Related Experiment Video
Updated: Sep 8, 2025
07:59
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
9.9K
Sesquiterpenoids from Euphorbia esula L
Defeng Yan1, Miaomiao Zhang1, Dan Tang2
1State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, People's Republic of China; University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.
Phytochemistry
|September 6, 2025
Summary
Six new sesquiterpene esters, euphoresulins A-F, were isolated from Euphorbia esula. Some compounds showed anti-inflammatory and cytotoxic activities, offering potential for new drug development.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Organic Chemistry
Background:
- Euphorbia esula is a plant species known for its diverse chemical constituents.
- Sesquiterpene esters represent a class of natural products with a wide range of biological activities.
- Investigating novel compounds from medicinal plants is crucial for drug discovery.
Purpose of the Study:
- To isolate and characterize new sesquiterpene esters from Euphorbia esula.
- To evaluate the anti-inflammatory and cytotoxic potential of isolated compounds.
- To contribute to the understanding of the chemical diversity within the Euphorbia genus.
Main Methods:
- Isolation of compounds using chromatographic techniques.
- Structure elucidation via extensive spectroscopic analyses (NMR, MS).
- Determination of absolute configurations using ECD data and X-ray crystallography.
Main Results:
- Six new sesquiterpene esters, euphoresulins A-F, were identified, along with fourteen known daucane analogues.
- Compounds 3, 9, and 10 exhibited anti-inflammatory activity by inhibiting nitric oxide (NO) release.
- Compounds 3, 9, 11, 14, and 18 displayed cytotoxic effects against various cancer cell lines.
Conclusions:
- The study successfully identified novel sesquiterpene esters from Euphorbia esula.
- The isolated compounds demonstrate promising anti-inflammatory and cytotoxic properties.
- These findings highlight the potential of Euphorbia esula as a source for bioactive natural products.
Keywords:
Anti-inflammatory activityAromadendraneCytotoxicityDaucaneECD calculationEuphorbia esula L.EuphorbiaceaeSesquiterpenoidX-ray diffractionMore Related Videos
Related Concept Videos
02:43E1 Reaction: Stereochemistry and Regiochemistry
9.9K
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
9.9K
02:38Structure and Nomenclature of Epoxides
6.9K
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
6.9K
02:43E2 Reaction: Stereochemistry and Regiochemistry
11.9K
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
11.9K
02:45E2 Reaction: Kinetics and Mechanism
10.6K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.6K
01:17Thermal Electrocyclic Reactions: Stereochemistry
2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
03:00Preparation of Epoxides
8.1K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
8.1K