Related Experiment Video
Updated: Sep 8, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
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.
Abstract:
Six undescribed sesquiterpene esters, euphoresulins A-F, along with fourteen known daucane analogues were isolated from the aerial parts of Euphorbia esula growing in Uzbekistan. Their structures were determined on the basis of extensive spectroscopic analyses, with absolute configurations established by comparison of experimental and calculated ECD data, in addition to single-crystal X-ray diffraction crystallography. Euphoresulins A-F (1-6) presented sesquiterpene ester types of daucane for euphoresulins A-D (1-4) and aromadendrane for euphoresulins E-F (5-6). Compounds 7-20 were firstly isolated from the genus Euphorbia, wherein compound 7 was naturally unprecedented. Bioactivity assays revealed that three compounds (3, 9 and 10) carrying 9-keto group and 6-acyloxy residue of trisubstituted benzoyloxy moiety demonstrated anti-inflammatory effects by inhibiting the release of NO in LPS-induced RAW 264.7 macrophages, with IC50 values ranging from 22.49 ± 0.21 to 30.31 ± 1.19 μM. Additionally, five esters (3, 9, 11, 14 and 18) bearing Δ9, Δ8 or 8β-OH, and 6-benzoyloxy groups with versatile substitution patterns displayed certain cytotoxic activities against HeLa, HT-29 and MCF-7 cell lines, representing IC50 values of 14.71 ± 0.75, 15.30 ± 0.75 and 26.36 ± 1.84 μM, respectively for compound 18.
More Related Videos
Related Concept Videos
E1 Reaction: Stereochemistry and Regiochemistry
Structure and Nomenclature of Epoxides
E2 Reaction: Stereochemistry and Regiochemistry
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...
E2 Reaction: Kinetics and Mechanism
Thermal Electrocyclic Reactions: Stereochemistry
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.
Preparation of Epoxides
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...

