.5K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
3.5K